diff --git a/apps/sim/app/api/v1/admin/types.ts b/apps/sim/app/api/v1/admin/types.ts
index 0f2dfd814..615e02d78 100644
--- a/apps/sim/app/api/v1/admin/types.ts
+++ b/apps/sim/app/api/v1/admin/types.ts
@@ -640,6 +640,7 @@ export interface AdminDeployResult {
   isDeployed: boolean
   version: number
   deployedAt: string
+  warnings?: string[]
 }
 
 export interface AdminUndeployResult {
diff --git a/apps/sim/app/api/v1/admin/workflows/[id]/deploy/route.ts b/apps/sim/app/api/v1/admin/workflows/[id]/deploy/route.ts
index 4f9f517ae..3eab0374d 100644
--- a/apps/sim/app/api/v1/admin/workflows/[id]/deploy/route.ts
+++ b/apps/sim/app/api/v1/admin/workflows/[id]/deploy/route.ts
@@ -1,14 +1,23 @@
-import { db, workflow } from '@sim/db'
+import { db, workflow, workflowDeploymentVersion } from '@sim/db'
 import { createLogger } from '@sim/logger'
-import { eq } from 'drizzle-orm'
+import { and, eq } from 'drizzle-orm'
 import { generateRequestId } from '@/lib/core/utils/request'
-import { cleanupWebhooksForWorkflow } from '@/lib/webhooks/deploy'
+import { removeMcpToolsForWorkflow, syncMcpToolsForWorkflow } from '@/lib/mcp/workflow-mcp-sync'
+import {
+  cleanupWebhooksForWorkflow,
+  restorePreviousVersionWebhooks,
+  saveTriggerWebhooksForDeploy,
+} from '@/lib/webhooks/deploy'
 import {
   deployWorkflow,
   loadWorkflowFromNormalizedTables,
   undeployWorkflow,
 } from '@/lib/workflows/persistence/utils'
-import { createSchedulesForDeploy, validateWorkflowSchedules } from '@/lib/workflows/schedules'
+import {
+  cleanupDeploymentVersion,
+  createSchedulesForDeploy,
+  validateWorkflowSchedules,
+} from '@/lib/workflows/schedules'
 import { withAdminAuthParams } from '@/app/api/v1/admin/middleware'
 import {
   badRequestResponse,
@@ -28,10 +37,11 @@ interface RouteParams {
 
 export const POST = withAdminAuthParams<RouteParams>(async (request, context) => {
   const { id: workflowId } = await context.params
+  const requestId = generateRequestId()
 
   try {
     const [workflowRecord] = await db
-      .select({ id: workflow.id, name: workflow.name })
+      .select()
       .from(workflow)
       .where(eq(workflow.id, workflowId))
       .limit(1)
@@ -50,6 +60,18 @@ export const POST = withAdminAuthParams<RouteParams>(async (request, context) =>
       return badRequestResponse(`Invalid schedule configuration: ${scheduleValidation.error}`)
     }
 
+    const [currentActiveVersion] = await db
+      .select({ id: workflowDeploymentVersion.id })
+      .from(workflowDeploymentVersion)
+      .where(
+        and(
+          eq(workflowDeploymentVersion.workflowId, workflowId),
+          eq(workflowDeploymentVersion.isActive, true)
+        )
+      )
+      .limit(1)
+    const previousVersionId = currentActiveVersion?.id
+
     const deployResult = await deployWorkflow({
       workflowId,
       deployedBy: ADMIN_ACTOR_ID,
@@ -65,6 +87,32 @@ export const POST = withAdminAuthParams<RouteParams>(async (request, context) =>
       return internalErrorResponse('Failed to resolve deployment version')
     }
 
+    const workflowData = workflowRecord as Record<string, unknown>
+
+    const triggerSaveResult = await saveTriggerWebhooksForDeploy({
+      request,
+      workflowId,
+      workflow: workflowData,
+      userId: workflowRecord.userId,
+      blocks: normalizedData.blocks,
+      requestId,
+      deploymentVersionId: deployResult.deploymentVersionId,
+      previousVersionId,
+    })
+
+    if (!triggerSaveResult.success) {
+      await cleanupDeploymentVersion({
+        workflowId,
+        workflow: workflowData,
+        requestId,
+        deploymentVersionId: deployResult.deploymentVersionId,
+      })
+      await undeployWorkflow({ workflowId })
+      return internalErrorResponse(
+        triggerSaveResult.error?.message || 'Failed to sync trigger configuration'
+      )
+    }
+
     const scheduleResult = await createSchedulesForDeploy(
       workflowId,
       normalizedData.blocks,
@@ -72,15 +120,58 @@ export const POST = withAdminAuthParams<RouteParams>(async (request, context) =>
       deployResult.deploymentVersionId
     )
     if (!scheduleResult.success) {
-      logger.warn(`Schedule creation failed for workflow ${workflowId}: ${scheduleResult.error}`)
+      logger.error(
+        `[${requestId}] Admin API: Schedule creation failed for workflow ${workflowId}: ${scheduleResult.error}`
+      )
+      await cleanupDeploymentVersion({
+        workflowId,
+        workflow: workflowData,
+        requestId,
+        deploymentVersionId: deployResult.deploymentVersionId,
+      })
+      if (previousVersionId) {
+        await restorePreviousVersionWebhooks({
+          request,
+          workflow: workflowData,
+          userId: workflowRecord.userId,
+          previousVersionId,
+          requestId,
+        })
+      }
+      await undeployWorkflow({ workflowId })
+      return internalErrorResponse(scheduleResult.error || 'Failed to create schedule')
     }
 
-    logger.info(`Admin API: Deployed workflow ${workflowId} as v${deployResult.version}`)
+    if (previousVersionId && previousVersionId !== deployResult.deploymentVersionId) {
+      try {
+        logger.info(`[${requestId}] Admin API: Cleaning up previous version ${previousVersionId}`)
+        await cleanupDeploymentVersion({
+          workflowId,
+          workflow: workflowData,
+          requestId,
+          deploymentVersionId: previousVersionId,
+          skipExternalCleanup: true,
+        })
+      } catch (cleanupError) {
+        logger.error(
+          `[${requestId}] Admin API: Failed to clean up previous version ${previousVersionId}`,
+          cleanupError
+        )
+      }
+    }
+
+    logger.info(
+      `[${requestId}] Admin API: Deployed workflow ${workflowId} as v${deployResult.version}`
+    )
+
+    // Sync MCP tools with the latest parameter schema
+    await syncMcpToolsForWorkflow({ workflowId, requestId, context: 'deploy' })
 
     const response: AdminDeployResult = {
       isDeployed: true,
       version: deployResult.version!,
       deployedAt: deployResult.deployedAt!.toISOString(),
+      warnings: triggerSaveResult.warnings,
     }
 
     return singleResponse(response)
@@ -105,7 +196,6 @@ export const DELETE = withAdminAuthParams<RouteParams>(async (request, context)
       return notFoundResponse('Workflow')
     }
 
-    // Clean up external webhook subscriptions before undeploying
     await cleanupWebhooksForWorkflow(
       workflowId,
       workflowRecord as Record<string, unknown>,
@@ -117,6 +207,8 @@ export const DELETE = withAdminAuthParams<RouteParams>(async (request, context)
       return internalErrorResponse(result.error || 'Failed to undeploy workflow')
     }
 
+    await removeMcpToolsForWorkflow(workflowId, requestId)
+
     logger.info(`Admin API: Undeployed workflow ${workflowId}`)
 
     const response: AdminUndeployResult = {
diff --git a/apps/sim/app/api/v1/admin/workflows/[id]/versions/[versionId]/activate/route.ts b/apps/sim/app/api/v1/admin/workflows/[id]/versions/[versionId]/activate/route.ts
index 9b5ac90f1..a1406ca83 100644
--- a/apps/sim/app/api/v1/admin/workflows/[id]/versions/[versionId]/activate/route.ts
+++ b/apps/sim/app/api/v1/admin/workflows/[id]/versions/[versionId]/activate/route.ts
@@ -1,7 +1,15 @@
-import { db, workflow } from '@sim/db'
+import { db, workflow, workflowDeploymentVersion } from '@sim/db'
 import { createLogger } from '@sim/logger'
-import { eq } from 'drizzle-orm'
+import { and, eq } from 'drizzle-orm'
+import { generateRequestId } from '@/lib/core/utils/request'
+import { syncMcpToolsForWorkflow } from '@/lib/mcp/workflow-mcp-sync'
+import { restorePreviousVersionWebhooks, saveTriggerWebhooksForDeploy } from '@/lib/webhooks/deploy'
 import { activateWorkflowVersion } from '@/lib/workflows/persistence/utils'
+import {
+  cleanupDeploymentVersion,
+  createSchedulesForDeploy,
+  validateWorkflowSchedules,
+} from '@/lib/workflows/schedules'
 import { withAdminAuthParams } from '@/app/api/v1/admin/middleware'
 import {
   badRequestResponse,
@@ -9,6 +17,7 @@ import {
   notFoundResponse,
   singleResponse,
 } from '@/app/api/v1/admin/responses'
+import type { BlockState } from '@/stores/workflows/workflow/types'
 
 const logger = createLogger('AdminWorkflowActivateVersionAPI')
 
@@ -18,11 +27,12 @@ interface RouteParams {
 }
 
 export const POST = withAdminAuthParams<RouteParams>(async (request, context) => {
+  const requestId = generateRequestId()
   const { id: workflowId, versionId } = await context.params
 
   try {
     const [workflowRecord] = await db
-      .select({ id: workflow.id })
+      .select()
       .from(workflow)
       .where(eq(workflow.id, workflowId))
       .limit(1)
@@ -36,23 +46,161 @@ export const POST = withAdminAuthParams<RouteParams>(async (request, context) =>
       return badRequestResponse('Invalid version number')
     }
 
+    const [versionRow] = await db
+      .select({
+        id: workflowDeploymentVersion.id,
+        state: workflowDeploymentVersion.state,
+      })
+      .from(workflowDeploymentVersion)
+      .where(
+        and(
+          eq(workflowDeploymentVersion.workflowId, workflowId),
+          eq(workflowDeploymentVersion.version, versionNum)
+        )
+      )
+      .limit(1)
+
+    if (!versionRow?.state) {
+      return notFoundResponse('Deployment version')
+    }
+
+    const [currentActiveVersion] = await db
+      .select({ id: workflowDeploymentVersion.id })
+      .from(workflowDeploymentVersion)
+      .where(
+        and(
+          eq(workflowDeploymentVersion.workflowId, workflowId),
+          eq(workflowDeploymentVersion.isActive, true)
+        )
+      )
+      .limit(1)
+
+    const previousVersionId = currentActiveVersion?.id
+
+    const deployedState = versionRow.state as { blocks?: Record<string, BlockState> }
+    const blocks = deployedState.blocks
+    if (!blocks || typeof blocks !== 'object') {
+      return internalErrorResponse('Invalid deployed state structure')
+    }
+
+    const workflowData = workflowRecord as Record<string, unknown>
+
+    const scheduleValidation = validateWorkflowSchedules(blocks)
+    if (!scheduleValidation.isValid) {
+      return badRequestResponse(`Invalid schedule configuration: ${scheduleValidation.error}`)
+    }
+
+    const triggerSaveResult = await saveTriggerWebhooksForDeploy({
+      request,
+      workflowId,
+      workflow: workflowData,
+      userId: workflowRecord.userId,
+      blocks,
+      requestId,
+      deploymentVersionId: versionRow.id,
+      previousVersionId,
+      forceRecreateSubscriptions: true,
+    })
+
+    if (!triggerSaveResult.success) {
+      logger.error(
+        `[${requestId}] Admin API: Failed to sync triggers for workflow ${workflowId}`,
+        triggerSaveResult.error
+      )
+      return internalErrorResponse(
+        triggerSaveResult.error?.message || 'Failed to sync trigger configuration'
+      )
+    }
+
+    const scheduleResult = await createSchedulesForDeploy(workflowId, blocks, db, versionRow.id)
+
+    if (!scheduleResult.success) {
+      await cleanupDeploymentVersion({
+        workflowId,
+        workflow: workflowData,
+        requestId,
+        deploymentVersionId: versionRow.id,
+      })
+      if (previousVersionId) {
+        await restorePreviousVersionWebhooks({
+          request,
+          workflow: workflowData,
+          userId: workflowRecord.userId,
+          previousVersionId,
+          requestId,
+        })
+      }
+      return internalErrorResponse(scheduleResult.error || 'Failed to sync schedules')
+    }
+
     const result = await activateWorkflowVersion({ workflowId, version: versionNum })
     if (!result.success) {
+      await cleanupDeploymentVersion({
+        workflowId,
+        workflow: workflowData,
+        requestId,
+        deploymentVersionId: versionRow.id,
+      })
+      if (previousVersionId) {
+        await restorePreviousVersionWebhooks({
+          request,
+          workflow: workflowData,
+          userId: workflowRecord.userId,
+          previousVersionId,
+          requestId,
+        })
+      }
       if (result.error === 'Deployment version not found') {
         return notFoundResponse('Deployment version')
       }
       return internalErrorResponse(result.error || 'Failed to activate version')
     }
 
-    logger.info(`Admin API: Activated version ${versionNum} for workflow ${workflowId}`)
+    if (previousVersionId && previousVersionId !== versionRow.id) {
+      try {
+        logger.info(
+          `[${requestId}] Admin API: Cleaning up previous version ${previousVersionId} webhooks/schedules`
+        )
+        await cleanupDeploymentVersion({
+          workflowId,
+          workflow: workflowData,
+          requestId,
+          deploymentVersionId: previousVersionId,
+          skipExternalCleanup: true,
+        })
+        logger.info(`[${requestId}] Admin API: Previous version cleanup completed`)
+      } catch (cleanupError) {
+        logger.error(
+          `[${requestId}] Admin API: Failed to clean up previous version ${previousVersionId}`,
+          cleanupError
+        )
+      }
+    }
+
+    await syncMcpToolsForWorkflow({
+      workflowId,
+      requestId,
+      state: versionRow.state,
+      context: 'activate',
+    })
+
+    logger.info(
+      `[${requestId}] Admin API: Activated version ${versionNum} for workflow ${workflowId}`
+    )
 
     return singleResponse({
       success: true,
       version: versionNum,
       deployedAt: result.deployedAt!.toISOString(),
+      warnings: triggerSaveResult.warnings,
     })
   } catch (error) {
-    logger.error(`Admin API: Failed to activate version for workflow ${workflowId}`, { error })
+    logger.error(
+      `[${requestId}] Admin API: Failed to activate version for workflow ${workflowId}`,
+      {
+        error,
+      }
+    )
     return internalErrorResponse('Failed to activate deployment version')
   }
 })
diff --git a/apps/sim/app/api/webhooks/[id]/route.ts b/apps/sim/app/api/webhooks/[id]/route.ts
index ddc588e98..e4c381cad 100644
--- a/apps/sim/app/api/webhooks/[id]/route.ts
+++ b/apps/sim/app/api/webhooks/[id]/route.ts
@@ -7,12 +7,7 @@ import { getSession } from '@/lib/auth'
 import { validateInteger } from '@/lib/core/security/input-validation'
 import { PlatformEvents } from '@/lib/core/telemetry'
 import { generateRequestId } from '@/lib/core/utils/request'
-import { resolveEnvVarsInObject } from '@/lib/webhooks/env-resolver'
-import {
-  cleanupExternalWebhook,
-  createExternalWebhookSubscription,
-  shouldRecreateExternalWebhookSubscription,
-} from '@/lib/webhooks/provider-subscriptions'
+import { cleanupExternalWebhook } from '@/lib/webhooks/provider-subscriptions'
 import { getUserEntityPermissions } from '@/lib/workspaces/permissions/utils'
 
 const logger = createLogger('WebhookAPI')
@@ -88,7 +83,6 @@ export async function GET(request: NextRequest, { params }: { params: Promise<{
   }
 }
 
-// Update a webhook
 export async function PATCH(request: NextRequest, { params }: { params: Promise<{ id: string }> }) {
   const requestId = generateRequestId()
 
@@ -103,7 +97,7 @@ export async function PATCH(request: NextRequest, { params }: { params: Promise<
     }
 
     const body = await request.json()
-    const { path, provider, providerConfig, isActive, failedCount } = body
+    const { isActive, failedCount } = body
 
     if (failedCount !== undefined) {
       const validation = validateInteger(failedCount, 'failedCount', { min: 0 })
@@ -113,28 +107,6 @@ export async function PATCH(request: NextRequest, { params }: { params: Promise<
       }
     }
 
-    const originalProviderConfig = providerConfig
-    let resolvedProviderConfig = providerConfig
-    if (providerConfig) {
-      const webhookDataForResolve = await db
-        .select({
-          workspaceId: workflow.workspaceId,
-        })
-        .from(webhook)
-        .innerJoin(workflow, eq(webhook.workflowId, workflow.id))
-        .where(eq(webhook.id, id))
-        .limit(1)
-
-      if (webhookDataForResolve.length > 0) {
-        resolvedProviderConfig = await resolveEnvVarsInObject(
-          providerConfig,
-          session.user.id,
-          webhookDataForResolve[0].workspaceId || undefined
-        )
-      }
-    }
-
-    // Find the webhook and check permissions
     const webhooks = await db
       .select({
         webhook: webhook,
@@ -155,16 +127,12 @@ export async function PATCH(request: NextRequest, { params }: { params: Promise<
     }
 
     const webhookData = webhooks[0]
-
-    // Check if user has permission to modify this webhook
     let canModify = false
 
-    // Case 1: User owns the workflow
     if (webhookData.workflow.userId === session.user.id) {
       canModify = true
     }
 
-    // Case 2: Workflow belongs to a workspace and user has write or admin permission
     if (!canModify && webhookData.workflow.workspaceId) {
       const userPermission = await getUserEntityPermissions(
         session.user.id,
@@ -183,80 +151,14 @@ export async function PATCH(request: NextRequest, { params }: { params: Promise<
       return NextResponse.json({ error: 'Access denied' }, { status: 403 })
     }
 
-    const existingProviderConfig =
-      (webhookData.webhook.providerConfig as Record<string, unknown>) || {}
-    let nextProviderConfig =
-      providerConfig !== undefined &&
-      resolvedProviderConfig &&
-      typeof resolvedProviderConfig === 'object'
-        ? (resolvedProviderConfig as Record<string, unknown>)
-        : existingProviderConfig
-    const nextProvider = (provider ?? webhookData.webhook.provider) as string
-
-    if (
-      providerConfig !== undefined &&
-      shouldRecreateExternalWebhookSubscription({
-        previousProvider: webhookData.webhook.provider as string,
-        nextProvider,
-        previousConfig: existingProviderConfig,
-        nextConfig: nextProviderConfig,
-      })
-    ) {
-      await cleanupExternalWebhook(
-        { ...webhookData.webhook, providerConfig: existingProviderConfig },
-        webhookData.workflow,
-        requestId
-      )
-
-      const result = await createExternalWebhookSubscription(
-        request,
-        {
-          ...webhookData.webhook,
-          provider: nextProvider,
-          providerConfig: nextProviderConfig,
-        },
-        webhookData.workflow,
-        session.user.id,
-        requestId
-      )
-
-      nextProviderConfig = result.updatedProviderConfig as Record<string, unknown>
-    }
-
     logger.debug(`[${requestId}] Updating webhook properties`, {
-      hasPathUpdate: path !== undefined,
-      hasProviderUpdate: provider !== undefined,
-      hasConfigUpdate: providerConfig !== undefined,
       hasActiveUpdate: isActive !== undefined,
       hasFailedCountUpdate: failedCount !== undefined,
     })
 
-    let finalProviderConfig = webhooks[0].webhook.providerConfig
-    if (providerConfig !== undefined && originalProviderConfig) {
-      const existingConfig = existingProviderConfig
-      finalProviderConfig = {
-        ...originalProviderConfig,
-        credentialId: existingConfig.credentialId,
-        credentialSetId: existingConfig.credentialSetId,
-        userId: existingConfig.userId,
-        historyId: existingConfig.historyId,
-        lastCheckedTimestamp: existingConfig.lastCheckedTimestamp,
-        setupCompleted: existingConfig.setupCompleted,
-        externalId: existingConfig.externalId,
-      }
-      for (const [key, value] of Object.entries(nextProviderConfig)) {
-        if (!(key in originalProviderConfig)) {
-          ;(finalProviderConfig as Record<string, unknown>)[key] = value
-        }
-      }
-    }
-
     const updatedWebhook = await db
       .update(webhook)
       .set({
-        path: path !== undefined ? path : webhooks[0].webhook.path,
-        provider: provider !== undefined ? provider : webhooks[0].webhook.provider,
-        providerConfig: finalProviderConfig,
         isActive: isActive !== undefined ? isActive : webhooks[0].webhook.isActive,
         failedCount: failedCount !== undefined ? failedCount : webhooks[0].webhook.failedCount,
         updatedAt: new Date(),
@@ -339,11 +241,8 @@ export async function DELETE(
     }
 
     const foundWebhook = webhookData.webhook
-    const { cleanupExternalWebhook } = await import('@/lib/webhooks/provider-subscriptions')
-
-    const providerConfig = foundWebhook.providerConfig as Record<string, unknown> | null
-    const credentialSetId = providerConfig?.credentialSetId as string | undefined
-    const blockId = providerConfig?.blockId as string | undefined
+    const credentialSetId = foundWebhook.credentialSetId as string | undefined
+    const blockId = foundWebhook.blockId as string | undefined
 
     if (credentialSetId && blockId) {
       const allCredentialSetWebhooks = await db
@@ -351,10 +250,9 @@ export async function DELETE(
         .from(webhook)
         .where(and(eq(webhook.workflowId, webhookData.workflow.id), eq(webhook.blockId, blockId)))
 
-      const webhooksToDelete = allCredentialSetWebhooks.filter((w) => {
-        const config = w.providerConfig as Record<string, unknown> | null
-        return config?.credentialSetId === credentialSetId
-      })
+      const webhooksToDelete = allCredentialSetWebhooks.filter(
+        (w) => w.credentialSetId === credentialSetId
+      )
 
       for (const w of webhooksToDelete) {
         await cleanupExternalWebhook(w, webhookData.workflow, requestId)
diff --git a/apps/sim/app/api/webhooks/route.ts b/apps/sim/app/api/webhooks/route.ts
index 5f5d9eace..6cc9876f7 100644
--- a/apps/sim/app/api/webhooks/route.ts
+++ b/apps/sim/app/api/webhooks/route.ts
@@ -7,9 +7,21 @@ import { type NextRequest, NextResponse } from 'next/server'
 import { getSession } from '@/lib/auth'
 import { PlatformEvents } from '@/lib/core/telemetry'
 import { generateRequestId } from '@/lib/core/utils/request'
+import { getProviderIdFromServiceId } from '@/lib/oauth'
 import { resolveEnvVarsInObject } from '@/lib/webhooks/env-resolver'
-import { createExternalWebhookSubscription } from '@/lib/webhooks/provider-subscriptions'
+import {
+  cleanupExternalWebhook,
+  createExternalWebhookSubscription,
+} from '@/lib/webhooks/provider-subscriptions'
+import { mergeNonUserFields } from '@/lib/webhooks/utils'
+import {
+  configureGmailPolling,
+  configureOutlookPolling,
+  configureRssPolling,
+  syncWebhooksForCredentialSet,
+} from '@/lib/webhooks/utils.server'
 import { getUserEntityPermissions } from '@/lib/workspaces/permissions/utils'
+import { extractCredentialSetId, isCredentialSetValue } from '@/executor/constants'
 
 const logger = createLogger('WebhooksAPI')
 
@@ -316,8 +328,6 @@ export async function POST(request: NextRequest) {
     const directCredentialSetId = resolvedProviderConfig?.credentialSetId as string | undefined
 
     if (directCredentialSetId || rawCredentialId) {
-      const { isCredentialSetValue, extractCredentialSetId } = await import('@/executor/constants')
-
       const credentialSetId =
         directCredentialSetId ||
         (rawCredentialId && isCredentialSetValue(rawCredentialId)
@@ -329,11 +339,6 @@ export async function POST(request: NextRequest) {
           `[${requestId}] Credential set detected for ${provider} trigger. Syncing webhooks for set ${credentialSetId}`
         )
 
-        const { getProviderIdFromServiceId } = await import('@/lib/oauth')
-        const { syncWebhooksForCredentialSet, configureGmailPolling, configureOutlookPolling } =
-          await import('@/lib/webhooks/utils.server')
-
-        // Map provider to OAuth provider ID
         const oauthProviderId = getProviderIdFromServiceId(provider)
 
         const {
@@ -466,7 +471,8 @@ export async function POST(request: NextRequest) {
       providerConfig: providerConfigOverride,
     })
 
-    const configToSave = { ...originalProviderConfig }
+    const userProvided = originalProviderConfig as Record<string, unknown>
+    const configToSave: Record<string, unknown> = { ...userProvided }
 
     try {
       const result = await createExternalWebhookSubscription(
@@ -477,11 +483,7 @@ export async function POST(request: NextRequest) {
         requestId
       )
       const updatedConfig = result.updatedProviderConfig as Record<string, unknown>
-      for (const [key, value] of Object.entries(updatedConfig)) {
-        if (!(key in originalProviderConfig)) {
-          configToSave[key] = value
-        }
-      }
+      mergeNonUserFields(configToSave, updatedConfig, userProvided)
       resolvedProviderConfig = updatedConfig
       externalSubscriptionCreated = result.externalSubscriptionCreated
     } catch (err) {
@@ -547,7 +549,6 @@ export async function POST(request: NextRequest) {
       if (externalSubscriptionCreated) {
         logger.error(`[${requestId}] DB save failed, cleaning up external subscription`, dbError)
         try {
-          const { cleanupExternalWebhook } = await import('@/lib/webhooks/provider-subscriptions')
           await cleanupExternalWebhook(
             createTempWebhookData(configToSave),
             workflowRecord,
@@ -567,7 +568,6 @@ export async function POST(request: NextRequest) {
     if (savedWebhook && provider === 'gmail') {
       logger.info(`[${requestId}] Gmail provider detected. Setting up Gmail webhook configuration.`)
       try {
-        const { configureGmailPolling } = await import('@/lib/webhooks/utils.server')
         const success = await configureGmailPolling(savedWebhook, requestId)
 
         if (!success) {
@@ -606,7 +606,6 @@ export async function POST(request: NextRequest) {
         `[${requestId}] Outlook provider detected. Setting up Outlook webhook configuration.`
       )
       try {
-        const { configureOutlookPolling } = await import('@/lib/webhooks/utils.server')
         const success = await configureOutlookPolling(savedWebhook, requestId)
 
         if (!success) {
@@ -643,7 +642,6 @@ export async function POST(request: NextRequest) {
     if (savedWebhook && provider === 'rss') {
       logger.info(`[${requestId}] RSS provider detected. Setting up RSS webhook configuration.`)
       try {
-        const { configureRssPolling } = await import('@/lib/webhooks/utils.server')
         const success = await configureRssPolling(savedWebhook, requestId)
 
         if (!success) {
diff --git a/apps/sim/app/api/workflows/[id]/deploy/route.ts b/apps/sim/app/api/workflows/[id]/deploy/route.ts
index 6e1172c04..9fd15eb60 100644
--- a/apps/sim/app/api/workflows/[id]/deploy/route.ts
+++ b/apps/sim/app/api/workflows/[id]/deploy/route.ts
@@ -4,7 +4,11 @@ import { and, desc, eq } from 'drizzle-orm'
 import type { NextRequest } from 'next/server'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { removeMcpToolsForWorkflow, syncMcpToolsForWorkflow } from '@/lib/mcp/workflow-mcp-sync'
-import { cleanupWebhooksForWorkflow, saveTriggerWebhooksForDeploy } from '@/lib/webhooks/deploy'
+import {
+  cleanupWebhooksForWorkflow,
+  restorePreviousVersionWebhooks,
+  saveTriggerWebhooksForDeploy,
+} from '@/lib/webhooks/deploy'
 import {
   deployWorkflow,
   loadWorkflowFromNormalizedTables,
@@ -135,6 +139,18 @@ export async function POST(request: NextRequest, { params }: { params: Promise<{
       return createErrorResponse(`Invalid schedule configuration: ${scheduleValidation.error}`, 400)
     }
 
+    const [currentActiveVersion] = await db
+      .select({ id: workflowDeploymentVersion.id })
+      .from(workflowDeploymentVersion)
+      .where(
+        and(
+          eq(workflowDeploymentVersion.workflowId, id),
+          eq(workflowDeploymentVersion.isActive, true)
+        )
+      )
+      .limit(1)
+    const previousVersionId = currentActiveVersion?.id
+
     const deployResult = await deployWorkflow({
       workflowId: id,
       deployedBy: actorUserId,
@@ -161,6 +177,7 @@ export async function POST(request: NextRequest, { params }: { params: Promise<{
       blocks: normalizedData.blocks,
       requestId,
       deploymentVersionId,
+      previousVersionId,
     })
 
     if (!triggerSaveResult.success) {
@@ -194,6 +211,15 @@ export async function POST(request: NextRequest, { params }: { params: Promise<{
         requestId,
         deploymentVersionId,
       })
+      if (previousVersionId) {
+        await restorePreviousVersionWebhooks({
+          request,
+          workflow: workflowData as Record<string, unknown>,
+          userId: actorUserId,
+          previousVersionId,
+          requestId,
+        })
+      }
       await undeployWorkflow({ workflowId: id })
       return createErrorResponse(scheduleResult.error || 'Failed to create schedule', 500)
     }
@@ -208,6 +234,25 @@ export async function POST(request: NextRequest, { params }: { params: Promise<{
       )
     }
 
+    if (previousVersionId && previousVersionId !== deploymentVersionId) {
+      try {
+        logger.info(`[${requestId}] Cleaning up previous version ${previousVersionId} DB records`)
+        await cleanupDeploymentVersion({
+          workflowId: id,
+          workflow: workflowData as Record<string, unknown>,
+          requestId,
+          deploymentVersionId: previousVersionId,
+          skipExternalCleanup: true,
+        })
+      } catch (cleanupError) {
+        logger.error(
+          `[${requestId}] Failed to clean up previous version ${previousVersionId}`,
+          cleanupError
+        )
+        // Non-fatal - continue with success response
+      }
+    }
+
     logger.info(`[${requestId}] Workflow deployed successfully: ${id}`)
 
     // Sync MCP tools with the latest parameter schema
@@ -228,6 +273,7 @@ export async function POST(request: NextRequest, { params }: { params: Promise<{
             nextRunAt: scheduleInfo.nextRunAt,
           }
         : undefined,
+      warnings: triggerSaveResult.warnings,
     })
   } catch (error: any) {
     logger.error(`[${requestId}] Error deploying workflow: ${id}`, {
diff --git a/apps/sim/app/api/workflows/[id]/deployments/[version]/activate/route.ts b/apps/sim/app/api/workflows/[id]/deployments/[version]/activate/route.ts
index d3e5abb55..782b65e33 100644
--- a/apps/sim/app/api/workflows/[id]/deployments/[version]/activate/route.ts
+++ b/apps/sim/app/api/workflows/[id]/deployments/[version]/activate/route.ts
@@ -4,7 +4,7 @@ import { and, eq } from 'drizzle-orm'
 import type { NextRequest } from 'next/server'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { syncMcpToolsForWorkflow } from '@/lib/mcp/workflow-mcp-sync'
-import { saveTriggerWebhooksForDeploy } from '@/lib/webhooks/deploy'
+import { restorePreviousVersionWebhooks, saveTriggerWebhooksForDeploy } from '@/lib/webhooks/deploy'
 import { activateWorkflowVersion } from '@/lib/workflows/persistence/utils'
 import {
   cleanupDeploymentVersion,
@@ -85,6 +85,11 @@ export async function POST(
       return createErrorResponse('Invalid deployed state structure', 500)
     }
 
+    const scheduleValidation = validateWorkflowSchedules(blocks)
+    if (!scheduleValidation.isValid) {
+      return createErrorResponse(`Invalid schedule configuration: ${scheduleValidation.error}`, 400)
+    }
+
     const triggerSaveResult = await saveTriggerWebhooksForDeploy({
       request,
       workflowId: id,
@@ -93,6 +98,8 @@ export async function POST(
       blocks,
       requestId,
       deploymentVersionId: versionRow.id,
+      previousVersionId,
+      forceRecreateSubscriptions: true,
     })
 
     if (!triggerSaveResult.success) {
@@ -102,11 +109,6 @@ export async function POST(
       )
     }
 
-    const scheduleValidation = validateWorkflowSchedules(blocks)
-    if (!scheduleValidation.isValid) {
-      return createErrorResponse(`Invalid schedule configuration: ${scheduleValidation.error}`, 400)
-    }
-
     const scheduleResult = await createSchedulesForDeploy(id, blocks, db, versionRow.id)
 
     if (!scheduleResult.success) {
@@ -116,6 +118,15 @@ export async function POST(
         requestId,
         deploymentVersionId: versionRow.id,
       })
+      if (previousVersionId) {
+        await restorePreviousVersionWebhooks({
+          request,
+          workflow: workflowData as Record<string, unknown>,
+          userId: actorUserId,
+          previousVersionId,
+          requestId,
+        })
+      }
       return createErrorResponse(scheduleResult.error || 'Failed to sync schedules', 500)
     }
 
@@ -127,6 +138,15 @@ export async function POST(
         requestId,
         deploymentVersionId: versionRow.id,
       })
+      if (previousVersionId) {
+        await restorePreviousVersionWebhooks({
+          request,
+          workflow: workflowData as Record<string, unknown>,
+          userId: actorUserId,
+          previousVersionId,
+          requestId,
+        })
+      }
       return createErrorResponse(result.error || 'Failed to activate deployment', 400)
     }
 
@@ -140,6 +160,7 @@ export async function POST(
           workflow: workflowData as Record<string, unknown>,
           requestId,
           deploymentVersionId: previousVersionId,
+          skipExternalCleanup: true,
         })
         logger.info(`[${requestId}] Previous version cleanup completed`)
       } catch (cleanupError) {
@@ -157,7 +178,11 @@ export async function POST(
       context: 'activate',
     })
 
-    return createSuccessResponse({ success: true, deployedAt: result.deployedAt })
+    return createSuccessResponse({
+      success: true,
+      deployedAt: result.deployedAt,
+      warnings: triggerSaveResult.warnings,
+    })
   } catch (error: any) {
     logger.error(`[${requestId}] Error activating deployment for workflow: ${id}`, error)
     return createErrorResponse(error.message || 'Failed to activate deployment', 500)
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/deploy/components/deploy-modal/deploy-modal.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/deploy/components/deploy-modal/deploy-modal.tsx
index 09138be70..e90fbee6b 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/deploy/components/deploy-modal/deploy-modal.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/deploy/components/deploy-modal/deploy-modal.tsx
@@ -95,6 +95,7 @@ export function DeployModal({
   const [activeTab, setActiveTab] = useState<TabView>('general')
   const [chatSubmitting, setChatSubmitting] = useState(false)
   const [apiDeployError, setApiDeployError] = useState<string | null>(null)
+  const [apiDeployWarnings, setApiDeployWarnings] = useState<string[]>([])
   const [isChatFormValid, setIsChatFormValid] = useState(false)
   const [selectedStreamingOutputs, setSelectedStreamingOutputs] = useState<string[]>([])
 
@@ -227,6 +228,7 @@ export function DeployModal({
     if (open && workflowId) {
       setActiveTab('general')
       setApiDeployError(null)
+      setApiDeployWarnings([])
     }
   }, [open, workflowId])
 
@@ -282,9 +284,13 @@ export function DeployModal({
     if (!workflowId) return
 
     setApiDeployError(null)
+    setApiDeployWarnings([])
 
     try {
-      await deployMutation.mutateAsync({ workflowId, deployChatEnabled: false })
+      const result = await deployMutation.mutateAsync({ workflowId, deployChatEnabled: false })
+      if (result.warnings && result.warnings.length > 0) {
+        setApiDeployWarnings(result.warnings)
+      }
       await refetchDeployedState()
     } catch (error: unknown) {
       logger.error('Error deploying workflow:', { error })
@@ -297,8 +303,13 @@ export function DeployModal({
     async (version: number) => {
       if (!workflowId) return
 
+      setApiDeployWarnings([])
+
       try {
-        await activateVersionMutation.mutateAsync({ workflowId, version })
+        const result = await activateVersionMutation.mutateAsync({ workflowId, version })
+        if (result.warnings && result.warnings.length > 0) {
+          setApiDeployWarnings(result.warnings)
+        }
         await refetchDeployedState()
       } catch (error) {
         logger.error('Error promoting version:', { error })
@@ -324,9 +335,13 @@ export function DeployModal({
     if (!workflowId) return
 
     setApiDeployError(null)
+    setApiDeployWarnings([])
 
     try {
-      await deployMutation.mutateAsync({ workflowId, deployChatEnabled: false })
+      const result = await deployMutation.mutateAsync({ workflowId, deployChatEnabled: false })
+      if (result.warnings && result.warnings.length > 0) {
+        setApiDeployWarnings(result.warnings)
+      }
       await refetchDeployedState()
     } catch (error: unknown) {
       logger.error('Error redeploying workflow:', { error })
@@ -338,6 +353,7 @@ export function DeployModal({
   const handleCloseModal = useCallback(() => {
     setChatSubmitting(false)
     setApiDeployError(null)
+    setApiDeployWarnings([])
     onOpenChange(false)
   }, [onOpenChange])
 
@@ -479,6 +495,14 @@ export function DeployModal({
                   <div>{apiDeployError}</div>
                 </div>
               )}
+              {apiDeployWarnings.length > 0 && (
+                <div className='mb-3 rounded-[4px] border border-amber-500/30 bg-amber-500/10 p-3 text-amber-700 dark:text-amber-400 text-sm'>
+                  <div className='font-semibold'>Deployment Warning</div>
+                  {apiDeployWarnings.map((warning, index) => (
+                    <div key={index}>{warning}</div>
+                  ))}
+                </div>
+              )}
               <ModalTabsContent value='general'>
                 <GeneralDeploy
                   workflowId={workflowId}
diff --git a/apps/sim/hooks/queries/deployments.ts b/apps/sim/hooks/queries/deployments.ts
index 40982e66c..5aa088aad 100644
--- a/apps/sim/hooks/queries/deployments.ts
+++ b/apps/sim/hooks/queries/deployments.ts
@@ -237,6 +237,7 @@ interface DeployWorkflowResult {
   isDeployed: boolean
   deployedAt?: string
   apiKey?: string
+  warnings?: string[]
 }
 
 /**
@@ -272,6 +273,7 @@ export function useDeployWorkflow() {
         isDeployed: data.isDeployed ?? false,
         deployedAt: data.deployedAt,
         apiKey: data.apiKey,
+        warnings: data.warnings,
       }
     },
     onSuccess: (data, variables) => {
@@ -360,6 +362,7 @@ interface ActivateVersionVariables {
 interface ActivateVersionResult {
   deployedAt?: string
   apiKey?: string
+  warnings?: string[]
 }
 
 /**
diff --git a/apps/sim/hooks/use-webhook-management.ts b/apps/sim/hooks/use-webhook-management.ts
index 3df45eee0..3c8ef5a4d 100644
--- a/apps/sim/hooks/use-webhook-management.ts
+++ b/apps/sim/hooks/use-webhook-management.ts
@@ -1,4 +1,4 @@
-import { useCallback, useEffect, useMemo, useState } from 'react'
+import { useCallback, useEffect, useMemo } from 'react'
 import { createLogger } from '@sim/logger'
 import { useParams } from 'next/navigation'
 import { getBaseUrl } from '@/lib/core/utils/urls'
@@ -6,12 +6,10 @@ import { getBlock } from '@/blocks'
 import { populateTriggerFieldsFromConfig } from '@/hooks/use-trigger-config-aggregation'
 import { useSubBlockStore } from '@/stores/workflows/subblock/store'
 import { useWorkflowStore } from '@/stores/workflows/workflow/store'
-import { getTrigger, isTriggerValid } from '@/triggers'
+import { isTriggerValid } from '@/triggers'
 
 const logger = createLogger('useWebhookManagement')
 
-const CREDENTIAL_SET_PREFIX = 'credentialSet:'
-
 interface UseWebhookManagementProps {
   blockId: string
   triggerId?: string
@@ -24,9 +22,6 @@ interface WebhookManagementState {
   webhookPath: string
   webhookId: string | null
   isLoading: boolean
-  isSaving: boolean
-  saveConfig: () => Promise<boolean>
-  deleteConfig: () => Promise<boolean>
 }
 
 /**
@@ -83,11 +78,9 @@ function resolveEffectiveTriggerId(
 }
 
 /**
- * Hook to manage webhook lifecycle for trigger blocks
- * Handles:
- * - Pre-generating webhook URLs based on blockId (without creating webhook)
- * - Loading existing webhooks from the API
- * - Saving and deleting webhook configurations
+ * Hook to load webhook info for trigger blocks.
+ * Used for displaying webhook URLs in the UI.
+ * Webhook creation/updates are handled by the deploy flow.
  */
 export function useWebhookManagement({
   blockId,
@@ -98,8 +91,6 @@ export function useWebhookManagement({
   const params = useParams()
   const workflowId = params.workflowId as string
 
-  const triggerDef = triggerId && isTriggerValid(triggerId) ? getTrigger(triggerId) : null
-
   const webhookId = useSubBlockStore(
     useCallback((state) => state.getValue(blockId, 'webhookId') as string | null, [blockId])
   )
@@ -107,7 +98,6 @@ export function useWebhookManagement({
     useCallback((state) => state.getValue(blockId, 'triggerPath') as string | null, [blockId])
   )
   const isLoading = useSubBlockStore((state) => state.loadingWebhooks.has(blockId))
-  const isChecked = useSubBlockStore((state) => state.checkedWebhooks.has(blockId))
 
   const webhookUrl = useMemo(() => {
     if (!webhookPath) {
@@ -118,8 +108,6 @@ export function useWebhookManagement({
     return `${baseUrl}/api/webhooks/trigger/${webhookPath}`
   }, [webhookPath, blockId])
 
-  const [isSaving, setIsSaving] = useState(false)
-
   useEffect(() => {
     if (triggerId && !isPreview) {
       const storedTriggerId = useSubBlockStore.getState().getValue(blockId, 'triggerId')
@@ -143,7 +131,7 @@ export function useWebhookManagement({
       return
     }
 
-    const loadWebhookOrGenerateUrl = async () => {
+    const loadWebhookInfo = async () => {
       useSubBlockStore.setState((state) => ({
         loadingWebhooks: new Set([...state.loadingWebhooks, blockId]),
       }))
@@ -171,8 +159,6 @@ export function useWebhookManagement({
             if (webhook.providerConfig) {
               const effectiveTriggerId = resolveEffectiveTriggerId(blockId, triggerId, webhook)
 
-              // Filter out runtime/system fields from providerConfig before storing as triggerConfig
-              // These fields are managed by the system and should not be included in change detection
               const {
                 credentialId: _credId,
                 credentialSetId: _credSetId,
@@ -224,202 +210,14 @@ export function useWebhookManagement({
       }
     }
     if (useWebhookUrl) {
-      loadWebhookOrGenerateUrl()
+      loadWebhookInfo()
     }
   }, [isPreview, triggerId, workflowId, blockId, useWebhookUrl])
 
-  const createWebhook = async (
-    effectiveTriggerId: string | undefined,
-    selectedCredentialId: string | null
-  ): Promise<boolean> => {
-    if (!triggerDef || !effectiveTriggerId) {
-      return false
-    }
-
-    const triggerConfig = useSubBlockStore.getState().getValue(blockId, 'triggerConfig')
-
-    const isCredentialSet = selectedCredentialId?.startsWith(CREDENTIAL_SET_PREFIX)
-    const credentialSetId = isCredentialSet
-      ? selectedCredentialId!.slice(CREDENTIAL_SET_PREFIX.length)
-      : undefined
-    const credentialId = isCredentialSet ? undefined : selectedCredentialId
-
-    const webhookConfig = {
-      ...(triggerConfig || {}),
-      ...(credentialId ? { credentialId } : {}),
-      ...(credentialSetId ? { credentialSetId } : {}),
-      triggerId: effectiveTriggerId,
-    }
-
-    const path = blockId
-
-    const response = await fetch('/api/webhooks', {
-      method: 'POST',
-      headers: { 'Content-Type': 'application/json' },
-      body: JSON.stringify({
-        workflowId,
-        blockId,
-        path,
-        provider: triggerDef.provider,
-        providerConfig: webhookConfig,
-      }),
-    })
-
-    if (!response.ok) {
-      let errorMessage = 'Failed to create webhook'
-      try {
-        const errorData = await response.json()
-        errorMessage = errorData.details || errorData.error || errorMessage
-      } catch {
-        // If response is not JSON, use default message
-      }
-      logger.error('Failed to create webhook', { errorMessage })
-      throw new Error(errorMessage)
-    }
-
-    const data = await response.json()
-    const savedWebhookId = data.webhook.id
-
-    useSubBlockStore.getState().setValue(blockId, 'triggerPath', path)
-    useSubBlockStore.getState().setValue(blockId, 'triggerId', effectiveTriggerId)
-    useSubBlockStore.getState().setValue(blockId, 'webhookId', savedWebhookId)
-    useSubBlockStore.setState((state) => ({
-      checkedWebhooks: new Set([...state.checkedWebhooks, blockId]),
-    }))
-
-    logger.info('Trigger webhook created successfully', {
-      webhookId: savedWebhookId,
-      triggerId: effectiveTriggerId,
-      provider: triggerDef.provider,
-      blockId,
-    })
-
-    return true
-  }
-
-  const updateWebhook = async (
-    webhookIdToUpdate: string,
-    effectiveTriggerId: string | undefined,
-    selectedCredentialId: string | null
-  ): Promise<boolean> => {
-    const triggerConfigRaw = useSubBlockStore.getState().getValue(blockId, 'triggerConfig')
-    const triggerConfig =
-      typeof triggerConfigRaw === 'object' && triggerConfigRaw !== null
-        ? (triggerConfigRaw as Record<string, unknown>)
-        : {}
-
-    const isCredentialSet = selectedCredentialId?.startsWith(CREDENTIAL_SET_PREFIX)
-    const credentialSetId = isCredentialSet
-      ? selectedCredentialId!.slice(CREDENTIAL_SET_PREFIX.length)
-      : undefined
-    const credentialId = isCredentialSet ? undefined : selectedCredentialId
-
-    const response = await fetch(`/api/webhooks/${webhookIdToUpdate}`, {
-      method: 'PATCH',
-      headers: { 'Content-Type': 'application/json' },
-      body: JSON.stringify({
-        providerConfig: {
-          ...triggerConfig,
-          ...(credentialId ? { credentialId } : {}),
-          ...(credentialSetId ? { credentialSetId } : {}),
-          triggerId: effectiveTriggerId,
-        },
-      }),
-    })
-
-    if (response.status === 404) {
-      logger.warn('Webhook not found while updating, recreating', {
-        blockId,
-        lostWebhookId: webhookIdToUpdate,
-      })
-      useSubBlockStore.getState().setValue(blockId, 'webhookId', null)
-      return createWebhook(effectiveTriggerId, selectedCredentialId)
-    }
-
-    if (!response.ok) {
-      let errorMessage = 'Failed to save trigger configuration'
-      try {
-        const errorData = await response.json()
-        errorMessage = errorData.details || errorData.error || errorMessage
-      } catch {
-        // If response is not JSON, use default message
-      }
-      logger.error('Failed to save trigger config', { errorMessage })
-      throw new Error(errorMessage)
-    }
-
-    logger.info('Trigger config saved successfully', { blockId, webhookId: webhookIdToUpdate })
-    return true
-  }
-
-  const saveConfig = async (): Promise<boolean> => {
-    if (isPreview || !triggerDef) {
-      return false
-    }
-
-    const effectiveTriggerId = resolveEffectiveTriggerId(blockId, triggerId)
-
-    try {
-      setIsSaving(true)
-
-      const triggerCredentials = useSubBlockStore.getState().getValue(blockId, 'triggerCredentials')
-      const selectedCredentialId = (triggerCredentials as string | null) || null
-
-      if (!webhookId) {
-        return createWebhook(effectiveTriggerId, selectedCredentialId)
-      }
-
-      return updateWebhook(webhookId, effectiveTriggerId, selectedCredentialId)
-    } catch (error) {
-      logger.error('Error saving trigger config:', error)
-      throw error
-    } finally {
-      setIsSaving(false)
-    }
-  }
-
-  const deleteConfig = async (): Promise<boolean> => {
-    if (isPreview || !webhookId) {
-      return false
-    }
-
-    try {
-      setIsSaving(true)
-
-      const response = await fetch(`/api/webhooks/${webhookId}`, {
-        method: 'DELETE',
-      })
-
-      if (!response.ok) {
-        logger.error('Failed to delete webhook')
-        return false
-      }
-
-      useSubBlockStore.getState().setValue(blockId, 'triggerPath', '')
-      useSubBlockStore.getState().setValue(blockId, 'webhookId', null)
-      useSubBlockStore.setState((state) => {
-        const newSet = new Set(state.checkedWebhooks)
-        newSet.delete(blockId)
-        return { checkedWebhooks: newSet }
-      })
-
-      logger.info('Webhook deleted successfully')
-      return true
-    } catch (error) {
-      logger.error('Error deleting webhook:', error)
-      return false
-    } finally {
-      setIsSaving(false)
-    }
-  }
-
   return {
     webhookUrl,
     webhookPath: webhookPath || blockId,
     webhookId,
     isLoading,
-    isSaving,
-    saveConfig,
-    deleteConfig,
   }
 }
diff --git a/apps/sim/lib/webhooks/deploy.ts b/apps/sim/lib/webhooks/deploy.ts
index 4b7208362..d991894c1 100644
--- a/apps/sim/lib/webhooks/deploy.ts
+++ b/apps/sim/lib/webhooks/deploy.ts
@@ -32,6 +32,12 @@ interface TriggerSaveError {
 interface TriggerSaveResult {
   success: boolean
   error?: TriggerSaveError
+  warnings?: string[]
+}
+
+interface CredentialSetSyncResult {
+  error: TriggerSaveError | null
+  warnings: string[]
 }
 
 interface SaveTriggerWebhooksInput {
@@ -42,6 +48,16 @@ interface SaveTriggerWebhooksInput {
   blocks: Record<string, BlockState>
   requestId: string
   deploymentVersionId?: string
+  /**
+   * The previous active version's ID. Only this version's external subscriptions
+   * will be cleaned up (along with draft webhooks). If not provided, skips cleanup.
+   */
+  previousVersionId?: string
+  /**
+   * When true, forces recreation of external subscriptions even if webhook config is unchanged.
+   * Used when activating a previous deployment version whose subscriptions were cleaned up.
+   */
+  forceRecreateSubscriptions?: boolean
 }
 
 function getSubBlockValue(block: BlockState, subBlockId: string): unknown {
@@ -248,7 +264,7 @@ async function syncCredentialSetWebhooks(params: {
   providerConfig: Record<string, unknown>
   requestId: string
   deploymentVersionId?: string
-}): Promise<TriggerSaveError | null> {
+}): Promise<CredentialSetSyncResult> {
   const {
     workflowId,
     blockId,
@@ -261,7 +277,7 @@ async function syncCredentialSetWebhooks(params: {
 
   const credentialSetId = providerConfig.credentialSetId as string | undefined
   if (!credentialSetId) {
-    return null
+    return { error: null, warnings: [] }
   }
 
   const oauthProviderId = getProviderIdFromServiceId(provider)
@@ -280,10 +296,23 @@ async function syncCredentialSetWebhooks(params: {
     deploymentVersionId,
   })
 
+  const warnings: string[] = []
+
+  if (syncResult.failed.length > 0) {
+    const failedCount = syncResult.failed.length
+    const totalCount = syncResult.webhooks.length + failedCount
+    warnings.push(
+      `${failedCount} of ${totalCount} credentials in the set failed to sync for ${provider}. Some team members may not receive triggers.`
+    )
+  }
+
   if (syncResult.webhooks.length === 0) {
     return {
-      message: `No valid credentials found in credential set for ${provider}. Please connect accounts and try again.`,
-      status: 400,
+      error: {
+        message: `No valid credentials found in credential set for ${provider}. Please connect accounts and try again.`,
+        status: 400,
+      },
+      warnings,
     }
   }
 
@@ -297,8 +326,11 @@ async function syncCredentialSetWebhooks(params: {
           if (!success) {
             await db.delete(webhook).where(eq(webhook.id, wh.id))
             return {
-              message: `Failed to configure ${provider} polling. Please check account permissions.`,
-              status: 500,
+              error: {
+                message: `Failed to configure ${provider} polling. Please check account permissions.`,
+                status: 500,
+              },
+              warnings,
             }
           }
         }
@@ -306,84 +338,7 @@ async function syncCredentialSetWebhooks(params: {
     }
   }
 
-  return null
-}
-
-async function createWebhookForBlock(params: {
-  request: NextRequest
-  workflowId: string
-  workflow: Record<string, unknown>
-  userId: string
-  block: BlockState
-  provider: string
-  providerConfig: Record<string, unknown>
-  triggerPath: string
-  requestId: string
-  deploymentVersionId?: string
-}): Promise<TriggerSaveError | null> {
-  const {
-    request,
-    workflowId,
-    workflow,
-    userId,
-    block,
-    provider,
-    providerConfig,
-    triggerPath,
-    requestId,
-    deploymentVersionId,
-  } = params
-
-  const webhookId = nanoid()
-  const createPayload = {
-    id: webhookId,
-    path: triggerPath,
-    provider,
-    providerConfig,
-  }
-
-  const result = await createExternalWebhookSubscription(
-    request,
-    createPayload,
-    workflow,
-    userId,
-    requestId
-  )
-
-  const updatedProviderConfig = result.updatedProviderConfig as Record<string, unknown>
-  let savedWebhook: any
-
-  try {
-    const createdRows = await db
-      .insert(webhook)
-      .values({
-        id: webhookId,
-        workflowId,
-        deploymentVersionId: deploymentVersionId || null,
-        blockId: block.id,
-        path: triggerPath,
-        provider,
-        providerConfig: updatedProviderConfig,
-        credentialSetId: (updatedProviderConfig.credentialSetId as string | undefined) || null,
-        isActive: true,
-        createdAt: new Date(),
-        updatedAt: new Date(),
-      })
-      .returning()
-    savedWebhook = createdRows[0]
-  } catch (error) {
-    if (result.externalSubscriptionCreated) {
-      await cleanupExternalWebhook(createPayload, workflow, requestId)
-    }
-    throw error
-  }
-
-  const pollingError = await configurePollingIfNeeded(provider, savedWebhook, requestId)
-  if (pollingError) {
-    return pollingError
-  }
-
-  return null
+  return { error: null, warnings }
 }
 
 /**
@@ -398,23 +353,57 @@ export async function saveTriggerWebhooksForDeploy({
   blocks,
   requestId,
   deploymentVersionId,
+  previousVersionId,
+  forceRecreateSubscriptions = false,
 }: SaveTriggerWebhooksInput): Promise<TriggerSaveResult> {
-  const triggerBlocks = Object.values(blocks || {}).filter(Boolean)
+  const triggerBlocks = Object.values(blocks || {}).filter((b) => b && b.enabled !== false)
   const currentBlockIds = new Set(triggerBlocks.map((b) => b.id))
 
-  // 1. Get all existing webhooks for this workflow
-  const existingWebhooks = await db
+  // 1. Get ALL webhooks for this workflow (all versions including draft)
+  const allWorkflowWebhooks = await db
     .select()
     .from(webhook)
-    .where(
-      deploymentVersionId
-        ? and(
-            eq(webhook.workflowId, workflowId),
-            eq(webhook.deploymentVersionId, deploymentVersionId)
-          )
-        : eq(webhook.workflowId, workflowId)
+    .where(eq(webhook.workflowId, workflowId))
+
+  // Separate webhooks by version: current deployment vs others
+  const existingWebhooks: typeof allWorkflowWebhooks = []
+
+  for (const wh of allWorkflowWebhooks) {
+    if (deploymentVersionId && wh.deploymentVersionId === deploymentVersionId) {
+      existingWebhooks.push(wh)
+    }
+  }
+
+  if (previousVersionId) {
+    const webhooksToCleanup = allWorkflowWebhooks.filter(
+      (wh) => wh.deploymentVersionId === previousVersionId
     )
 
+    if (webhooksToCleanup.length > 0) {
+      logger.info(
+        `[${requestId}] Cleaning up ${webhooksToCleanup.length} external subscription(s) from previous version`
+      )
+      for (const wh of webhooksToCleanup) {
+        try {
+          await cleanupExternalWebhook(wh, workflow, requestId)
+        } catch (cleanupError) {
+          logger.warn(`[${requestId}] Failed to cleanup external webhook ${wh.id}`, cleanupError)
+        }
+      }
+    }
+  }
+
+  const restorePreviousSubscriptions = async () => {
+    if (!previousVersionId) return
+    await restorePreviousVersionWebhooks({
+      request,
+      workflow,
+      userId,
+      previousVersionId,
+      requestId,
+    })
+  }
+
   const webhooksByBlockId = new Map<string, typeof existingWebhooks>()
   for (const wh of existingWebhooks) {
     if (!wh.blockId) continue
@@ -429,7 +418,14 @@ export async function saveTriggerWebhooksForDeploy({
     existingWebhookBlockIds: Array.from(webhooksByBlockId.keys()),
   })
 
-  // 2. Determine which webhooks to delete (orphaned or config changed)
+  type WebhookConfig = {
+    provider: string
+    providerConfig: Record<string, unknown>
+    triggerPath: string
+    triggerDef: ReturnType<typeof getTrigger>
+  }
+  const webhookConfigs = new Map<string, WebhookConfig>()
+
   const webhooksToDelete: typeof existingWebhooks = []
   const blocksNeedingWebhook: BlockState[] = []
   const blocksNeedingCredentialSetSync: BlockState[] = []
@@ -447,6 +443,7 @@ export async function saveTriggerWebhooksForDeploy({
     )
 
     if (missingFields.length > 0) {
+      await restorePreviousSubscriptions()
       return {
         success: false,
         error: {
@@ -455,9 +452,8 @@ export async function saveTriggerWebhooksForDeploy({
         },
       }
     }
-    // Store config for later use
 
-    ;(block as any)._webhookConfig = { provider, providerConfig, triggerPath, triggerDef }
+    webhookConfigs.set(block.id, { provider, providerConfig, triggerPath, triggerDef })
 
     if (providerConfig.credentialSetId) {
       blocksNeedingCredentialSetSync.push(block)
@@ -477,22 +473,29 @@ export async function saveTriggerWebhooksForDeploy({
         )
       }
 
-      // Check if config changed
+      // Check if config changed or if we're forcing recreation (e.g., activating old version)
       const existingConfig = (existingWh.providerConfig as Record<string, unknown>) || {}
-      if (
+      const needsRecreation =
+        forceRecreateSubscriptions ||
         shouldRecreateExternalWebhookSubscription({
           previousProvider: existingWh.provider as string,
           nextProvider: provider,
           previousConfig: existingConfig,
           nextConfig: providerConfig,
         })
-      ) {
-        // Config changed - delete and recreate
+
+      if (needsRecreation) {
         webhooksToDelete.push(existingWh)
         blocksNeedingWebhook.push(block)
-        logger.info(`[${requestId}] Webhook config changed for block ${block.id}, will recreate`)
+        if (forceRecreateSubscriptions) {
+          logger.info(
+            `[${requestId}] Forcing webhook recreation for block ${block.id} (reactivating version)`
+          )
+        } else {
+          logger.info(`[${requestId}] Webhook config changed for block ${block.id}, will recreate`)
+        }
       }
-      // else: config unchanged, keep existing webhook
+      // else: config unchanged and not forcing recreation, keep existing webhook
     }
   }
 
@@ -522,15 +525,16 @@ export async function saveTriggerWebhooksForDeploy({
     await db.delete(webhook).where(inArray(webhook.id, idsToDelete))
   }
 
-  // 4. Sync credential set webhooks
+  const collectedWarnings: string[] = []
+
   for (const block of blocksNeedingCredentialSetSync) {
-    const config = (block as any)._webhookConfig
+    const config = webhookConfigs.get(block.id)
     if (!config) continue
 
     const { provider, providerConfig, triggerPath } = config
 
     try {
-      const credentialSetError = await syncCredentialSetWebhooks({
+      const syncResult = await syncCredentialSetWebhooks({
         workflowId,
         blockId: block.id,
         provider,
@@ -540,74 +544,214 @@ export async function saveTriggerWebhooksForDeploy({
         deploymentVersionId,
       })
 
-      if (credentialSetError) {
-        return { success: false, error: credentialSetError }
+      if (syncResult.warnings.length > 0) {
+        collectedWarnings.push(...syncResult.warnings)
+      }
+
+      if (syncResult.error) {
+        await restorePreviousSubscriptions()
+        return { success: false, error: syncResult.error, warnings: collectedWarnings }
       }
     } catch (error: any) {
       logger.error(`[${requestId}] Failed to create webhook for ${block.id}`, error)
+      await restorePreviousSubscriptions()
       return {
         success: false,
         error: {
           message: error?.message || 'Failed to save trigger configuration',
           status: 500,
         },
+        warnings: collectedWarnings,
       }
     }
   }
 
-  // 5. Create webhooks for blocks that need them
+  // 5. Create webhooks for blocks that need them (two-phase approach for atomicity)
+  const createdSubscriptions: Array<{
+    webhookId: string
+    block: BlockState
+    provider: string
+    triggerPath: string
+    updatedProviderConfig: Record<string, unknown>
+    externalSubscriptionCreated: boolean
+  }> = []
+
   for (const block of blocksNeedingWebhook) {
-    const config = (block as any)._webhookConfig
+    const config = webhookConfigs.get(block.id)
     if (!config) continue
 
     const { provider, providerConfig, triggerPath } = config
+    const webhookId = nanoid()
+    const createPayload = {
+      id: webhookId,
+      path: triggerPath,
+      provider,
+      providerConfig,
+    }
 
     try {
-      const createError = await createWebhookForBlock({
+      const result = await createExternalWebhookSubscription(
         request,
-        workflowId,
+        createPayload,
         workflow,
         userId,
+        requestId
+      )
+
+      createdSubscriptions.push({
+        webhookId,
         block,
         provider,
-        providerConfig,
         triggerPath,
-        requestId,
-        deploymentVersionId,
+        updatedProviderConfig: result.updatedProviderConfig as Record<string, unknown>,
+        externalSubscriptionCreated: result.externalSubscriptionCreated,
       })
-
-      if (createError) {
-        return { success: false, error: createError }
-      }
     } catch (error: any) {
-      logger.error(`[${requestId}] Failed to create webhook for ${block.id}`, error)
+      logger.error(`[${requestId}] Failed to create external subscription for ${block.id}`, error)
+      for (const sub of createdSubscriptions) {
+        if (sub.externalSubscriptionCreated) {
+          try {
+            await cleanupExternalWebhook(
+              {
+                id: sub.webhookId,
+                path: sub.triggerPath,
+                provider: sub.provider,
+                providerConfig: sub.updatedProviderConfig,
+              },
+              workflow,
+              requestId
+            )
+          } catch (cleanupError) {
+            logger.warn(
+              `[${requestId}] Failed to cleanup external subscription for ${sub.block.id}`,
+              cleanupError
+            )
+          }
+        }
+      }
+      await restorePreviousSubscriptions()
       return {
         success: false,
         error: {
-          message: error?.message || 'Failed to save trigger configuration',
+          message: error?.message || 'Failed to create external subscription',
           status: 500,
         },
       }
     }
   }
 
-  // Clean up temp config
-  for (const block of triggerBlocks) {
-    ;(block as any)._webhookConfig = undefined
+  // Phase 2: Insert all DB records in a transaction
+  try {
+    await db.transaction(async (tx) => {
+      for (const sub of createdSubscriptions) {
+        await tx.insert(webhook).values({
+          id: sub.webhookId,
+          workflowId,
+          deploymentVersionId: deploymentVersionId || null,
+          blockId: sub.block.id,
+          path: sub.triggerPath,
+          provider: sub.provider,
+          providerConfig: sub.updatedProviderConfig,
+          credentialSetId:
+            (sub.updatedProviderConfig.credentialSetId as string | undefined) || null,
+          isActive: true,
+          createdAt: new Date(),
+          updatedAt: new Date(),
+        })
+      }
+    })
+
+    for (const sub of createdSubscriptions) {
+      const pollingError = await configurePollingIfNeeded(
+        sub.provider,
+        { id: sub.webhookId, path: sub.triggerPath, providerConfig: sub.updatedProviderConfig },
+        requestId
+      )
+      if (pollingError) {
+        logger.error(
+          `[${requestId}] Polling configuration failed for ${sub.block.id}`,
+          pollingError
+        )
+        for (const otherSub of createdSubscriptions) {
+          if (otherSub.webhookId === sub.webhookId) continue
+          if (otherSub.externalSubscriptionCreated) {
+            try {
+              await cleanupExternalWebhook(
+                {
+                  id: otherSub.webhookId,
+                  path: otherSub.triggerPath,
+                  provider: otherSub.provider,
+                  providerConfig: otherSub.updatedProviderConfig,
+                },
+                workflow,
+                requestId
+              )
+            } catch (cleanupError) {
+              logger.warn(
+                `[${requestId}] Failed to cleanup external subscription for ${otherSub.block.id}`,
+                cleanupError
+              )
+            }
+          }
+        }
+        const otherWebhookIds = createdSubscriptions
+          .filter((s) => s.webhookId !== sub.webhookId)
+          .map((s) => s.webhookId)
+        if (otherWebhookIds.length > 0) {
+          await db.delete(webhook).where(inArray(webhook.id, otherWebhookIds))
+        }
+        await restorePreviousSubscriptions()
+        return { success: false, error: pollingError }
+      }
+    }
+  } catch (error: any) {
+    logger.error(`[${requestId}] Failed to insert webhook records`, error)
+    for (const sub of createdSubscriptions) {
+      if (sub.externalSubscriptionCreated) {
+        try {
+          await cleanupExternalWebhook(
+            {
+              id: sub.webhookId,
+              path: sub.triggerPath,
+              provider: sub.provider,
+              providerConfig: sub.updatedProviderConfig,
+            },
+            workflow,
+            requestId
+          )
+        } catch (cleanupError) {
+          logger.warn(
+            `[${requestId}] Failed to cleanup external subscription for ${sub.block.id}`,
+            cleanupError
+          )
+        }
+      }
+    }
+    await restorePreviousSubscriptions()
+    return {
+      success: false,
+      error: {
+        message: error?.message || 'Failed to save webhook records',
+        status: 500,
+      },
+    }
   }
 
-  return { success: true }
+  return { success: true, warnings: collectedWarnings.length > 0 ? collectedWarnings : undefined }
 }
 
 /**
  * Clean up all webhooks for a workflow during undeploy.
  * Removes external subscriptions and deletes webhook records from the database.
+ *
+ * @param skipExternalCleanup - If true, skip external subscription cleanup (already done elsewhere)
  */
 export async function cleanupWebhooksForWorkflow(
   workflowId: string,
   workflow: Record<string, unknown>,
   requestId: string,
-  deploymentVersionId?: string
+  deploymentVersionId?: string,
+  skipExternalCleanup = false
 ): Promise<void> {
   const existingWebhooks = await db
     .select()
@@ -626,23 +770,26 @@ export async function cleanupWebhooksForWorkflow(
     return
   }
 
-  logger.info(`[${requestId}] Cleaning up ${existingWebhooks.length} webhook(s) for undeploy`, {
-    workflowId,
-    deploymentVersionId,
-    webhookIds: existingWebhooks.map((wh) => wh.id),
-  })
+  logger.info(
+    `[${requestId}] Cleaning up ${existingWebhooks.length} webhook(s) for ${skipExternalCleanup ? 'DB records only' : 'undeploy'}`,
+    {
+      workflowId,
+      deploymentVersionId,
+      webhookIds: existingWebhooks.map((wh) => wh.id),
+    }
+  )
 
-  // Clean up external subscriptions
-  for (const wh of existingWebhooks) {
-    try {
-      await cleanupExternalWebhook(wh, workflow, requestId)
-    } catch (cleanupError) {
-      logger.warn(`[${requestId}] Failed to cleanup external webhook ${wh.id}`, cleanupError)
-      // Continue with other webhooks even if one fails
+  if (!skipExternalCleanup) {
+    for (const wh of existingWebhooks) {
+      try {
+        await cleanupExternalWebhook(wh, workflow, requestId)
+      } catch (cleanupError) {
+        logger.warn(`[${requestId}] Failed to cleanup external webhook ${wh.id}`, cleanupError)
+        // Continue with other webhooks even if one fails
+      }
     }
   }
 
-  // Delete all webhook records
   await db
     .delete(webhook)
     .where(
@@ -660,3 +807,55 @@ export async function cleanupWebhooksForWorkflow(
       : `[${requestId}] Cleaned up all webhooks for workflow ${workflowId}`
   )
 }
+
+/**
+ * Restore external subscriptions for a previous deployment version.
+ * Used when activation/deployment fails after webhooks were created,
+ * to restore the previous version's external subscriptions.
+ */
+export async function restorePreviousVersionWebhooks(params: {
+  request: NextRequest
+  workflow: Record<string, unknown>
+  userId: string
+  previousVersionId: string
+  requestId: string
+}): Promise<void> {
+  const { request, workflow, userId, previousVersionId, requestId } = params
+
+  const previousWebhooks = await db
+    .select()
+    .from(webhook)
+    .where(eq(webhook.deploymentVersionId, previousVersionId))
+
+  if (previousWebhooks.length === 0) {
+    logger.debug(`[${requestId}] No previous webhooks to restore for version ${previousVersionId}`)
+    return
+  }
+
+  logger.info(
+    `[${requestId}] Restoring ${previousWebhooks.length} external subscription(s) for previous version ${previousVersionId}`
+  )
+
+  for (const wh of previousWebhooks) {
+    try {
+      await createExternalWebhookSubscription(
+        request,
+        {
+          id: wh.id,
+          path: wh.path,
+          provider: wh.provider,
+          providerConfig: (wh.providerConfig as Record<string, unknown>) || {},
+        },
+        workflow,
+        userId,
+        requestId
+      )
+      logger.info(`[${requestId}] Restored external subscription for webhook ${wh.id}`)
+    } catch (restoreError) {
+      logger.error(
+        `[${requestId}] Failed to restore external subscription for webhook ${wh.id}`,
+        restoreError
+      )
+    }
+  }
+}
diff --git a/apps/sim/lib/webhooks/gmail-polling-service.ts b/apps/sim/lib/webhooks/gmail-polling-service.ts
index 0c4ce378e..7e3bcca5d 100644
--- a/apps/sim/lib/webhooks/gmail-polling-service.ts
+++ b/apps/sim/lib/webhooks/gmail-polling-service.ts
@@ -161,7 +161,7 @@ export async function pollGmailWebhooks() {
         const metadata = webhookData.providerConfig as any
         const credentialId: string | undefined = metadata?.credentialId
         const userId: string | undefined = metadata?.userId
-        const credentialSetId: string | undefined = metadata?.credentialSetId
+        const credentialSetId: string | undefined = webhookData.credentialSetId ?? undefined
 
         if (!credentialId && !userId) {
           logger.error(`[${requestId}] Missing credential info for webhook ${webhookId}`)
@@ -697,7 +697,6 @@ async function processEmails(
             method: 'POST',
             headers: {
               'Content-Type': 'application/json',
-              'X-Webhook-Secret': webhookData.secret || '',
               'User-Agent': 'Sim/1.0',
             },
             body: JSON.stringify(payload),
@@ -766,17 +765,21 @@ async function markEmailAsRead(accessToken: string, messageId: string) {
 }
 
 async function updateWebhookLastChecked(webhookId: string, timestamp: string, historyId?: string) {
-  const result = await db.select().from(webhook).where(eq(webhook.id, webhookId))
-  const existingConfig = (result[0]?.providerConfig as Record<string, any>) || {}
-  await db
-    .update(webhook)
-    .set({
-      providerConfig: {
-        ...existingConfig,
-        lastCheckedTimestamp: timestamp,
-        ...(historyId ? { historyId } : {}),
-      } as any,
-      updatedAt: new Date(),
-    })
-    .where(eq(webhook.id, webhookId))
+  try {
+    const result = await db.select().from(webhook).where(eq(webhook.id, webhookId))
+    const existingConfig = (result[0]?.providerConfig as Record<string, any>) || {}
+    await db
+      .update(webhook)
+      .set({
+        providerConfig: {
+          ...existingConfig,
+          lastCheckedTimestamp: timestamp,
+          ...(historyId ? { historyId } : {}),
+        } as any,
+        updatedAt: new Date(),
+      })
+      .where(eq(webhook.id, webhookId))
+  } catch (error) {
+    logger.error(`Error updating webhook ${webhookId} last checked timestamp:`, error)
+  }
 }
diff --git a/apps/sim/lib/webhooks/imap-polling-service.ts b/apps/sim/lib/webhooks/imap-polling-service.ts
index 49185f9d9..9d664531f 100644
--- a/apps/sim/lib/webhooks/imap-polling-service.ts
+++ b/apps/sim/lib/webhooks/imap-polling-service.ts
@@ -645,7 +645,6 @@ async function processEmails(
               method: 'POST',
               headers: {
                 'Content-Type': 'application/json',
-                'X-Webhook-Secret': '',
                 'User-Agent': 'Sim/1.0',
               },
               body: JSON.stringify(payload),
diff --git a/apps/sim/lib/webhooks/outlook-polling-service.ts b/apps/sim/lib/webhooks/outlook-polling-service.ts
index 801d22182..1f1b48e0c 100644
--- a/apps/sim/lib/webhooks/outlook-polling-service.ts
+++ b/apps/sim/lib/webhooks/outlook-polling-service.ts
@@ -210,7 +210,7 @@ export async function pollOutlookWebhooks() {
         const metadata = webhookData.providerConfig as any
         const credentialId: string | undefined = metadata?.credentialId
         const userId: string | undefined = metadata?.userId
-        const credentialSetId: string | undefined = metadata?.credentialSetId
+        const credentialSetId: string | undefined = webhookData.credentialSetId ?? undefined
 
         if (!credentialId && !userId) {
           logger.error(`[${requestId}] Missing credentialId and userId for webhook ${webhookId}`)
@@ -607,7 +607,6 @@ async function processOutlookEmails(
             method: 'POST',
             headers: {
               'Content-Type': 'application/json',
-              'X-Webhook-Secret': webhookData.secret || '',
               'User-Agent': 'Sim/1.0',
             },
             body: JSON.stringify(payload),
diff --git a/apps/sim/lib/webhooks/processor.ts b/apps/sim/lib/webhooks/processor.ts
index fa4e295bb..709fa05d2 100644
--- a/apps/sim/lib/webhooks/processor.ts
+++ b/apps/sim/lib/webhooks/processor.ts
@@ -7,16 +7,27 @@ import { type NextRequest, NextResponse } from 'next/server'
 import { v4 as uuidv4 } from 'uuid'
 import { checkEnterprisePlan, checkTeamPlan } from '@/lib/billing/subscriptions/utils'
 import { isProd, isTriggerDevEnabled } from '@/lib/core/config/feature-flags'
+import { getEffectiveDecryptedEnv } from '@/lib/environment/utils'
 import { preprocessExecution } from '@/lib/execution/preprocessing'
 import { convertSquareBracketsToTwiML } from '@/lib/webhooks/utils'
 import {
   handleSlackChallenge,
   handleWhatsAppVerification,
+  validateCirclebackSignature,
+  validateFirefliesSignature,
+  validateGitHubSignature,
+  validateJiraSignature,
+  validateLinearSignature,
   validateMicrosoftTeamsSignature,
+  validateTwilioSignature,
+  validateTypeformSignature,
   verifyProviderWebhook,
 } from '@/lib/webhooks/utils.server'
 import { executeWebhookJob } from '@/background/webhook-execution'
 import { resolveEnvVarReferences } from '@/executor/utils/reference-validation'
+import { isGitHubEventMatch } from '@/triggers/github/utils'
+import { isHubSpotContactEventMatch } from '@/triggers/hubspot/utils'
+import { isJiraEventMatch } from '@/triggers/jira/utils'
 
 const logger = createLogger('WebhookProcessor')
 
@@ -451,7 +462,6 @@ export async function verifyProviderAuth(
   // Step 1: Fetch and decrypt environment variables for signature verification
   let decryptedEnvVars: Record<string, string> = {}
   try {
-    const { getEffectiveDecryptedEnv } = await import('@/lib/environment/utils')
     decryptedEnvVars = await getEffectiveDecryptedEnv(
       foundWorkflow.userId,
       foundWorkflow.workspaceId
@@ -553,9 +563,6 @@ export async function verifyProviderAuth(
       }
 
       const fullUrl = getExternalUrl(request)
-
-      const { validateTwilioSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = await validateTwilioSignature(authToken, signature, fullUrl, params)
 
       if (!isValidSignature) {
@@ -583,8 +590,6 @@ export async function verifyProviderAuth(
         return new NextResponse('Unauthorized - Missing Typeform signature', { status: 401 })
       }
 
-      const { validateTypeformSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = validateTypeformSignature(secret, signature, rawBody)
 
       if (!isValidSignature) {
@@ -610,8 +615,6 @@ export async function verifyProviderAuth(
         return new NextResponse('Unauthorized - Missing Linear signature', { status: 401 })
       }
 
-      const { validateLinearSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = validateLinearSignature(secret, signature, rawBody)
 
       if (!isValidSignature) {
@@ -637,8 +640,6 @@ export async function verifyProviderAuth(
         return new NextResponse('Unauthorized - Missing Circleback signature', { status: 401 })
       }
 
-      const { validateCirclebackSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = validateCirclebackSignature(secret, signature, rawBody)
 
       if (!isValidSignature) {
@@ -664,8 +665,6 @@ export async function verifyProviderAuth(
         return new NextResponse('Unauthorized - Missing Jira signature', { status: 401 })
       }
 
-      const { validateJiraSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = validateJiraSignature(secret, signature, rawBody)
 
       if (!isValidSignature) {
@@ -694,8 +693,6 @@ export async function verifyProviderAuth(
         return new NextResponse('Unauthorized - Missing GitHub signature', { status: 401 })
       }
 
-      const { validateGitHubSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = validateGitHubSignature(secret, signature, rawBody)
 
       if (!isValidSignature) {
@@ -724,8 +721,6 @@ export async function verifyProviderAuth(
         return new NextResponse('Unauthorized - Missing Fireflies signature', { status: 401 })
       }
 
-      const { validateFirefliesSignature } = await import('@/lib/webhooks/utils.server')
-
       const isValidSignature = validateFirefliesSignature(secret, signature, rawBody)
 
       if (!isValidSignature) {
@@ -860,8 +855,6 @@ export async function queueWebhookExecution(
         const eventType = request.headers.get('x-github-event')
         const action = body.action
 
-        const { isGitHubEventMatch } = await import('@/triggers/github/utils')
-
         if (!isGitHubEventMatch(triggerId, eventType || '', action, body)) {
           logger.debug(
             `[${options.requestId}] GitHub event mismatch for trigger ${triggerId}. Event: ${eventType}, Action: ${action}. Skipping execution.`,
@@ -890,8 +883,6 @@ export async function queueWebhookExecution(
       if (triggerId && triggerId !== 'jira_webhook') {
         const webhookEvent = body.webhookEvent as string | undefined
 
-        const { isJiraEventMatch } = await import('@/triggers/jira/utils')
-
         if (!isJiraEventMatch(triggerId, webhookEvent || '', body)) {
           logger.debug(
             `[${options.requestId}] Jira event mismatch for trigger ${triggerId}. Event: ${webhookEvent}. Skipping execution.`,
@@ -921,8 +912,6 @@ export async function queueWebhookExecution(
 
         const subscriptionType = firstEvent?.subscriptionType as string | undefined
 
-        const { isHubSpotContactEventMatch } = await import('@/triggers/hubspot/utils')
-
         if (!isHubSpotContactEventMatch(triggerId, subscriptionType || '')) {
           logger.debug(
             `[${options.requestId}] HubSpot event mismatch for trigger ${triggerId}. Event: ${subscriptionType}. Skipping execution.`,
@@ -974,7 +963,8 @@ export async function queueWebhookExecution(
     // Note: Each webhook now has its own credentialId (credential sets are fanned out at save time)
     const providerConfig = (foundWebhook.providerConfig as Record<string, any>) || {}
     const credentialId = providerConfig.credentialId as string | undefined
-    const credentialSetId = providerConfig.credentialSetId as string | undefined
+    // credentialSetId is a direct field on webhook table, not in providerConfig
+    const credentialSetId = foundWebhook.credentialSetId as string | undefined
 
     // Verify billing for credential sets
     if (credentialSetId) {
diff --git a/apps/sim/lib/webhooks/provider-subscriptions.ts b/apps/sim/lib/webhooks/provider-subscriptions.ts
index 6461eb1e2..a3e049f76 100644
--- a/apps/sim/lib/webhooks/provider-subscriptions.ts
+++ b/apps/sim/lib/webhooks/provider-subscriptions.ts
@@ -30,11 +30,11 @@ export async function createTeamsSubscription(
   webhook: any,
   workflow: any,
   requestId: string
-): Promise<void> {
+): Promise<string | undefined> {
   const config = getProviderConfig(webhook)
 
   if (config.triggerId !== 'microsoftteams_chat_subscription') {
-    return
+    return undefined
   }
 
   const credentialId = config.credentialId as string | undefined
@@ -77,7 +77,7 @@ export async function createTeamsSubscription(
         teamsLogger.info(
           `[${requestId}] Teams subscription ${existingSubscriptionId} already exists for webhook ${webhook.id}`
         )
-        return
+        return existingSubscriptionId
       }
     } catch {
       teamsLogger.debug(`[${requestId}] Existing subscription check failed, will create new one`)
@@ -140,6 +140,7 @@ export async function createTeamsSubscription(
     teamsLogger.info(
       `[${requestId}] Successfully created Teams subscription ${payload.id} for webhook ${webhook.id}`
     )
+    return payload.id as string
   } catch (error: any) {
     if (
       error instanceof Error &&
@@ -1600,9 +1601,11 @@ export async function createExternalWebhookSubscription(
       externalSubscriptionCreated = true
     }
   } else if (provider === 'microsoft-teams') {
-    await createTeamsSubscription(request, webhookData, workflow, requestId)
-    externalSubscriptionCreated =
-      (providerConfig.triggerId as string | undefined) === 'microsoftteams_chat_subscription'
+    const subscriptionId = await createTeamsSubscription(request, webhookData, workflow, requestId)
+    if (subscriptionId) {
+      updatedProviderConfig = { ...updatedProviderConfig, externalSubscriptionId: subscriptionId }
+      externalSubscriptionCreated = true
+    }
   } else if (provider === 'telegram') {
     await createTelegramWebhook(request, webhookData, requestId)
     externalSubscriptionCreated = true
diff --git a/apps/sim/lib/webhooks/rss-polling-service.ts b/apps/sim/lib/webhooks/rss-polling-service.ts
index 1b4e56993..ce282ef0d 100644
--- a/apps/sim/lib/webhooks/rss-polling-service.ts
+++ b/apps/sim/lib/webhooks/rss-polling-service.ts
@@ -379,7 +379,6 @@ async function processRssItems(
             method: 'POST',
             headers: {
               'Content-Type': 'application/json',
-              'X-Webhook-Secret': webhookData.secret || '',
               'User-Agent': 'Sim/1.0',
             },
             body: JSON.stringify(payload),
diff --git a/apps/sim/lib/webhooks/utils.server.ts b/apps/sim/lib/webhooks/utils.server.ts
index fd0eb12a0..368b36f9f 100644
--- a/apps/sim/lib/webhooks/utils.server.ts
+++ b/apps/sim/lib/webhooks/utils.server.ts
@@ -2,6 +2,7 @@ import { db, workflowDeploymentVersion } from '@sim/db'
 import { account, webhook } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
 import { and, eq, isNull, or } from 'drizzle-orm'
+import { nanoid } from 'nanoid'
 import { type NextRequest, NextResponse } from 'next/server'
 import {
   type SecureFetchResponse,
@@ -9,7 +10,11 @@ import {
   validateUrlWithDNS,
 } from '@/lib/core/security/input-validation'
 import type { DbOrTx } from '@/lib/db/types'
-import { refreshAccessTokenIfNeeded } from '@/app/api/auth/oauth/utils'
+import { getProviderIdFromServiceId } from '@/lib/oauth'
+import {
+  getCredentialsForCredentialSet,
+  refreshAccessTokenIfNeeded,
+} from '@/app/api/auth/oauth/utils'
 
 const logger = createLogger('WebhookUtils')
 
@@ -1388,21 +1393,6 @@ export function verifyProviderWebhook(
     case 'stripe':
       break
     case 'gmail':
-      if (providerConfig.secret) {
-        const secretHeader = request.headers.get('X-Webhook-Secret')
-        if (!secretHeader || secretHeader.length !== providerConfig.secret.length) {
-          logger.warn(`[${requestId}] Invalid Gmail webhook secret`)
-          return new NextResponse('Unauthorized', { status: 401 })
-        }
-        let result = 0
-        for (let i = 0; i < secretHeader.length; i++) {
-          result |= secretHeader.charCodeAt(i) ^ providerConfig.secret.charCodeAt(i)
-        }
-        if (result !== 0) {
-          logger.warn(`[${requestId}] Invalid Gmail webhook secret`)
-          return new NextResponse('Unauthorized', { status: 401 })
-        }
-      }
       break
     case 'telegram': {
       // Check User-Agent to ensure it's not blocked by middleware
@@ -1946,6 +1936,10 @@ export interface CredentialSetWebhookSyncResult {
   created: number
   updated: number
   deleted: number
+  failed: Array<{
+    credentialId: string
+    error: string
+  }>
 }
 
 /**
@@ -1997,9 +1991,6 @@ export async function syncWebhooksForCredentialSet(params: {
     `[${requestId}] Syncing webhooks for credential set ${credentialSetId}, provider ${provider}`
   )
 
-  const { getCredentialsForCredentialSet } = await import('@/app/api/auth/oauth/utils')
-  const { nanoid } = await import('nanoid')
-
   // Polling providers get unique paths per credential (for independent state)
   // External webhook providers share the same path (external service sends to one URL)
   const pollingProviders = ['gmail', 'outlook', 'rss', 'imap']
@@ -2011,7 +2002,7 @@ export async function syncWebhooksForCredentialSet(params: {
     syncLogger.warn(
       `[${requestId}] No credentials found in credential set ${credentialSetId} for provider ${oauthProviderId}`
     )
-    return { webhooks: [], created: 0, updated: 0, deleted: 0 }
+    return { webhooks: [], created: 0, updated: 0, deleted: 0, failed: [] }
   }
 
   syncLogger.info(
@@ -2033,10 +2024,9 @@ export async function syncWebhooksForCredentialSet(params: {
     )
 
   // Filter to only webhooks belonging to this credential set
-  const credentialSetWebhooks = existingWebhooks.filter((wh) => {
-    const config = wh.providerConfig as Record<string, any>
-    return config?.credentialSetId === credentialSetId
-  })
+  const credentialSetWebhooks = existingWebhooks.filter(
+    (wh) => wh.credentialSetId === credentialSetId
+  )
 
   syncLogger.info(
     `[${requestId}] Found ${credentialSetWebhooks.length} existing webhooks for credential set`
@@ -2058,103 +2048,128 @@ export async function syncWebhooksForCredentialSet(params: {
     created: 0,
     updated: 0,
     deleted: 0,
+    failed: [],
   }
 
   // Process each credential in the set
   for (const cred of credentials) {
-    const existingWebhook = existingByCredentialId.get(cred.credentialId)
+    try {
+      const existingWebhook = existingByCredentialId.get(cred.credentialId)
 
-    if (existingWebhook) {
-      // Update existing webhook - preserve state fields
-      const existingConfig = existingWebhook.providerConfig as Record<string, any>
+      if (existingWebhook) {
+        // Update existing webhook - preserve state fields
+        const existingConfig = existingWebhook.providerConfig as Record<string, any>
 
-      const updatedConfig = {
-        ...providerConfig,
-        basePath, // Store basePath for reliable reconstruction during membership sync
-        credentialId: cred.credentialId,
-        credentialSetId: credentialSetId,
-        // Preserve state fields from existing config
-        historyId: existingConfig.historyId,
-        lastCheckedTimestamp: existingConfig.lastCheckedTimestamp,
-        setupCompleted: existingConfig.setupCompleted,
-        externalId: existingConfig.externalId,
-        userId: cred.userId,
-      }
+        const updatedConfig = {
+          ...providerConfig,
+          basePath, // Store basePath for reliable reconstruction during membership sync
+          credentialId: cred.credentialId,
+          credentialSetId: credentialSetId,
+          // Preserve state fields from existing config
+          historyId: existingConfig?.historyId,
+          lastCheckedTimestamp: existingConfig?.lastCheckedTimestamp,
+          setupCompleted: existingConfig?.setupCompleted,
+          externalId: existingConfig?.externalId,
+          userId: cred.userId,
+        }
 
-      await dbCtx
-        .update(webhook)
-        .set({
-          ...(deploymentVersionId ? { deploymentVersionId } : {}),
-          providerConfig: updatedConfig,
+        await dbCtx
+          .update(webhook)
+          .set({
+            ...(deploymentVersionId ? { deploymentVersionId } : {}),
+            providerConfig: updatedConfig,
+            isActive: true,
+            updatedAt: new Date(),
+          })
+          .where(eq(webhook.id, existingWebhook.id))
+
+        result.webhooks.push({
+          id: existingWebhook.id,
+          credentialId: cred.credentialId,
+          isNew: false,
+        })
+        result.updated++
+
+        syncLogger.debug(
+          `[${requestId}] Updated webhook ${existingWebhook.id} for credential ${cred.credentialId}`
+        )
+      } else {
+        // Create new webhook for this credential
+        const webhookId = nanoid()
+        const webhookPath = useUniquePaths
+          ? `${basePath}-${cred.credentialId.slice(0, 8)}`
+          : basePath
+
+        const newConfig = {
+          ...providerConfig,
+          basePath, // Store basePath for reliable reconstruction during membership sync
+          credentialId: cred.credentialId,
+          credentialSetId: credentialSetId,
+          userId: cred.userId,
+        }
+
+        await dbCtx.insert(webhook).values({
+          id: webhookId,
+          workflowId,
+          blockId,
+          path: webhookPath,
+          provider,
+          providerConfig: newConfig,
+          credentialSetId, // Indexed column for efficient credential set queries
           isActive: true,
+          ...(deploymentVersionId ? { deploymentVersionId } : {}),
+          createdAt: new Date(),
           updatedAt: new Date(),
         })
-        .where(eq(webhook.id, existingWebhook.id))
 
-      result.webhooks.push({
-        id: existingWebhook.id,
-        credentialId: cred.credentialId,
-        isNew: false,
-      })
-      result.updated++
+        result.webhooks.push({
+          id: webhookId,
+          credentialId: cred.credentialId,
+          isNew: true,
+        })
+        result.created++
 
-      syncLogger.debug(
-        `[${requestId}] Updated webhook ${existingWebhook.id} for credential ${cred.credentialId}`
-      )
-    } else {
-      // Create new webhook for this credential
-      const webhookId = nanoid()
-      const webhookPath = useUniquePaths ? `${basePath}-${cred.credentialId.slice(0, 8)}` : basePath
-
-      const newConfig = {
-        ...providerConfig,
-        basePath, // Store basePath for reliable reconstruction during membership sync
-        credentialId: cred.credentialId,
-        credentialSetId: credentialSetId,
-        userId: cred.userId,
+        syncLogger.debug(
+          `[${requestId}] Created webhook ${webhookId} for credential ${cred.credentialId}`
+        )
       }
-
-      await dbCtx.insert(webhook).values({
-        id: webhookId,
-        workflowId,
-        blockId,
-        path: webhookPath,
-        provider,
-        providerConfig: newConfig,
-        credentialSetId, // Indexed column for efficient credential set queries
-        isActive: true,
-        ...(deploymentVersionId ? { deploymentVersionId } : {}),
-        createdAt: new Date(),
-        updatedAt: new Date(),
-      })
-
-      result.webhooks.push({
-        id: webhookId,
-        credentialId: cred.credentialId,
-        isNew: true,
-      })
-      result.created++
-
-      syncLogger.debug(
-        `[${requestId}] Created webhook ${webhookId} for credential ${cred.credentialId}`
+    } catch (error) {
+      const errorMessage = error instanceof Error ? error.message : 'Unknown error'
+      syncLogger.error(
+        `[${requestId}] Failed to sync webhook for credential ${cred.credentialId}: ${errorMessage}`
       )
+      result.failed.push({
+        credentialId: cred.credentialId,
+        error: errorMessage,
+      })
     }
   }
 
   // Delete webhooks for credentials no longer in the set
   for (const [credentialId, existingWebhook] of existingByCredentialId) {
     if (!credentialIdsInSet.has(credentialId)) {
-      await dbCtx.delete(webhook).where(eq(webhook.id, existingWebhook.id))
-      result.deleted++
+      try {
+        await dbCtx.delete(webhook).where(eq(webhook.id, existingWebhook.id))
+        result.deleted++
 
-      syncLogger.debug(
-        `[${requestId}] Deleted webhook ${existingWebhook.id} for removed credential ${credentialId}`
-      )
+        syncLogger.debug(
+          `[${requestId}] Deleted webhook ${existingWebhook.id} for removed credential ${credentialId}`
+        )
+      } catch (error) {
+        const errorMessage = error instanceof Error ? error.message : 'Unknown error'
+        syncLogger.error(
+          `[${requestId}] Failed to delete webhook ${existingWebhook.id} for credential ${credentialId}: ${errorMessage}`
+        )
+        result.failed.push({
+          credentialId,
+          error: `Failed to delete: ${errorMessage}`,
+        })
+      }
     }
   }
 
   syncLogger.info(
-    `[${requestId}] Credential set webhook sync complete: ${result.created} created, ${result.updated} updated, ${result.deleted} deleted`
+    `[${requestId}] Credential set webhook sync complete: ${result.created} created, ${result.updated} updated, ${result.deleted} deleted, ${result.failed.length} failed`
   )
 
   return result
@@ -2175,8 +2190,6 @@ export async function syncAllWebhooksForCredentialSet(
   const syncLogger = createLogger('CredentialSetMembershipSync')
   syncLogger.info(`[${requestId}] Syncing all webhooks for credential set ${credentialSetId}`)
 
-  const { getProviderIdFromServiceId } = await import('@/lib/oauth')
-
   // Find all webhooks that use this credential set using the indexed column
   const webhooksForSet = await dbCtx
     .select({ webhook })
diff --git a/apps/sim/lib/webhooks/utils.ts b/apps/sim/lib/webhooks/utils.ts
index 916045b34..d411f6b84 100644
--- a/apps/sim/lib/webhooks/utils.ts
+++ b/apps/sim/lib/webhooks/utils.ts
@@ -1,5 +1,5 @@
 /**
- * Pure utility functions for TwiML processing
+ * Pure utility functions for webhook processing
  * This file has NO server-side dependencies to ensure it can be safely imported in client-side code
  */
 
@@ -18,3 +18,19 @@ export function convertSquareBracketsToTwiML(twiml: string | undefined): string
   // Replace [Tag] with <Tag> and [/Tag] with </Tag>
   return twiml.replace(/\[(\/?[^\]]+)\]/g, '<$1>')
 }
+
+/**
+ * Merges fields from source into target, but only if they don't exist in the base config.
+ * Used to preserve system-managed fields while respecting user-provided values.
+ */
+export function mergeNonUserFields(
+  target: Record<string, unknown>,
+  source: Record<string, unknown>,
+  userProvided: Record<string, unknown>
+): void {
+  for (const [key, value] of Object.entries(source)) {
+    if (!(key in userProvided)) {
+      target[key] = value
+    }
+  }
+}
diff --git a/apps/sim/lib/workflows/schedules/deploy.test.ts b/apps/sim/lib/workflows/schedules/deploy.test.ts
index a18bd5adf..b5039c031 100644
--- a/apps/sim/lib/workflows/schedules/deploy.test.ts
+++ b/apps/sim/lib/workflows/schedules/deploy.test.ts
@@ -17,6 +17,9 @@ const {
   mockValidateCronExpression,
   mockGetScheduleTimeValues,
   mockRandomUUID,
+  mockTransaction,
+  mockSelect,
+  mockFrom,
 } = vi.hoisted(() => ({
   mockInsert: vi.fn(),
   mockDelete: vi.fn(),
@@ -28,20 +31,27 @@ const {
   mockValidateCronExpression: vi.fn(),
   mockGetScheduleTimeValues: vi.fn(),
   mockRandomUUID: vi.fn(),
+  mockTransaction: vi.fn(),
+  mockSelect: vi.fn(),
+  mockFrom: vi.fn(),
 }))
 
 vi.mock('@sim/db', () => ({
-  db: {},
+  db: {
+    transaction: mockTransaction,
+  },
   workflowSchedule: {
     workflowId: 'workflow_id',
     blockId: 'block_id',
     deploymentVersionId: 'deployment_version_id',
+    id: 'id',
   },
 }))
 
 vi.mock('drizzle-orm', () => ({
   eq: vi.fn((...args) => ({ type: 'eq', args })),
   and: vi.fn((...args) => ({ type: 'and', args })),
+  inArray: vi.fn((...args) => ({ type: 'inArray', args })),
   sql: vi.fn((strings, ...values) => ({ type: 'sql', strings, values })),
 }))
 
@@ -100,6 +110,20 @@ describe('Schedule Deploy Utilities', () => {
     // Setup mock chain for delete
     mockWhere.mockResolvedValue({})
     mockDelete.mockReturnValue({ where: mockWhere })
+
+    // Setup mock chain for select
+    mockFrom.mockReturnValue({ where: vi.fn().mockResolvedValue([]) })
+    mockSelect.mockReturnValue({ from: mockFrom })
+
+    // Setup transaction mock to execute callback with mock tx
+    mockTransaction.mockImplementation(async (callback) => {
+      const mockTx = {
+        insert: mockInsert,
+        delete: mockDelete,
+        select: mockSelect,
+      }
+      return callback(mockTx)
+    })
   })
 
   afterEach(() => {
@@ -135,6 +159,19 @@ describe('Schedule Deploy Utilities', () => {
       const result = findScheduleBlocks({})
       expect(result).toHaveLength(0)
     })
+
+    it('should exclude disabled schedule blocks', () => {
+      const blocks: Record<string, BlockState> = {
+        'block-1': { id: 'block-1', type: 'schedule', enabled: true, subBlocks: {} } as BlockState,
+        'block-2': { id: 'block-2', type: 'schedule', enabled: false, subBlocks: {} } as BlockState,
+        'block-3': { id: 'block-3', type: 'schedule', subBlocks: {} } as BlockState, // enabled undefined = enabled
+      }
+
+      const result = findScheduleBlocks(blocks)
+
+      expect(result).toHaveLength(2)
+      expect(result.map((b) => b.id)).toEqual(['block-1', 'block-3'])
+    })
   })
 
   describe('validateScheduleBlock', () => {
@@ -671,20 +708,24 @@ describe('Schedule Deploy Utilities', () => {
   })
 
   describe('createSchedulesForDeploy', () => {
+    const setupMockTransaction = (
+      existingSchedules: Array<{ id: string; blockId: string }> = []
+    ) => {
+      mockFrom.mockReturnValue({ where: vi.fn().mockResolvedValue(existingSchedules) })
+      mockSelect.mockReturnValue({ from: mockFrom })
+    }
+
     it('should return success with no schedule blocks', async () => {
       const blocks: Record<string, BlockState> = {
         'block-1': { id: 'block-1', type: 'agent', subBlocks: {} } as BlockState,
       }
 
-      const mockTx = {
-        insert: mockInsert,
-        delete: mockDelete,
-      }
+      setupMockTransaction()
 
-      const result = await createSchedulesForDeploy('workflow-1', blocks, mockTx as any)
+      const result = await createSchedulesForDeploy('workflow-1', blocks, {} as any)
 
       expect(result.success).toBe(true)
-      expect(mockInsert).not.toHaveBeenCalled()
+      expect(mockTransaction).not.toHaveBeenCalled()
     })
 
     it('should create schedule for valid schedule block', async () => {
@@ -700,17 +741,15 @@ describe('Schedule Deploy Utilities', () => {
         } as BlockState,
       }
 
-      const mockTx = {
-        insert: mockInsert,
-        delete: mockDelete,
-      }
+      setupMockTransaction()
 
-      const result = await createSchedulesForDeploy('workflow-1', blocks, mockTx as any)
+      const result = await createSchedulesForDeploy('workflow-1', blocks, {} as any)
 
       expect(result.success).toBe(true)
       expect(result.scheduleId).toBe('test-uuid')
       expect(result.cronExpression).toBe('0 9 * * *')
       expect(result.nextRunAt).toEqual(new Date('2025-04-15T09:00:00Z'))
+      expect(mockTransaction).toHaveBeenCalled()
       expect(mockInsert).toHaveBeenCalled()
       expect(mockOnConflictDoUpdate).toHaveBeenCalled()
     })
@@ -727,16 +766,13 @@ describe('Schedule Deploy Utilities', () => {
         } as BlockState,
       }
 
-      const mockTx = {
-        insert: mockInsert,
-        delete: mockDelete,
-      }
+      setupMockTransaction()
 
-      const result = await createSchedulesForDeploy('workflow-1', blocks, mockTx as any)
+      const result = await createSchedulesForDeploy('workflow-1', blocks, {} as any)
 
       expect(result.success).toBe(false)
       expect(result.error).toBe('Time is required for daily schedules')
-      expect(mockInsert).not.toHaveBeenCalled()
+      expect(mockTransaction).not.toHaveBeenCalled()
     })
 
     it('should use onConflictDoUpdate for existing schedules', async () => {
@@ -752,12 +788,9 @@ describe('Schedule Deploy Utilities', () => {
         } as BlockState,
       }
 
-      const mockTx = {
-        insert: mockInsert,
-        delete: mockDelete,
-      }
+      setupMockTransaction()
 
-      await createSchedulesForDeploy('workflow-1', blocks, mockTx as any)
+      await createSchedulesForDeploy('workflow-1', blocks, {} as any)
 
       expect(mockOnConflictDoUpdate).toHaveBeenCalledWith({
         target: expect.any(Array),
@@ -769,6 +802,27 @@ describe('Schedule Deploy Utilities', () => {
         }),
       })
     })
+
+    it('should rollback on database error', async () => {
+      const blocks: Record<string, BlockState> = {
+        'block-1': {
+          id: 'block-1',
+          type: 'schedule',
+          subBlocks: {
+            scheduleType: { value: 'daily' },
+            dailyTime: { value: '09:00' },
+            timezone: { value: 'UTC' },
+          },
+        } as BlockState,
+      }
+
+      mockTransaction.mockRejectedValueOnce(new Error('Database error'))
+
+      const result = await createSchedulesForDeploy('workflow-1', blocks, {} as any)
+
+      expect(result.success).toBe(false)
+      expect(result.error).toBe('Database error')
+    })
   })
 
   describe('deleteSchedulesForWorkflow', () => {
diff --git a/apps/sim/lib/workflows/schedules/deploy.ts b/apps/sim/lib/workflows/schedules/deploy.ts
index 659affda9..9344b018e 100644
--- a/apps/sim/lib/workflows/schedules/deploy.ts
+++ b/apps/sim/lib/workflows/schedules/deploy.ts
@@ -1,6 +1,6 @@
 import { db, workflowSchedule } from '@sim/db'
 import { createLogger } from '@sim/logger'
-import { and, eq } from 'drizzle-orm'
+import { and, eq, inArray } from 'drizzle-orm'
 import type { DbOrTx } from '@/lib/db/types'
 import { cleanupWebhooksForWorkflow } from '@/lib/webhooks/deploy'
 import type { BlockState } from '@/lib/workflows/schedules/utils'
@@ -21,13 +21,13 @@ export interface ScheduleDeployResult {
 }
 
 /**
- * Create or update schedule records for a workflow during deployment
- * This should be called within a database transaction
+ * Create or update schedule records for a workflow during deployment.
+ * Uses a transaction to ensure atomicity - all schedules are created or none are.
  */
 export async function createSchedulesForDeploy(
   workflowId: string,
   blocks: Record<string, BlockState>,
-  tx: DbOrTx,
+  _tx: DbOrTx,
   deploymentVersionId?: string
 ): Promise<ScheduleDeployResult> {
   const scheduleBlocks = findScheduleBlocks(blocks)
@@ -37,16 +37,16 @@ export async function createSchedulesForDeploy(
     return { success: true }
   }
 
-  let lastScheduleInfo: {
-    scheduleId: string
-    cronExpression?: string
-    nextRunAt?: Date
-    timezone?: string
-  } | null = null
+  // Phase 1: Validate ALL blocks before making any DB changes
+  const validatedBlocks: Array<{
+    blockId: string
+    cronExpression: string
+    nextRunAt: Date
+    timezone: string
+  }> = []
 
   for (const block of scheduleBlocks) {
     const blockId = block.id as string
-
     const validation = validateScheduleBlock(block)
     if (!validation.isValid) {
       return {
@@ -54,62 +54,112 @@ export async function createSchedulesForDeploy(
         error: validation.error,
       }
     }
-
-    const { cronExpression, nextRunAt, timezone } = validation
-
-    const scheduleId = crypto.randomUUID()
-    const now = new Date()
-
-    const values = {
-      id: scheduleId,
-      workflowId,
-      deploymentVersionId: deploymentVersionId || null,
+    validatedBlocks.push({
       blockId,
-      cronExpression: cronExpression!,
-      triggerType: 'schedule',
-      createdAt: now,
-      updatedAt: now,
-      nextRunAt: nextRunAt!,
-      timezone: timezone!,
-      status: 'active',
-      failedCount: 0,
-    }
-
-    const setValues = {
-      blockId,
-      cronExpression: cronExpression!,
-      ...(deploymentVersionId ? { deploymentVersionId } : {}),
-      updatedAt: now,
-      nextRunAt: nextRunAt!,
-      timezone: timezone!,
-      status: 'active',
-      failedCount: 0,
-    }
-
-    await tx
-      .insert(workflowSchedule)
-      .values(values)
-      .onConflictDoUpdate({
-        target: [
-          workflowSchedule.workflowId,
-          workflowSchedule.blockId,
-          workflowSchedule.deploymentVersionId,
-        ],
-        set: setValues,
-      })
-
-    logger.info(`Schedule created/updated for workflow ${workflowId}, block ${blockId}`, {
-      scheduleId: values.id,
-      cronExpression,
-      nextRunAt: nextRunAt?.toISOString(),
+      cronExpression: validation.cronExpression!,
+      nextRunAt: validation.nextRunAt!,
+      timezone: validation.timezone!,
     })
+  }
 
-    lastScheduleInfo = { scheduleId: values.id, cronExpression, nextRunAt, timezone }
+  // Phase 2: All validations passed - now do DB operations in a transaction
+  let lastScheduleInfo: {
+    scheduleId: string
+    cronExpression?: string
+    nextRunAt?: Date
+    timezone?: string
+  } | null = null
+
+  try {
+    await db.transaction(async (tx) => {
+      const currentBlockIds = new Set(validatedBlocks.map((b) => b.blockId))
+
+      const existingSchedules = await tx
+        .select({ id: workflowSchedule.id, blockId: workflowSchedule.blockId })
+        .from(workflowSchedule)
+        .where(
+          deploymentVersionId
+            ? and(
+                eq(workflowSchedule.workflowId, workflowId),
+                eq(workflowSchedule.deploymentVersionId, deploymentVersionId)
+              )
+            : eq(workflowSchedule.workflowId, workflowId)
+        )
+
+      const orphanedScheduleIds = existingSchedules
+        .filter((s) => s.blockId && !currentBlockIds.has(s.blockId))
+        .map((s) => s.id)
+
+      if (orphanedScheduleIds.length > 0) {
+        logger.info(
+          `Deleting ${orphanedScheduleIds.length} orphaned schedule(s) for workflow ${workflowId}`
+        )
+        await tx.delete(workflowSchedule).where(inArray(workflowSchedule.id, orphanedScheduleIds))
+      }
+
+      for (const validated of validatedBlocks) {
+        const { blockId, cronExpression, nextRunAt, timezone } = validated
+        const scheduleId = crypto.randomUUID()
+        const now = new Date()
+
+        const values = {
+          id: scheduleId,
+          workflowId,
+          deploymentVersionId: deploymentVersionId || null,
+          blockId,
+          cronExpression,
+          triggerType: 'schedule',
+          createdAt: now,
+          updatedAt: now,
+          nextRunAt,
+          timezone,
+          status: 'active',
+          failedCount: 0,
+        }
+
+        const setValues = {
+          blockId,
+          cronExpression,
+          ...(deploymentVersionId ? { deploymentVersionId } : {}),
+          updatedAt: now,
+          nextRunAt,
+          timezone,
+          status: 'active',
+          failedCount: 0,
+        }
+
+        await tx
+          .insert(workflowSchedule)
+          .values(values)
+          .onConflictDoUpdate({
+            target: [
+              workflowSchedule.workflowId,
+              workflowSchedule.blockId,
+              workflowSchedule.deploymentVersionId,
+            ],
+            set: setValues,
+          })
+
+        logger.info(`Schedule created/updated for workflow ${workflowId}, block ${blockId}`, {
+          scheduleId: values.id,
+          cronExpression,
+          nextRunAt: nextRunAt?.toISOString(),
+        })
+
+        lastScheduleInfo = { scheduleId: values.id, cronExpression, nextRunAt, timezone }
+      }
+    })
+  } catch (error) {
+    logger.error(`Failed to create schedules for workflow ${workflowId}`, error)
+    return {
+      success: false,
+      error: error instanceof Error ? error.message : 'Failed to create schedules',
+    }
   }
 
   return {
     success: true,
-    ...lastScheduleInfo,
+    ...(lastScheduleInfo ?? {}),
   }
 }
 
@@ -145,8 +195,25 @@ export async function cleanupDeploymentVersion(params: {
   workflow: Record<string, unknown>
   requestId: string
   deploymentVersionId: string
+  /**
+   * If true, skip external subscription cleanup (already done by saveTriggerWebhooksForDeploy).
+   * Only deletes DB records.
+   */
+  skipExternalCleanup?: boolean
 }): Promise<void> {
-  const { workflowId, workflow, requestId, deploymentVersionId } = params
-  await cleanupWebhooksForWorkflow(workflowId, workflow, requestId, deploymentVersionId)
+  const {
+    workflowId,
+    workflow,
+    requestId,
+    deploymentVersionId,
+    skipExternalCleanup = false,
+  } = params
+  await cleanupWebhooksForWorkflow(
+    workflowId,
+    workflow,
+    requestId,
+    deploymentVersionId,
+    skipExternalCleanup
+  )
   await deleteSchedulesForWorkflow(workflowId, db, deploymentVersionId)
 }
diff --git a/apps/sim/lib/workflows/schedules/validation.ts b/apps/sim/lib/workflows/schedules/validation.ts
index 2ad436983..2c8356c0b 100644
--- a/apps/sim/lib/workflows/schedules/validation.ts
+++ b/apps/sim/lib/workflows/schedules/validation.ts
@@ -98,9 +98,12 @@ function getMissingConfigError(scheduleType: string): string {
 
 /**
  * Find schedule blocks in a workflow's blocks
+ * Only returns enabled schedule blocks (disabled blocks are skipped)
  */
 export function findScheduleBlocks(blocks: Record<string, BlockState>): BlockState[] {
-  return Object.values(blocks).filter((block) => block.type === 'schedule')
+  return Object.values(blocks).filter(
+    (block) => block.type === 'schedule' && block.enabled !== false
+  )
 }
 
 /**
diff --git a/apps/sim/stores/workflows/workflow/store.ts b/apps/sim/stores/workflows/workflow/store.ts
index 9c40fffc4..3fc3438cf 100644
--- a/apps/sim/stores/workflows/workflow/store.ts
+++ b/apps/sim/stores/workflows/workflow/store.ts
@@ -4,7 +4,6 @@ import { create } from 'zustand'
 import { devtools } from 'zustand/middleware'
 import { DEFAULT_DUPLICATE_OFFSET } from '@/lib/workflows/autolayout/constants'
 import { getBlockOutputs } from '@/lib/workflows/blocks/block-outputs'
-import { TriggerUtils } from '@/lib/workflows/triggers/triggers'
 import { getBlock } from '@/blocks'
 import type { SubBlockConfig } from '@/blocks/types'
 import { normalizeName, RESERVED_BLOCK_NAMES } from '@/executor/constants'
@@ -1171,93 +1170,6 @@ export const useWorkflowStore = create<WorkflowStore>()(
         // Note: Socket.IO handles real-time sync automatically
       },
 
-      toggleBlockTriggerMode: (id: string) => {
-        const block = get().blocks[id]
-        if (!block) return
-
-        const newTriggerMode = !block.triggerMode
-
-        // When switching TO trigger mode, check if block is inside a subflow
-        if (newTriggerMode && TriggerUtils.isBlockInSubflow(id, get().blocks)) {
-          logger.warn('Cannot enable trigger mode for block inside loop or parallel subflow', {
-            blockId: id,
-            blockType: block.type,
-          })
-          return
-        }
-
-        // When switching TO trigger mode, remove all incoming connections
-        let filteredEdges = [...get().edges]
-        if (newTriggerMode) {
-          // Remove edges where this block is the target
-          filteredEdges = filteredEdges.filter((edge) => edge.target !== id)
-          logger.info(
-            `Removed ${get().edges.length - filteredEdges.length} incoming connections for trigger mode`,
-            {
-              blockId: id,
-              blockType: block.type,
-            }
-          )
-        }
-
-        const newState = {
-          blocks: {
-            ...get().blocks,
-            [id]: {
-              ...block,
-              triggerMode: newTriggerMode,
-            },
-          },
-          edges: filteredEdges,
-          loops: { ...get().loops },
-          parallels: { ...get().parallels },
-        }
-
-        set(newState)
-        get().updateLastSaved()
-
-        // Handle webhook enable/disable when toggling trigger mode
-        const handleWebhookToggle = async () => {
-          try {
-            const activeWorkflowId = useWorkflowRegistry.getState().activeWorkflowId
-            if (!activeWorkflowId) return
-
-            // Check if there's a webhook for this block
-            const response = await fetch(
-              `/api/webhooks?workflowId=${activeWorkflowId}&blockId=${id}`
-            )
-            if (response.ok) {
-              const data = await response.json()
-              if (data.webhooks && data.webhooks.length > 0) {
-                const webhook = data.webhooks[0].webhook
-
-                // Update webhook's isActive status based on trigger mode
-                const updateResponse = await fetch(`/api/webhooks/${webhook.id}`, {
-                  method: 'PATCH',
-                  headers: {
-                    'Content-Type': 'application/json',
-                  },
-                  body: JSON.stringify({
-                    isActive: newTriggerMode,
-                  }),
-                })
-
-                if (!updateResponse.ok) {
-                  logger.error('Failed to update webhook status')
-                }
-              }
-            }
-          } catch (error) {
-            logger.error('Error toggling webhook status:', error)
-          }
-        }
-
-        // Handle webhook toggle asynchronously
-        handleWebhookToggle()
-
-        // Note: Socket.IO handles real-time sync automatically
-      },
-
       // Parallel block methods implementation
       updateParallelCount: (parallelId: string, count: number) => {
         const block = get().blocks[parallelId]
diff --git a/apps/sim/stores/workflows/workflow/types.ts b/apps/sim/stores/workflows/workflow/types.ts
index c5d99e17a..e978999a8 100644
--- a/apps/sim/stores/workflows/workflow/types.ts
+++ b/apps/sim/stores/workflows/workflow/types.ts
@@ -241,7 +241,6 @@ export interface WorkflowActions {
   setNeedsRedeploymentFlag: (needsRedeployment: boolean) => void
   revertToDeployedState: (deployedState: WorkflowState) => void
   toggleBlockAdvancedMode: (id: string) => void
-  toggleBlockTriggerMode: (id: string) => void
   setDragStartPosition: (position: DragStartPosition | null) => void
   getDragStartPosition: () => DragStartPosition | null
   getWorkflowState: () => WorkflowState