diff --git a/apps/sim/app/api/webhooks/route.ts b/apps/sim/app/api/webhooks/route.ts
index 4c2d2735f..62ad40db0 100644
--- a/apps/sim/app/api/webhooks/route.ts
+++ b/apps/sim/app/api/webhooks/route.ts
@@ -581,6 +581,56 @@ export async function POST(request: NextRequest) {
     }
     // --- End RSS specific logic ---
 
+    if (savedWebhook && provider === 'grain') {
+      logger.info(`[${requestId}] Grain provider detected. Creating Grain webhook subscription.`)
+      try {
+        const grainHookId = await createGrainWebhookSubscription(
+          request,
+          {
+            id: savedWebhook.id,
+            path: savedWebhook.path,
+            providerConfig: savedWebhook.providerConfig,
+          },
+          requestId
+        )
+
+        if (grainHookId) {
+          // Update the webhook record with the external Grain hook ID
+          const updatedConfig = {
+            ...(savedWebhook.providerConfig as Record<string, any>),
+            externalId: grainHookId,
+          }
+          await db
+            .update(webhook)
+            .set({
+              providerConfig: updatedConfig,
+              updatedAt: new Date(),
+            })
+            .where(eq(webhook.id, savedWebhook.id))
+
+          savedWebhook.providerConfig = updatedConfig
+          logger.info(`[${requestId}] Successfully created Grain webhook`, {
+            grainHookId,
+            webhookId: savedWebhook.id,
+          })
+        }
+      } catch (err) {
+        logger.error(
+          `[${requestId}] Error creating Grain webhook subscription, rolling back webhook`,
+          err
+        )
+        await db.delete(webhook).where(eq(webhook.id, savedWebhook.id))
+        return NextResponse.json(
+          {
+            error: 'Failed to create webhook in Grain',
+            details: err instanceof Error ? err.message : 'Unknown error',
+          },
+          { status: 500 }
+        )
+      }
+    }
+    // --- End Grain specific logic ---
+
     const status = targetWebhookId ? 200 : 201
     return NextResponse.json({ webhook: savedWebhook }, { status })
   } catch (error: any) {
@@ -947,3 +997,103 @@ async function createWebflowWebhookSubscription(
     throw error
   }
 }
+
+// Helper function to create the webhook subscription in Grain
+async function createGrainWebhookSubscription(
+  request: NextRequest,
+  webhookData: any,
+  requestId: string
+): Promise<string | undefined> {
+  try {
+    const { path, providerConfig } = webhookData
+    const { apiKey, includeHighlights, includeParticipants, includeAiSummary } =
+      providerConfig || {}
+
+    if (!apiKey) {
+      logger.warn(`[${requestId}] Missing apiKey for Grain webhook creation.`, {
+        webhookId: webhookData.id,
+      })
+      throw new Error(
+        'Grain API Key is required. Please provide your Grain Personal Access Token in the trigger configuration.'
+      )
+    }
+
+    const notificationUrl = `${getBaseUrl()}/api/webhooks/trigger/${path}`
+
+    const grainApiUrl = 'https://api.grain.com/_/public-api/v2/hooks/create'
+
+    const requestBody: Record<string, any> = {
+      hook_url: notificationUrl,
+    }
+
+    // Build include object based on configuration
+    const include: Record<string, boolean> = {}
+    if (includeHighlights) {
+      include.highlights = true
+    }
+    if (includeParticipants) {
+      include.participants = true
+    }
+    if (includeAiSummary) {
+      include.ai_summary = true
+    }
+    if (Object.keys(include).length > 0) {
+      requestBody.include = include
+    }
+
+    const grainResponse = await fetch(grainApiUrl, {
+      method: 'POST',
+      headers: {
+        Authorization: `Bearer ${apiKey}`,
+        'Content-Type': 'application/json',
+        'Public-Api-Version': '2025-10-31',
+      },
+      body: JSON.stringify(requestBody),
+    })
+
+    const responseBody = await grainResponse.json()
+
+    if (!grainResponse.ok || responseBody.error) {
+      const errorMessage =
+        responseBody.error?.message ||
+        responseBody.error ||
+        responseBody.message ||
+        'Unknown Grain API error'
+      logger.error(
+        `[${requestId}] Failed to create webhook in Grain for webhook ${webhookData.id}. Status: ${grainResponse.status}`,
+        { message: errorMessage, response: responseBody }
+      )
+
+      let userFriendlyMessage = 'Failed to create webhook subscription in Grain'
+      if (grainResponse.status === 401) {
+        userFriendlyMessage =
+          'Invalid Grain API Key. Please verify your Personal Access Token is correct.'
+      } else if (grainResponse.status === 403) {
+        userFriendlyMessage =
+          'Access denied. Please ensure your Grain API Key has appropriate permissions.'
+      } else if (errorMessage && errorMessage !== 'Unknown Grain API error') {
+        userFriendlyMessage = `Grain error: ${errorMessage}`
+      }
+
+      throw new Error(userFriendlyMessage)
+    }
+
+    logger.info(
+      `[${requestId}] Successfully created webhook in Grain for webhook ${webhookData.id}.`,
+      {
+        grainWebhookId: responseBody.id,
+      }
+    )
+
+    return responseBody.id
+  } catch (error: any) {
+    logger.error(
+      `[${requestId}] Exception during Grain webhook creation for webhook ${webhookData.id}.`,
+      {
+        message: error.message,
+        stack: error.stack,
+      }
+    )
+    throw error
+  }
+}
diff --git a/apps/sim/lib/webhooks/provider-subscriptions.ts b/apps/sim/lib/webhooks/provider-subscriptions.ts
index 2772b9c8b..7b4566935 100644
--- a/apps/sim/lib/webhooks/provider-subscriptions.ts
+++ b/apps/sim/lib/webhooks/provider-subscriptions.ts
@@ -8,6 +8,7 @@ const telegramLogger = createLogger('TelegramWebhook')
 const airtableLogger = createLogger('AirtableWebhook')
 const typeformLogger = createLogger('TypeformWebhook')
 const calendlyLogger = createLogger('CalendlyWebhook')
+const grainLogger = createLogger('GrainWebhook')
 
 function getProviderConfig(webhook: any): Record<string, any> {
   return (webhook.providerConfig as Record<string, any>) || {}
@@ -661,9 +662,58 @@ export async function deleteCalendlyWebhook(webhook: any, requestId: string): Pr
   }
 }
 
+/**
+ * Delete a Grain webhook
+ * Don't fail webhook deletion if cleanup fails
+ */
+export async function deleteGrainWebhook(webhook: any, requestId: string): Promise<void> {
+  try {
+    const config = getProviderConfig(webhook)
+    const apiKey = config.apiKey as string | undefined
+    const externalId = config.externalId as string | undefined
+
+    if (!apiKey) {
+      grainLogger.warn(
+        `[${requestId}] Missing apiKey for Grain webhook deletion ${webhook.id}, skipping cleanup`
+      )
+      return
+    }
+
+    if (!externalId) {
+      grainLogger.warn(
+        `[${requestId}] Missing externalId for Grain webhook deletion ${webhook.id}, skipping cleanup`
+      )
+      return
+    }
+
+    const grainApiUrl = `https://api.grain.com/_/public-api/v2/hooks/${externalId}`
+
+    const grainResponse = await fetch(grainApiUrl, {
+      method: 'DELETE',
+      headers: {
+        Authorization: `Bearer ${apiKey}`,
+        'Content-Type': 'application/json',
+        'Public-Api-Version': '2025-10-31',
+      },
+    })
+
+    if (!grainResponse.ok && grainResponse.status !== 404) {
+      const responseBody = await grainResponse.json().catch(() => ({}))
+      grainLogger.warn(
+        `[${requestId}] Failed to delete Grain webhook (non-fatal): ${grainResponse.status}`,
+        { response: responseBody }
+      )
+    } else {
+      grainLogger.info(`[${requestId}] Successfully deleted Grain webhook ${externalId}`)
+    }
+  } catch (error) {
+    grainLogger.warn(`[${requestId}] Error deleting Grain webhook (non-fatal)`, error)
+  }
+}
+
 /**
  * Clean up external webhook subscriptions for a webhook
- * Handles Airtable, Teams, Telegram, Typeform, and Calendly cleanup
+ * Handles Airtable, Teams, Telegram, Typeform, Calendly, and Grain cleanup
  * Don't fail deletion if cleanup fails
  */
 export async function cleanupExternalWebhook(
@@ -681,5 +731,7 @@ export async function cleanupExternalWebhook(
     await deleteTypeformWebhook(webhook, requestId)
   } else if (webhook.provider === 'calendly') {
     await deleteCalendlyWebhook(webhook, requestId)
+  } else if (webhook.provider === 'grain') {
+    await deleteGrainWebhook(webhook, requestId)
   }
 }
diff --git a/apps/sim/triggers/grain/highlight_created.ts b/apps/sim/triggers/grain/highlight_created.ts
index b59338ac7..12ab02d26 100644
--- a/apps/sim/triggers/grain/highlight_created.ts
+++ b/apps/sim/triggers/grain/highlight_created.ts
@@ -12,13 +12,13 @@ export const grainHighlightCreatedTrigger: TriggerConfig = {
 
   subBlocks: [
     {
-      id: 'webhookUrlDisplay',
-      title: 'Webhook URL',
+      id: 'apiKey',
+      title: 'API Key',
       type: 'short-input',
-      readOnly: true,
-      showCopyButton: true,
-      useWebhookUrl: true,
-      placeholder: 'Webhook URL will be generated',
+      placeholder: 'Enter your Grain API key (Personal Access Token)',
+      description: 'Required to create the webhook in Grain.',
+      password: true,
+      required: true,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
@@ -26,13 +26,35 @@ export const grainHighlightCreatedTrigger: TriggerConfig = {
       },
     },
     {
-      id: 'webhookSecret',
-      title: 'Webhook Secret',
-      type: 'short-input',
-      placeholder: 'Enter a strong secret',
-      description: 'Validates that webhook deliveries originate from Grain.',
-      password: true,
-      required: false,
+      id: 'includeHighlights',
+      title: 'Include Highlights',
+      type: 'switch',
+      description: 'Include highlights/clips in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_highlight_created',
+      },
+    },
+    {
+      id: 'includeParticipants',
+      title: 'Include Participants',
+      type: 'switch',
+      description: 'Include participant list in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_highlight_created',
+      },
+    },
+    {
+      id: 'includeAiSummary',
+      title: 'Include AI Summary',
+      type: 'switch',
+      description: 'Include AI-generated summary in webhook payload.',
+      defaultValue: false,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
diff --git a/apps/sim/triggers/grain/highlight_updated.ts b/apps/sim/triggers/grain/highlight_updated.ts
index e3c7f7378..cf8e77158 100644
--- a/apps/sim/triggers/grain/highlight_updated.ts
+++ b/apps/sim/triggers/grain/highlight_updated.ts
@@ -12,13 +12,13 @@ export const grainHighlightUpdatedTrigger: TriggerConfig = {
 
   subBlocks: [
     {
-      id: 'webhookUrlDisplay',
-      title: 'Webhook URL',
+      id: 'apiKey',
+      title: 'API Key',
       type: 'short-input',
-      readOnly: true,
-      showCopyButton: true,
-      useWebhookUrl: true,
-      placeholder: 'Webhook URL will be generated',
+      placeholder: 'Enter your Grain API key (Personal Access Token)',
+      description: 'Required to create the webhook in Grain.',
+      password: true,
+      required: true,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
@@ -26,13 +26,35 @@ export const grainHighlightUpdatedTrigger: TriggerConfig = {
       },
     },
     {
-      id: 'webhookSecret',
-      title: 'Webhook Secret',
-      type: 'short-input',
-      placeholder: 'Enter a strong secret',
-      description: 'Validates that webhook deliveries originate from Grain.',
-      password: true,
-      required: false,
+      id: 'includeHighlights',
+      title: 'Include Highlights',
+      type: 'switch',
+      description: 'Include highlights/clips in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_highlight_updated',
+      },
+    },
+    {
+      id: 'includeParticipants',
+      title: 'Include Participants',
+      type: 'switch',
+      description: 'Include participant list in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_highlight_updated',
+      },
+    },
+    {
+      id: 'includeAiSummary',
+      title: 'Include AI Summary',
+      type: 'switch',
+      description: 'Include AI-generated summary in webhook payload.',
+      defaultValue: false,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
diff --git a/apps/sim/triggers/grain/recording_created.ts b/apps/sim/triggers/grain/recording_created.ts
index 6fe67aa5e..4085f0c75 100644
--- a/apps/sim/triggers/grain/recording_created.ts
+++ b/apps/sim/triggers/grain/recording_created.ts
@@ -12,13 +12,13 @@ export const grainRecordingCreatedTrigger: TriggerConfig = {
 
   subBlocks: [
     {
-      id: 'webhookUrlDisplay',
-      title: 'Webhook URL',
+      id: 'apiKey',
+      title: 'API Key',
       type: 'short-input',
-      readOnly: true,
-      showCopyButton: true,
-      useWebhookUrl: true,
-      placeholder: 'Webhook URL will be generated',
+      placeholder: 'Enter your Grain API key (Personal Access Token)',
+      description: 'Required to create the webhook in Grain.',
+      password: true,
+      required: true,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
@@ -26,13 +26,35 @@ export const grainRecordingCreatedTrigger: TriggerConfig = {
       },
     },
     {
-      id: 'webhookSecret',
-      title: 'Webhook Secret',
-      type: 'short-input',
-      placeholder: 'Enter a strong secret',
-      description: 'Validates that webhook deliveries originate from Grain.',
-      password: true,
-      required: false,
+      id: 'includeHighlights',
+      title: 'Include Highlights',
+      type: 'switch',
+      description: 'Include highlights/clips in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_recording_created',
+      },
+    },
+    {
+      id: 'includeParticipants',
+      title: 'Include Participants',
+      type: 'switch',
+      description: 'Include participant list in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_recording_created',
+      },
+    },
+    {
+      id: 'includeAiSummary',
+      title: 'Include AI Summary',
+      type: 'switch',
+      description: 'Include AI-generated summary in webhook payload.',
+      defaultValue: false,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
diff --git a/apps/sim/triggers/grain/recording_updated.ts b/apps/sim/triggers/grain/recording_updated.ts
index d541fe132..799424f2e 100644
--- a/apps/sim/triggers/grain/recording_updated.ts
+++ b/apps/sim/triggers/grain/recording_updated.ts
@@ -12,13 +12,13 @@ export const grainRecordingUpdatedTrigger: TriggerConfig = {
 
   subBlocks: [
     {
-      id: 'webhookUrlDisplay',
-      title: 'Webhook URL',
+      id: 'apiKey',
+      title: 'API Key',
       type: 'short-input',
-      readOnly: true,
-      showCopyButton: true,
-      useWebhookUrl: true,
-      placeholder: 'Webhook URL will be generated',
+      placeholder: 'Enter your Grain API key (Personal Access Token)',
+      description: 'Required to create the webhook in Grain.',
+      password: true,
+      required: true,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
@@ -26,13 +26,35 @@ export const grainRecordingUpdatedTrigger: TriggerConfig = {
       },
     },
     {
-      id: 'webhookSecret',
-      title: 'Webhook Secret',
-      type: 'short-input',
-      placeholder: 'Enter a strong secret',
-      description: 'Validates that webhook deliveries originate from Grain.',
-      password: true,
-      required: false,
+      id: 'includeHighlights',
+      title: 'Include Highlights',
+      type: 'switch',
+      description: 'Include highlights/clips in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_recording_updated',
+      },
+    },
+    {
+      id: 'includeParticipants',
+      title: 'Include Participants',
+      type: 'switch',
+      description: 'Include participant list in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_recording_updated',
+      },
+    },
+    {
+      id: 'includeAiSummary',
+      title: 'Include AI Summary',
+      type: 'switch',
+      description: 'Include AI-generated summary in webhook payload.',
+      defaultValue: false,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
diff --git a/apps/sim/triggers/grain/story_created.ts b/apps/sim/triggers/grain/story_created.ts
index 8e43051be..e9b7306b8 100644
--- a/apps/sim/triggers/grain/story_created.ts
+++ b/apps/sim/triggers/grain/story_created.ts
@@ -12,13 +12,13 @@ export const grainStoryCreatedTrigger: TriggerConfig = {
 
   subBlocks: [
     {
-      id: 'webhookUrlDisplay',
-      title: 'Webhook URL',
+      id: 'apiKey',
+      title: 'API Key',
       type: 'short-input',
-      readOnly: true,
-      showCopyButton: true,
-      useWebhookUrl: true,
-      placeholder: 'Webhook URL will be generated',
+      placeholder: 'Enter your Grain API key (Personal Access Token)',
+      description: 'Required to create the webhook in Grain.',
+      password: true,
+      required: true,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
@@ -26,13 +26,35 @@ export const grainStoryCreatedTrigger: TriggerConfig = {
       },
     },
     {
-      id: 'webhookSecret',
-      title: 'Webhook Secret',
-      type: 'short-input',
-      placeholder: 'Enter a strong secret',
-      description: 'Validates that webhook deliveries originate from Grain.',
-      password: true,
-      required: false,
+      id: 'includeHighlights',
+      title: 'Include Highlights',
+      type: 'switch',
+      description: 'Include highlights/clips in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_story_created',
+      },
+    },
+    {
+      id: 'includeParticipants',
+      title: 'Include Participants',
+      type: 'switch',
+      description: 'Include participant list in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_story_created',
+      },
+    },
+    {
+      id: 'includeAiSummary',
+      title: 'Include AI Summary',
+      type: 'switch',
+      description: 'Include AI-generated summary in webhook payload.',
+      defaultValue: false,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
diff --git a/apps/sim/triggers/grain/utils.ts b/apps/sim/triggers/grain/utils.ts
index c9fa593ec..3c77dd026 100644
--- a/apps/sim/triggers/grain/utils.ts
+++ b/apps/sim/triggers/grain/utils.ts
@@ -17,19 +17,17 @@ export const grainTriggerOptions = [
  */
 export function grainSetupInstructions(eventType: string): string {
   const instructions = [
-    '<strong>Note:</strong> You need admin permissions in your Grain workspace to create webhooks.',
-    'In Grain, navigate to <strong>Settings > Integrations > Webhooks</strong>.',
-    'Click <strong>"Create webhook"</strong> or <strong>"Add webhook"</strong>.',
-    'Paste the <strong>Webhook URL</strong> from above into the URL field.',
-    'Optionally, enter the <strong>Webhook Secret</strong> from above for signature validation.',
-    `Select the event types this webhook should listen to. For this trigger, select <strong>${eventType}</strong>.`,
-    'Click <strong>"Save"</strong> to activate the webhook.',
+    'Enter your Grain API Key (Personal Access Token) above.',
+    'You can find or create your API key in Grain at <strong>Settings > Integrations > API</strong>.',
+    'Optionally configure filters to narrow which recordings trigger the webhook.',
+    `Click <strong>"Save Configuration"</strong> to automatically create the webhook in Grain for <strong>${eventType}</strong> events.`,
+    'The webhook will be automatically deleted when you remove this trigger.',
   ]
 
   return instructions
     .map(
       (instruction, index) =>
-        `<div class="mb-3">${index === 0 ? instruction : `<strong>${index}.</strong> ${instruction}`}</div>`
+        `<div class="mb-3"><strong>${index + 1}.</strong> ${instruction}</div>`
     )
     .join('')
 }
diff --git a/apps/sim/triggers/grain/webhook.ts b/apps/sim/triggers/grain/webhook.ts
index 872a2ea93..88f968682 100644
--- a/apps/sim/triggers/grain/webhook.ts
+++ b/apps/sim/triggers/grain/webhook.ts
@@ -21,13 +21,13 @@ export const grainWebhookTrigger: TriggerConfig = {
       required: true,
     },
     {
-      id: 'webhookUrlDisplay',
-      title: 'Webhook URL',
+      id: 'apiKey',
+      title: 'API Key',
       type: 'short-input',
-      readOnly: true,
-      showCopyButton: true,
-      useWebhookUrl: true,
-      placeholder: 'Webhook URL will be generated',
+      placeholder: 'Enter your Grain API key (Personal Access Token)',
+      description: 'Required to create the webhook in Grain.',
+      password: true,
+      required: true,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',
@@ -35,13 +35,35 @@ export const grainWebhookTrigger: TriggerConfig = {
       },
     },
     {
-      id: 'webhookSecret',
-      title: 'Webhook Secret',
-      type: 'short-input',
-      placeholder: 'Enter a strong secret',
-      description: 'Validates that webhook deliveries originate from Grain.',
-      password: true,
-      required: false,
+      id: 'includeHighlights',
+      title: 'Include Highlights',
+      type: 'switch',
+      description: 'Include highlights/clips in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_webhook',
+      },
+    },
+    {
+      id: 'includeParticipants',
+      title: 'Include Participants',
+      type: 'switch',
+      description: 'Include participant list in webhook payload.',
+      defaultValue: false,
+      mode: 'trigger',
+      condition: {
+        field: 'selectedTriggerId',
+        value: 'grain_webhook',
+      },
+    },
+    {
+      id: 'includeAiSummary',
+      title: 'Include AI Summary',
+      type: 'switch',
+      description: 'Include AI-generated summary in webhook payload.',
+      defaultValue: false,
       mode: 'trigger',
       condition: {
         field: 'selectedTriggerId',