diff --git a/apps/sim/app/api/files/parse/route.ts b/apps/sim/app/api/files/parse/route.ts
index 50dc55572..89d5867bf 100644
--- a/apps/sim/app/api/files/parse/route.ts
+++ b/apps/sim/app/api/files/parse/route.ts
@@ -7,6 +7,7 @@ import binaryExtensionsList from 'binary-extensions'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkHybridAuth } from '@/lib/auth/hybrid'
 import { secureFetchWithPinnedIP, validateUrlWithDNS } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { isSupportedFileType, parseFile } from '@/lib/file-parsers'
 import { isUsingCloudStorage, type StorageContext, StorageService } from '@/lib/uploads'
 import { uploadExecutionFile } from '@/lib/uploads/contexts/execution'
@@ -367,7 +368,7 @@ async function handleExternalUrl(
       throw new Error(`File too large: ${buffer.length} bytes (max: ${MAX_DOWNLOAD_SIZE_BYTES})`)
     }
 
-    logger.info(`Downloaded file from URL: ${url}, size: ${buffer.length} bytes`)
+    logger.info(`Downloaded file from URL: ${sanitizeUrlForLog(url)}, size: ${buffer.length} bytes`)
 
     let userFile: UserFile | undefined
     const mimeType = response.headers.get('content-type') || getMimeTypeFromExtension(extension)
@@ -420,7 +421,7 @@ async function handleExternalUrl(
 
     return parseResult
   } catch (error) {
-    logger.error(`Error handling external URL ${url}:`, error)
+    logger.error(`Error handling external URL ${sanitizeUrlForLog(url)}:`, error)
     return {
       success: false,
       error: `Error fetching URL: ${(error as Error).message}`,
diff --git a/apps/sim/app/api/tools/discord/send-message/route.ts b/apps/sim/app/api/tools/discord/send-message/route.ts
index c597ae467..f5bf7d27f 100644
--- a/apps/sim/app/api/tools/discord/send-message/route.ts
+++ b/apps/sim/app/api/tools/discord/send-message/route.ts
@@ -102,6 +102,12 @@ export async function POST(request: NextRequest) {
     logger.info(`[${requestId}] Processing ${validatedData.files.length} file(s)`)
 
     const userFiles = processFilesToUserFiles(validatedData.files, requestId, logger)
+    const filesOutput: Array<{
+      name: string
+      mimeType: string
+      data: string
+      size: number
+    }> = []
 
     if (userFiles.length === 0) {
       logger.warn(`[${requestId}] No valid files to upload, falling back to text-only`)
@@ -138,6 +144,12 @@ export async function POST(request: NextRequest) {
       logger.info(`[${requestId}] Downloading file ${i}: ${userFile.name}`)
 
       const buffer = await downloadFileFromStorage(userFile, requestId, logger)
+      filesOutput.push({
+        name: userFile.name,
+        mimeType: userFile.type || 'application/octet-stream',
+        data: buffer.toString('base64'),
+        size: buffer.length,
+      })
 
       const blob = new Blob([new Uint8Array(buffer)], { type: userFile.type })
       formData.append(`files[${i}]`, blob, userFile.name)
@@ -174,6 +186,7 @@ export async function POST(request: NextRequest) {
         message: data.content,
         data: data,
         fileCount: userFiles.length,
+        files: filesOutput,
       },
     })
   } catch (error) {
diff --git a/apps/sim/app/api/tools/image/route.ts b/apps/sim/app/api/tools/image/route.ts
index 633e61068..96dc58cad 100644
--- a/apps/sim/app/api/tools/image/route.ts
+++ b/apps/sim/app/api/tools/image/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateImageUrl } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { generateRequestId } from '@/lib/core/utils/request'
 
 const logger = createLogger('ImageProxyAPI')
@@ -29,13 +30,13 @@ export async function GET(request: NextRequest) {
   const urlValidation = validateImageUrl(imageUrl)
   if (!urlValidation.isValid) {
     logger.warn(`[${requestId}] Blocked image proxy request`, {
-      url: imageUrl.substring(0, 100),
+      url: sanitizeUrlForLog(imageUrl),
       error: urlValidation.error,
     })
     return new NextResponse(urlValidation.error || 'Invalid image URL', { status: 403 })
   }
 
-  logger.info(`[${requestId}] Proxying image request for: ${imageUrl}`)
+  logger.info(`[${requestId}] Proxying image request for: ${sanitizeUrlForLog(imageUrl)}`)
 
   try {
     const imageResponse = await fetch(imageUrl, {
diff --git a/apps/sim/app/api/tools/jira/add-attachment/route.ts b/apps/sim/app/api/tools/jira/add-attachment/route.ts
new file mode 100644
index 000000000..52b36b24a
--- /dev/null
+++ b/apps/sim/app/api/tools/jira/add-attachment/route.ts
@@ -0,0 +1,121 @@
+import { createLogger } from '@sim/logger'
+import { type NextRequest, NextResponse } from 'next/server'
+import { z } from 'zod'
+import { checkInternalAuth } from '@/lib/auth/hybrid'
+import { RawFileInputArraySchema } from '@/lib/uploads/utils/file-schemas'
+import { processFilesToUserFiles } from '@/lib/uploads/utils/file-utils'
+import { downloadFileFromStorage } from '@/lib/uploads/utils/file-utils.server'
+import { getJiraCloudId } from '@/tools/jira/utils'
+
+const logger = createLogger('JiraAddAttachmentAPI')
+
+export const dynamic = 'force-dynamic'
+
+const JiraAddAttachmentSchema = z.object({
+  accessToken: z.string().min(1, 'Access token is required'),
+  domain: z.string().min(1, 'Domain is required'),
+  issueKey: z.string().min(1, 'Issue key is required'),
+  files: RawFileInputArraySchema,
+  cloudId: z.string().optional().nullable(),
+})
+
+export async function POST(request: NextRequest) {
+  const requestId = `jira-attach-${Date.now()}`
+
+  try {
+    const authResult = await checkInternalAuth(request, { requireWorkflowId: false })
+    if (!authResult.success) {
+      return NextResponse.json(
+        { success: false, error: authResult.error || 'Unauthorized' },
+        { status: 401 }
+      )
+    }
+
+    const body = await request.json()
+    const validatedData = JiraAddAttachmentSchema.parse(body)
+
+    const userFiles = processFilesToUserFiles(validatedData.files, requestId, logger)
+    if (userFiles.length === 0) {
+      return NextResponse.json(
+        { success: false, error: 'No valid files provided for upload' },
+        { status: 400 }
+      )
+    }
+
+    const cloudId =
+      validatedData.cloudId ||
+      (await getJiraCloudId(validatedData.domain, validatedData.accessToken))
+
+    const formData = new FormData()
+    const filesOutput: Array<{ name: string; mimeType: string; data: string; size: number }> = []
+
+    for (const file of userFiles) {
+      const buffer = await downloadFileFromStorage(file, requestId, logger)
+      filesOutput.push({
+        name: file.name,
+        mimeType: file.type || 'application/octet-stream',
+        data: buffer.toString('base64'),
+        size: buffer.length,
+      })
+      const blob = new Blob([new Uint8Array(buffer)], {
+        type: file.type || 'application/octet-stream',
+      })
+      formData.append('file', blob, file.name)
+    }
+
+    const url = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${validatedData.issueKey}/attachments`
+
+    const response = await fetch(url, {
+      method: 'POST',
+      headers: {
+        Authorization: `Bearer ${validatedData.accessToken}`,
+        'X-Atlassian-Token': 'no-check',
+      },
+      body: formData,
+    })
+
+    if (!response.ok) {
+      const errorText = await response.text()
+      logger.error(`[${requestId}] Jira attachment upload failed`, {
+        status: response.status,
+        statusText: response.statusText,
+        error: errorText,
+      })
+      return NextResponse.json(
+        {
+          success: false,
+          error: `Failed to upload attachments: ${response.statusText}`,
+        },
+        { status: response.status }
+      )
+    }
+
+    const attachments = await response.json()
+    const attachmentIds = Array.isArray(attachments)
+      ? attachments.map((attachment) => attachment.id).filter(Boolean)
+      : []
+
+    return NextResponse.json({
+      success: true,
+      output: {
+        ts: new Date().toISOString(),
+        issueKey: validatedData.issueKey,
+        attachmentIds,
+        files: filesOutput,
+      },
+    })
+  } catch (error) {
+    if (error instanceof z.ZodError) {
+      return NextResponse.json(
+        { success: false, error: 'Invalid request data', details: error.errors },
+        { status: 400 }
+      )
+    }
+
+    logger.error(`[${requestId}] Jira attachment upload error`, error)
+    return NextResponse.json(
+      { success: false, error: error instanceof Error ? error.message : 'Internal server error' },
+      { status: 500 }
+    )
+  }
+}
diff --git a/apps/sim/app/api/tools/jsm/queues/route.ts b/apps/sim/app/api/tools/jsm/queues/route.ts
index 2921008ef..f7dc234f3 100644
--- a/apps/sim/app/api/tools/jsm/queues/route.ts
+++ b/apps/sim/app/api/tools/jsm/queues/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateAlphanumericId, validateJiraCloudId } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -62,7 +63,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/servicedesk/${serviceDeskId}/queue${params.toString() ? `?${params.toString()}` : ''}`
 
-    logger.info('Fetching queues from:', url)
+    logger.info('Fetching queues from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/jsm/request/route.ts b/apps/sim/app/api/tools/jsm/request/route.ts
index 92e5e9f4c..213786706 100644
--- a/apps/sim/app/api/tools/jsm/request/route.ts
+++ b/apps/sim/app/api/tools/jsm/request/route.ts
@@ -6,6 +6,7 @@ import {
   validateJiraCloudId,
   validateJiraIssueKey,
 } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -66,7 +67,7 @@ export async function POST(request: NextRequest) {
       }
       const url = `${baseUrl}/request`
 
-      logger.info('Creating request at:', url)
+      logger.info('Creating request at:', sanitizeUrlForLog(url))
 
       const requestBody: Record<string, unknown> = {
         serviceDeskId,
@@ -128,7 +129,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/request/${issueIdOrKey}`
 
-    logger.info('Fetching request from:', url)
+    logger.info('Fetching request from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/jsm/requests/route.ts b/apps/sim/app/api/tools/jsm/requests/route.ts
index f2f0dc0e7..fff27fe82 100644
--- a/apps/sim/app/api/tools/jsm/requests/route.ts
+++ b/apps/sim/app/api/tools/jsm/requests/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateAlphanumericId, validateJiraCloudId } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -68,7 +69,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/request${params.toString() ? `?${params.toString()}` : ''}`
 
-    logger.info('Fetching requests from:', url)
+    logger.info('Fetching requests from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/jsm/requesttypes/route.ts b/apps/sim/app/api/tools/jsm/requesttypes/route.ts
index 8591f116b..fa7f826ae 100644
--- a/apps/sim/app/api/tools/jsm/requesttypes/route.ts
+++ b/apps/sim/app/api/tools/jsm/requesttypes/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateAlphanumericId, validateJiraCloudId } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -53,7 +54,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/servicedesk/${serviceDeskId}/requesttype${params.toString() ? `?${params.toString()}` : ''}`
 
-    logger.info('Fetching request types from:', url)
+    logger.info('Fetching request types from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/jsm/servicedesks/route.ts b/apps/sim/app/api/tools/jsm/servicedesks/route.ts
index 607508a61..875280575 100644
--- a/apps/sim/app/api/tools/jsm/servicedesks/route.ts
+++ b/apps/sim/app/api/tools/jsm/servicedesks/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateJiraCloudId } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -43,7 +44,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/servicedesk${params.toString() ? `?${params.toString()}` : ''}`
 
-    logger.info('Fetching service desks from:', url)
+    logger.info('Fetching service desks from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/jsm/sla/route.ts b/apps/sim/app/api/tools/jsm/sla/route.ts
index dc414ac83..ea5b88559 100644
--- a/apps/sim/app/api/tools/jsm/sla/route.ts
+++ b/apps/sim/app/api/tools/jsm/sla/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateJiraCloudId, validateJiraIssueKey } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -53,7 +54,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/request/${issueIdOrKey}/sla${params.toString() ? `?${params.toString()}` : ''}`
 
-    logger.info('Fetching SLA info from:', url)
+    logger.info('Fetching SLA info from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/jsm/transition/route.ts b/apps/sim/app/api/tools/jsm/transition/route.ts
index 45a9e3a5c..5f1065b6f 100644
--- a/apps/sim/app/api/tools/jsm/transition/route.ts
+++ b/apps/sim/app/api/tools/jsm/transition/route.ts
@@ -6,6 +6,7 @@ import {
   validateJiraCloudId,
   validateJiraIssueKey,
 } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -69,7 +70,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/request/${issueIdOrKey}/transition`
 
-    logger.info('Transitioning request at:', url)
+    logger.info('Transitioning request at:', sanitizeUrlForLog(url))
 
     const body: Record<string, unknown> = {
       id: transitionId,
diff --git a/apps/sim/app/api/tools/jsm/transitions/route.ts b/apps/sim/app/api/tools/jsm/transitions/route.ts
index 5d5f2e260..c80a27ab8 100644
--- a/apps/sim/app/api/tools/jsm/transitions/route.ts
+++ b/apps/sim/app/api/tools/jsm/transitions/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { validateJiraCloudId, validateJiraIssueKey } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { getJiraCloudId, getJsmApiBaseUrl, getJsmHeaders } from '@/tools/jsm/utils'
 
 export const dynamic = 'force-dynamic'
@@ -49,7 +50,7 @@ export async function POST(request: NextRequest) {
 
     const url = `${baseUrl}/request/${issueIdOrKey}/transition`
 
-    logger.info('Fetching transitions from:', url)
+    logger.info('Fetching transitions from:', sanitizeUrlForLog(url))
 
     const response = await fetch(url, {
       method: 'GET',
diff --git a/apps/sim/app/api/tools/microsoft_teams/write_channel/route.ts b/apps/sim/app/api/tools/microsoft_teams/write_channel/route.ts
index bcfcb0b40..a3789ca99 100644
--- a/apps/sim/app/api/tools/microsoft_teams/write_channel/route.ts
+++ b/apps/sim/app/api/tools/microsoft_teams/write_channel/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { RawFileInputArraySchema } from '@/lib/uploads/utils/file-schemas'
 import { processFilesToUserFiles } from '@/lib/uploads/utils/file-utils'
@@ -55,6 +56,12 @@ export async function POST(request: NextRequest) {
     })
 
     const attachments: any[] = []
+    const filesOutput: Array<{
+      name: string
+      mimeType: string
+      data: string
+      size: number
+    }> = []
     if (validatedData.files && validatedData.files.length > 0) {
       const rawFiles = validatedData.files
       logger.info(`[${requestId}] Processing ${rawFiles.length} file(s) for upload to OneDrive`)
@@ -66,13 +73,19 @@ export async function POST(request: NextRequest) {
           logger.info(`[${requestId}] Uploading file to Teams: ${file.name} (${file.size} bytes)`)
 
           const buffer = await downloadFileFromStorage(file, requestId, logger)
+          filesOutput.push({
+            name: file.name,
+            mimeType: file.type || 'application/octet-stream',
+            data: buffer.toString('base64'),
+            size: buffer.length,
+          })
 
           const uploadUrl =
             'https://graph.microsoft.com/v1.0/me/drive/root:/TeamsAttachments/' +
             encodeURIComponent(file.name) +
             ':/content'
 
-          logger.info(`[${requestId}] Uploading to Teams: ${uploadUrl}`)
+          logger.info(`[${requestId}] Uploading to Teams: ${sanitizeUrlForLog(uploadUrl)}`)
 
           const uploadResponse = await fetch(uploadUrl, {
             method: 'PUT',
@@ -238,6 +251,7 @@ export async function POST(request: NextRequest) {
           url: responseData.webUrl || '',
           attachmentCount: attachments.length,
         },
+        files: filesOutput,
       },
     })
   } catch (error) {
diff --git a/apps/sim/app/api/tools/microsoft_teams/write_chat/route.ts b/apps/sim/app/api/tools/microsoft_teams/write_chat/route.ts
index 6b940e17c..1137cc9a1 100644
--- a/apps/sim/app/api/tools/microsoft_teams/write_chat/route.ts
+++ b/apps/sim/app/api/tools/microsoft_teams/write_chat/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { RawFileInputArraySchema } from '@/lib/uploads/utils/file-schemas'
 import { processFilesToUserFiles } from '@/lib/uploads/utils/file-utils'
@@ -53,6 +54,12 @@ export async function POST(request: NextRequest) {
     })
 
     const attachments: any[] = []
+    const filesOutput: Array<{
+      name: string
+      mimeType: string
+      data: string
+      size: number
+    }> = []
     if (validatedData.files && validatedData.files.length > 0) {
       const rawFiles = validatedData.files
       logger.info(`[${requestId}] Processing ${rawFiles.length} file(s) for upload to Teams`)
@@ -64,13 +71,19 @@ export async function POST(request: NextRequest) {
           logger.info(`[${requestId}] Uploading file to Teams: ${file.name} (${file.size} bytes)`)
 
           const buffer = await downloadFileFromStorage(file, requestId, logger)
+          filesOutput.push({
+            name: file.name,
+            mimeType: file.type || 'application/octet-stream',
+            data: buffer.toString('base64'),
+            size: buffer.length,
+          })
 
           const uploadUrl =
             'https://graph.microsoft.com/v1.0/me/drive/root:/TeamsAttachments/' +
             encodeURIComponent(file.name) +
             ':/content'
 
-          logger.info(`[${requestId}] Uploading to Teams: ${uploadUrl}`)
+          logger.info(`[${requestId}] Uploading to Teams: ${sanitizeUrlForLog(uploadUrl)}`)
 
           const uploadResponse = await fetch(uploadUrl, {
             method: 'PUT',
@@ -234,6 +247,7 @@ export async function POST(request: NextRequest) {
           url: responseData.webUrl || '',
           attachmentCount: attachments.length,
         },
+        files: filesOutput,
       },
     })
   } catch (error) {
diff --git a/apps/sim/app/api/tools/mistral/parse/route.ts b/apps/sim/app/api/tools/mistral/parse/route.ts
index 89ff35b77..642bb15e2 100644
--- a/apps/sim/app/api/tools/mistral/parse/route.ts
+++ b/apps/sim/app/api/tools/mistral/parse/route.ts
@@ -5,6 +5,7 @@ import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { getBaseUrl } from '@/lib/core/utils/urls'
 import { StorageService } from '@/lib/uploads'
+import { FileInputSchema } from '@/lib/uploads/utils/file-schemas'
 import {
   extractStorageKey,
   inferContextFromKey,
@@ -19,7 +20,7 @@ const logger = createLogger('MistralParseAPI')
 const MistralParseSchema = z.object({
   apiKey: z.string().min(1, 'API key is required'),
   filePath: z.string().min(1, 'File path is required').optional(),
-  fileData: z.unknown().optional(),
+  fileData: FileInputSchema.optional(),
   resultType: z.string().optional(),
   pages: z.array(z.number()).optional(),
   includeImageBase64: z.boolean().optional(),
diff --git a/apps/sim/app/api/tools/sftp/download/route.ts b/apps/sim/app/api/tools/sftp/download/route.ts
index 4914703fc..849e1ee09 100644
--- a/apps/sim/app/api/tools/sftp/download/route.ts
+++ b/apps/sim/app/api/tools/sftp/download/route.ts
@@ -4,6 +4,7 @@ import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { generateRequestId } from '@/lib/core/utils/request'
+import { getFileExtension, getMimeTypeFromExtension } from '@/lib/uploads/utils/file-utils'
 import { createSftpConnection, getSftp, isPathSafe, sanitizePath } from '@/app/api/tools/sftp/utils'
 
 export const dynamic = 'force-dynamic'
@@ -111,6 +112,8 @@ export async function POST(request: NextRequest) {
 
       const buffer = Buffer.concat(chunks)
       const fileName = path.basename(remotePath)
+      const extension = getFileExtension(fileName)
+      const mimeType = getMimeTypeFromExtension(extension)
 
       let content: string
       if (params.encoding === 'base64') {
@@ -124,6 +127,12 @@ export async function POST(request: NextRequest) {
       return NextResponse.json({
         success: true,
         fileName,
+        file: {
+          name: fileName,
+          mimeType,
+          data: buffer.toString('base64'),
+          size: buffer.length,
+        },
         content,
         size: buffer.length,
         encoding: params.encoding,
diff --git a/apps/sim/app/api/tools/sharepoint/upload/route.ts b/apps/sim/app/api/tools/sharepoint/upload/route.ts
index b5826c6ec..b15421d00 100644
--- a/apps/sim/app/api/tools/sharepoint/upload/route.ts
+++ b/apps/sim/app/api/tools/sharepoint/upload/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { RawFileInputArraySchema } from '@/lib/uploads/utils/file-schemas'
 import { processFilesToUserFiles } from '@/lib/uploads/utils/file-utils'
@@ -144,7 +145,7 @@ export async function POST(request: NextRequest) {
 
       const uploadUrl = `https://graph.microsoft.com/v1.0/sites/${validatedData.siteId}/drives/${effectiveDriveId}/root:${encodedPath}:/content`
 
-      logger.info(`[${requestId}] Uploading to: ${uploadUrl}`)
+      logger.info(`[${requestId}] Uploading to: ${sanitizeUrlForLog(uploadUrl)}`)
 
       const uploadResponse = await fetch(uploadUrl, {
         method: 'PUT',
diff --git a/apps/sim/app/api/tools/slack/utils.ts b/apps/sim/app/api/tools/slack/utils.ts
index 4a18071bf..a5527d95d 100644
--- a/apps/sim/app/api/tools/slack/utils.ts
+++ b/apps/sim/app/api/tools/slack/utils.ts
@@ -1,6 +1,7 @@
 import type { Logger } from '@sim/logger'
 import { processFilesToUserFiles } from '@/lib/uploads/utils/file-utils'
 import { downloadFileFromStorage } from '@/lib/uploads/utils/file-utils.server'
+import type { ToolFileData } from '@/tools/types'
 
 /**
  * Sends a message to a Slack channel using chat.postMessage
@@ -70,14 +71,21 @@ export async function uploadFilesToSlack(
   accessToken: string,
   requestId: string,
   logger: Logger
-): Promise<string[]> {
+): Promise<{ fileIds: string[]; files: ToolFileData[] }> {
   const userFiles = processFilesToUserFiles(files, requestId, logger)
   const uploadedFileIds: string[] = []
+  const uploadedFiles: ToolFileData[] = []
 
   for (const userFile of userFiles) {
     logger.info(`[${requestId}] Uploading file: ${userFile.name}`)
 
     const buffer = await downloadFileFromStorage(userFile, requestId, logger)
+    uploadedFiles.push({
+      name: userFile.name,
+      mimeType: userFile.type || 'application/octet-stream',
+      data: buffer.toString('base64'),
+      size: buffer.length,
+    })
 
     const getUrlResponse = await fetch('https://slack.com/api/files.getUploadURLExternal', {
       method: 'POST',
@@ -114,7 +122,7 @@ export async function uploadFilesToSlack(
     uploadedFileIds.push(urlData.file_id)
   }
 
-  return uploadedFileIds
+  return { fileIds: uploadedFileIds, files: uploadedFiles }
 }
 
 /**
@@ -217,7 +225,13 @@ export async function sendSlackMessage(
   logger: Logger
 ): Promise<{
   success: boolean
-  output?: { message: any; ts: string; channel: string; fileCount?: number }
+  output?: {
+    message: any
+    ts: string
+    channel: string
+    fileCount?: number
+    files?: ToolFileData[]
+  }
   error?: string
 }> {
   const { accessToken, text, threadTs, files } = params
@@ -249,10 +263,15 @@ export async function sendSlackMessage(
 
   // Process files
   logger.info(`[${requestId}] Processing ${files.length} file(s)`)
-  const uploadedFileIds = await uploadFilesToSlack(files, accessToken, requestId, logger)
+  const { fileIds, files: uploadedFiles } = await uploadFilesToSlack(
+    files,
+    accessToken,
+    requestId,
+    logger
+  )
 
   // No valid files uploaded - send text-only
-  if (uploadedFileIds.length === 0) {
+  if (fileIds.length === 0) {
     logger.warn(`[${requestId}] No valid files to upload, sending text-only message`)
 
     const data = await postSlackMessage(accessToken, channel, text, threadTs)
@@ -265,7 +284,7 @@ export async function sendSlackMessage(
   }
 
   // Complete file upload
-  const completeData = await completeSlackFileUpload(uploadedFileIds, channel, text, accessToken)
+  const completeData = await completeSlackFileUpload(fileIds, channel, text, accessToken)
 
   if (!completeData.ok) {
     logger.error(`[${requestId}] Failed to complete upload:`, completeData.error)
@@ -282,7 +301,8 @@ export async function sendSlackMessage(
       message: fileMessage,
       ts: fileMessage.ts,
       channel,
-      fileCount: uploadedFileIds.length,
+      fileCount: fileIds.length,
+      files: uploadedFiles,
     },
   }
 }
diff --git a/apps/sim/app/api/tools/ssh/download-file/route.ts b/apps/sim/app/api/tools/ssh/download-file/route.ts
index e3bffd29d..818d0ed41 100644
--- a/apps/sim/app/api/tools/ssh/download-file/route.ts
+++ b/apps/sim/app/api/tools/ssh/download-file/route.ts
@@ -5,6 +5,7 @@ import { type NextRequest, NextResponse } from 'next/server'
 import type { Client, SFTPWrapper } from 'ssh2'
 import { z } from 'zod'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
+import { getFileExtension, getMimeTypeFromExtension } from '@/lib/uploads/utils/file-utils'
 import { createSSHConnection, sanitizePath } from '@/app/api/tools/ssh/utils'
 
 const logger = createLogger('SSHDownloadFileAPI')
@@ -96,6 +97,8 @@ export async function POST(request: NextRequest) {
       })
 
       const fileName = path.basename(remotePath)
+      const extension = getFileExtension(fileName)
+      const mimeType = getMimeTypeFromExtension(extension)
 
       // Encode content as base64 for binary safety
       const base64Content = content.toString('base64')
@@ -104,6 +107,12 @@ export async function POST(request: NextRequest) {
 
       return NextResponse.json({
         downloaded: true,
+        file: {
+          name: fileName,
+          mimeType,
+          data: base64Content,
+          size: stats.size,
+        },
         content: base64Content,
         fileName: fileName,
         remotePath: remotePath,
diff --git a/apps/sim/app/api/tools/stagehand/extract/route.ts b/apps/sim/app/api/tools/stagehand/extract/route.ts
index b663f575d..db0d2848a 100644
--- a/apps/sim/app/api/tools/stagehand/extract/route.ts
+++ b/apps/sim/app/api/tools/stagehand/extract/route.ts
@@ -3,6 +3,7 @@ import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
 import { env } from '@/lib/core/config/env'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { ensureZodObject, normalizeUrl } from '@/app/api/tools/stagehand/utils'
 
 const logger = createLogger('StagehandExtractAPI')
@@ -120,7 +121,7 @@ export async function POST(request: NextRequest) {
 
       const page = stagehand.context.pages()[0]
 
-      logger.info(`Navigating to ${url}`)
+      logger.info(`Navigating to ${sanitizeUrlForLog(url)}`)
       await page.goto(url, { waitUntil: 'networkidle' })
       logger.info('Navigation complete')
 
diff --git a/apps/sim/app/api/tools/stt/route.ts b/apps/sim/app/api/tools/stt/route.ts
index 8a3ed3ef2..d14db9175 100644
--- a/apps/sim/app/api/tools/stt/route.ts
+++ b/apps/sim/app/api/tools/stt/route.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { extractAudioFromVideo, isVideoFile } from '@/lib/audio/extractor'
 import { checkInternalAuth } from '@/lib/auth/hybrid'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { downloadFileFromStorage } from '@/lib/uploads/utils/file-utils.server'
 import type { UserFile } from '@/executor/types'
 import type { TranscriptSegment } from '@/tools/stt/types'
@@ -88,7 +89,7 @@ export async function POST(request: NextRequest) {
       audioFileName = file.name
       audioMimeType = file.type
     } else if (body.audioUrl) {
-      logger.info(`[${requestId}] Downloading from URL: ${body.audioUrl}`)
+      logger.info(`[${requestId}] Downloading from URL: ${sanitizeUrlForLog(body.audioUrl)}`)
 
       const response = await fetch(body.audioUrl)
       if (!response.ok) {
diff --git a/apps/sim/app/api/tools/telegram/send-document/route.ts b/apps/sim/app/api/tools/telegram/send-document/route.ts
index 27d3277d4..0ddaac702 100644
--- a/apps/sim/app/api/tools/telegram/send-document/route.ts
+++ b/apps/sim/app/api/tools/telegram/send-document/route.ts
@@ -94,6 +94,14 @@ export async function POST(request: NextRequest) {
     logger.info(`[${requestId}] Uploading document: ${userFile.name}`)
 
     const buffer = await downloadFileFromStorage(userFile, requestId, logger)
+    const filesOutput = [
+      {
+        name: userFile.name,
+        mimeType: userFile.type || 'application/octet-stream',
+        data: buffer.toString('base64'),
+        size: buffer.length,
+      },
+    ]
 
     logger.info(`[${requestId}] Downloaded file: ${buffer.length} bytes`)
 
@@ -136,6 +144,7 @@ export async function POST(request: NextRequest) {
       output: {
         message: 'Document sent successfully',
         data: data.result,
+        files: filesOutput,
       },
     })
   } catch (error) {
diff --git a/apps/sim/app/workspace/[workspaceId]/logs/components/log-details/components/file-download/file-download.tsx b/apps/sim/app/workspace/[workspaceId]/logs/components/log-details/components/file-download/file-download.tsx
index 74397b9bb..9e3b163a5 100644
--- a/apps/sim/app/workspace/[workspaceId]/logs/components/log-details/components/file-download/file-download.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/logs/components/log-details/components/file-download/file-download.tsx
@@ -5,6 +5,7 @@ import { createLogger } from '@sim/logger'
 import { ArrowDown, Loader2 } from 'lucide-react'
 import { useRouter } from 'next/navigation'
 import { Button } from '@/components/emcn'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { extractWorkspaceIdFromExecutionKey, getViewerUrl } from '@/lib/uploads/utils/file-utils'
 
 const logger = createLogger('FileCards')
@@ -57,7 +58,7 @@ function FileCard({ file, isExecutionFile = false, workspaceId }: FileCardProps)
       if (file.key.startsWith('url/')) {
         if (file.url) {
           window.open(file.url, '_blank')
-          logger.info(`Opened URL-type file directly: ${file.url}`)
+          logger.info(`Opened URL-type file directly: ${sanitizeUrlForLog(file.url)}`)
           return
         }
         throw new Error('URL is required for URL-type files')
@@ -77,13 +78,13 @@ function FileCard({ file, isExecutionFile = false, workspaceId }: FileCardProps)
         const serveUrl =
           file.url || `/api/files/serve/${encodeURIComponent(file.key)}?context=execution`
         window.open(serveUrl, '_blank')
-        logger.info(`Opened execution file serve URL: ${serveUrl}`)
+        logger.info(`Opened execution file serve URL: ${sanitizeUrlForLog(serveUrl)}`)
       } else {
         const viewerUrl = resolvedWorkspaceId ? getViewerUrl(file.key, resolvedWorkspaceId) : null
 
         if (viewerUrl) {
           router.push(viewerUrl)
-          logger.info(`Navigated to viewer URL: ${viewerUrl}`)
+          logger.info(`Navigated to viewer URL: ${sanitizeUrlForLog(viewerUrl)}`)
         } else {
           logger.warn(
             `Could not construct viewer URL for file: ${file.name}, falling back to serve URL`
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/chat/chat.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/chat/chat.tsx
index 1c1d468be..7b66b8369 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/chat/chat.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/chat/chat.tsx
@@ -807,7 +807,7 @@ export function Chat() {
 
       const newReservedFields: StartInputFormatField[] = missingStartReservedFields.map(
         (fieldName) => {
-          const defaultType = fieldName === 'files' ? 'files' : 'string'
+          const defaultType = fieldName === 'files' ? 'file[]' : 'string'
 
           return {
             id: crypto.randomUUID(),
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tag-dropdown/tag-dropdown.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tag-dropdown/tag-dropdown.tsx
index 0d2569690..770dd3f17 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tag-dropdown/tag-dropdown.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tag-dropdown/tag-dropdown.tsx
@@ -225,7 +225,7 @@ const getOutputTypeForPath = (
       const chatModeTypes: Record<string, string> = {
         input: 'string',
         conversationId: 'string',
-        files: 'files',
+        files: 'file[]',
       }
       return chatModeTypes[outputPath] || 'any'
     }
@@ -1563,16 +1563,11 @@ export const TagDropdown: React.FC<TagDropdownProps> = ({
     blockTagGroups.sort((a, b) => a.distance - b.distance)
     finalBlockTagGroups.push(...blockTagGroups)
 
-    const contextualTags: string[] = []
-    if (loopBlockGroup) {
-      contextualTags.push(...loopBlockGroup.tags)
-    }
-    if (parallelBlockGroup) {
-      contextualTags.push(...parallelBlockGroup.tags)
-    }
+    const groupTags = finalBlockTagGroups.flatMap((group) => group.tags)
+    const tags = [...groupTags, ...variableTags]
 
     return {
-      tags: [...allBlockTags, ...variableTags, ...contextualTags],
+      tags,
       variableInfoMap,
       blockTagGroups: finalBlockTagGroups,
     }
diff --git a/apps/sim/blocks/blocks/discord.ts b/apps/sim/blocks/blocks/discord.ts
index 0d1108a09..94c27d448 100644
--- a/apps/sim/blocks/blocks/discord.ts
+++ b/apps/sim/blocks/blocks/discord.ts
@@ -578,13 +578,20 @@ export const DiscordBlock: BlockConfig<DiscordResponse> = {
         if (!params.serverId) throw new Error('Server ID is required')
 
         switch (params.operation) {
-          case 'discord_send_message':
+          case 'discord_send_message': {
+            const fileParam = params.attachmentFiles || params.files
+            const normalizedFiles = fileParam
+              ? Array.isArray(fileParam)
+                ? fileParam
+                : [fileParam]
+              : undefined
             return {
               ...commonParams,
               channelId: params.channelId,
               content: params.content,
-              files: params.attachmentFiles || params.files,
+              files: normalizedFiles,
             }
+          }
           case 'discord_get_messages':
             return {
               ...commonParams,
@@ -789,6 +796,7 @@ export const DiscordBlock: BlockConfig<DiscordResponse> = {
   },
   outputs: {
     message: { type: 'string', description: 'Status message' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
     data: { type: 'json', description: 'Response data' },
   },
 }
diff --git a/apps/sim/blocks/blocks/elevenlabs.ts b/apps/sim/blocks/blocks/elevenlabs.ts
index 9589a9f47..58d79fe67 100644
--- a/apps/sim/blocks/blocks/elevenlabs.ts
+++ b/apps/sim/blocks/blocks/elevenlabs.ts
@@ -73,5 +73,6 @@ export const ElevenLabsBlock: BlockConfig<ElevenLabsBlockResponse> = {
 
   outputs: {
     audioUrl: { type: 'string', description: 'Generated audio URL' },
+    audioFile: { type: 'file', description: 'Generated audio file' },
   },
 }
diff --git a/apps/sim/blocks/blocks/jira.ts b/apps/sim/blocks/blocks/jira.ts
index 66d42a43d..c2e64ce1e 100644
--- a/apps/sim/blocks/blocks/jira.ts
+++ b/apps/sim/blocks/blocks/jira.ts
@@ -34,6 +34,7 @@ export const JiraBlock: BlockConfig<JiraResponse> = {
         { label: 'Update Comment', id: 'update_comment' },
         { label: 'Delete Comment', id: 'delete_comment' },
         { label: 'Get Attachments', id: 'get_attachments' },
+        { label: 'Add Attachment', id: 'add_attachment' },
         { label: 'Delete Attachment', id: 'delete_attachment' },
         { label: 'Add Worklog', id: 'add_worklog' },
         { label: 'Get Worklogs', id: 'get_worklogs' },
@@ -137,6 +138,7 @@ export const JiraBlock: BlockConfig<JiraResponse> = {
           'update_comment',
           'delete_comment',
           'get_attachments',
+          'add_attachment',
           'add_worklog',
           'get_worklogs',
           'update_worklog',
@@ -168,6 +170,7 @@ export const JiraBlock: BlockConfig<JiraResponse> = {
           'update_comment',
           'delete_comment',
           'get_attachments',
+          'add_attachment',
           'add_worklog',
           'get_worklogs',
           'update_worklog',
@@ -407,6 +410,27 @@ Return ONLY the comment text - no explanations.`,
       condition: { field: 'operation', value: ['update_comment', 'delete_comment'] },
     },
     // Attachment fields
+    {
+      id: 'attachmentFiles',
+      title: 'Attachments',
+      type: 'file-upload',
+      canonicalParamId: 'files',
+      placeholder: 'Upload files',
+      condition: { field: 'operation', value: 'add_attachment' },
+      mode: 'basic',
+      multiple: true,
+      required: true,
+    },
+    {
+      id: 'files',
+      title: 'File References',
+      type: 'short-input',
+      canonicalParamId: 'files',
+      placeholder: 'File reference from previous block',
+      condition: { field: 'operation', value: 'add_attachment' },
+      mode: 'advanced',
+      required: true,
+    },
     {
       id: 'attachmentId',
       title: 'Attachment ID',
@@ -576,6 +600,7 @@ Return ONLY the comment text - no explanations.`,
       'jira_update_comment',
       'jira_delete_comment',
       'jira_get_attachments',
+      'jira_add_attachment',
       'jira_delete_attachment',
       'jira_add_worklog',
       'jira_get_worklogs',
@@ -623,6 +648,8 @@ Return ONLY the comment text - no explanations.`,
             return 'jira_delete_comment'
           case 'get_attachments':
             return 'jira_get_attachments'
+          case 'add_attachment':
+            return 'jira_add_attachment'
           case 'delete_attachment':
             return 'jira_delete_attachment'
           case 'add_worklog':
@@ -838,6 +865,21 @@ Return ONLY the comment text - no explanations.`,
               issueKey: effectiveIssueKey,
             }
           }
+          case 'add_attachment': {
+            if (!effectiveIssueKey) {
+              throw new Error('Issue Key is required to add attachments.')
+            }
+            const fileParam = params.attachmentFiles || params.files
+            if (!fileParam || (Array.isArray(fileParam) && fileParam.length === 0)) {
+              throw new Error('At least one attachment file is required.')
+            }
+            const normalizedFiles = Array.isArray(fileParam) ? fileParam : [fileParam]
+            return {
+              ...baseParams,
+              issueKey: effectiveIssueKey,
+              files: normalizedFiles,
+            }
+          }
           case 'delete_attachment': {
             return {
               ...baseParams,
@@ -982,6 +1024,8 @@ Return ONLY the comment text - no explanations.`,
     commentBody: { type: 'string', description: 'Text content for comment operations' },
     commentId: { type: 'string', description: 'Comment ID for update/delete operations' },
     // Attachment operation inputs
+    attachmentFiles: { type: 'json', description: 'Files to attach (UI upload)' },
+    files: { type: 'array', description: 'Files to attach (UserFile array)' },
     attachmentId: { type: 'string', description: 'Attachment ID for delete operation' },
     // Worklog operation inputs
     timeSpentSeconds: {
@@ -1049,9 +1093,11 @@ Return ONLY the comment text - no explanations.`,
 
     // jira_get_attachments outputs
     attachments: {
-      type: 'file[]',
+      type: 'json',
       description: 'Array of attachments with id, filename, size, mimeType, created, author',
     },
+    files: { type: 'file[]', description: 'Uploaded attachment files' },
+    attachmentIds: { type: 'json', description: 'Uploaded attachment IDs' },
 
     // jira_delete_attachment, jira_delete_comment, jira_delete_issue, jira_delete_worklog, jira_delete_issue_link outputs
     attachmentId: { type: 'string', description: 'Deleted attachment ID' },
diff --git a/apps/sim/blocks/blocks/linear.ts b/apps/sim/blocks/blocks/linear.ts
index 300c51b70..fefe38bc9 100644
--- a/apps/sim/blocks/blocks/linear.ts
+++ b/apps/sim/blocks/blocks/linear.ts
@@ -668,17 +668,44 @@ Return ONLY the date string in YYYY-MM-DD format - no explanations, no quotes, n
         generationType: 'timestamp',
       },
     },
+    // Attachment file
+    {
+      id: 'attachmentFileUpload',
+      title: 'Attachment',
+      type: 'file-upload',
+      canonicalParamId: 'file',
+      placeholder: 'Upload attachment',
+      condition: {
+        field: 'operation',
+        value: ['linear_create_attachment'],
+      },
+      mode: 'basic',
+      multiple: false,
+    },
+    {
+      id: 'file',
+      title: 'File Reference',
+      type: 'short-input',
+      canonicalParamId: 'file',
+      placeholder: 'File reference from previous block',
+      condition: {
+        field: 'operation',
+        value: ['linear_create_attachment'],
+      },
+      mode: 'advanced',
+    },
     // Attachment URL
     {
       id: 'url',
       title: 'URL',
       type: 'short-input',
       placeholder: 'Enter URL',
-      required: true,
+      required: false,
       condition: {
         field: 'operation',
         value: ['linear_create_attachment'],
       },
+      mode: 'advanced',
     },
     // Attachment title
     {
@@ -1742,16 +1769,31 @@ Return ONLY the date string in YYYY-MM-DD format - no explanations, no quotes, n
               teamId: effectiveTeamId,
             }
 
-          case 'linear_create_attachment':
-            if (!params.issueId?.trim() || !params.url?.trim()) {
-              throw new Error('Issue ID and URL are required.')
+          case 'linear_create_attachment': {
+            if (!params.issueId?.trim()) {
+              throw new Error('Issue ID is required.')
+            }
+            if (Array.isArray(params.file)) {
+              throw new Error('Attachment file must be a single file.')
+            }
+            if (Array.isArray(params.attachmentFileUpload)) {
+              throw new Error('Attachment file must be a single file.')
+            }
+            const attachmentFile = params.attachmentFileUpload || params.file
+            const attachmentUrl =
+              params.url?.trim() ||
+              (attachmentFile && !Array.isArray(attachmentFile) ? attachmentFile.url : undefined)
+            if (!attachmentUrl) {
+              throw new Error('URL or file is required.')
             }
             return {
               ...baseParams,
               issueId: params.issueId.trim(),
-              url: params.url.trim(),
+              url: attachmentUrl,
+              file: attachmentFile,
               title: params.attachmentTitle,
             }
+          }
 
           case 'linear_list_attachments':
             if (!params.issueId?.trim()) {
@@ -2248,6 +2290,8 @@ Return ONLY the date string in YYYY-MM-DD format - no explanations, no quotes, n
     endDate: { type: 'string', description: 'End date' },
     targetDate: { type: 'string', description: 'Target date' },
     url: { type: 'string', description: 'URL' },
+    attachmentFileUpload: { type: 'json', description: 'File to attach (UI upload)' },
+    file: { type: 'json', description: 'File to attach (UserFile)' },
     attachmentTitle: { type: 'string', description: 'Attachment title' },
     attachmentId: { type: 'string', description: 'Attachment identifier' },
     relationType: { type: 'string', description: 'Relation type' },
@@ -2341,7 +2385,7 @@ Return ONLY the date string in YYYY-MM-DD format - no explanations, no quotes, n
     cycles: { type: 'json', description: 'Cycles list' },
     // Attachment outputs
     attachment: { type: 'json', description: 'Attachment data' },
-    attachments: { type: 'file[]', description: 'Attachments list' },
+    attachments: { type: 'json', description: 'Attachments list' },
     // Relation outputs
     relation: { type: 'json', description: 'Issue relation data' },
     relations: { type: 'json', description: 'Issue relations list' },
diff --git a/apps/sim/blocks/blocks/microsoft_teams.ts b/apps/sim/blocks/blocks/microsoft_teams.ts
index 69dedc8af..04cb2d242 100644
--- a/apps/sim/blocks/blocks/microsoft_teams.ts
+++ b/apps/sim/blocks/blocks/microsoft_teams.ts
@@ -346,7 +346,10 @@ export const MicrosoftTeamsBlock: BlockConfig<MicrosoftTeamsResponse> = {
         // Add files if provided
         const fileParam = attachmentFiles || files
         if (fileParam && (operation === 'write_chat' || operation === 'write_channel')) {
-          baseParams.files = fileParam
+          const normalizedFiles = Array.isArray(fileParam) ? fileParam : [fileParam]
+          if (normalizedFiles.length > 0) {
+            baseParams.files = normalizedFiles
+          }
         }
 
         // Add messageId if provided
@@ -463,6 +466,7 @@ export const MicrosoftTeamsBlock: BlockConfig<MicrosoftTeamsResponse> = {
     totalAttachments: { type: 'number', description: 'Total number of attachments' },
     attachmentTypes: { type: 'json', description: 'Array of attachment content types' },
     attachments: { type: 'file[]', description: 'Downloaded message attachments' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
     updatedContent: {
       type: 'boolean',
       description: 'Whether content was successfully updated/sent',
diff --git a/apps/sim/blocks/blocks/pipedrive.ts b/apps/sim/blocks/blocks/pipedrive.ts
index 1d3b939d4..b6bd6fb8e 100644
--- a/apps/sim/blocks/blocks/pipedrive.ts
+++ b/apps/sim/blocks/blocks/pipedrive.ts
@@ -803,7 +803,7 @@ Return ONLY the date string in YYYY-MM-DD format - no explanations, no quotes, n
   outputs: {
     deals: { type: 'json', description: 'Array of deal objects' },
     deal: { type: 'json', description: 'Single deal object' },
-    files: { type: 'file[]', description: 'Array of file objects' },
+    files: { type: 'json', description: 'Array of file objects' },
     messages: { type: 'json', description: 'Array of mail message objects' },
     pipelines: { type: 'json', description: 'Array of pipeline objects' },
     projects: { type: 'json', description: 'Array of project objects' },
diff --git a/apps/sim/blocks/blocks/sftp.ts b/apps/sim/blocks/blocks/sftp.ts
index f459c1a03..3621ee5b4 100644
--- a/apps/sim/blocks/blocks/sftp.ts
+++ b/apps/sim/blocks/blocks/sftp.ts
@@ -293,6 +293,7 @@ export const SftpBlock: BlockConfig<SftpUploadResult> = {
   outputs: {
     success: { type: 'boolean', description: 'Whether the operation was successful' },
     uploadedFiles: { type: 'json', description: 'Array of uploaded file details' },
+    file: { type: 'file', description: 'Downloaded file stored in execution files' },
     fileName: { type: 'string', description: 'Downloaded file name' },
     content: { type: 'string', description: 'Downloaded file content' },
     size: { type: 'number', description: 'File size in bytes' },
diff --git a/apps/sim/blocks/blocks/sharepoint.ts b/apps/sim/blocks/blocks/sharepoint.ts
index b6cdbfbda..5fe1dfb6d 100644
--- a/apps/sim/blocks/blocks/sharepoint.ts
+++ b/apps/sim/blocks/blocks/sharepoint.ts
@@ -522,7 +522,7 @@ Return ONLY the JSON object - no explanations, no markdown, no extra text.`,
       description: 'Array of SharePoint list items with fields',
     },
     uploadedFiles: {
-      type: 'file[]',
+      type: 'json',
       description: 'Array of uploaded file objects with id, name, webUrl, size',
     },
     fileCount: {
diff --git a/apps/sim/blocks/blocks/slack.ts b/apps/sim/blocks/blocks/slack.ts
index 9bd6292b7..0ce640032 100644
--- a/apps/sim/blocks/blocks/slack.ts
+++ b/apps/sim/blocks/blocks/slack.ts
@@ -622,7 +622,10 @@ Return ONLY the timestamp string - no explanations, no quotes, no extra text.`,
             }
             const fileParam = attachmentFiles || files
             if (fileParam) {
-              baseParams.files = fileParam
+              const normalizedFiles = Array.isArray(fileParam) ? fileParam : [fileParam]
+              if (normalizedFiles.length > 0) {
+                baseParams.files = normalizedFiles
+              }
             }
             break
           }
@@ -796,6 +799,7 @@ Return ONLY the timestamp string - no explanations, no quotes, no extra text.`,
       type: 'number',
       description: 'Number of files uploaded (when files are attached)',
     },
+    files: { type: 'file[]', description: 'Files attached to the message' },
 
     // slack_canvas outputs
     canvas_id: { type: 'string', description: 'Canvas identifier for created canvases' },
diff --git a/apps/sim/blocks/blocks/ssh.ts b/apps/sim/blocks/blocks/ssh.ts
index 924b26c45..32dbffd72 100644
--- a/apps/sim/blocks/blocks/ssh.ts
+++ b/apps/sim/blocks/blocks/ssh.ts
@@ -507,6 +507,7 @@ export const SSHBlock: BlockConfig<SSHResponse> = {
     stderr: { type: 'string', description: 'Command standard error' },
     exitCode: { type: 'number', description: 'Command exit code' },
     success: { type: 'boolean', description: 'Operation success status' },
+    file: { type: 'file', description: 'Downloaded file stored in execution files' },
     fileContent: { type: 'string', description: 'Downloaded/read file content' },
     entries: { type: 'json', description: 'Directory entries' },
     exists: { type: 'boolean', description: 'File/directory existence' },
diff --git a/apps/sim/blocks/blocks/telegram.ts b/apps/sim/blocks/blocks/telegram.ts
index e45f27cee..65b18677a 100644
--- a/apps/sim/blocks/blocks/telegram.ts
+++ b/apps/sim/blocks/blocks/telegram.ts
@@ -314,9 +314,14 @@ export const TelegramBlock: BlockConfig<TelegramResponse> = {
           case 'telegram_send_document': {
             // Handle file upload
             const fileParam = params.attachmentFiles || params.files
+            const normalizedFiles = fileParam
+              ? Array.isArray(fileParam)
+                ? fileParam
+                : [fileParam]
+              : undefined
             return {
               ...commonParams,
-              files: fileParam,
+              files: normalizedFiles,
               caption: params.caption,
             }
           }
@@ -359,6 +364,7 @@ export const TelegramBlock: BlockConfig<TelegramResponse> = {
     },
     message: { type: 'string', description: 'Success or error message' },
     data: { type: 'json', description: 'Response data' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
     // Specific result fields
     messageId: { type: 'number', description: 'Sent message ID' },
     chatId: { type: 'number', description: 'Chat ID where message was sent' },
diff --git a/apps/sim/lib/core/utils/logging.ts b/apps/sim/lib/core/utils/logging.ts
new file mode 100644
index 000000000..5670d6a5d
--- /dev/null
+++ b/apps/sim/lib/core/utils/logging.ts
@@ -0,0 +1,19 @@
+/**
+ * Sanitize URLs for logging by stripping query/hash and truncating.
+ */
+export function sanitizeUrlForLog(url: string, maxLength = 120): string {
+  if (!url) return ''
+
+  const trimmed = url.trim()
+  try {
+    const hasProtocol = /^[a-zA-Z][a-zA-Z\d+\-.]*:/.test(trimmed)
+    const parsed = new URL(trimmed, hasProtocol ? undefined : 'http://localhost')
+    const origin = parsed.origin === 'null' ? '' : parsed.origin
+    const sanitized = `${origin}${parsed.pathname}`
+    const result = sanitized || parsed.pathname || trimmed
+    return result.length > maxLength ? `${result.slice(0, maxLength)}...` : result
+  } catch {
+    const withoutQuery = trimmed.split('?')[0].split('#')[0]
+    return withoutQuery.length > maxLength ? `${withoutQuery.slice(0, maxLength)}...` : withoutQuery
+  }
+}
diff --git a/apps/sim/lib/knowledge/documents/document-processor.ts b/apps/sim/lib/knowledge/documents/document-processor.ts
index 632e91fa8..fadd43fa1 100644
--- a/apps/sim/lib/knowledge/documents/document-processor.ts
+++ b/apps/sim/lib/knowledge/documents/document-processor.ts
@@ -3,6 +3,7 @@ import { PDFDocument } from 'pdf-lib'
 import { getBYOKKey } from '@/lib/api-key/byok'
 import { type Chunk, JsonYamlChunker, StructuredDataChunker, TextChunker } from '@/lib/chunkers'
 import { env } from '@/lib/core/config/env'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import { parseBuffer, parseFile } from '@/lib/file-parsers'
 import type { FileParseMetadata } from '@/lib/file-parsers/types'
 import { retryWithExponentialBackoff } from '@/lib/knowledge/documents/utils'
@@ -489,7 +490,7 @@ async function parseWithMistralOCR(
     workspaceId
   )
 
-  logger.info(`Mistral OCR: Using presigned URL for ${filename}: ${httpsUrl.substring(0, 120)}...`)
+  logger.info(`Mistral OCR: Using presigned URL for ${filename}: ${sanitizeUrlForLog(httpsUrl)}`)
 
   let pageCount = 0
   if (mimeType === 'application/pdf' && buffer) {
diff --git a/apps/sim/lib/webhooks/utils.server.ts b/apps/sim/lib/webhooks/utils.server.ts
index f3cd6b436..ad17cd774 100644
--- a/apps/sim/lib/webhooks/utils.server.ts
+++ b/apps/sim/lib/webhooks/utils.server.ts
@@ -11,6 +11,7 @@ import {
   secureFetchWithPinnedIP,
   validateUrlWithDNS,
 } from '@/lib/core/security/input-validation'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import type { DbOrTx } from '@/lib/db/types'
 import { getProviderIdFromServiceId } from '@/lib/oauth'
 import {
@@ -114,7 +115,7 @@ async function fetchWithDNSPinning(
     const urlValidation = await validateUrlWithDNS(url, 'contentUrl')
     if (!urlValidation.isValid) {
       logger.warn(`[${requestId}] Invalid content URL: ${urlValidation.error}`, {
-        url: url.substring(0, 100),
+        url: sanitizeUrlForLog(url),
       })
       return null
     }
@@ -133,7 +134,7 @@ async function fetchWithDNSPinning(
   } catch (error) {
     logger.error(`[${requestId}] Error fetching URL with DNS pinning`, {
       error: error instanceof Error ? error.message : String(error),
-      url: url.substring(0, 100),
+      url: sanitizeUrlForLog(url),
     })
     return null
   }
diff --git a/apps/sim/tools/browser_use/run_task.ts b/apps/sim/tools/browser_use/run_task.ts
index 9dbeeb5b6..76edcfe8b 100644
--- a/apps/sim/tools/browser_use/run_task.ts
+++ b/apps/sim/tools/browser_use/run_task.ts
@@ -1,4 +1,5 @@
 import { createLogger } from '@sim/logger'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import type { BrowserUseRunTaskParams, BrowserUseRunTaskResponse } from '@/tools/browser_use/types'
 import type { ToolConfig, ToolResponse } from '@/tools/types'
 
@@ -183,7 +184,7 @@ async function pollForCompletion(
     }
 
     if (!liveUrlLogged && taskData.live_url) {
-      logger.info(`BrowserUse task ${taskId} live URL: ${taskData.live_url}`)
+      logger.info(`BrowserUse task ${taskId} live URL: ${sanitizeUrlForLog(taskData.live_url)}`)
       liveUrlLogged = true
     }
 
diff --git a/apps/sim/tools/discord/send_message.ts b/apps/sim/tools/discord/send_message.ts
index 074285e48..abe95515d 100644
--- a/apps/sim/tools/discord/send_message.ts
+++ b/apps/sim/tools/discord/send_message.ts
@@ -72,6 +72,7 @@ export const discordSendMessageTool: ToolConfig<
 
   outputs: {
     message: { type: 'string', description: 'Success or error message' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
     data: {
       type: 'object',
       description: 'Discord message data',
diff --git a/apps/sim/tools/discord/types.ts b/apps/sim/tools/discord/types.ts
index 9573309e9..76a5d016e 100644
--- a/apps/sim/tools/discord/types.ts
+++ b/apps/sim/tools/discord/types.ts
@@ -1,4 +1,5 @@
 import type { UserFile } from '@/executor/types'
+import type { ToolFileData } from '@/tools/types'
 
 export interface DiscordMessage {
   id: string
@@ -85,6 +86,7 @@ interface BaseDiscordResponse {
 export interface DiscordSendMessageResponse extends BaseDiscordResponse {
   output: {
     message: string
+    files?: ToolFileData[]
     data?: DiscordMessage
   }
 }
diff --git a/apps/sim/tools/elevenlabs/types.ts b/apps/sim/tools/elevenlabs/types.ts
index 06d043698..5627d1f72 100644
--- a/apps/sim/tools/elevenlabs/types.ts
+++ b/apps/sim/tools/elevenlabs/types.ts
@@ -1,3 +1,4 @@
+import type { UserFile } from '@/executor/types'
 import type { ToolResponse } from '@/tools/types'
 
 export interface ElevenLabsTtsParams {
@@ -12,11 +13,13 @@ export interface ElevenLabsTtsParams {
 export interface ElevenLabsTtsResponse extends ToolResponse {
   output: {
     audioUrl: string
+    audioFile?: UserFile
   }
 }
 
 export interface ElevenLabsBlockResponse extends ToolResponse {
   output: {
     audioUrl: string
+    audioFile?: UserFile
   }
 }
diff --git a/apps/sim/tools/jira/add_attachment.ts b/apps/sim/tools/jira/add_attachment.ts
new file mode 100644
index 000000000..8055c7230
--- /dev/null
+++ b/apps/sim/tools/jira/add_attachment.ts
@@ -0,0 +1,83 @@
+import type { JiraAddAttachmentParams, JiraAddAttachmentResponse } from '@/tools/jira/types'
+import type { ToolConfig } from '@/tools/types'
+
+export const jiraAddAttachmentTool: ToolConfig<JiraAddAttachmentParams, JiraAddAttachmentResponse> =
+  {
+    id: 'jira_add_attachment',
+    name: 'Jira Add Attachment',
+    description: 'Add attachments to a Jira issue',
+    version: '1.0.0',
+
+    oauth: {
+      required: true,
+      provider: 'jira',
+    },
+
+    params: {
+      accessToken: {
+        type: 'string',
+        required: true,
+        visibility: 'hidden',
+        description: 'OAuth access token for Jira',
+      },
+      domain: {
+        type: 'string',
+        required: true,
+        visibility: 'user-only',
+        description: 'Your Jira domain (e.g., yourcompany.atlassian.net)',
+      },
+      issueKey: {
+        type: 'string',
+        required: true,
+        visibility: 'user-or-llm',
+        description: 'Jira issue key to add attachments to (e.g., PROJ-123)',
+      },
+      files: {
+        type: 'file[]',
+        required: true,
+        visibility: 'user-only',
+        description: 'Files to attach to the Jira issue',
+      },
+      cloudId: {
+        type: 'string',
+        required: false,
+        visibility: 'hidden',
+        description:
+          'Jira Cloud ID for the instance. If not provided, it will be fetched using the domain.',
+      },
+    },
+
+    request: {
+      url: '/api/tools/jira/add-attachment',
+      method: 'POST',
+      headers: () => ({
+        'Content-Type': 'application/json',
+      }),
+      body: (params: JiraAddAttachmentParams) => ({
+        accessToken: params.accessToken,
+        domain: params.domain,
+        issueKey: params.issueKey,
+        files: params.files,
+        cloudId: params.cloudId,
+      }),
+    },
+
+    transformResponse: async (response: Response) => {
+      const data = await response.json()
+      if (!response.ok || !data.success) {
+        throw new Error(data.error || 'Failed to add Jira attachment')
+      }
+
+      return {
+        success: true,
+        output: data.output,
+      }
+    },
+
+    outputs: {
+      ts: { type: 'string', description: 'Timestamp of the operation' },
+      issueKey: { type: 'string', description: 'Issue key' },
+      attachmentIds: { type: 'json', description: 'IDs of uploaded attachments' },
+      files: { type: 'file[]', description: 'Uploaded attachment files' },
+    },
+  }
diff --git a/apps/sim/tools/jira/index.ts b/apps/sim/tools/jira/index.ts
index a9bed6699..ced24d2d0 100644
--- a/apps/sim/tools/jira/index.ts
+++ b/apps/sim/tools/jira/index.ts
@@ -1,3 +1,4 @@
+import { jiraAddAttachmentTool } from '@/tools/jira/add_attachment'
 import { jiraAddCommentTool } from '@/tools/jira/add_comment'
 import { jiraAddWatcherTool } from '@/tools/jira/add_watcher'
 import { jiraAddWorklogTool } from '@/tools/jira/add_worklog'
@@ -32,6 +33,7 @@ export {
   jiraTransitionIssueTool,
   jiraSearchIssuesTool,
   jiraAddCommentTool,
+  jiraAddAttachmentTool,
   jiraGetCommentsTool,
   jiraUpdateCommentTool,
   jiraDeleteCommentTool,
diff --git a/apps/sim/tools/jira/types.ts b/apps/sim/tools/jira/types.ts
index b7d840f95..0ed2ba646 100644
--- a/apps/sim/tools/jira/types.ts
+++ b/apps/sim/tools/jira/types.ts
@@ -1,4 +1,5 @@
-import type { ToolResponse } from '@/tools/types'
+import type { UserFile } from '@/executor/types'
+import type { ToolFileData, ToolResponse } from '@/tools/types'
 
 export interface JiraRetrieveParams {
   accessToken: string
@@ -312,6 +313,23 @@ export interface JiraDeleteAttachmentResponse extends ToolResponse {
   }
 }
 
+export interface JiraAddAttachmentParams {
+  accessToken: string
+  domain: string
+  issueKey: string
+  files: UserFile[]
+  cloudId?: string
+}
+
+export interface JiraAddAttachmentResponse extends ToolResponse {
+  output: {
+    ts: string
+    issueKey: string
+    attachmentIds: string[]
+    files: ToolFileData[]
+  }
+}
+
 // Worklogs
 export interface JiraAddWorklogParams {
   accessToken: string
@@ -482,6 +500,7 @@ export type JiraResponse =
   | JiraUpdateCommentResponse
   | JiraDeleteCommentResponse
   | JiraGetAttachmentsResponse
+  | JiraAddAttachmentResponse
   | JiraDeleteAttachmentResponse
   | JiraAddWorklogResponse
   | JiraGetWorklogsResponse
diff --git a/apps/sim/tools/linear/create_attachment.ts b/apps/sim/tools/linear/create_attachment.ts
index 5e366c5c6..03019de91 100644
--- a/apps/sim/tools/linear/create_attachment.ts
+++ b/apps/sim/tools/linear/create_attachment.ts
@@ -28,10 +28,16 @@ export const linearCreateAttachmentTool: ToolConfig<
     },
     url: {
       type: 'string',
-      required: true,
+      required: false,
       visibility: 'user-or-llm',
       description: 'URL of the attachment',
     },
+    file: {
+      type: 'file',
+      required: false,
+      visibility: 'user-only',
+      description: 'File to attach',
+    },
     title: {
       type: 'string',
       required: true,
@@ -59,9 +65,14 @@ export const linearCreateAttachmentTool: ToolConfig<
       }
     },
     body: (params) => {
+      const attachmentUrl = params.url || params.file?.url
+      if (!attachmentUrl) {
+        throw new Error('URL or file is required')
+      }
+
       const input: Record<string, any> = {
         issueId: params.issueId,
-        url: params.url,
+        url: attachmentUrl,
         title: params.title,
       }
 
diff --git a/apps/sim/tools/linear/types.ts b/apps/sim/tools/linear/types.ts
index 5a24f0a82..b66bae5b4 100644
--- a/apps/sim/tools/linear/types.ts
+++ b/apps/sim/tools/linear/types.ts
@@ -1,3 +1,4 @@
+import type { UserFile } from '@/executor/types'
 import type { OutputProperty, ToolResponse } from '@/tools/types'
 
 /**
@@ -875,7 +876,8 @@ export interface LinearGetActiveCycleParams {
 
 export interface LinearCreateAttachmentParams {
   issueId: string
-  url: string
+  url?: string
+  file?: UserFile
   title?: string
   subtitle?: string
   accessToken?: string
diff --git a/apps/sim/tools/microsoft_planner/read_task.ts b/apps/sim/tools/microsoft_planner/read_task.ts
index e44d5e175..730d3f788 100644
--- a/apps/sim/tools/microsoft_planner/read_task.ts
+++ b/apps/sim/tools/microsoft_planner/read_task.ts
@@ -1,4 +1,5 @@
 import { createLogger } from '@sim/logger'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import type {
   MicrosoftPlannerReadResponse,
   MicrosoftPlannerToolParams,
@@ -76,7 +77,7 @@ export const readTaskTool: ToolConfig<MicrosoftPlannerToolParams, MicrosoftPlann
         finalUrl = 'https://graph.microsoft.com/v1.0/me/planner/tasks'
       }
 
-      logger.info('Microsoft Planner URL:', finalUrl)
+      logger.info('Microsoft Planner URL:', sanitizeUrlForLog(finalUrl))
       return finalUrl
     },
     method: 'GET',
diff --git a/apps/sim/tools/microsoft_teams/types.ts b/apps/sim/tools/microsoft_teams/types.ts
index dac19fb8c..756d8f5d5 100644
--- a/apps/sim/tools/microsoft_teams/types.ts
+++ b/apps/sim/tools/microsoft_teams/types.ts
@@ -1,5 +1,5 @@
 import type { UserFile } from '@/executor/types'
-import type { ToolResponse } from '@/tools/types'
+import type { ToolFileData, ToolResponse } from '@/tools/types'
 
 export interface MicrosoftTeamsAttachment {
   id: string
@@ -61,6 +61,7 @@ export interface MicrosoftTeamsWriteResponse extends ToolResponse {
   output: {
     updatedContent: boolean
     metadata: MicrosoftTeamsMetadata
+    files?: ToolFileData[]
   }
 }
 
diff --git a/apps/sim/tools/microsoft_teams/write_channel.ts b/apps/sim/tools/microsoft_teams/write_channel.ts
index 08ffac1fe..c4bffeb35 100644
--- a/apps/sim/tools/microsoft_teams/write_channel.ts
+++ b/apps/sim/tools/microsoft_teams/write_channel.ts
@@ -58,6 +58,7 @@ export const writeChannelTool: ToolConfig<MicrosoftTeamsToolParams, MicrosoftTea
     createdTime: { type: 'string', description: 'Timestamp when message was created' },
     url: { type: 'string', description: 'Web URL to the message' },
     updatedContent: { type: 'boolean', description: 'Whether content was successfully updated' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
   },
 
   request: {
diff --git a/apps/sim/tools/microsoft_teams/write_chat.ts b/apps/sim/tools/microsoft_teams/write_chat.ts
index 132337fe0..e5c9b0c2c 100644
--- a/apps/sim/tools/microsoft_teams/write_chat.ts
+++ b/apps/sim/tools/microsoft_teams/write_chat.ts
@@ -50,6 +50,7 @@ export const writeChatTool: ToolConfig<MicrosoftTeamsToolParams, MicrosoftTeamsW
     createdTime: { type: 'string', description: 'Timestamp when message was created' },
     url: { type: 'string', description: 'Web URL to the message' },
     updatedContent: { type: 'boolean', description: 'Whether content was successfully updated' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
   },
 
   request: {
diff --git a/apps/sim/tools/mistral/parser.ts b/apps/sim/tools/mistral/parser.ts
index f7db85e5f..125c5b21f 100644
--- a/apps/sim/tools/mistral/parser.ts
+++ b/apps/sim/tools/mistral/parser.ts
@@ -98,10 +98,10 @@ export const mistralParserTool: ToolConfig<MistralParserInput, MistralParserOutp
         if (
           typeof params.fileUpload === 'object' &&
           params.fileUpload !== null &&
-          (params.fileUpload.url || params.fileUpload.path)
+          params.fileUpload.url
         ) {
-          // Get the full URL to the file - prefer url over path for UserFile compatibility
-          let uploadedFilePath = params.fileUpload.url || params.fileUpload.path
+          // Get the full URL to the file
+          let uploadedFilePath = params.fileUpload.url
 
           // Make sure the file path is an absolute URL
           if (uploadedFilePath.startsWith('/')) {
@@ -184,9 +184,9 @@ export const mistralParserTool: ToolConfig<MistralParserInput, MistralParserOutp
       }
 
       // Check if this is an internal workspace file path
-      if (params.fileUpload?.path?.startsWith('/api/files/serve/')) {
+      if (params.fileUpload?.url?.startsWith('/api/files/serve/')) {
         // Update filePath to the internal path for workspace files
-        requestBody.filePath = params.fileUpload.path
+        requestBody.filePath = params.fileUpload.url
       }
 
       // Add optional parameters with proper validation
diff --git a/apps/sim/tools/registry.ts b/apps/sim/tools/registry.ts
index 4f342e027..2d538beb9 100644
--- a/apps/sim/tools/registry.ts
+++ b/apps/sim/tools/registry.ts
@@ -763,6 +763,7 @@ import {
 } from '@/tools/intercom'
 import { jinaReadUrlTool, jinaSearchTool } from '@/tools/jina'
 import {
+  jiraAddAttachmentTool,
   jiraAddCommentTool,
   jiraAddWatcherTool,
   jiraAddWorklogTool,
@@ -1879,6 +1880,7 @@ export const tools: Record<string, ToolConfig> = {
   jira_update_comment: jiraUpdateCommentTool,
   jira_delete_comment: jiraDeleteCommentTool,
   jira_get_attachments: jiraGetAttachmentsTool,
+  jira_add_attachment: jiraAddAttachmentTool,
   jira_delete_attachment: jiraDeleteAttachmentTool,
   jira_add_worklog: jiraAddWorklogTool,
   jira_get_worklogs: jiraGetWorklogsTool,
diff --git a/apps/sim/tools/sftp/download.ts b/apps/sim/tools/sftp/download.ts
index d02532e86..0c026258d 100644
--- a/apps/sim/tools/sftp/download.ts
+++ b/apps/sim/tools/sftp/download.ts
@@ -94,6 +94,7 @@ export const sftpDownloadTool: ToolConfig<SftpDownloadParams, SftpDownloadResult
       output: {
         success: true,
         fileName: data.fileName,
+        file: data.file,
         content: data.content,
         size: data.size,
         encoding: data.encoding,
@@ -104,6 +105,7 @@ export const sftpDownloadTool: ToolConfig<SftpDownloadParams, SftpDownloadResult
 
   outputs: {
     success: { type: 'boolean', description: 'Whether the download was successful' },
+    file: { type: 'file', description: 'Downloaded file stored in execution files' },
     fileName: { type: 'string', description: 'Name of the downloaded file' },
     content: { type: 'string', description: 'File content (text or base64 encoded)' },
     size: { type: 'number', description: 'File size in bytes' },
diff --git a/apps/sim/tools/sftp/types.ts b/apps/sim/tools/sftp/types.ts
index de32d3cc2..357a2c4e4 100644
--- a/apps/sim/tools/sftp/types.ts
+++ b/apps/sim/tools/sftp/types.ts
@@ -1,5 +1,5 @@
 import type { UserFile } from '@/executor/types'
-import type { ToolResponse } from '@/tools/types'
+import type { ToolFileData, ToolResponse } from '@/tools/types'
 
 export interface SftpConnectionConfig {
   host: string
@@ -42,6 +42,7 @@ export interface SftpDownloadResult extends ToolResponse {
   output: {
     success: boolean
     fileName?: string
+    file?: ToolFileData
     content?: string
     size?: number
     encoding?: string
diff --git a/apps/sim/tools/sharepoint/get_list.ts b/apps/sim/tools/sharepoint/get_list.ts
index 90b9168c6..0dc540223 100644
--- a/apps/sim/tools/sharepoint/get_list.ts
+++ b/apps/sim/tools/sharepoint/get_list.ts
@@ -1,4 +1,5 @@
 import { createLogger } from '@sim/logger'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import type {
   SharepointGetListResponse,
   SharepointList,
@@ -56,7 +57,10 @@ export const getListTool: ToolConfig<SharepointToolParams, SharepointGetListResp
         const baseUrl = `https://graph.microsoft.com/v1.0/sites/${siteId}/lists`
         const url = new URL(baseUrl)
         const finalUrl = url.toString()
-        logger.info('SharePoint List All Lists URL', { finalUrl, siteId })
+        logger.info('SharePoint List All Lists URL', {
+          finalUrl: sanitizeUrlForLog(finalUrl),
+          siteId,
+        })
         return finalUrl
       }
 
@@ -72,7 +76,7 @@ export const getListTool: ToolConfig<SharepointToolParams, SharepointGetListResp
         itemsUrl.searchParams.set('$expand', 'fields')
         const finalItemsUrl = itemsUrl.toString()
         logger.info('SharePoint Get List Items URL', {
-          finalUrl: finalItemsUrl,
+          finalUrl: sanitizeUrlForLog(finalItemsUrl),
           siteId,
           listId: params.listId,
         })
@@ -89,7 +93,7 @@ export const getListTool: ToolConfig<SharepointToolParams, SharepointGetListResp
 
       const finalUrl = url.toString()
       logger.info('SharePoint Get List URL', {
-        finalUrl,
+        finalUrl: sanitizeUrlForLog(finalUrl),
         siteId,
         listId: params.listId,
         includeColumns: !!params.includeColumns,
diff --git a/apps/sim/tools/slack/message.ts b/apps/sim/tools/slack/message.ts
index 5849292a6..1fd60b685 100644
--- a/apps/sim/tools/slack/message.ts
+++ b/apps/sim/tools/slack/message.ts
@@ -114,5 +114,6 @@ export const slackMessageTool: ToolConfig<SlackMessageParams, SlackMessageRespon
       type: 'number',
       description: 'Number of files uploaded (when files are attached)',
     },
+    files: { type: 'file[]', description: 'Files attached to the message' },
   },
 }
diff --git a/apps/sim/tools/slack/types.ts b/apps/sim/tools/slack/types.ts
index 54c9bc21f..874ea59c4 100644
--- a/apps/sim/tools/slack/types.ts
+++ b/apps/sim/tools/slack/types.ts
@@ -1,5 +1,5 @@
 import type { UserFile } from '@/executor/types'
-import type { OutputProperty, ToolResponse } from '@/tools/types'
+import type { OutputProperty, ToolFileData, ToolResponse } from '@/tools/types'
 
 /**
  * Shared output property definitions for Slack API responses.
@@ -596,6 +596,7 @@ export interface SlackMessageResponse extends ToolResponse {
     ts: string
     channel: string
     fileCount?: number
+    files?: ToolFileData[]
     // New comprehensive message object
     message: SlackMessage
   }
diff --git a/apps/sim/tools/ssh/download_file.ts b/apps/sim/tools/ssh/download_file.ts
index e7ed207f0..f6171a193 100644
--- a/apps/sim/tools/ssh/download_file.ts
+++ b/apps/sim/tools/ssh/download_file.ts
@@ -80,6 +80,7 @@ export const downloadFileTool: ToolConfig<SSHDownloadFileParams, SSHResponse> =
       success: true,
       output: {
         downloaded: true,
+        file: data.file,
         fileContent: data.content,
         fileName: data.fileName,
         remotePath: data.remotePath,
@@ -91,6 +92,7 @@ export const downloadFileTool: ToolConfig<SSHDownloadFileParams, SSHResponse> =
 
   outputs: {
     downloaded: { type: 'boolean', description: 'Whether the file was downloaded successfully' },
+    file: { type: 'file', description: 'Downloaded file stored in execution files' },
     fileContent: { type: 'string', description: 'File content (base64 encoded for binary files)' },
     fileName: { type: 'string', description: 'Name of the downloaded file' },
     remotePath: { type: 'string', description: 'Source path on the remote server' },
diff --git a/apps/sim/tools/ssh/types.ts b/apps/sim/tools/ssh/types.ts
index e68f6302f..5c4267f98 100644
--- a/apps/sim/tools/ssh/types.ts
+++ b/apps/sim/tools/ssh/types.ts
@@ -1,4 +1,4 @@
-import type { ToolResponse } from '@/tools/types'
+import type { ToolFileData, ToolResponse } from '@/tools/types'
 
 // Base SSH connection configuration
 export interface SSHConnectionConfig {
@@ -149,6 +149,7 @@ export interface SSHResponse extends ToolResponse {
 
     uploaded?: boolean
     downloaded?: boolean
+    file?: ToolFileData
     fileContent?: string
     fileName?: string
     remotePath?: string
diff --git a/apps/sim/tools/stagehand/agent.ts b/apps/sim/tools/stagehand/agent.ts
index f3d055a8e..7884b4575 100644
--- a/apps/sim/tools/stagehand/agent.ts
+++ b/apps/sim/tools/stagehand/agent.ts
@@ -1,4 +1,5 @@
 import { createLogger } from '@sim/logger'
+import { sanitizeUrlForLog } from '@/lib/core/utils/logging'
 import type { StagehandAgentParams, StagehandAgentResponse } from '@/tools/stagehand/types'
 import { STAGEHAND_AGENT_RESULT_OUTPUT_PROPERTIES } from '@/tools/stagehand/types'
 import type { ToolConfig } from '@/tools/types'
@@ -61,7 +62,9 @@ export const agentTool: ToolConfig<StagehandAgentParams, StagehandAgentResponse>
       let startUrl = params.startUrl
       if (startUrl && !startUrl.match(/^https?:\/\//i)) {
         startUrl = `https://${startUrl.trim()}`
-        logger.info(`Normalized URL from ${params.startUrl} to ${startUrl}`)
+        logger.info(
+          `Normalized URL from ${sanitizeUrlForLog(params.startUrl)} to ${sanitizeUrlForLog(startUrl)}`
+        )
       }
 
       return {
diff --git a/apps/sim/tools/supabase/types.ts b/apps/sim/tools/supabase/types.ts
index b26e065b4..cf2ca9c00 100644
--- a/apps/sim/tools/supabase/types.ts
+++ b/apps/sim/tools/supabase/types.ts
@@ -1,3 +1,4 @@
+import type { UserFile } from '@/executor/types'
 import type { OutputProperty, ToolResponse } from '@/tools/types'
 
 /**
@@ -441,7 +442,7 @@ export interface SupabaseStorageUploadParams {
   bucket: string
   fileName: string
   path?: string
-  fileData: any // UserFile object (basic mode) or string (advanced mode: base64/plain text)
+  fileData: UserFile | string
   contentType?: string
   upsert?: boolean
 }
diff --git a/apps/sim/tools/telegram/send_document.ts b/apps/sim/tools/telegram/send_document.ts
index a9800e809..85c3724a8 100644
--- a/apps/sim/tools/telegram/send_document.ts
+++ b/apps/sim/tools/telegram/send_document.ts
@@ -75,6 +75,7 @@ export const telegramSendDocumentTool: ToolConfig<
 
   outputs: {
     message: { type: 'string', description: 'Success or error message' },
+    files: { type: 'file[]', description: 'Files attached to the message' },
     data: {
       type: 'object',
       description: 'Telegram message data including document',
diff --git a/apps/sim/tools/telegram/types.ts b/apps/sim/tools/telegram/types.ts
index 0e54deeb4..b7a887856 100644
--- a/apps/sim/tools/telegram/types.ts
+++ b/apps/sim/tools/telegram/types.ts
@@ -1,5 +1,5 @@
 import type { UserFile } from '@/executor/types'
-import type { ToolResponse } from '@/tools/types'
+import type { ToolFileData, ToolResponse } from '@/tools/types'
 
 export interface TelegramMessage {
   message_id: number
@@ -167,6 +167,7 @@ export interface TelegramSendDocumentResponse extends ToolResponse {
   output: {
     message: string
     data?: TelegramMedia
+    files?: ToolFileData[]
   }
 }
 
diff --git a/apps/sim/tools/wordpress/types.ts b/apps/sim/tools/wordpress/types.ts
index fbb948335..595e9e3e6 100644
--- a/apps/sim/tools/wordpress/types.ts
+++ b/apps/sim/tools/wordpress/types.ts
@@ -1,4 +1,5 @@
 // Common types for WordPress REST API tools
+import type { UserFile } from '@/executor/types'
 import type { ToolResponse } from '@/tools/types'
 
 // Common parameters for all WordPress tools (WordPress.com OAuth)
@@ -254,7 +255,7 @@ export interface WordPressListPagesResponse extends ToolResponse {
 
 // Upload Media
 export interface WordPressUploadMediaParams extends WordPressBaseParams {
-  file: any // UserFile object from file upload
+  file: UserFile
   filename?: string // Optional filename override
   title?: string
   caption?: string
diff --git a/apps/sim/triggers/microsoftteams/webhook.ts b/apps/sim/triggers/microsoftteams/webhook.ts
index abec61982..1f17a7719 100644
--- a/apps/sim/triggers/microsoftteams/webhook.ts
+++ b/apps/sim/triggers/microsoftteams/webhook.ts
@@ -98,7 +98,7 @@ export const microsoftTeamsWebhookTrigger: TriggerConfig = {
     },
     message: {
       raw: {
-        attachments: { type: 'file[]', description: 'Array of attachments' },
+        attachments: { type: 'json', description: 'Array of attachments' },
         channelData: {
           team: { id: { type: 'string', description: 'Team ID' } },
           tenant: { id: { type: 'string', description: 'Tenant ID' } },