diff --git a/apps/sim/app/api/billing/update-cost/route.ts b/apps/sim/app/api/billing/update-cost/route.ts
index 743ddb17011..f01ec13f939 100644
--- a/apps/sim/app/api/billing/update-cost/route.ts
+++ b/apps/sim/app/api/billing/update-cost/route.ts
@@ -6,6 +6,7 @@ import { recordUsage } from '@/lib/billing/core/usage-log'
 import { checkAndBillOverageThreshold } from '@/lib/billing/threshold-billing'
 import { checkInternalApiKey } from '@/lib/copilot/request/http'
 import { isBillingEnabled } from '@/lib/core/config/feature-flags'
+import { type AtomicClaimResult, billingIdempotency } from '@/lib/core/idempotency/service'
 import { generateRequestId } from '@/lib/core/utils/request'
 
 const logger = createLogger('BillingUpdateCostAPI')
@@ -19,6 +20,7 @@ const UpdateCostSchema = z.object({
   source: z
     .enum(['copilot', 'workspace-chat', 'mcp_copilot', 'mothership_block'])
     .default('copilot'),
+  idempotencyKey: z.string().min(1).optional(),
 })
 
 /**
@@ -28,6 +30,8 @@ const UpdateCostSchema = z.object({
 export async function POST(req: NextRequest) {
   const requestId = generateRequestId()
   const startTime = Date.now()
+  let claim: AtomicClaimResult | null = null
+  let usageCommitted = false
 
   try {
     logger.info(`[${requestId}] Update cost request started`)
@@ -75,9 +79,30 @@ export async function POST(req: NextRequest) {
       )
     }
 
-    const { userId, cost, model, inputTokens, outputTokens, source } = validation.data
+    const { userId, cost, model, inputTokens, outputTokens, source, idempotencyKey } =
+      validation.data
     const isMcp = source === 'mcp_copilot'
 
+    claim = idempotencyKey
+      ? await billingIdempotency.atomicallyClaim('update-cost', idempotencyKey)
+      : null
+
+    if (claim && !claim.claimed) {
+      logger.warn(`[${requestId}] Duplicate billing update rejected`, {
+        idempotencyKey,
+        userId,
+        source,
+      })
+      return NextResponse.json(
+        {
+          success: false,
+          error: 'Duplicate request: idempotency key already processed',
+          requestId,
+        },
+        { status: 409 }
+      )
+    }
+
     logger.info(`[${requestId}] Processing cost update`, {
       userId,
       cost,
@@ -113,6 +138,7 @@ export async function POST(req: NextRequest) {
       ],
       additionalStats,
     })
+    usageCommitted = true
 
     logger.info(`[${requestId}] Recorded usage`, {
       userId,
@@ -149,6 +175,22 @@ export async function POST(req: NextRequest) {
       duration,
     })
 
+    if (claim?.claimed && !usageCommitted) {
+      await billingIdempotency
+        .release(claim.normalizedKey, claim.storageMethod)
+        .catch((releaseErr) => {
+          logger.warn(`[${requestId}] Failed to release idempotency claim`, {
+            error: releaseErr instanceof Error ? releaseErr.message : String(releaseErr),
+            normalizedKey: claim?.normalizedKey,
+          })
+        })
+    } else if (claim?.claimed && usageCommitted) {
+      logger.warn(
+        `[${requestId}] Error occurred after usage committed; retaining idempotency claim to prevent double-billing`,
+        { normalizedKey: claim.normalizedKey }
+      )
+    }
+
     return NextResponse.json(
       {
         success: false,
diff --git a/apps/sim/app/api/tools/google_drive/download/route.ts b/apps/sim/app/api/tools/google_drive/download/route.ts
index e4131423f91..e2733e73abc 100644
--- a/apps/sim/app/api/tools/google_drive/download/route.ts
+++ b/apps/sim/app/api/tools/google_drive/download/route.ts
@@ -13,6 +13,7 @@ import {
   ALL_REVISION_FIELDS,
   DEFAULT_EXPORT_FORMATS,
   GOOGLE_WORKSPACE_MIME_TYPES,
+  VALID_EXPORT_FORMATS,
 } from '@/tools/google_drive/utils'
 
 export const dynamic = 'force-dynamic'
@@ -65,10 +66,12 @@ export async function POST(request: NextRequest) {
     const {
       accessToken,
       fileId,
-      mimeType: exportMimeType,
+      mimeType: rawExportMimeType,
       fileName,
       includeRevisions,
     } = validatedData
+    const exportMimeType =
+      rawExportMimeType && rawExportMimeType !== 'auto' ? rawExportMimeType : null
     const authHeader = `Bearer ${accessToken}`
 
     logger.info(`[${requestId}] Getting file metadata from Google Drive`, { fileId })
@@ -112,6 +115,24 @@ export async function POST(request: NextRequest) {
 
     if (GOOGLE_WORKSPACE_MIME_TYPES.includes(fileMimeType)) {
       const exportFormat = exportMimeType || DEFAULT_EXPORT_FORMATS[fileMimeType] || 'text/plain'
+
+      const validFormats = VALID_EXPORT_FORMATS[fileMimeType]
+      if (validFormats && !validFormats.includes(exportFormat)) {
+        logger.warn(`[${requestId}] Unsupported export format requested`, {
+          fileId,
+          fileMimeType,
+          requestedFormat: exportFormat,
+          validFormats,
+        })
+        return NextResponse.json(
+          {
+            success: false,
+            error: `Export format "${exportFormat}" is not supported for this file type. Supported formats: ${validFormats.join(', ')}`,
+          },
+          { status: 400 }
+        )
+      }
+
       finalMimeType = exportFormat
 
       logger.info(`[${requestId}] Exporting Google Workspace file`, {
diff --git a/apps/sim/app/api/tools/jira/update/route.ts b/apps/sim/app/api/tools/jira/update/route.ts
index 8ad96ba3d0c..2c0f5dcb4ab 100644
--- a/apps/sim/app/api/tools/jira/update/route.ts
+++ b/apps/sim/app/api/tools/jira/update/route.ts
@@ -3,7 +3,7 @@ import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { checkSessionOrInternalAuth } from '@/lib/auth/hybrid'
 import { validateJiraCloudId, validateJiraIssueKey } from '@/lib/core/security/input-validation'
-import { getJiraCloudId, parseAtlassianErrorMessage } from '@/tools/jira/utils'
+import { getJiraCloudId, parseAtlassianErrorMessage, toAdf } from '@/tools/jira/utils'
 
 export const dynamic = 'force-dynamic'
 
@@ -15,14 +15,14 @@ const jiraUpdateSchema = z.object({
   issueKey: z.string().min(1, 'Issue key is required'),
   summary: z.string().optional(),
   title: z.string().optional(),
-  description: z.string().optional(),
+  description: z.union([z.string(), z.record(z.unknown())]).optional(),
   priority: z.string().optional(),
   assignee: z.string().optional(),
   labels: z.array(z.string()).optional(),
   components: z.array(z.string()).optional(),
   duedate: z.string().optional(),
   fixVersions: z.array(z.string()).optional(),
-  environment: z.string().optional(),
+  environment: z.union([z.string(), z.record(z.unknown())]).optional(),
   customFieldId: z.string().optional(),
   customFieldValue: z.string().optional(),
   notifyUsers: z.boolean().optional(),
@@ -91,21 +91,7 @@ export async function PUT(request: NextRequest) {
     }
 
     if (description !== undefined && description !== null && description !== '') {
-      fields.description = {
-        type: 'doc',
-        version: 1,
-        content: [
-          {
-            type: 'paragraph',
-            content: [
-              {
-                type: 'text',
-                text: description,
-              },
-            ],
-          },
-        ],
-      }
+      fields.description = toAdf(description)
     }
 
     if (priority !== undefined && priority !== null && priority !== '') {
@@ -136,21 +122,7 @@ export async function PUT(request: NextRequest) {
     }
 
     if (environment !== undefined && environment !== null && environment !== '') {
-      fields.environment = {
-        type: 'doc',
-        version: 1,
-        content: [
-          {
-            type: 'paragraph',
-            content: [
-              {
-                type: 'text',
-                text: environment,
-              },
-            ],
-          },
-        ],
-      }
+      fields.environment = toAdf(environment)
     }
 
     if (
diff --git a/apps/sim/app/api/tools/jira/write/route.ts b/apps/sim/app/api/tools/jira/write/route.ts
index 6ecb49553c6..d63689b267f 100644
--- a/apps/sim/app/api/tools/jira/write/route.ts
+++ b/apps/sim/app/api/tools/jira/write/route.ts
@@ -2,7 +2,7 @@ import { createLogger } from '@sim/logger'
 import { type NextRequest, NextResponse } from 'next/server'
 import { checkSessionOrInternalAuth } from '@/lib/auth/hybrid'
 import { validateAlphanumericId, validateJiraCloudId } from '@/lib/core/security/input-validation'
-import { getJiraCloudId, parseAtlassianErrorMessage } from '@/tools/jira/utils'
+import { getJiraCloudId, parseAtlassianErrorMessage, toAdf } from '@/tools/jira/utils'
 
 export const dynamic = 'force-dynamic'
 
@@ -85,21 +85,7 @@ export async function POST(request: NextRequest) {
     }
 
     if (description !== undefined && description !== null && description !== '') {
-      fields.description = {
-        type: 'doc',
-        version: 1,
-        content: [
-          {
-            type: 'paragraph',
-            content: [
-              {
-                type: 'text',
-                text: description,
-              },
-            ],
-          },
-        ],
-      }
+      fields.description = toAdf(description)
     }
 
     if (parent !== undefined && parent !== null && parent !== '') {
@@ -144,21 +130,7 @@ export async function POST(request: NextRequest) {
     }
 
     if (environment !== undefined && environment !== null && environment !== '') {
-      fields.environment = {
-        type: 'doc',
-        version: 1,
-        content: [
-          {
-            type: 'paragraph',
-            content: [
-              {
-                type: 'text',
-                text: environment,
-              },
-            ],
-          },
-        ],
-      }
+      fields.environment = toAdf(environment)
     }
 
     if (
diff --git a/apps/sim/background/webhook-execution.test.ts b/apps/sim/background/webhook-execution.test.ts
new file mode 100644
index 00000000000..620c073ac0d
--- /dev/null
+++ b/apps/sim/background/webhook-execution.test.ts
@@ -0,0 +1,68 @@
+/**
+ * @vitest-environment node
+ */
+
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+
+const { mockResolveWebhookRecordProviderConfig } = vi.hoisted(() => ({
+  mockResolveWebhookRecordProviderConfig: vi.fn(),
+}))
+
+vi.mock('@/lib/webhooks/env-resolver', () => ({
+  resolveWebhookRecordProviderConfig: mockResolveWebhookRecordProviderConfig,
+}))
+
+import { resolveWebhookExecutionProviderConfig } from './webhook-execution'
+
+describe('resolveWebhookExecutionProviderConfig', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+  })
+
+  it('returns the resolved webhook record when provider config resolution succeeds', async () => {
+    const webhookRecord = {
+      id: 'webhook-1',
+      providerConfig: {
+        botToken: '{{SLACK_BOT_TOKEN}}',
+      },
+    }
+    const resolvedWebhookRecord = {
+      ...webhookRecord,
+      providerConfig: {
+        botToken: 'xoxb-resolved',
+      },
+    }
+
+    mockResolveWebhookRecordProviderConfig.mockResolvedValue(resolvedWebhookRecord)
+
+    await expect(
+      resolveWebhookExecutionProviderConfig(webhookRecord, 'slack', 'user-1', 'workspace-1')
+    ).resolves.toEqual(resolvedWebhookRecord)
+
+    expect(mockResolveWebhookRecordProviderConfig).toHaveBeenCalledWith(
+      webhookRecord,
+      'user-1',
+      'workspace-1'
+    )
+  })
+
+  it('throws a contextual error when provider config resolution fails', async () => {
+    mockResolveWebhookRecordProviderConfig.mockRejectedValue(new Error('env lookup failed'))
+
+    await expect(
+      resolveWebhookExecutionProviderConfig(
+        {
+          id: 'webhook-1',
+          providerConfig: {
+            botToken: '{{SLACK_BOT_TOKEN}}',
+          },
+        },
+        'slack',
+        'user-1',
+        'workspace-1'
+      )
+    ).rejects.toThrow(
+      'Failed to resolve webhook provider config for slack webhook webhook-1: env lookup failed'
+    )
+  })
+})
diff --git a/apps/sim/background/webhook-execution.ts b/apps/sim/background/webhook-execution.ts
index d78a1401389..843de822019 100644
--- a/apps/sim/background/webhook-execution.ts
+++ b/apps/sim/background/webhook-execution.ts
@@ -11,6 +11,7 @@ import { preprocessExecution } from '@/lib/execution/preprocessing'
 import { LoggingSession } from '@/lib/logs/execution/logging-session'
 import { buildTraceSpans } from '@/lib/logs/execution/trace-spans/trace-spans'
 import { WebhookAttachmentProcessor } from '@/lib/webhooks/attachment-processor'
+import { resolveWebhookRecordProviderConfig } from '@/lib/webhooks/env-resolver'
 import { getProviderHandler } from '@/lib/webhooks/providers'
 import {
   executeWorkflowCore,
@@ -168,6 +169,24 @@ export async function executeWebhookJob(payload: WebhookExecutionPayload) {
   )
 }
 
+export async function resolveWebhookExecutionProviderConfig<
+  T extends { id: string; providerConfig?: unknown },
+>(
+  webhookRecord: T,
+  provider: string,
+  userId: string,
+  workspaceId?: string
+): Promise<T & { providerConfig: Record<string, unknown> }> {
+  try {
+    return await resolveWebhookRecordProviderConfig(webhookRecord, userId, workspaceId)
+  } catch (error) {
+    const errorMessage = error instanceof Error ? error.message : String(error)
+    throw new Error(
+      `Failed to resolve webhook provider config for ${provider} webhook ${webhookRecord.id}: ${errorMessage}`
+    )
+  }
+}
+
 async function resolveCredentialAccountUserId(credentialId: string): Promise<string | undefined> {
   const resolved = await resolveOAuthAccountId(credentialId)
   if (!resolved) {
@@ -300,9 +319,16 @@ async function executeWebhookJobInternal(
       throw new Error(`Webhook record not found: ${payload.webhookId}`)
     }
 
+    const resolvedWebhookRecord = await resolveWebhookExecutionProviderConfig(
+      webhookRecord,
+      payload.provider,
+      workflowRecord.userId,
+      workspaceId
+    )
+
     if (handler.formatInput) {
       const result = await handler.formatInput({
-        webhook: webhookRecord,
+        webhook: resolvedWebhookRecord,
         workflow: { id: payload.workflowId, userId: payload.userId },
         body: payload.body,
         headers: payload.headers,
diff --git a/apps/sim/blocks/blocks/google_drive.ts b/apps/sim/blocks/blocks/google_drive.ts
index 79ab814e04e..6feff2d80f9 100644
--- a/apps/sim/blocks/blocks/google_drive.ts
+++ b/apps/sim/blocks/blocks/google_drive.ts
@@ -316,6 +316,7 @@ Return ONLY the query string - no explanations, no quotes around the whole thing
       title: 'Export Format',
       type: 'dropdown',
       options: [
+        { label: 'Auto (best format for file type)', id: 'auto' },
         { label: 'Plain Text (text/plain)', id: 'text/plain' },
         { label: 'HTML (text/html)', id: 'text/html' },
         { label: 'PDF (application/pdf)', id: 'application/pdf' },
@@ -333,7 +334,8 @@ Return ONLY the query string - no explanations, no quotes around the whole thing
         },
         { label: 'CSV (text/csv)', id: 'text/csv' },
       ],
-      placeholder: 'Optional: Choose export format for Google Docs/Sheets/Slides',
+      value: () => 'auto',
+      placeholder: 'Export format for Google Docs/Sheets/Slides',
       condition: { field: 'operation', value: 'download' },
     },
     {
@@ -867,7 +869,7 @@ Return ONLY the message text - no subject line, no greetings/signatures, no extr
           destinationFolderId: effectiveDestinationFolderId,
           file: normalizedFile,
           pageSize: rest.pageSize ? Number.parseInt(rest.pageSize as string, 10) : undefined,
-          mimeType: mimeType,
+          mimeType: mimeType === 'auto' ? undefined : mimeType,
           type: shareType, // Map shareType to type for share tool
           starred: starredValue,
           sendNotification: sendNotificationValue,
diff --git a/apps/sim/lib/core/idempotency/service.ts b/apps/sim/lib/core/idempotency/service.ts
index a96627bba34..b9920f49e81 100644
--- a/apps/sim/lib/core/idempotency/service.ts
+++ b/apps/sim/lib/core/idempotency/service.ts
@@ -343,6 +343,10 @@ export class IdempotencyService {
     logger.debug(`Stored idempotency result in database: ${normalizedKey}`)
   }
 
+  async release(normalizedKey: string, storageMethod: 'redis' | 'database'): Promise<void> {
+    return this.deleteKey(normalizedKey, storageMethod)
+  }
+
   private async deleteKey(
     normalizedKey: string,
     storageMethod: 'redis' | 'database'
@@ -482,3 +486,8 @@ export const pollingIdempotency = new IdempotencyService({
   ttlSeconds: 60 * 60 * 24 * 3, // 3 days
   retryFailures: true,
 })
+
+export const billingIdempotency = new IdempotencyService({
+  namespace: 'billing',
+  ttlSeconds: 60 * 60, // 1 hour
+})
diff --git a/apps/sim/lib/webhooks/env-resolver.test.ts b/apps/sim/lib/webhooks/env-resolver.test.ts
new file mode 100644
index 00000000000..6da44a32fb3
--- /dev/null
+++ b/apps/sim/lib/webhooks/env-resolver.test.ts
@@ -0,0 +1,74 @@
+/**
+ * @vitest-environment node
+ */
+
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+
+const { mockGetEffectiveDecryptedEnv } = vi.hoisted(() => ({
+  mockGetEffectiveDecryptedEnv: vi.fn(),
+}))
+
+vi.mock('@/lib/environment/utils', () => ({
+  getEffectiveDecryptedEnv: mockGetEffectiveDecryptedEnv,
+}))
+
+import {
+  resolveWebhookProviderConfig,
+  resolveWebhookRecordProviderConfig,
+} from '@/lib/webhooks/env-resolver'
+
+describe('webhook env resolver', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+    mockGetEffectiveDecryptedEnv.mockResolvedValue({
+      SLACK_BOT_TOKEN: 'xoxb-resolved',
+      SLACK_HOST: 'files.slack.com',
+    })
+  })
+
+  it('resolves environment variables inside webhook provider config', async () => {
+    const result = await resolveWebhookProviderConfig(
+      {
+        botToken: '{{SLACK_BOT_TOKEN}}',
+        includeFiles: true,
+        nested: {
+          url: 'https://{{SLACK_HOST}}/api/files.info',
+        },
+      },
+      'user-1',
+      'workspace-1'
+    )
+
+    expect(result).toEqual({
+      botToken: 'xoxb-resolved',
+      includeFiles: true,
+      nested: {
+        url: 'https://files.slack.com/api/files.info',
+      },
+    })
+    expect(mockGetEffectiveDecryptedEnv).toHaveBeenCalledWith('user-1', 'workspace-1')
+  })
+
+  it('returns a cloned webhook record with resolved provider config', async () => {
+    const webhookRecord = {
+      id: 'webhook-1',
+      provider: 'slack',
+      providerConfig: {
+        botToken: '{{SLACK_BOT_TOKEN}}',
+        includeFiles: true,
+      },
+    }
+
+    const result = await resolveWebhookRecordProviderConfig(webhookRecord, 'user-1', 'workspace-1')
+
+    expect(result).toEqual({
+      ...webhookRecord,
+      providerConfig: {
+        botToken: 'xoxb-resolved',
+        includeFiles: true,
+      },
+    })
+    expect(result).not.toBe(webhookRecord)
+    expect(result.providerConfig).not.toBe(webhookRecord.providerConfig)
+  })
+})
diff --git a/apps/sim/lib/webhooks/env-resolver.ts b/apps/sim/lib/webhooks/env-resolver.ts
index 23b83b63493..1537879e7d0 100644
--- a/apps/sim/lib/webhooks/env-resolver.ts
+++ b/apps/sim/lib/webhooks/env-resolver.ts
@@ -20,3 +20,43 @@ export async function resolveEnvVarsInObject<T extends Record<string, unknown>>(
   const envVars = await getEffectiveDecryptedEnv(userId, workspaceId)
   return resolveEnvVarReferences(config, envVars, { deep: true }) as T
 }
+
+/**
+ * Normalizes webhook provider config into a plain object for runtime resolution.
+ */
+export function normalizeWebhookProviderConfig(providerConfig: unknown): Record<string, unknown> {
+  if (providerConfig && typeof providerConfig === 'object' && !Array.isArray(providerConfig)) {
+    return providerConfig as Record<string, unknown>
+  }
+
+  return {}
+}
+
+/**
+ * Resolves environment variable references inside a webhook provider config object.
+ */
+export async function resolveWebhookProviderConfig(
+  providerConfig: unknown,
+  userId: string,
+  workspaceId?: string
+): Promise<Record<string, unknown>> {
+  return resolveEnvVarsInObject(normalizeWebhookProviderConfig(providerConfig), userId, workspaceId)
+}
+
+/**
+ * Clones a webhook-like record with its provider config resolved for runtime use.
+ */
+export async function resolveWebhookRecordProviderConfig<T extends { providerConfig?: unknown }>(
+  webhookRecord: T,
+  userId: string,
+  workspaceId?: string
+): Promise<T & { providerConfig: Record<string, unknown> }> {
+  return {
+    ...webhookRecord,
+    providerConfig: await resolveWebhookProviderConfig(
+      webhookRecord.providerConfig,
+      userId,
+      workspaceId
+    ),
+  }
+}
diff --git a/apps/sim/tools/google_drive/utils.ts b/apps/sim/tools/google_drive/utils.ts
index e58b27eb989..fd046cf1b83 100644
--- a/apps/sim/tools/google_drive/utils.ts
+++ b/apps/sim/tools/google_drive/utils.ts
@@ -111,8 +111,50 @@ export const DEFAULT_EXPORT_FORMATS: Record<string, string> = {
   'application/vnd.google-apps.spreadsheet': 'text/csv',
   'application/vnd.google-apps.presentation': 'text/plain',
   'application/vnd.google-apps.drawing': 'image/png',
-  'application/vnd.google-apps.form': 'application/pdf',
-  'application/vnd.google-apps.script': 'application/json',
+  'application/vnd.google-apps.form': 'application/zip',
+  'application/vnd.google-apps.script': 'application/vnd.google-apps.script+json',
+}
+
+/**
+ * Valid export formats per Google Workspace file type.
+ * See: https://developers.google.com/drive/api/guides/ref-export-formats
+ */
+export const VALID_EXPORT_FORMATS: Record<string, string[]> = {
+  'application/vnd.google-apps.document': [
+    'text/plain',
+    'text/html',
+    'application/pdf',
+    'application/vnd.openxmlformats-officedocument.wordprocessingml.document',
+    'application/vnd.oasis.opendocument.text',
+    'application/rtf',
+    'application/epub+zip',
+    'text/markdown',
+  ],
+  'application/vnd.google-apps.spreadsheet': [
+    'text/csv',
+    'text/tab-separated-values',
+    'application/pdf',
+    'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',
+    'application/vnd.oasis.opendocument.spreadsheet',
+    'application/zip',
+  ],
+  'application/vnd.google-apps.presentation': [
+    'text/plain',
+    'application/pdf',
+    'application/vnd.openxmlformats-officedocument.presentationml.presentation',
+    'application/vnd.oasis.opendocument.presentation',
+    'image/jpeg',
+    'image/png',
+    'image/svg+xml',
+  ],
+  'application/vnd.google-apps.drawing': [
+    'application/pdf',
+    'image/jpeg',
+    'image/png',
+    'image/svg+xml',
+  ],
+  'application/vnd.google-apps.form': ['application/zip'],
+  'application/vnd.google-apps.script': ['application/vnd.google-apps.script+json'],
 }
 
 export const SOURCE_MIME_TYPES: Record<string, string> = {
diff --git a/apps/sim/tools/jira/update.ts b/apps/sim/tools/jira/update.ts
index 75f53fc8765..47e8e26693a 100644
--- a/apps/sim/tools/jira/update.ts
+++ b/apps/sim/tools/jira/update.ts
@@ -42,7 +42,8 @@ export const jiraUpdateTool: ToolConfig<JiraUpdateParams, JiraUpdateResponse> =
       type: 'string',
       required: false,
       visibility: 'user-or-llm',
-      description: 'New description for the issue',
+      description:
+        'New description for the issue. Accepts plain text (auto-wrapped in ADF) or a raw ADF document object',
     },
     priority: {
       type: 'string',
diff --git a/apps/sim/tools/jira/utils.ts b/apps/sim/tools/jira/utils.ts
index d29f9c792b7..02f5a28b0b9 100644
--- a/apps/sim/tools/jira/utils.ts
+++ b/apps/sim/tools/jira/utils.ts
@@ -5,6 +5,51 @@ const logger = createLogger('JiraUtils')
 
 const MAX_ATTACHMENT_SIZE = 50 * 1024 * 1024
 
+/**
+ * Converts a value to ADF format. If the value is already an ADF document object,
+ * it is returned as-is. If it is a plain string, it is wrapped in a single-paragraph ADF doc.
+ */
+export function toAdf(value: string | Record<string, unknown>): Record<string, unknown> {
+  if (typeof value === 'object') {
+    if (value.type === 'doc') {
+      return value
+    }
+    if (value.type && Array.isArray(value.content)) {
+      return { type: 'doc', version: 1, content: [value] }
+    }
+  }
+  if (typeof value === 'string') {
+    try {
+      const parsed = JSON.parse(value)
+      if (typeof parsed === 'object' && parsed !== null && parsed.type === 'doc') {
+        return parsed
+      }
+      if (
+        typeof parsed === 'object' &&
+        parsed !== null &&
+        parsed.type &&
+        Array.isArray(parsed.content)
+      ) {
+        return { type: 'doc', version: 1, content: [parsed] }
+      }
+    } catch {
+      // Not JSON — treat as plain text below
+    }
+  }
+  return {
+    type: 'doc',
+    version: 1,
+    content: [
+      {
+        type: 'paragraph',
+        content: [
+          { type: 'text', text: typeof value === 'string' ? value : JSON.stringify(value) },
+        ],
+      },
+    ],
+  }
+}
+
 /**
  * Extracts plain text from Atlassian Document Format (ADF) content.
  * Returns null if content is falsy.
diff --git a/apps/sim/tools/jira/write.ts b/apps/sim/tools/jira/write.ts
index 42a5f9391c5..db1fac87f86 100644
--- a/apps/sim/tools/jira/write.ts
+++ b/apps/sim/tools/jira/write.ts
@@ -42,7 +42,8 @@ export const jiraWriteTool: ToolConfig<JiraWriteParams, JiraWriteResponse> = {
       type: 'string',
       required: false,
       visibility: 'user-or-llm',
-      description: 'Description for the issue',
+      description:
+        'Description for the issue. Accepts plain text (auto-wrapped in ADF) or a raw ADF document object',
     },
     priority: {
       type: 'string',