diff --git a/apps/sim/app/api/webhooks/route.ts b/apps/sim/app/api/webhooks/route.ts
index 61f8d30c54d..22468160cb5 100644
--- a/apps/sim/app/api/webhooks/route.ts
+++ b/apps/sim/app/api/webhooks/route.ts
@@ -33,6 +33,7 @@ import {
   shouldRecreateExternalWebhookSubscription,
 } from '@/lib/webhooks/provider-subscriptions'
 import { getProviderHandler } from '@/lib/webhooks/providers'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import { mergeNonUserFields } from '@/lib/webhooks/utils'
 import { findConflictingWebhookPathOwner } from '@/lib/webhooks/utils.server'
 import { listAccessibleWorkspaceRowsForUser } from '@/lib/workspaces/utils'
@@ -573,13 +574,20 @@ export const POST = withRouteHandler(async (request: NextRequest) => {
           }
         }
       } catch (err) {
-        logger.error(`[${requestId}] Error creating external webhook subscription`, err)
+        const isConfigurationError = err instanceof WebhookDeploymentConfigurationError
+        if (isConfigurationError) {
+          logger.warn(`[${requestId}] Rejected webhook trigger configuration`, {
+            error: err.message,
+          })
+        } else {
+          logger.error(`[${requestId}] Error creating external webhook subscription`, err)
+        }
         return NextResponse.json(
           {
             error: 'Failed to create external webhook subscription',
             details: getErrorMessage(err, 'Unknown error'),
           },
-          { status: 500 }
+          { status: isConfigurationError ? 400 : 500 }
         )
       }
     } else {
diff --git a/apps/sim/lib/webhooks/providers/airtable.ts b/apps/sim/lib/webhooks/providers/airtable.ts
index 63f609e2ee3..0c9a2ccbc03 100644
--- a/apps/sim/lib/webhooks/providers/airtable.ts
+++ b/apps/sim/lib/webhooks/providers/airtable.ts
@@ -1,6 +1,7 @@
 import { db } from '@sim/db'
 import { account, webhook } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
+import { toStringOrNull } from '@sim/utils/coerce'
 import { toRecord } from '@sim/utils/object'
 import { eq } from 'drizzle-orm'
 import { validateAirtableId } from '@/lib/core/security/input-validation'
@@ -14,6 +15,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   FormatInputContext,
@@ -435,30 +437,30 @@ export const airtableHandler: WebhookProviderHandler = {
   }: SubscriptionContext): Promise<SubscriptionResult | undefined> {
     try {
       const config = getProviderConfig(webhookRecord)
-      const { baseId, tableId, includeCellValuesInFieldIds, credentialId } = config as {
-        baseId?: string
-        tableId?: string
+      const { includeCellValuesInFieldIds, credentialId } = config as {
         includeCellValuesInFieldIds?: string
         credentialId?: string
       }
+      const baseId = toStringOrNull(config.baseId)
+      const tableId = toStringOrNull(config.tableId)
 
       if (!baseId || !tableId) {
         logger.warn(`[${requestId}] Missing baseId or tableId for Airtable webhook creation.`, {
           webhookId: webhookRecord.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Base ID and Table ID are required to create Airtable webhook. Please provide valid Airtable base and table IDs.'
         )
       }
 
       const baseIdValidation = validateAirtableId(baseId, 'app', 'baseId')
       if (!baseIdValidation.isValid) {
-        throw new Error(baseIdValidation.error)
+        throw new WebhookDeploymentConfigurationError(baseIdValidation.error)
       }
 
       const tableIdValidation = validateAirtableId(tableId, 'tbl', 'tableId')
       if (!tableIdValidation.isValid) {
-        throw new Error(tableIdValidation.error)
+        throw new WebhookDeploymentConfigurationError(tableIdValidation.error)
       }
 
       const accessToken = credentialId
@@ -535,6 +537,7 @@ export const airtableHandler: WebhookProviderHandler = {
       )
       return { providerConfigUpdates: { externalId: responseBody.id } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Airtable webhook creation for webhook ${webhookRecord.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/ashby.ts b/apps/sim/lib/webhooks/providers/ashby.ts
index 18315250edf..c42c042414f 100644
--- a/apps/sim/lib/webhooks/providers/ashby.ts
+++ b/apps/sim/lib/webhooks/providers/ashby.ts
@@ -6,6 +6,7 @@ import { isRecordLike, omit, toRecord } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { isPayloadSizeLimitError, readResponseJsonWithLimit } from '@/lib/core/utils/stream-limits'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -235,13 +236,15 @@ export const ashbyHandler: WebhookProviderHandler = {
       }
 
       if (!apiKey) {
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Ashby API Key is required. Please provide your API Key with apiKeysWrite permission in the trigger configuration.'
         )
       }
 
       if (!triggerId) {
-        throw new Error('Trigger ID is required to create Ashby webhook.')
+        throw new WebhookDeploymentConfigurationError(
+          'Trigger ID is required to create Ashby webhook.'
+        )
       }
 
       const { ASHBY_TRIGGER_ACTION_MAP } = await import('@/triggers/ashby/utils')
@@ -322,6 +325,7 @@ export const ashbyHandler: WebhookProviderHandler = {
       )
       return { providerConfigUpdates: { externalId, secretToken } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${ctx.requestId}] Exception during Ashby webhook creation for webhook ${ctx.webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/attio.ts b/apps/sim/lib/webhooks/providers/attio.ts
index c8fde94a4cd..5b3fb473ce8 100644
--- a/apps/sim/lib/webhooks/providers/attio.ts
+++ b/apps/sim/lib/webhooks/providers/attio.ts
@@ -9,6 +9,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -116,7 +117,7 @@ export const attioHandler: WebhookProviderHandler = {
         logger.warn(`[${requestId}] Missing credentialId for Attio webhook creation.`, {
           webhookId: webhookRecord.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Attio account connection required. Please connect your Attio account in the trigger configuration and try again.'
         )
       }
@@ -222,6 +223,7 @@ export const attioHandler: WebhookProviderHandler = {
 
       return { providerConfigUpdates: { externalId: webhookId, webhookSecret: secret || '' } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const message = toError(error).message
       logger.error(
         `[${requestId}] Exception during Attio webhook creation for webhook ${webhookRecord.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/bitbucket.ts b/apps/sim/lib/webhooks/providers/bitbucket.ts
index 2f61d11825c..3ded1288f57 100644
--- a/apps/sim/lib/webhooks/providers/bitbucket.ts
+++ b/apps/sim/lib/webhooks/providers/bitbucket.ts
@@ -11,6 +11,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   EventMatchContext,
@@ -89,7 +90,7 @@ async function resolveBitbucketAccessToken(
   requestId: string
 ): Promise<string> {
   if (!credentialId) {
-    throw new Error(
+    throw new WebhookDeploymentConfigurationError(
       'Bitbucket account connection required. Connect or reconnect Bitbucket in the trigger configuration and try again.'
     )
   }
@@ -112,7 +113,9 @@ function readRequiredConfigString(
 ): string {
   const value = config[key]
   if (typeof value !== 'string' || !value.trim()) {
-    throw new Error(`Bitbucket ${label} is required to manage the repository webhook.`)
+    throw new WebhookDeploymentConfigurationError(
+      `Bitbucket ${label} is required to manage the repository webhook.`
+    )
   }
   return value.trim()
 }
diff --git a/apps/sim/lib/webhooks/providers/calendly.ts b/apps/sim/lib/webhooks/providers/calendly.ts
index d574d6e9534..83445bf7cfc 100644
--- a/apps/sim/lib/webhooks/providers/calendly.ts
+++ b/apps/sim/lib/webhooks/providers/calendly.ts
@@ -1,5 +1,6 @@
 import { createLogger } from '@sim/logger'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   FormatInputContext,
@@ -37,7 +38,7 @@ export const calendlyHandler: WebhookProviderHandler = {
         logger.warn(`[${ctx.requestId}] Missing apiKey for Calendly webhook creation.`, {
           webhookId: ctx.webhook.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Personal Access Token is required to create Calendly webhook. Please provide your Calendly Personal Access Token.'
         )
       }
@@ -46,7 +47,7 @@ export const calendlyHandler: WebhookProviderHandler = {
         logger.warn(`[${ctx.requestId}] Missing organization URI for Calendly webhook creation.`, {
           webhookId: ctx.webhook.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Organization URI is required to create Calendly webhook. Please provide your Organization URI from the "Get Current User" operation.'
         )
       }
@@ -55,7 +56,9 @@ export const calendlyHandler: WebhookProviderHandler = {
         logger.warn(`[${ctx.requestId}] Missing triggerId for Calendly webhook creation.`, {
           webhookId: ctx.webhook.id,
         })
-        throw new Error('Trigger ID is required to create Calendly webhook')
+        throw new WebhookDeploymentConfigurationError(
+          'Trigger ID is required to create Calendly webhook'
+        )
       }
 
       const notificationUrl = getNotificationUrl(ctx.webhook)
@@ -152,6 +155,7 @@ export const calendlyHandler: WebhookProviderHandler = {
       )
       return { providerConfigUpdates: { externalId: webhookId } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${ctx.requestId}] Exception during Calendly webhook creation for webhook ${ctx.webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/checkr.ts b/apps/sim/lib/webhooks/providers/checkr.ts
index 5bfb6b8b180..2896636da71 100644
--- a/apps/sim/lib/webhooks/providers/checkr.ts
+++ b/apps/sim/lib/webhooks/providers/checkr.ts
@@ -8,6 +8,7 @@ import { and, eq, isNull, ne } from 'drizzle-orm'
 import { NextResponse } from 'next/server'
 import { isPayloadSizeLimitError, readResponseJsonWithLimit } from '@/lib/core/utils/stream-limits'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -198,7 +199,9 @@ export const checkrHandler: WebhookProviderHandler = {
     const providerConfig = getProviderConfig(ctx.webhook)
     const apiKey = typeof providerConfig.apiKey === 'string' ? providerConfig.apiKey.trim() : ''
     if (!apiKey) {
-      throw new Error('Checkr API key is required to register the webhook.')
+      throw new WebhookDeploymentConfigurationError(
+        'Checkr API key is required to register the webhook.'
+      )
     }
 
     const notificationUrl = getNotificationUrl(ctx.webhook)
diff --git a/apps/sim/lib/webhooks/providers/clickup.ts b/apps/sim/lib/webhooks/providers/clickup.ts
index 1f97de6ee3f..a411b4be055 100644
--- a/apps/sim/lib/webhooks/providers/clickup.ts
+++ b/apps/sim/lib/webhooks/providers/clickup.ts
@@ -9,6 +9,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   EventMatchContext,
@@ -46,7 +47,7 @@ async function resolveClickUpAccessToken(
   requestId: string
 ): Promise<string> {
   if (!credentialId) {
-    throw new Error(
+    throw new WebhookDeploymentConfigurationError(
       'ClickUp account connection required. Please connect your ClickUp account in the trigger configuration and try again.'
     )
   }
@@ -72,7 +73,9 @@ function parseOptionalNumericId(value: unknown, label: string): number | undefin
   if (!raw) return undefined
   const parsed = Number(raw)
   if (!Number.isInteger(parsed)) {
-    throw new Error(`ClickUp ${label} must be a whole number. Received: ${raw}`)
+    throw new WebhookDeploymentConfigurationError(
+      `ClickUp ${label} must be a whole number. Received: ${raw}`
+    )
   }
   return parsed
 }
@@ -154,7 +157,7 @@ export const clickupHandler: WebhookProviderHandler = {
 
       const workspaceId = parseOptionalStringId(config.triggerWorkspaceId)
       if (!workspaceId) {
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'ClickUp workspace is required. Please select a workspace in the trigger configuration and try again.'
         )
       }
@@ -271,6 +274,7 @@ export const clickupHandler: WebhookProviderHandler = {
 
       return { providerConfigUpdates: { externalId, webhookSecret: secret } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const message = toError(error).message
       logger.error(
         `[${requestId}] Exception during ClickUp webhook creation for webhook ${webhookRecord.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/emailbison.ts b/apps/sim/lib/webhooks/providers/emailbison.ts
index 43dc7c9f999..cdbcce6dfcd 100644
--- a/apps/sim/lib/webhooks/providers/emailbison.ts
+++ b/apps/sim/lib/webhooks/providers/emailbison.ts
@@ -7,6 +7,7 @@ import {
   validateUrlWithDNS,
 } from '@/lib/core/security/input-validation.server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   EventMatchContext,
@@ -127,15 +128,15 @@ export const emailBisonHandler: WebhookProviderHandler = {
     const triggerId = providerConfig.triggerId as string | undefined
 
     if (!apiKey?.trim()) {
-      throw new Error('Email Bison API Key is required.')
+      throw new WebhookDeploymentConfigurationError('Email Bison API Key is required.')
     }
 
     if (!apiBaseUrl?.trim()) {
-      throw new Error('Email Bison Instance URL is required.')
+      throw new WebhookDeploymentConfigurationError('Email Bison Instance URL is required.')
     }
 
     if (!triggerId) {
-      throw new Error('Email Bison trigger ID is required.')
+      throw new WebhookDeploymentConfigurationError('Email Bison trigger ID is required.')
     }
 
     const { getEmailBisonEventTypeForTrigger } = await import('@/triggers/emailbison/utils')
diff --git a/apps/sim/lib/webhooks/providers/errors.ts b/apps/sim/lib/webhooks/providers/errors.ts
index 77fe674ed81..1ce9f67921a 100644
--- a/apps/sim/lib/webhooks/providers/errors.ts
+++ b/apps/sim/lib/webhooks/providers/errors.ts
@@ -1,5 +1,5 @@
 export class WebhookDeploymentConfigurationError extends Error {
-  constructor(message: string) {
+  constructor(message?: string) {
     super(message)
     this.name = 'WebhookDeploymentConfigurationError'
   }
diff --git a/apps/sim/lib/webhooks/providers/fathom.ts b/apps/sim/lib/webhooks/providers/fathom.ts
index 341f50c4592..5299edadeb2 100644
--- a/apps/sim/lib/webhooks/providers/fathom.ts
+++ b/apps/sim/lib/webhooks/providers/fathom.ts
@@ -1,6 +1,7 @@
 import { createLogger } from '@sim/logger'
 import { validateAlphanumericId } from '@/lib/core/security/input-validation'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   SubscriptionContext,
@@ -27,7 +28,7 @@ export const fathomHandler: WebhookProviderHandler = {
         logger.warn(`[${requestId}] Missing apiKey for Fathom webhook creation.`, {
           webhookId: webhook.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Fathom API Key is required. Please provide your API key in the trigger configuration.'
         )
       }
@@ -108,6 +109,7 @@ export const fathomHandler: WebhookProviderHandler = {
 
       return { providerConfigUpdates: { externalId: responseBody.id } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Fathom webhook creation for webhook ${webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/fivetran.ts b/apps/sim/lib/webhooks/providers/fivetran.ts
index 1069e383676..f17ded3337c 100644
--- a/apps/sim/lib/webhooks/providers/fivetran.ts
+++ b/apps/sim/lib/webhooks/providers/fivetran.ts
@@ -8,6 +8,7 @@ import { generateRandomHex } from '@sim/utils/random'
 import { NextResponse } from 'next/server'
 import { isPayloadSizeLimitError, readResponseJsonWithLimit } from '@/lib/core/utils/stream-limits'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -228,7 +229,9 @@ export const fivetranHandler: WebhookProviderHandler = {
     const providerConfig = getProviderConfig(ctx.webhook)
     const credentials = readCredentials(providerConfig)
     if (!credentials) {
-      throw new Error('A Fivetran API key and secret are required to register the webhook.')
+      throw new WebhookDeploymentConfigurationError(
+        'A Fivetran API key and secret are required to register the webhook.'
+      )
     }
 
     const triggerId = readString(providerConfig, 'triggerId')
diff --git a/apps/sim/lib/webhooks/providers/gitlab.ts b/apps/sim/lib/webhooks/providers/gitlab.ts
index 41d71d758e1..cbb99aed691 100644
--- a/apps/sim/lib/webhooks/providers/gitlab.ts
+++ b/apps/sim/lib/webhooks/providers/gitlab.ts
@@ -5,6 +5,7 @@ import { isRecordLike, toRecord } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { secureFetchWithValidation } from '@/lib/core/security/input-validation.server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -182,15 +183,22 @@ export const gitlabHandler: WebhookProviderHandler = {
     const triggerId = config.triggerId as string | undefined
     const host = config.host as string | undefined
 
-    if (!accessToken)
-      throw new Error('GitLab Personal Access Token is required to create the webhook.')
-    if (!projectId) throw new Error('GitLab Project ID is required to create the webhook.')
+    if (!accessToken) {
+      throw new WebhookDeploymentConfigurationError(
+        'GitLab Personal Access Token is required to create the webhook.'
+      )
+    }
+    if (!projectId) {
+      throw new WebhookDeploymentConfigurationError(
+        'GitLab Project ID is required to create the webhook.'
+      )
+    }
 
     try {
       getGitLabApiBase(host)
     } catch (error) {
       if (error instanceof UnsafeGitLabHostError) {
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'GitLab host is invalid. Provide a domain like gitlab.example.com (no protocol, path, or credentials).'
         )
       }
diff --git a/apps/sim/lib/webhooks/providers/grain.ts b/apps/sim/lib/webhooks/providers/grain.ts
index 4270b6babe5..8a7820694d4 100644
--- a/apps/sim/lib/webhooks/providers/grain.ts
+++ b/apps/sim/lib/webhooks/providers/grain.ts
@@ -1,6 +1,7 @@
 import { createLogger } from '@sim/logger'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   EventFilterContext,
@@ -141,7 +142,7 @@ async function createLegacyV1Subscription(params: {
       webhookId,
       triggerId,
     })
-    throw new Error(
+    throw new WebhookDeploymentConfigurationError(
       'Grain view ID is required. Please provide the Grain view ID from GET /_/public-api/views in the trigger configuration.'
     )
   }
@@ -303,7 +304,7 @@ export const grainHandler: WebhookProviderHandler = {
         logger.warn(`[${requestId}] Missing apiKey for Grain webhook creation.`, {
           webhookId: webhook.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Grain API Key is required. Please provide your Grain access token in the trigger configuration.'
         )
       }
@@ -352,6 +353,7 @@ export const grainHandler: WebhookProviderHandler = {
         webhookId: webhook.id as string,
       })
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Grain webhook creation for webhook ${webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/granola.ts b/apps/sim/lib/webhooks/providers/granola.ts
index b8dfb7dcb9f..70905343420 100644
--- a/apps/sim/lib/webhooks/providers/granola.ts
+++ b/apps/sim/lib/webhooks/providers/granola.ts
@@ -2,6 +2,7 @@ import { createLogger } from '@sim/logger'
 import { toRecordOrNull } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -215,7 +216,7 @@ export const granolaHandler: WebhookProviderHandler = {
       logger.warn(`[${requestId}] Missing apiKey for Granola webhook creation.`, {
         webhookId: webhook.id,
       })
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Granola API Key is required. Please provide your Granola API key in the trigger configuration.'
       )
     }
diff --git a/apps/sim/lib/webhooks/providers/instantly.ts b/apps/sim/lib/webhooks/providers/instantly.ts
index ff8089a867e..5b62fad2c42 100644
--- a/apps/sim/lib/webhooks/providers/instantly.ts
+++ b/apps/sim/lib/webhooks/providers/instantly.ts
@@ -5,6 +5,7 @@ import { generateShortId } from '@sim/utils/id'
 import { isRecordLike, toRecord, toRecordOrNull } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -127,11 +128,11 @@ export const instantlyHandler: WebhookProviderHandler = {
     const campaignId = optionalId(providerConfig.triggerCampaignId)
 
     if (!apiKey?.trim()) {
-      throw new Error('Instantly API Key is required.')
+      throw new WebhookDeploymentConfigurationError('Instantly API Key is required.')
     }
 
     if (!triggerId) {
-      throw new Error('Instantly trigger ID is required.')
+      throw new WebhookDeploymentConfigurationError('Instantly trigger ID is required.')
     }
 
     const { getInstantlySubscriptionEventTypeForTrigger } = await import(
diff --git a/apps/sim/lib/webhooks/providers/jotform.ts b/apps/sim/lib/webhooks/providers/jotform.ts
index 39de88e8a9b..97ba5d5e1a9 100644
--- a/apps/sim/lib/webhooks/providers/jotform.ts
+++ b/apps/sim/lib/webhooks/providers/jotform.ts
@@ -4,6 +4,7 @@ import { getErrorMessage } from '@sim/utils/errors'
 import { isRecordLike, toRecord } from '@sim/utils/object'
 import { and, eq, isNull, ne } from 'drizzle-orm'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   FormatInputContext,
@@ -167,7 +168,7 @@ export const jotformHandler: WebhookProviderHandler = {
     const credentials = readCredentials(ctx.webhook)
     if ('error' in credentials) {
       logger.warn(`[${ctx.requestId}] ${credentials.error}`, { webhookId: ctx.webhook.id })
-      throw new Error(credentials.error)
+      throw new WebhookDeploymentConfigurationError(credentials.error)
     }
 
     const notificationUrl = getNotificationUrl(ctx.webhook)
diff --git a/apps/sim/lib/webhooks/providers/lemlist.ts b/apps/sim/lib/webhooks/providers/lemlist.ts
index 24759354a36..46fdfab2d54 100644
--- a/apps/sim/lib/webhooks/providers/lemlist.ts
+++ b/apps/sim/lib/webhooks/providers/lemlist.ts
@@ -1,6 +1,7 @@
 import { createLogger } from '@sim/logger'
 import { validateAlphanumericId } from '@/lib/core/security/input-validation'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   SubscriptionContext,
@@ -23,7 +24,7 @@ export const lemlistHandler: WebhookProviderHandler = {
         logger.warn(`[${requestId}] Missing apiKey for Lemlist webhook creation.`, {
           webhookId: webhook.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Lemlist API Key is required. Please provide your Lemlist API Key in the trigger configuration.'
         )
       }
@@ -108,6 +109,7 @@ export const lemlistHandler: WebhookProviderHandler = {
 
       return { providerConfigUpdates: { externalId: responseBody._id } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Lemlist webhook creation for webhook ${webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/linear.ts b/apps/sim/lib/webhooks/providers/linear.ts
index 5b9af23aaff..5b5d09a341b 100644
--- a/apps/sim/lib/webhooks/providers/linear.ts
+++ b/apps/sim/lib/webhooks/providers/linear.ts
@@ -6,6 +6,7 @@ import { generateId } from '@sim/utils/id'
 import { isRecordLike, toRecord } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -183,7 +184,7 @@ export const linearHandler: WebhookProviderHandler = {
     const apiKey = config.apiKey as string | undefined
     if (!apiKey) {
       logger.warn(`[${ctx.requestId}] Missing API key for Linear webhook ${ctx.webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Linear API key is required. Please provide a valid API key in the trigger configuration.'
       )
     }
diff --git a/apps/sim/lib/webhooks/providers/linq.ts b/apps/sim/lib/webhooks/providers/linq.ts
index 56ac42570fd..5337dee92d3 100644
--- a/apps/sim/lib/webhooks/providers/linq.ts
+++ b/apps/sim/lib/webhooks/providers/linq.ts
@@ -1,6 +1,7 @@
 import { createLogger } from '@sim/logger'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -102,7 +103,7 @@ export const linqHandler: WebhookProviderHandler = {
       logger.warn(`[${requestId}] Missing apiKey for Linq webhook creation.`, {
         webhookId: webhook.id,
       })
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Linq API Key is required. Please provide your Linq API Key in the trigger configuration.'
       )
     }
diff --git a/apps/sim/lib/webhooks/providers/microsoft-teams.ts b/apps/sim/lib/webhooks/providers/microsoft-teams.ts
index fa9e9b632d1..1d441b991b5 100644
--- a/apps/sim/lib/webhooks/providers/microsoft-teams.ts
+++ b/apps/sim/lib/webhooks/providers/microsoft-teams.ts
@@ -20,6 +20,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -603,14 +604,14 @@ export const microsoftTeamsHandler: WebhookProviderHandler = {
 
     if (!credentialId) {
       logger.warn(`[${requestId}] Missing credentialId for Teams chat subscription ${webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Microsoft Teams credentials are required. Please connect your Microsoft account in the trigger configuration.'
       )
     }
 
     if (!chatId) {
       logger.warn(`[${requestId}] Missing chatId for Teams chat subscription ${webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Chat ID is required to create a Teams subscription. Please provide a valid chat ID.'
       )
     }
diff --git a/apps/sim/lib/webhooks/providers/monday.ts b/apps/sim/lib/webhooks/providers/monday.ts
index 3d9ebafc470..9b10e78d1cf 100644
--- a/apps/sim/lib/webhooks/providers/monday.ts
+++ b/apps/sim/lib/webhooks/providers/monday.ts
@@ -8,6 +8,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   FormatInputContext,
@@ -73,19 +74,21 @@ export const mondayHandler: WebhookProviderHandler = {
 
     if (!triggerId) {
       logger.warn(`[${ctx.requestId}] Missing triggerId for Monday webhook ${ctx.webhook.id}`)
-      throw new Error('Trigger type is required for Monday.com webhook creation.')
+      throw new WebhookDeploymentConfigurationError(
+        'Trigger type is required for Monday.com webhook creation.'
+      )
     }
 
     if (!boardId) {
       logger.warn(`[${ctx.requestId}] Missing boardId for Monday webhook ${ctx.webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Board ID is required. Please provide a valid Monday.com board ID in the trigger configuration.'
       )
     }
 
     const boardIdValidation = validateMondayNumericId(boardId, 'boardId')
     if (!boardIdValidation.isValid) {
-      throw new Error(boardIdValidation.error!)
+      throw new WebhookDeploymentConfigurationError(boardIdValidation.error!)
     }
 
     const { MONDAY_EVENT_TYPE_MAP } = await import('@/triggers/monday/utils')
diff --git a/apps/sim/lib/webhooks/providers/pagerduty.ts b/apps/sim/lib/webhooks/providers/pagerduty.ts
index fe15d0d475c..9f3d318d4e9 100644
--- a/apps/sim/lib/webhooks/providers/pagerduty.ts
+++ b/apps/sim/lib/webhooks/providers/pagerduty.ts
@@ -3,6 +3,7 @@ import { createLogger } from '@sim/logger'
 import { safeCompare } from '@sim/security/compare'
 import { toRecord } from '@sim/utils/object'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   EventMatchContext,
@@ -145,8 +146,11 @@ export const pagerdutyHandler: WebhookProviderHandler = {
     const apiKey = config.apiKey as string | undefined
     const triggerId = config.triggerId as string | undefined
 
-    if (!apiKey)
-      throw new Error('PagerDuty API Key is required to create the webhook subscription.')
+    if (!apiKey) {
+      throw new WebhookDeploymentConfigurationError(
+        'PagerDuty API Key is required to create the webhook subscription.'
+      )
+    }
 
     const { getPagerDutyEvents } = await import('@/triggers/pagerduty/utils')
     const res = await fetch(`${PAGERDUTY_API_BASE}/webhook_subscriptions`, {
diff --git a/apps/sim/lib/webhooks/providers/plane.ts b/apps/sim/lib/webhooks/providers/plane.ts
index 8bbf999e555..ff23a291f5a 100644
--- a/apps/sim/lib/webhooks/providers/plane.ts
+++ b/apps/sim/lib/webhooks/providers/plane.ts
@@ -5,6 +5,7 @@ import { getErrorMessage } from '@sim/utils/errors'
 import { isRecordLike, toRecord } from '@sim/utils/object'
 import { secureFetchWithValidation } from '@/lib/core/security/input-validation.server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type { WebhookProviderHandler } from '@/lib/webhooks/providers/types'
 import {
   buildFallbackDeliveryFingerprint,
@@ -40,8 +41,16 @@ async function planeWebhookRequest(
 ) {
   const slug = config.triggerWorkspaceSlug
   const apiKey = config.triggerApiKey
-  if (typeof slug !== 'string' || !slug.trim() || typeof apiKey !== 'string') {
-    throw new Error('Plane workspace slug and API token are required for automatic registration')
+  if (
+    typeof slug !== 'string' ||
+    !slug.trim() ||
+    typeof apiKey !== 'string' ||
+    !apiKey.trim() ||
+    /[\r\n]/.test(apiKey.trim())
+  ) {
+    throw new WebhookDeploymentConfigurationError(
+      'Plane workspace slug and API token are required for automatic registration'
+    )
   }
   const baseUrl = typeof config.triggerBaseUrl === 'string' ? config.triggerBaseUrl : undefined
   return secureFetchWithValidation(
diff --git a/apps/sim/lib/webhooks/providers/resend.ts b/apps/sim/lib/webhooks/providers/resend.ts
index d3045a5ab96..e532540123c 100644
--- a/apps/sim/lib/webhooks/providers/resend.ts
+++ b/apps/sim/lib/webhooks/providers/resend.ts
@@ -1,6 +1,7 @@
 import { createLogger } from '@sim/logger'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -117,7 +118,7 @@ export const resendHandler: WebhookProviderHandler = {
         logger.warn(`[${requestId}] Missing apiKey for Resend webhook creation.`, {
           webhookId: webhook.id,
         })
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Resend API Key is required. Please provide your Resend API Key in the trigger configuration.'
         )
       }
@@ -203,6 +204,7 @@ export const resendHandler: WebhookProviderHandler = {
         },
       }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Resend webhook creation for webhook ${webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/revenuecat.ts b/apps/sim/lib/webhooks/providers/revenuecat.ts
index 54ed8c5e499..14ff48b7010 100644
--- a/apps/sim/lib/webhooks/providers/revenuecat.ts
+++ b/apps/sim/lib/webhooks/providers/revenuecat.ts
@@ -3,6 +3,7 @@ import { safeCompare } from '@sim/security/compare'
 import { generateId } from '@sim/utils/id'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -81,13 +82,15 @@ export const revenueCatHandler: WebhookProviderHandler = {
     }
 
     if (!apiKey) {
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'RevenueCat Secret API key is required to create the webhook. Provide a v2 Secret API key with the project_configuration:integrations:read_write permission.'
       )
     }
 
     if (!projectId) {
-      throw new Error('RevenueCat Project ID is required to create the webhook.')
+      throw new WebhookDeploymentConfigurationError(
+        'RevenueCat Project ID is required to create the webhook.'
+      )
     }
 
     const { REVENUECAT_TRIGGER_TO_API_EVENT_TYPE } = await import('@/triggers/revenuecat/utils')
diff --git a/apps/sim/lib/webhooks/providers/rootly.ts b/apps/sim/lib/webhooks/providers/rootly.ts
index a0f99798541..79bbc026f8a 100644
--- a/apps/sim/lib/webhooks/providers/rootly.ts
+++ b/apps/sim/lib/webhooks/providers/rootly.ts
@@ -4,6 +4,7 @@ import { hmacSha256Hex } from '@sim/security/hmac'
 import { generateId } from '@sim/utils/id'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -144,7 +145,7 @@ export const rootlyHandler: WebhookProviderHandler = {
       }
 
       if (!apiKey) {
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Rootly API key is required. Please provide your Rootly API key in the trigger configuration.'
         )
       }
@@ -221,6 +222,7 @@ export const rootlyHandler: WebhookProviderHandler = {
       )
       return { providerConfigUpdates: { externalId, webhookSecret: signingSecret } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${ctx.requestId}] Exception during Rootly webhook creation for webhook ${ctx.webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/telegram.ts b/apps/sim/lib/webhooks/providers/telegram.ts
index 41a2e03adc3..afd30d9fa93 100644
--- a/apps/sim/lib/webhooks/providers/telegram.ts
+++ b/apps/sim/lib/webhooks/providers/telegram.ts
@@ -7,6 +7,7 @@ import { NextResponse } from 'next/server'
 import { getEffectiveDecryptedEnv } from '@/lib/environment/utils'
 import { resolveBackgroundWebhookEnv } from '@/lib/webhooks/env-resolver'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -147,7 +148,7 @@ export const telegramHandler: WebhookProviderHandler = {
 
     if (!botToken) {
       logger.warn(`[${ctx.requestId}] Missing botToken for Telegram webhook ${ctx.webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Bot token is required to create a Telegram webhook. Please provide a valid Telegram bot token.'
       )
     }
diff --git a/apps/sim/lib/webhooks/providers/typeform.ts b/apps/sim/lib/webhooks/providers/typeform.ts
index aa4f2181c02..492e3c83981 100644
--- a/apps/sim/lib/webhooks/providers/typeform.ts
+++ b/apps/sim/lib/webhooks/providers/typeform.ts
@@ -4,6 +4,7 @@ import { hmacSha256Base64 } from '@sim/security/hmac'
 import { getErrorMessage } from '@sim/utils/errors'
 import { toRecord } from '@sim/utils/object'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   FormatInputContext,
@@ -74,14 +75,14 @@ export const typeformHandler: WebhookProviderHandler = {
 
     if (!formId) {
       logger.warn(`[${ctx.requestId}] Missing formId for Typeform webhook ${ctx.webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Form ID is required to create a Typeform webhook. Please provide a valid form ID.'
       )
     }
 
     if (!apiKey) {
       logger.warn(`[${ctx.requestId}] Missing apiKey for Typeform webhook ${ctx.webhook.id}`)
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Personal Access Token is required to create a Typeform webhook. Please provide your Typeform API key.'
       )
     }
diff --git a/apps/sim/lib/webhooks/providers/vercel.ts b/apps/sim/lib/webhooks/providers/vercel.ts
index 93319493703..2bafc09f8e3 100644
--- a/apps/sim/lib/webhooks/providers/vercel.ts
+++ b/apps/sim/lib/webhooks/providers/vercel.ts
@@ -4,6 +4,7 @@ import { safeCompare } from '@sim/security/compare'
 import { isRecordLike } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -86,7 +87,7 @@ export const vercelHandler: WebhookProviderHandler = {
       const filterProjectIds = providerConfig.filterProjectIds as string | undefined
 
       if (!apiKey) {
-        throw new Error(
+        throw new WebhookDeploymentConfigurationError(
           'Vercel Access Token is required. Please provide your access token in the trigger configuration.'
         )
       }
@@ -199,6 +200,7 @@ export const vercelHandler: WebhookProviderHandler = {
         },
       }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Vercel webhook creation for webhook ${webhook.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/webflow.ts b/apps/sim/lib/webhooks/providers/webflow.ts
index dfbea875859..2a806ce70d0 100644
--- a/apps/sim/lib/webhooks/providers/webflow.ts
+++ b/apps/sim/lib/webhooks/providers/webflow.ts
@@ -7,6 +7,7 @@ import {
   getNotificationUrl,
   getProviderConfig,
 } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   DeleteSubscriptionContext,
   EventFilterContext,
@@ -38,19 +39,23 @@ export const webflowHandler: WebhookProviderHandler = {
         logger.warn(`[${requestId}] Missing siteId for Webflow webhook creation.`, {
           webhookId: webhookRecord.id,
         })
-        throw new Error('Site ID is required to create Webflow webhook')
+        throw new WebhookDeploymentConfigurationError(
+          'Site ID is required to create Webflow webhook'
+        )
       }
 
       const siteIdValidation = validateAlphanumericId(siteId, 'siteId', 100)
       if (!siteIdValidation.isValid) {
-        throw new Error(siteIdValidation.error)
+        throw new WebhookDeploymentConfigurationError(siteIdValidation.error)
       }
 
       if (!triggerId) {
         logger.warn(`[${requestId}] Missing triggerId for Webflow webhook creation.`, {
           webhookId: webhookRecord.id,
         })
-        throw new Error('Trigger type is required to create Webflow webhook')
+        throw new WebhookDeploymentConfigurationError(
+          'Trigger type is required to create Webflow webhook'
+        )
       }
 
       const accessToken = credentialId
@@ -126,6 +131,7 @@ export const webflowHandler: WebhookProviderHandler = {
 
       return { providerConfigUpdates: { externalId: responseBody.id || responseBody._id } }
     } catch (error: unknown) {
+      if (error instanceof WebhookDeploymentConfigurationError) throw error
       const err = error as Error
       logger.error(
         `[${requestId}] Exception during Webflow webhook creation for webhook ${webhookRecord.id}.`,
diff --git a/apps/sim/lib/webhooks/providers/zendesk.ts b/apps/sim/lib/webhooks/providers/zendesk.ts
index 452eec0ef37..c231c654578 100644
--- a/apps/sim/lib/webhooks/providers/zendesk.ts
+++ b/apps/sim/lib/webhooks/providers/zendesk.ts
@@ -4,6 +4,7 @@ import { safeCompare } from '@sim/security/compare'
 import { toRecord } from '@sim/utils/object'
 import { NextResponse } from 'next/server'
 import { getNotificationUrl, getProviderConfig } from '@/lib/webhooks/provider-subscription-utils'
+import { WebhookDeploymentConfigurationError } from '@/lib/webhooks/providers/errors'
 import type {
   AuthContext,
   DeleteSubscriptionContext,
@@ -174,14 +175,26 @@ export const zendeskHandler: WebhookProviderHandler = {
     const apiToken = config.apiToken as string | undefined
     const triggerId = config.triggerId as string | undefined
 
-    if (!subdomain) throw new Error('Zendesk subdomain is required to create the webhook.')
+    if (!subdomain) {
+      throw new WebhookDeploymentConfigurationError(
+        'Zendesk subdomain is required to create the webhook.'
+      )
+    }
     if (!isValidZendeskSubdomain(subdomain)) {
-      throw new Error(
+      throw new WebhookDeploymentConfigurationError(
         'Zendesk subdomain must contain only letters, numbers, and hyphens (e.g. "yourcompany").'
       )
     }
-    if (!email) throw new Error('Zendesk admin email is required to create the webhook.')
-    if (!apiToken) throw new Error('Zendesk API token is required to create the webhook.')
+    if (!email) {
+      throw new WebhookDeploymentConfigurationError(
+        'Zendesk admin email is required to create the webhook.'
+      )
+    }
+    if (!apiToken) {
+      throw new WebhookDeploymentConfigurationError(
+        'Zendesk API token is required to create the webhook.'
+      )
+    }
 
     const { getZendeskSubscriptions } = await import('@/triggers/zendesk/utils')
     const apiBase = zendeskApiBase(subdomain)
diff --git a/apps/sim/lib/workflows/executor/resume-execution.ts b/apps/sim/lib/workflows/executor/resume-execution.ts
index 2f523769258..4a4d6e6311b 100644
--- a/apps/sim/lib/workflows/executor/resume-execution.ts
+++ b/apps/sim/lib/workflows/executor/resume-execution.ts
@@ -8,6 +8,7 @@ import {
 } from '@/lib/billing/core/attribution'
 import { getJobQueue, shouldExecuteInline } from '@/lib/core/async-jobs'
 import type { AsyncExecutionCorrelation } from '@/lib/core/async-jobs/types'
+import { logFailureOnce, markFailureKind } from '@/lib/core/errors/failure-log'
 import { toTriggerMaxDurationSeconds } from '@/lib/core/execution-limits'
 import type { OrchestrationRequestContext } from '@/lib/core/orchestration/types'
 import { generateRequestId } from '@/lib/core/utils/request'
@@ -434,16 +435,14 @@ export async function executeResumeWorkflow({
     return { kind: 'started', executionId: enqueueResult.resumeExecutionId }
   } catch (error) {
     if (error instanceof ResumeWorkflowExecutionError) throw error
-    logger.error(
-      'Resume request failed',
-      projectResolvedSecretDiagnosticError(error, undefined, {
-        workflowId,
-        executionId,
-        contextId,
-      })
-    )
     const statusCode =
       isRecordLike(error) && typeof error.statusCode === 'number' ? error.statusCode : undefined
+    if (statusCode !== undefined && statusCode < 500) markFailureKind(error, 'user')
+    logFailureOnce(logger, 'Resume request failed', error, {
+      executionId,
+      metadata: () =>
+        projectResolvedSecretDiagnosticError(error, undefined, { workflowId, contextId }),
+    })
     if (statusCode !== undefined) {
       throw new ResumeWorkflowExecutionError(statusCode, toError(error).message, statusCode < 500)
     }