diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx
index 90cababca5b..a8d6a80ca83 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx
@@ -900,7 +900,11 @@ export function KnowledgeBase({
               onClick={() => setShowConnectorsModal(true)}
               className='flex shrink-0 cursor-pointer items-center gap-1.5 rounded-md px-2 py-1 text-[var(--text-secondary)] text-caption shadow-[inset_0_0_0_1px_var(--border)] transition-colors hover-hover:bg-[var(--surface-3)]'
             >
-              {ConnectorIcon && <ConnectorIcon className='h-[14px] w-[14px]' />}
+              {connector.status === 'syncing' ? (
+                <Loader2 className='h-[14px] w-[14px] animate-spin' />
+              ) : (
+                ConnectorIcon && <ConnectorIcon className='h-[14px] w-[14px]' />
+              )}
               {def?.name || connector.connectorType}
             </button>
           )
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/add-connector-modal/add-connector-modal.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/add-connector-modal/add-connector-modal.tsx
index 5144ce5d8ab..9e266ec4e80 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/add-connector-modal/add-connector-modal.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/add-connector-modal/add-connector-modal.tsx
@@ -19,21 +19,17 @@ import {
   ModalHeader,
   Tooltip,
 } from '@/components/emcn'
-import { useSession } from '@/lib/auth/auth-client'
-import { consumeOAuthReturnContext, writeOAuthReturnContext } from '@/lib/credentials/client-state'
-import {
-  getCanonicalScopesForProvider,
-  getProviderIdFromServiceId,
-  type OAuthProvider,
-} from '@/lib/oauth'
+import { consumeOAuthReturnContext } from '@/lib/credentials/client-state'
+import { getProviderIdFromServiceId, type OAuthProvider } from '@/lib/oauth'
 import { ConnectorSelectorField } from '@/app/workspace/[workspaceId]/knowledge/[id]/components/add-connector-modal/components/connector-selector-field'
-import { OAuthRequiredModal } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/oauth-required-modal'
+import { ConnectCredentialModal } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/connect-credential-modal'
 import { getDependsOnFields } from '@/blocks/utils'
 import { CONNECTOR_REGISTRY } from '@/connectors/registry'
 import type { ConnectorConfig, ConnectorConfigField } from '@/connectors/types'
 import { useCreateConnector } from '@/hooks/queries/kb/connectors'
 import { useOAuthCredentials } from '@/hooks/queries/oauth/oauth-credentials'
 import type { SelectorKey } from '@/hooks/selectors/types'
+import { useCredentialRefreshTriggers } from '@/hooks/use-credential-refresh-triggers'
 
 const SYNC_INTERVALS = [
   { label: 'Every hour', value: 60 },
@@ -69,7 +65,6 @@ export function AddConnectorModal({ open, onOpenChange, knowledgeBaseId }: AddCo
   const [searchTerm, setSearchTerm] = useState('')
 
   const { workspaceId } = useParams<{ workspaceId: string }>()
-  const { data: session } = useSession()
   const { mutate: createConnector, isPending: isCreating } = useCreateConnector()
 
   const connectorConfig = selectedType ? CONNECTOR_REGISTRY[selectedType] : null
@@ -82,10 +77,16 @@ export function AddConnectorModal({ open, onOpenChange, knowledgeBaseId }: AddCo
     [connectorConfig]
   )
 
-  const { data: credentials = [], isLoading: credentialsLoading } = useOAuthCredentials(
-    connectorProviderId ?? undefined,
-    { enabled: Boolean(connectorConfig) && !isApiKeyMode, workspaceId }
-  )
+  const {
+    data: credentials = [],
+    isLoading: credentialsLoading,
+    refetch: refetchCredentials,
+  } = useOAuthCredentials(connectorProviderId ?? undefined, {
+    enabled: Boolean(connectorConfig) && !isApiKeyMode,
+    workspaceId,
+  })
+
+  useCredentialRefreshTriggers(refetchCredentials, connectorProviderId ?? '', workspaceId)
 
   const effectiveCredentialId =
     selectedCredentialId ?? (credentials.length === 1 ? credentials[0].id : null)
@@ -263,51 +264,9 @@ export function AddConnectorModal({ open, onOpenChange, knowledgeBaseId }: AddCo
     )
   }
 
-  const handleConnectNewAccount = useCallback(async () => {
-    if (!connectorConfig || !connectorProviderId || !workspaceId) return
-
-    const userName = session?.user?.name
-    const integrationName = connectorConfig.name
-    const displayName = userName ? `${userName}'s ${integrationName}` : integrationName
-
-    try {
-      const res = await fetch('/api/credentials/draft', {
-        method: 'POST',
-        headers: { 'Content-Type': 'application/json' },
-        body: JSON.stringify({
-          workspaceId,
-          providerId: connectorProviderId,
-          displayName,
-        }),
-      })
-      if (!res.ok) {
-        setError('Failed to prepare credential. Please try again.')
-        return
-      }
-    } catch {
-      setError('Failed to prepare credential. Please try again.')
-      return
-    }
-
-    writeOAuthReturnContext({
-      origin: 'kb-connectors',
-      knowledgeBaseId,
-      displayName,
-      providerId: connectorProviderId,
-      preCount: credentials.length,
-      workspaceId,
-      requestedAt: Date.now(),
-    })
-
+  const handleConnectNewAccount = useCallback(() => {
     setShowOAuthModal(true)
-  }, [
-    connectorConfig,
-    connectorProviderId,
-    workspaceId,
-    session?.user?.name,
-    knowledgeBaseId,
-    credentials.length,
-  ])
+  }, [])
 
   const filteredEntries = useMemo(() => {
     const term = searchTerm.toLowerCase().trim()
@@ -396,40 +355,40 @@ export function AddConnectorModal({ open, onOpenChange, knowledgeBaseId }: AddCo
                 ) : (
                   <div className='flex flex-col gap-2'>
                     <Label>Account</Label>
-                    {credentialsLoading ? (
-                      <div className='flex items-center gap-2 text-[var(--text-muted)] text-small'>
-                        <Loader2 className='h-4 w-4 animate-spin' />
-                        Loading credentials...
-                      </div>
-                    ) : (
-                      <Combobox
-                        size='sm'
-                        options={[
-                          ...credentials.map(
-                            (cred): ComboboxOption => ({
-                              label: cred.name || cred.provider,
-                              value: cred.id,
-                              icon: connectorConfig.icon,
-                            })
-                          ),
-                          {
-                            label: 'Connect new account',
-                            value: '__connect_new__',
-                            icon: Plus,
-                            onSelect: () => {
-                              void handleConnectNewAccount()
-                            },
+                    <Combobox
+                      size='sm'
+                      options={[
+                        ...credentials.map(
+                          (cred): ComboboxOption => ({
+                            label: cred.name || cred.provider,
+                            value: cred.id,
+                            icon: connectorConfig.icon,
+                          })
+                        ),
+                        {
+                          label:
+                            credentials.length > 0
+                              ? `Connect another ${connectorConfig.name} account`
+                              : `Connect ${connectorConfig.name} account`,
+                          value: '__connect_new__',
+                          icon: Plus,
+                          onSelect: () => {
+                            void handleConnectNewAccount()
                           },
-                        ]}
-                        value={effectiveCredentialId ?? undefined}
-                        onChange={(value) => setSelectedCredentialId(value)}
-                        placeholder={
-                          credentials.length === 0
-                            ? `No ${connectorConfig.name} accounts`
-                            : 'Select account'
-                        }
-                      />
-                    )}
+                        },
+                      ]}
+                      value={effectiveCredentialId ?? undefined}
+                      onChange={(value) => setSelectedCredentialId(value)}
+                      onOpenChange={(isOpen) => {
+                        if (isOpen) void refetchCredentials()
+                      }}
+                      placeholder={
+                        credentials.length === 0
+                          ? `No ${connectorConfig.name} accounts`
+                          : 'Select account'
+                      }
+                      isLoading={credentialsLoading}
+                    />
                   </div>
                 )}
 
@@ -590,20 +549,23 @@ export function AddConnectorModal({ open, onOpenChange, knowledgeBaseId }: AddCo
           )}
         </ModalContent>
       </Modal>
-      {connectorConfig && connectorConfig.auth.mode === 'oauth' && connectorProviderId && (
-        <OAuthRequiredModal
-          isOpen={showOAuthModal}
-          onClose={() => {
-            consumeOAuthReturnContext()
-            setShowOAuthModal(false)
-          }}
-          provider={connectorProviderId}
-          toolName={connectorConfig.name}
-          requiredScopes={getCanonicalScopesForProvider(connectorProviderId)}
-          newScopes={[]}
-          serviceId={connectorConfig.auth.provider}
-        />
-      )}
+      {showOAuthModal &&
+        connectorConfig &&
+        connectorConfig.auth.mode === 'oauth' &&
+        connectorProviderId && (
+          <ConnectCredentialModal
+            isOpen={showOAuthModal}
+            onClose={() => {
+              consumeOAuthReturnContext()
+              setShowOAuthModal(false)
+            }}
+            provider={connectorProviderId}
+            serviceId={connectorConfig.auth.provider}
+            workspaceId={workspaceId}
+            knowledgeBaseId={knowledgeBaseId}
+            credentialCount={credentials.length}
+          />
+        )}
     </>
   )
 }
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/connectors-section/connectors-section.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/connectors-section/connectors-section.tsx
index f7eeac07c8b..37049a212d2 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/connectors-section/connectors-section.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/connectors-section/connectors-section.tsx
@@ -36,6 +36,7 @@ import {
 } from '@/lib/oauth'
 import { getMissingRequiredScopes } from '@/lib/oauth/utils'
 import { EditConnectorModal } from '@/app/workspace/[workspaceId]/knowledge/[id]/components/edit-connector-modal/edit-connector-modal'
+import { ConnectCredentialModal } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/connect-credential-modal'
 import { OAuthRequiredModal } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/oauth-required-modal'
 import { CONNECTOR_REGISTRY } from '@/connectors/registry'
 import type { ConnectorData, SyncLogData } from '@/hooks/queries/kb/connectors'
@@ -46,6 +47,7 @@ import {
   useUpdateConnector,
 } from '@/hooks/queries/kb/connectors'
 import { useOAuthCredentials } from '@/hooks/queries/oauth/oauth-credentials'
+import { useCredentialRefreshTriggers } from '@/hooks/use-credential-refresh-triggers'
 
 const logger = createLogger('ConnectorsSection')
 
@@ -328,11 +330,16 @@ function ConnectorCard({
   const requiredScopes =
     connectorDef?.auth.mode === 'oauth' ? (connectorDef.auth.requiredScopes ?? []) : []
 
-  const { data: credentials } = useOAuthCredentials(providerId, { workspaceId })
+  const { data: credentials, refetch: refetchCredentials } = useOAuthCredentials(providerId, {
+    workspaceId,
+  })
+
+  useCredentialRefreshTriggers(refetchCredentials, providerId ?? '', workspaceId)
 
   const missingScopes = useMemo(() => {
     if (!credentials || !connector.credentialId) return []
     const credential = credentials.find((c) => c.id === connector.credentialId)
+    if (!credential) return []
     return getMissingRequiredScopes(credential, requiredScopes)
   }, [credentials, connector.credentialId, requiredScopes])
 
@@ -484,15 +491,17 @@ function ConnectorCard({
               <Button
                 variant='active'
                 onClick={() => {
-                  writeOAuthReturnContext({
-                    origin: 'kb-connectors',
-                    knowledgeBaseId,
-                    displayName: connectorDef?.name ?? connector.connectorType,
-                    providerId: providerId!,
-                    preCount: credentials?.length ?? 0,
-                    workspaceId,
-                    requestedAt: Date.now(),
-                  })
+                  if (connector.credentialId) {
+                    writeOAuthReturnContext({
+                      origin: 'kb-connectors',
+                      knowledgeBaseId,
+                      displayName: connectorDef?.name ?? connector.connectorType,
+                      providerId: providerId!,
+                      preCount: credentials?.length ?? 0,
+                      workspaceId,
+                      requestedAt: Date.now(),
+                    })
+                  }
                   setShowOAuthModal(true)
                 }}
                 className='w-full px-2 py-1 font-medium text-caption'
@@ -510,7 +519,22 @@ function ConnectorCard({
         </div>
       )}
 
-      {showOAuthModal && serviceId && providerId && (
+      {showOAuthModal && serviceId && providerId && !connector.credentialId && (
+        <ConnectCredentialModal
+          isOpen={showOAuthModal}
+          onClose={() => {
+            consumeOAuthReturnContext()
+            setShowOAuthModal(false)
+          }}
+          provider={providerId as OAuthProvider}
+          serviceId={serviceId}
+          workspaceId={workspaceId}
+          knowledgeBaseId={knowledgeBaseId}
+          credentialCount={credentials?.length ?? 0}
+        />
+      )}
+
+      {showOAuthModal && serviceId && providerId && connector.credentialId && (
         <OAuthRequiredModal
           isOpen={showOAuthModal}
           onClose={() => {
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/connect-credential-modal.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/connect-credential-modal.tsx
index cc3a2306be8..c6574780423 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/connect-credential-modal.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/components/connect-credential-modal.tsx
@@ -14,6 +14,7 @@ import {
   ModalHeader,
 } from '@/components/emcn'
 import { client } from '@/lib/auth/auth-client'
+import type { OAuthReturnContext } from '@/lib/credentials/client-state'
 import { writeOAuthReturnContext } from '@/lib/credentials/client-state'
 import {
   getCanonicalScopesForProvider,
@@ -27,17 +28,22 @@ import { useCreateCredentialDraft } from '@/hooks/queries/credentials'
 
 const logger = createLogger('ConnectCredentialModal')
 
-export interface ConnectCredentialModalProps {
+interface ConnectCredentialModalBaseProps {
   isOpen: boolean
   onClose: () => void
   provider: OAuthProvider
   serviceId: string
   workspaceId: string
-  workflowId: string
   /** Number of existing credentials for this provider — used to detect a successful new connection. */
   credentialCount: number
 }
 
+export type ConnectCredentialModalProps = ConnectCredentialModalBaseProps &
+  (
+    | { workflowId: string; knowledgeBaseId?: never }
+    | { workflowId?: never; knowledgeBaseId: string }
+  )
+
 export function ConnectCredentialModal({
   isOpen,
   onClose,
@@ -45,6 +51,7 @@ export function ConnectCredentialModal({
   serviceId,
   workspaceId,
   workflowId,
+  knowledgeBaseId,
   credentialCount,
 }: ConnectCredentialModalProps) {
   const [displayName, setDisplayName] = useState('')
@@ -97,15 +104,19 @@ export function ConnectCredentialModal({
     try {
       await createDraft.mutateAsync({ workspaceId, providerId, displayName: trimmedName })
 
-      writeOAuthReturnContext({
-        origin: 'workflow',
-        workflowId,
+      const baseContext = {
         displayName: trimmedName,
         providerId,
         preCount: credentialCount,
         workspaceId,
         requestedAt: Date.now(),
-      })
+      }
+
+      const returnContext: OAuthReturnContext = knowledgeBaseId
+        ? { ...baseContext, origin: 'kb-connectors' as const, knowledgeBaseId }
+        : { ...baseContext, origin: 'workflow' as const, workflowId: workflowId! }
+
+      writeOAuthReturnContext(returnContext)
 
       if (providerId === 'trello') {
         window.location.href = '/api/auth/trello/authorize'
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/credential-selector.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/credential-selector.tsx
index e7915a6f907..26c897cf3d3 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/credential-selector.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/credential-selector/credential-selector.tsx
@@ -7,6 +7,7 @@ import { Button, Combobox } from '@/components/emcn/components'
 import { getSubscriptionAccessState } from '@/lib/billing/client'
 import { getEnv, isTruthy } from '@/lib/core/config/env'
 import { getPollingProviderFromOAuth } from '@/lib/credential-sets/providers'
+import { consumeOAuthReturnContext, writeOAuthReturnContext } from '@/lib/credentials/client-state'
 import {
   getCanonicalScopesForProvider,
   getProviderIdFromServiceId,
@@ -357,7 +358,18 @@ export function CredentialSelector({
           </div>
           <Button
             variant='active'
-            onClick={() => setShowOAuthModal(true)}
+            onClick={() => {
+              writeOAuthReturnContext({
+                origin: 'workflow',
+                workflowId: activeWorkflowId || '',
+                displayName: selectedCredential?.name ?? getProviderName(provider),
+                providerId: effectiveProviderId,
+                preCount: credentials.length,
+                workspaceId,
+                requestedAt: Date.now(),
+              })
+              setShowOAuthModal(true)
+            }}
             className='w-full px-2 py-1 font-medium text-caption'
           >
             Update access
@@ -380,7 +392,10 @@ export function CredentialSelector({
       {showOAuthModal && (
         <OAuthRequiredModal
           isOpen={showOAuthModal}
-          onClose={() => setShowOAuthModal(false)}
+          onClose={() => {
+            consumeOAuthReturnContext()
+            setShowOAuthModal(false)
+          }}
           provider={provider}
           toolName={getProviderName(provider)}
           requiredScopes={getCanonicalScopesForProvider(effectiveProviderId)}
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tool-input/components/tools/credential-selector.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tool-input/components/tools/credential-selector.tsx
index d7dce93c7f9..75db6bedffc 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tool-input/components/tools/credential-selector.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tool-input/components/tools/credential-selector.tsx
@@ -4,6 +4,7 @@ import { createElement, useCallback, useMemo, useRef, useState } from 'react'
 import { ExternalLink } from 'lucide-react'
 import { useParams } from 'next/navigation'
 import { Button, Combobox } from '@/components/emcn/components'
+import { consumeOAuthReturnContext, writeOAuthReturnContext } from '@/lib/credentials/client-state'
 import {
   getCanonicalScopesForProvider,
   getProviderIdFromServiceId,
@@ -222,7 +223,18 @@ export function ToolCredentialSelector({
           </div>
           <Button
             variant='active'
-            onClick={() => setShowOAuthModal(true)}
+            onClick={() => {
+              writeOAuthReturnContext({
+                origin: 'workflow',
+                workflowId: effectiveWorkflowId || '',
+                displayName: selectedCredential?.name ?? getProviderName(provider),
+                providerId: effectiveProviderId,
+                preCount: credentials.length,
+                workspaceId,
+                requestedAt: Date.now(),
+              })
+              setShowOAuthModal(true)
+            }}
             className='w-full px-2 py-1 font-medium text-caption'
           >
             Update access
@@ -245,7 +257,10 @@ export function ToolCredentialSelector({
       {showOAuthModal && (
         <OAuthRequiredModal
           isOpen={showOAuthModal}
-          onClose={() => setShowOAuthModal(false)}
+          onClose={() => {
+            consumeOAuthReturnContext()
+            setShowOAuthModal(false)
+          }}
           provider={provider}
           toolName={getProviderName(provider)}
           requiredScopes={getCanonicalScopesForProvider(effectiveProviderId)}
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/workflow.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/workflow.tsx
index fd69e48bbc8..c1a2b938077 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/workflow.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/workflow.tsx
@@ -19,6 +19,7 @@ import { createLogger } from '@sim/logger'
 import { useShallow } from 'zustand/react/shallow'
 import { useSession } from '@/lib/auth/auth-client'
 import type { OAuthConnectEventDetail } from '@/lib/copilot/tools/client/base-tool'
+import { consumeOAuthReturnContext, writeOAuthReturnContext } from '@/lib/credentials/client-state'
 import type { OAuthProvider } from '@/lib/oauth'
 import { BLOCK_DIMENSIONS, CONTAINER_DIMENSIONS } from '@/lib/workflows/blocks/block-dimensions'
 import { TriggerUtils } from '@/lib/workflows/triggers/triggers'
@@ -478,6 +479,17 @@ const WorkflowContent = React.memo(
       const handleOpenOAuthConnect = (event: Event) => {
         const detail = (event as CustomEvent<OAuthConnectEventDetail>).detail
         if (!detail) return
+
+        writeOAuthReturnContext({
+          origin: 'workflow',
+          workflowId: workflowIdParam,
+          displayName: detail.providerName,
+          providerId: detail.providerId,
+          preCount: 0,
+          workspaceId,
+          requestedAt: Date.now(),
+        })
+
         setOauthModal({
           provider: detail.providerId as OAuthProvider,
           serviceId: detail.serviceId,
@@ -490,7 +502,7 @@ const WorkflowContent = React.memo(
       window.addEventListener('open-oauth-connect', handleOpenOAuthConnect as EventListener)
       return () =>
         window.removeEventListener('open-oauth-connect', handleOpenOAuthConnect as EventListener)
-    }, [])
+    }, [workflowIdParam, workspaceId])
 
     const { diffAnalysis, isShowingDiff, isDiffReady, reapplyDiffMarkers, hasActiveDiff } =
       useWorkflowDiffStore(
@@ -4103,7 +4115,10 @@ const WorkflowContent = React.memo(
           <Suspense fallback={null}>
             <LazyOAuthRequiredModal
               isOpen={true}
-              onClose={() => setOauthModal(null)}
+              onClose={() => {
+                consumeOAuthReturnContext()
+                setOauthModal(null)
+              }}
               provider={oauthModal.provider}
               toolName={oauthModal.providerName}
               serviceId={oauthModal.serviceId}
diff --git a/apps/sim/lib/knowledge/connectors/sync-engine.ts b/apps/sim/lib/knowledge/connectors/sync-engine.ts
index 260ae7fc89c..e62e07179fc 100644
--- a/apps/sim/lib/knowledge/connectors/sync-engine.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-engine.ts
@@ -1,6 +1,7 @@
 import { db } from '@sim/db'
 import {
   document,
+  embedding,
   knowledgeBase,
   knowledgeConnector,
   knowledgeConnectorSyncLog,
@@ -658,6 +659,23 @@ export async function executeSync(
     if (stuckDocs.length > 0) {
       logger.info(`Retrying ${stuckDocs.length} stuck documents`, { connectorId })
       try {
+        const stuckDocIds = stuckDocs.map((doc) => doc.id)
+
+        await db.delete(embedding).where(inArray(embedding.documentId, stuckDocIds))
+
+        await db
+          .update(document)
+          .set({
+            processingStatus: 'pending',
+            processingStartedAt: null,
+            processingCompletedAt: null,
+            processingError: null,
+            chunkCount: 0,
+            tokenCount: 0,
+            characterCount: 0,
+          })
+          .where(inArray(document.id, stuckDocIds))
+
         await processDocumentsWithQueue(
           stuckDocs.map((doc) => ({
             documentId: doc.id,
diff --git a/apps/sim/lib/knowledge/documents/service.ts b/apps/sim/lib/knowledge/documents/service.ts
index 5c802d1e699..1c991b850f7 100644
--- a/apps/sim/lib/knowledge/documents/service.ts
+++ b/apps/sim/lib/knowledge/documents/service.ts
@@ -156,17 +156,12 @@ export async function dispatchDocumentProcessingJob(payload: DocumentJobData): P
     return
   }
 
-  void processDocumentAsync(
+  await processDocumentAsync(
     payload.knowledgeBaseId,
     payload.documentId,
     payload.docData,
     payload.processingOptions
-  ).catch((error) => {
-    logger.error(`[${payload.requestId}] Direct document processing failed`, {
-      documentId: payload.documentId,
-      error: error instanceof Error ? error.message : String(error),
-    })
-  })
+  )
 }
 
 export interface DocumentTagData {
@@ -385,9 +380,27 @@ export async function processDocumentsWithQueue(
     }
   )
 
-  await Promise.all(jobPayloads.map((payload) => dispatchDocumentProcessingJob(payload)))
+  const results = await Promise.allSettled(
+    jobPayloads.map((payload) => dispatchDocumentProcessingJob(payload))
+  )
+
+  const failures = results.filter((r): r is PromiseRejectedResult => r.status === 'rejected')
+  if (failures.length > 0) {
+    logger.error(`[${requestId}] ${failures.length}/${results.length} document dispatches failed`, {
+      errors: failures.map((f) =>
+        f.reason instanceof Error ? f.reason.message : String(f.reason)
+      ),
+    })
+  }
+
+  logger.info(
+    `[${requestId}] Document dispatch complete: ${results.length - failures.length}/${results.length} succeeded`
+  )
+
+  if (failures.length === results.length) {
+    throw new Error(`All ${failures.length} document processing dispatches failed`)
+  }
 
-  logger.info(`[${requestId}] All documents dispatched for processing`)
   return
 }
 
@@ -434,6 +447,7 @@ export async function processDocumentAsync(
       .set({
         processingStatus: 'processing',
         processingStartedAt: new Date(),
+        processingCompletedAt: null,
         processingError: null,
       })
       .where(
@@ -624,8 +638,9 @@ export async function processDocumentAsync(
     logger.info(`[${documentId}] Successfully processed document in ${processingTime}ms`)
   } catch (error) {
     const processingTime = Date.now() - startTime
+    const errorMessage = error instanceof Error ? error.message : 'Unknown error'
     logger.error(`[${documentId}] Failed to process document after ${processingTime}ms:`, {
-      error: error instanceof Error ? error.message : 'Unknown error',
+      error: errorMessage,
       stack: error instanceof Error ? error.stack : undefined,
       filename: docData.filename,
       fileUrl: docData.fileUrl,
@@ -636,10 +651,12 @@ export async function processDocumentAsync(
       .update(document)
       .set({
         processingStatus: 'failed',
-        processingError: error instanceof Error ? error.message : 'Unknown error',
+        processingError: errorMessage,
         processingCompletedAt: new Date(),
       })
       .where(eq(document.id, documentId))
+
+    throw error
   }
 }
 
@@ -1527,7 +1544,7 @@ export async function markDocumentAsFailedTimeout(
     .update(document)
     .set({
       processingStatus: 'failed',
-      processingError: 'Processing timed out - background process may have been terminated',
+      processingError: 'Processing timed out. Please retry or re-sync the connector.',
       processingCompletedAt: now,
     })
     .where(eq(document.id, documentId))
diff --git a/apps/sim/lib/knowledge/embeddings.ts b/apps/sim/lib/knowledge/embeddings.ts
index 1171065c75d..0499c71917c 100644
--- a/apps/sim/lib/knowledge/embeddings.ts
+++ b/apps/sim/lib/knowledge/embeddings.ts
@@ -101,6 +101,8 @@ async function getEmbeddingConfig(
   }
 }
 
+const EMBEDDING_REQUEST_TIMEOUT_MS = 60_000
+
 async function callEmbeddingAPI(inputs: string[], config: EmbeddingConfig): Promise<number[][]> {
   return retryWithExponentialBackoff(
     async () => {
@@ -119,11 +121,15 @@ async function callEmbeddingAPI(inputs: string[], config: EmbeddingConfig): Prom
             ...(useDimensions && { dimensions: EMBEDDING_DIMENSIONS }),
           }
 
+      const controller = new AbortController()
+      const timeout = setTimeout(() => controller.abort(), EMBEDDING_REQUEST_TIMEOUT_MS)
+
       const response = await fetch(config.apiUrl, {
         method: 'POST',
         headers: config.headers,
         body: JSON.stringify(requestBody),
-      })
+        signal: controller.signal,
+      }).finally(() => clearTimeout(timeout))
 
       if (!response.ok) {
         const errorText = await response.text()
diff --git a/apps/sim/lib/oauth/oauth.ts b/apps/sim/lib/oauth/oauth.ts
index ded48dc0800..c0bb54bdc92 100644
--- a/apps/sim/lib/oauth/oauth.ts
+++ b/apps/sim/lib/oauth/oauth.ts
@@ -1504,7 +1504,9 @@ export async function refreshOAuthToken(
       refreshToken: newRefreshToken || refreshToken, // Return new refresh token if available
     }
   } catch (error) {
-    logger.error('Error refreshing token:', { error })
+    logger.error('Error refreshing token:', {
+      error: error instanceof Error ? error.message : String(error),
+    })
     return null
   }
 }
diff --git a/bun.lock b/bun.lock
index 65639871af6..c2663c97fd3 100644
--- a/bun.lock
+++ b/bun.lock
@@ -10,7 +10,7 @@
         "glob": "13.0.0",
         "husky": "9.1.7",
         "lint-staged": "16.0.0",
-        "turbo": "2.8.20",
+        "turbo": "2.9.1",
       },
     },
     "apps/docs": {
@@ -1483,17 +1483,17 @@
 
     "@trigger.dev/sdk": ["@trigger.dev/sdk@4.4.3", "", { "dependencies": { "@opentelemetry/api": "1.9.0", "@opentelemetry/semantic-conventions": "1.36.0", "@trigger.dev/core": "4.4.3", "chalk": "^5.2.0", "cronstrue": "^2.21.0", "debug": "^4.3.4", "evt": "^2.4.13", "slug": "^6.0.0", "ulid": "^2.3.0", "uncrypto": "^0.1.3", "uuid": "^9.0.0", "ws": "^8.11.0" }, "peerDependencies": { "ai": "^4.2.0 || ^5.0.0 || ^6.0.0", "zod": "^3.0.0 || ^4.0.0" }, "optionalPeers": ["ai"] }, "sha512-ghJkak+PTBJJ9HiHMcnahJmzjsgCzYiIHu5Qj5R7I9q5LS6i7mkx169rB/tOE9HLadd4HSu3yYA5DrH4wXhZuw=="],
 
-    "@turbo/darwin-64": ["@turbo/darwin-64@2.8.20", "", { "os": "darwin", "cpu": "x64" }, "sha512-FQ9EX1xMU5nbwjxXxM3yU88AQQ6Sqc6S44exPRroMcx9XZHqqppl5ymJF0Ig/z3nvQNwDmz1Gsnvxubo+nXWjQ=="],
+    "@turbo/darwin-64": ["@turbo/darwin-64@2.9.1", "", { "os": "darwin", "cpu": "x64" }, "sha512-d1zTcIf6VWT7cdfjhi0X36C2PRsUi2HdEwYzVgkLHmuuYtL+1Y1Zu3JdlouoB/NjG2vX3q4NnKLMNhDOEweoIg=="],
 
-    "@turbo/darwin-arm64": ["@turbo/darwin-arm64@2.8.20", "", { "os": "darwin", "cpu": "arm64" }, "sha512-Gpyh9ATFGThD6/s9L95YWY54cizg/VRWl2B67h0yofG8BpHf67DFAh9nuJVKG7bY0+SBJDAo5cMur+wOl9YOYw=="],
+    "@turbo/darwin-arm64": ["@turbo/darwin-arm64@2.9.1", "", { "os": "darwin", "cpu": "arm64" }, "sha512-AwJ4mA++Kpem33Lcov093hS1LrgqbKxqq5FCReoqsA8ayEG6eAJAo8ItDd9qQTdBiXxZH8GHCspLAMIe1t3Xyw=="],
 
-    "@turbo/linux-64": ["@turbo/linux-64@2.8.20", "", { "os": "linux", "cpu": "x64" }, "sha512-p2QxWUYyYUgUFG0b0kR+pPi8t7c9uaVlRtjTTI1AbCvVqkpjUfCcReBn6DgG/Hu8xrWdKLuyQFaLYFzQskZbcA=="],
+    "@turbo/linux-64": ["@turbo/linux-64@2.9.1", "", { "os": "linux", "cpu": "x64" }, "sha512-HT9SjKkjEw9uvlgly/qwCGEm4wOXOwQPSPS+wkg+/O1Qan3F1uU/0PFYzxl3m4lfuV3CP9wr2Dq5dPrUX+B9Ag=="],
 
-    "@turbo/linux-arm64": ["@turbo/linux-arm64@2.8.20", "", { "os": "linux", "cpu": "arm64" }, "sha512-Gn5yjlZGLRZWarLWqdQzv0wMqyBNIdq1QLi48F1oY5Lo9kiohuf7BPQWtWxeNVS2NgJ1+nb/DzK1JduYC4AWOA=="],
+    "@turbo/linux-arm64": ["@turbo/linux-arm64@2.9.1", "", { "os": "linux", "cpu": "arm64" }, "sha512-+4s5GZs3kjxc1KMhLBhoQy4UBkXjOhgidA9ipNllkA4JLivSqUCuOgU1Xbyp6vzYrsqHJ9vvwo/2mXgEtD6ZHg=="],
 
-    "@turbo/windows-64": ["@turbo/windows-64@2.8.20", "", { "os": "win32", "cpu": "x64" }, "sha512-vyaDpYk/8T6Qz5V/X+ihKvKFEZFUoC0oxYpC1sZanK6gaESJlmV3cMRT3Qhcg4D2VxvtC2Jjs9IRkrZGL+exLw=="],
+    "@turbo/windows-64": ["@turbo/windows-64@2.9.1", "", { "os": "win32", "cpu": "x64" }, "sha512-ZO7GCyQd5HV564XWHc9KysjanFfM3DmnWquyEByu+hQMq42g9OMU/fYOCfHS6Xj2aXkIg2FHJeRV+iAck2YrbQ=="],
 
-    "@turbo/windows-arm64": ["@turbo/windows-arm64@2.8.20", "", { "os": "win32", "cpu": "arm64" }, "sha512-voicVULvUV5yaGXo0Iue13BcHGYW3u0VgqSbfQwBaHbpj1zLjYV4KIe+7fYIo6DO8FVUJzxFps3ODCQG/Wy2Qw=="],
+    "@turbo/windows-arm64": ["@turbo/windows-arm64@2.9.1", "", { "os": "win32", "cpu": "arm64" }, "sha512-BjX2fdz38mBb/H94JXrD5cJ+mEq8NmsCbYdC42JzQebJ0X8EdNgyFoEhOydPGViOmaRmhhdZnPZKKn6wahSpcA=="],
 
     "@tweenjs/tween.js": ["@tweenjs/tween.js@23.1.3", "", {}, "sha512-vJmvvwFxYuGnF2axRtPYocag6Clbb5YS7kLL+SO/TeVFzHqDIWrNKYtcsPMibjDx9O+bu+psAy9NKfWklassUA=="],
 
@@ -3629,7 +3629,7 @@
 
     "tunnel-agent": ["tunnel-agent@0.6.0", "", { "dependencies": { "safe-buffer": "^5.0.1" } }, "sha512-McnNiV1l8RYeY8tBgEpuodCC1mLUdbSN+CYBL7kJsJNInOP8UjDDEwdk6Mw60vdLLrr5NHKZhMAOSrR2NZuQ+w=="],
 
-    "turbo": ["turbo@2.8.20", "", { "optionalDependencies": { "@turbo/darwin-64": "2.8.20", "@turbo/darwin-arm64": "2.8.20", "@turbo/linux-64": "2.8.20", "@turbo/linux-arm64": "2.8.20", "@turbo/windows-64": "2.8.20", "@turbo/windows-arm64": "2.8.20" }, "bin": { "turbo": "bin/turbo" } }, "sha512-Rb4qk5YT8RUwwdXtkLpkVhNEe/lor6+WV7S5tTlLpxSz6MjV5Qi8jGNn4gS6NAvrYGA/rNrE6YUQM85sCZUDbQ=="],
+    "turbo": ["turbo@2.9.1", "", { "optionalDependencies": { "@turbo/darwin-64": "2.9.1", "@turbo/darwin-arm64": "2.9.1", "@turbo/linux-64": "2.9.1", "@turbo/linux-arm64": "2.9.1", "@turbo/windows-64": "2.9.1", "@turbo/windows-arm64": "2.9.1" }, "bin": { "turbo": "bin/turbo" } }, "sha512-TO9du8MwLTAKoXcGezekh9cPJabJUb0+8KxtpMR6kXdRASrmJ8qXf2GkVbCREgzbMQakzfNcux9cZtxheDY4RQ=="],
 
     "tweetnacl": ["tweetnacl@0.14.5", "", {}, "sha512-KXXFFdAbFXY4geFIwoyNK+f5Z1b7swfXABfL7HXCmoIWMKU3dmS26672A4EeQtDzLKy7SXmfBu51JolvEKwtGA=="],
 
diff --git a/package.json b/package.json
index 918b80ef331..84fff1afa0b 100644
--- a/package.json
+++ b/package.json
@@ -39,7 +39,7 @@
     "glob": "13.0.0",
     "husky": "9.1.7",
     "lint-staged": "16.0.0",
-    "turbo": "2.8.20"
+    "turbo": "2.9.1"
   },
   "lint-staged": {
     "*.{js,jsx,ts,tsx,json,css,scss}": [