improvement(billing): duplicate checks for bypasses, logger billing actor consistency, run from block

apps/sim/app/api/organizations/[id]/invitations/[invitationId]/route.ts

@@ -20,6 +20,7 @@ import { z } from 'zod'
 import { getEmailSubject, renderInvitationEmail } from '@/components/emails'
 import { getSession } from '@/lib/auth'
 import { hasAccessControlAccess } from '@/lib/billing'
+import { syncUsageLimitsFromSubscription } from '@/lib/billing/core/usage'
 import { requireStripeClient } from '@/lib/billing/stripe-client'
 import { getBaseUrl } from '@/lib/core/utils/urls'
 import { sendEmail } from '@/lib/messaging/email/mailer'
@@ -501,6 +502,18 @@ export async function PUT(
       }
     }
 
+    if (status === 'accepted') {
+      try {
+        await syncUsageLimitsFromSubscription(session.user.id)
+      } catch (syncError) {
+        logger.error('Failed to sync usage limits after joining org', {
+          userId: session.user.id,
+          organizationId,
+          error: syncError,
+        })
+      }
+    }
+
     logger.info(`Organization invitation ${status}`, {
       organizationId,
       invitationId,

apps/sim/app/api/users/me/subscription/[id]/transfer/route.ts

@@ -5,6 +5,7 @@ import { and, eq } from 'drizzle-orm'
 import { type NextRequest, NextResponse } from 'next/server'
 import { z } from 'zod'
 import { getSession } from '@/lib/auth'
+import { hasActiveSubscription } from '@/lib/billing'
 
 const logger = createLogger('SubscriptionTransferAPI')
 
@@ -88,6 +89,14 @@ export async function POST(request: NextRequest, { params }: { params: Promise<{
       )
     }
 
+    // Check if org already has an active subscription (prevent duplicates)
+    if (await hasActiveSubscription(organizationId)) {
+      return NextResponse.json(
+        { error: 'Organization already has an active subscription' },
+        { status: 409 }
+      )
+    }
+
     await db
       .update(subscription)
       .set({ referenceId: organizationId })

apps/sim/app/api/v1/admin/users/[id]/billing/route.ts

@@ -203,6 +203,10 @@ export const PATCH = withAdminAuthParams<RouteParams>(async (request, context) =
       }
 
       updateData.billingBlocked = body.billingBlocked
+      // Clear the reason when unblocking
+      if (body.billingBlocked === false) {
+        updateData.billingBlockedReason = null
+      }
       updated.push('billingBlocked')
     }
 

apps/sim/app/api/workflows/[id]/execute-from-block/route.ts

@@ -1,13 +1,12 @@
-import { db, workflow as workflowTable } from '@sim/db'
 import { createLogger } from '@sim/logger'
-import { eq } from 'drizzle-orm'
 import { type NextRequest, NextResponse } from 'next/server'
 import { v4 as uuidv4 } from 'uuid'
 import { z } from 'zod'
 import { checkHybridAuth } from '@/lib/auth/hybrid'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { SSE_HEADERS } from '@/lib/core/utils/sse'
 import { markExecutionCancelled } from '@/lib/execution/cancellation'
+import { preprocessExecution } from '@/lib/execution/preprocessing'
 import { LoggingSession } from '@/lib/logs/execution/logging-session'
 import { executeWorkflowCore } from '@/lib/workflows/executor/execution-core'
 import { createSSECallbacks } from '@/lib/workflows/executor/execution-events'
@@ -75,12 +74,31 @@ export async function POST(req: NextRequest, { params }: { params: Promise<{ id:
     const { startBlockId, sourceSnapshot, input } = validation.data
     const executionId = uuidv4()
 
-    const [workflowRecord] = await db
-      .select({ workspaceId: workflowTable.workspaceId, userId: workflowTable.userId })
-      .from(workflowTable)
-      .where(eq(workflowTable.id, workflowId))
-      .limit(1)
+    // Run preprocessing checks (billing, rate limits, usage limits)
+    const preprocessResult = await preprocessExecution({
+      workflowId,
+      userId,
+      triggerType: 'manual',
+      executionId,
+      requestId,
+      checkRateLimit: false, // Manual executions don't rate limit
+      checkDeployment: false, // Run-from-block doesn't require deployment
+    })
+
+    if (!preprocessResult.success) {
+      const { error } = preprocessResult
+      logger.warn(`[${requestId}] Preprocessing failed for run-from-block`, {
+        workflowId,
+        error: error?.message,
+        statusCode: error?.statusCode,
+      })
+      return NextResponse.json(
+        { error: error?.message || 'Execution blocked' },
+        { status: error?.statusCode || 500 }
+      )
+    }
 
+    const workflowRecord = preprocessResult.workflowRecord
     if (!workflowRecord?.workspaceId) {
       return NextResponse.json({ error: 'Workflow not found or has no workspace' }, { status: 404 })
     }
@@ -92,6 +110,7 @@ export async function POST(req: NextRequest, { params }: { params: Promise<{ id:
       workflowId,
       startBlockId,
       executedBlocksCount: sourceSnapshot.executedBlocks.length,
+      billingActorUserId: preprocessResult.actorUserId,
     })
 
     const loggingSession = new LoggingSession(workflowId, executionId, 'manual', requestId)

apps/sim/lib/billing/authorization.ts

@@ -1,20 +1,37 @@
 import { db } from '@sim/db'
 import * as schema from '@sim/db/schema'
+import { createLogger } from '@sim/logger'
 import { and, eq } from 'drizzle-orm'
+import { hasActiveSubscription } from '@/lib/billing'
+
+const logger = createLogger('BillingAuthorization')
 
 /**
  * Check if a user is authorized to manage billing for a given reference ID
  * Reference ID can be either a user ID (individual subscription) or organization ID (team subscription)
+ *
+ * This function also performs duplicate subscription validation for organizations:
+ * - Rejects if an organization already has an active subscription (prevents duplicates)
+ * - Personal subscriptions (referenceId === userId) skip this check to allow upgrades
  */
 export async function authorizeSubscriptionReference(
   userId: string,
   referenceId: string
 ): Promise<boolean> {
-  // User can always manage their own subscriptions
+  // User can always manage their own subscriptions (Pro upgrades, etc.)
   if (referenceId === userId) {
     return true
   }
 
+  // For organizations: check for existing active subscriptions to prevent duplicates
+  if (await hasActiveSubscription(referenceId)) {
+    logger.warn('Blocking checkout - active subscription already exists for organization', {
+      userId,
+      referenceId,
+    })
+    return false
+  }
+
   // Check if referenceId is an organizationId the user has admin rights to
   const members = await db
     .select()

apps/sim/lib/billing/client/upgrade.ts

@@ -25,9 +25,11 @@ export function useSubscriptionUpgrade() {
       }
 
       let currentSubscriptionId: string | undefined
+      let allSubscriptions: any[] = []
       try {
         const listResult = await client.subscription.list()
-        const activePersonalSub = listResult.data?.find(
+        allSubscriptions = listResult.data || []
+        const activePersonalSub = allSubscriptions.find(
           (sub: any) => sub.status === 'active' && sub.referenceId === userId
         )
         currentSubscriptionId = activePersonalSub?.id
@@ -50,6 +52,25 @@ export function useSubscriptionUpgrade() {
           )
 
           if (existingOrg) {
+            // Check if this org already has an active team subscription
+            const existingTeamSub = allSubscriptions.find(
+              (sub: any) =>
+                sub.status === 'active' &&
+                sub.referenceId === existingOrg.id &&
+                (sub.plan === 'team' || sub.plan === 'enterprise')
+            )
+
+            if (existingTeamSub) {
+              logger.warn('Organization already has an active team subscription', {
+                userId,
+                organizationId: existingOrg.id,
+                existingSubscriptionId: existingTeamSub.id,
+              })
+              throw new Error(
+                'This organization already has an active team subscription. Please manage it from the billing settings.'
+              )
+            }
+
             logger.info('Using existing organization for team plan upgrade', {
               userId,
               organizationId: existingOrg.id,

apps/sim/lib/billing/core/plan.ts

@@ -1,5 +1,5 @@
 import { db } from '@sim/db'
-import { member, subscription } from '@sim/db/schema'
+import { member, organization, subscription } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
 import { and, eq, inArray } from 'drizzle-orm'
 import { checkEnterprisePlan, checkProPlan, checkTeamPlan } from '@/lib/billing/subscriptions/utils'
@@ -26,10 +26,22 @@ export async function getHighestPrioritySubscription(userId: string) {
 
     let orgSubs: typeof personalSubs = []
     if (orgIds.length > 0) {
-      orgSubs = await db
-        .select()
-        .from(subscription)
-        .where(and(inArray(subscription.referenceId, orgIds), eq(subscription.status, 'active')))
+      // Verify orgs exist to filter out orphaned subscriptions
+      const existingOrgs = await db
+        .select({ id: organization.id })
+        .from(organization)
+        .where(inArray(organization.id, orgIds))
+
+      const validOrgIds = existingOrgs.map((o) => o.id)
+
+      if (validOrgIds.length > 0) {
+        orgSubs = await db
+          .select()
+          .from(subscription)
+          .where(
+            and(inArray(subscription.referenceId, validOrgIds), eq(subscription.status, 'active'))
+          )
+      }
     }
 
     const allSubs = [...personalSubs, ...orgSubs]

apps/sim/lib/billing/core/subscription.ts

@@ -25,6 +25,28 @@ const logger = createLogger('SubscriptionCore')
 
 export { getHighestPrioritySubscription }
 
+/**
+ * Check if a referenceId (user ID or org ID) has an active subscription
+ * Used for duplicate subscription prevention
+ *
+ * Fails closed: returns true on error to prevent duplicate creation
+ */
+export async function hasActiveSubscription(referenceId: string): Promise<boolean> {
+  try {
+    const [activeSub] = await db
+      .select({ id: subscription.id })
+      .from(subscription)
+      .where(and(eq(subscription.referenceId, referenceId), eq(subscription.status, 'active')))
+      .limit(1)
+
+    return !!activeSub
+  } catch (error) {
+    logger.error('Error checking active subscription', { error, referenceId })
+    // Fail closed: assume subscription exists to prevent duplicate creation
+    return true
+  }
+}
+
 /**
  * Check if user is on Pro plan (direct or via organization)
  */

apps/sim/lib/billing/index.ts

@@ -11,6 +11,7 @@ export {
   getHighestPrioritySubscription as getActiveSubscription,
   getUserSubscriptionState as getSubscriptionState,
   hasAccessControlAccess,
+  hasActiveSubscription,
   hasCredentialSetsAccess,
   hasSSOAccess,
   isEnterpriseOrgAdminOrOwner,
@@ -32,6 +33,11 @@ export {
 } from '@/lib/billing/core/usage'
 export * from '@/lib/billing/credits/balance'
 export * from '@/lib/billing/credits/purchase'
+export {
+  blockOrgMembers,
+  getOrgMemberIds,
+  unblockOrgMembers,
+} from '@/lib/billing/organizations/membership'
 export * from '@/lib/billing/subscriptions/utils'
 export { canEditUsageLimit as canEditLimit } from '@/lib/billing/subscriptions/utils'
 export * from '@/lib/billing/types'

apps/sim/lib/billing/organization.ts

@@ -8,6 +8,7 @@ import {
 } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
 import { and, eq } from 'drizzle-orm'
+import { hasActiveSubscription } from '@/lib/billing'
 import { getPlanPricing } from '@/lib/billing/core/billing'
 import { syncUsageLimitsFromSubscription } from '@/lib/billing/core/usage'
 
@@ -159,6 +160,16 @@ export async function ensureOrganizationForTeamSubscription(
   if (existingMembership.length > 0) {
     const membership = existingMembership[0]
     if (membership.role === 'owner' || membership.role === 'admin') {
+      // Check if org already has an active subscription (prevent duplicates)
+      if (await hasActiveSubscription(membership.organizationId)) {
+        logger.error('Organization already has an active subscription', {
+          userId,
+          organizationId: membership.organizationId,
+          newSubscriptionId: subscription.id,
+        })
+        throw new Error('Organization already has an active subscription')
+      }
+
       logger.info('User already owns/admins an org, using it', {
         userId,
         organizationId: membership.organizationId,

apps/sim/lib/billing/organizations/membership.ts

@@ -15,13 +15,86 @@ import {
   userStats,
 } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
-import { and, eq, sql } from 'drizzle-orm'
+import { and, eq, inArray, isNull, ne, or, sql } from 'drizzle-orm'
 import { syncUsageLimitsFromSubscription } from '@/lib/billing/core/usage'
 import { requireStripeClient } from '@/lib/billing/stripe-client'
 import { validateSeatAvailability } from '@/lib/billing/validation/seat-management'
 
 const logger = createLogger('OrganizationMembership')
 
+export type BillingBlockReason = 'payment_failed' | 'dispute'
+
+/**
+ * Get all member user IDs for an organization
+ */
+export async function getOrgMemberIds(organizationId: string): Promise<string[]> {
+  const members = await db
+    .select({ userId: member.userId })
+    .from(member)
+    .where(eq(member.organizationId, organizationId))
+
+  return members.map((m) => m.userId)
+}
+
+/**
+ * Block all members of an organization for billing reasons
+ * Returns the number of members actually blocked
+ *
+ * Reason priority: dispute > payment_failed
+ * A payment_failed block won't overwrite an existing dispute block
+ */
+export async function blockOrgMembers(
+  organizationId: string,
+  reason: BillingBlockReason
+): Promise<number> {
+  const memberIds = await getOrgMemberIds(organizationId)
+
+  if (memberIds.length === 0) {
+    return 0
+  }
+
+  // Don't overwrite dispute blocks with payment_failed (dispute is higher priority)
+  const whereClause =
+    reason === 'payment_failed'
+      ? and(
+          inArray(userStats.userId, memberIds),
+          or(ne(userStats.billingBlockedReason, 'dispute'), isNull(userStats.billingBlockedReason))
+        )
+      : inArray(userStats.userId, memberIds)
+
+  const result = await db
+    .update(userStats)
+    .set({ billingBlocked: true, billingBlockedReason: reason })
+    .where(whereClause)
+    .returning({ userId: userStats.userId })
+
+  return result.length
+}
+
+/**
+ * Unblock all members of an organization blocked for a specific reason
+ * Only unblocks members blocked for the specified reason (not other reasons)
+ * Returns the number of members actually unblocked
+ */
+export async function unblockOrgMembers(
+  organizationId: string,
+  reason: BillingBlockReason
+): Promise<number> {
+  const memberIds = await getOrgMemberIds(organizationId)
+
+  if (memberIds.length === 0) {
+    return 0
+  }
+
+  const result = await db
+    .update(userStats)
+    .set({ billingBlocked: false, billingBlockedReason: null })
+    .where(and(inArray(userStats.userId, memberIds), eq(userStats.billingBlockedReason, reason)))
+    .returning({ userId: userStats.userId })
+
+  return result.length
+}
+
 export interface RestoreProResult {
   restored: boolean
   usageRestored: boolean