diff --git a/apps/api/src/middlewares/org-admin.ts b/apps/api/src/middlewares/org-admin.ts
index 6197c378..8754e017 100644
--- a/apps/api/src/middlewares/org-admin.ts
+++ b/apps/api/src/middlewares/org-admin.ts
@@ -11,6 +11,7 @@ import { isUserOrgAdmin } from '@cio/db/queries/organization';
 export const orgAdminMiddleware = async (c: Context, next: Next) => {
   try {
     const user = c.get('user');
+    console.log('orgAdminMiddleware user', user);
     if (!user) {
       return c.json(
         {
@@ -23,6 +24,7 @@ export const orgAdminMiddleware = async (c: Context, next: Next) => {
     }
 
     const orgId = c.req.header('cio-org-id');
+    console.log('orgAdminMiddleware orgId', orgId);
 
     if (!orgId) {
       return c.json(
@@ -36,6 +38,7 @@ export const orgAdminMiddleware = async (c: Context, next: Next) => {
     }
 
     const isAdmin = await isUserOrgAdmin(orgId, user.id);
+    console.log('orgAdminMiddleware isAdmin', isAdmin);
     if (!isAdmin) {
       return c.json(
         {
diff --git a/apps/api/src/middlewares/org-member.ts b/apps/api/src/middlewares/org-member.ts
index bb4dc28b..930bc3a6 100644
--- a/apps/api/src/middlewares/org-member.ts
+++ b/apps/api/src/middlewares/org-member.ts
@@ -10,6 +10,7 @@ import { getUserOrgRole } from '@cio/db/queries/organization';
  */
 export const orgMemberMiddleware = async (c: Context, next: Next) => {
   try {
+    console.log('user', c.get('user'));
     const user = c.get('user');
     if (!user) {
       return c.json(
diff --git a/apps/api/src/middlewares/org-team-member.ts b/apps/api/src/middlewares/org-team-member.ts
index 6366fde1..dc5222ed 100644
--- a/apps/api/src/middlewares/org-team-member.ts
+++ b/apps/api/src/middlewares/org-team-member.ts
@@ -10,6 +10,8 @@ import { isUserOrgTeamMember } from '@cio/db/queries/organization';
  */
 export const orgTeamMemberMiddleware = async (c: Context, next: Next) => {
   try {
+    console.log('orgTeamMemberMiddleware user', c.get('user'));
+
     const user = c.get('user');
     if (!user) {
       return c.json(
diff --git a/apps/api/src/services/onboarding.ts b/apps/api/src/services/onboarding.ts
index 47320938..bc4f8ead 100644
--- a/apps/api/src/services/onboarding.ts
+++ b/apps/api/src/services/onboarding.ts
@@ -4,6 +4,7 @@ import {
   checkSiteNameExists,
   createOrganization,
   createOrganizationMember,
+  createOrganizationPlan,
   getOrganizationByProfileId,
   getOrganizationCount
 } from '@cio/db/queries';
@@ -11,6 +12,7 @@ import { getProfileById, updateProfile } from '@cio/db/queries/auth';
 
 import { env } from '@api/config/env';
 import { ROLE } from '@cio/utils/constants';
+import { PLAN } from '@cio/utils/plans';
 import { db } from '@cio/db/drizzle';
 import { sendEmail } from '@cio/email';
 
@@ -39,18 +41,40 @@ export async function createOrganizationWithOwner(
 
   // Business Logic: Create org and member in a transaction
   try {
-    const result = await db.transaction(async () => {
-      const organization = await createOrganization({
-        name: input.orgName,
-        siteName: input.siteName
-      });
+    const result = await db.transaction(async (tx) => {
+      const organization = await createOrganization(
+        {
+          name: input.orgName,
+          siteName: input.siteName
+        },
+        tx
+      );
 
-      const member = await createOrganizationMember({
-        organizationId: organization.id,
-        profileId,
-        roleId: ROLE.ADMIN,
-        verified: true
-      });
+      const member = await createOrganizationMember(
+        {
+          organizationId: organization.id,
+          profileId,
+          roleId: ROLE.ADMIN,
+          verified: true
+        },
+        tx
+      );
+
+      // Self-hosted: assign Enterprise plan to the new org
+      if (env.PUBLIC_IS_SELFHOSTED === 'true') {
+        await createOrganizationPlan(
+          {
+            orgId: organization.id,
+            planName: PLAN.ENTERPRISE as 'ENTERPRISE',
+            subscriptionId: `selfhosted-${organization.id}`,
+            triggeredBy: member.id,
+            payload: {},
+            isActive: true,
+            provider: 'selfhosted'
+          },
+          tx
+        );
+      }
 
       return { organization, member };
     });
diff --git a/apps/dashboard/src/lib/utils/services/api/index.ts b/apps/dashboard/src/lib/utils/services/api/index.ts
index a1269ab2..328bb4f0 100644
--- a/apps/dashboard/src/lib/utils/services/api/index.ts
+++ b/apps/dashboard/src/lib/utils/services/api/index.ts
@@ -228,6 +228,7 @@ export function getApiHeaders(
     .join('; ');
 
   console.log('cioCookies', cioCookies);
+  console.log('cookies', cookies.getAll());
   const headers: { cookie: string; 'cio-org-id'?: string } = {
     cookie: cioCookies || ''
   };
diff --git a/packages/db/src/queries/organization/organization.ts b/packages/db/src/queries/organization/organization.ts
index 1507bb18..d8434259 100644
--- a/packages/db/src/queries/organization/organization.ts
+++ b/packages/db/src/queries/organization/organization.ts
@@ -11,7 +11,7 @@ import type {
 import { and, eq, inArray, or, sql } from 'drizzle-orm';
 
 import { ROLE } from '@cio/utils/constants';
-import { db } from '@db/drizzle';
+import { db, type DbOrTxClient } from '@db/drizzle';
 
 export function getOrgIdBySiteName(siteName: string) {
   return db.select().from(schema.organization).where(eq(schema.organization.siteName, siteName)).limit(1);
@@ -82,14 +82,14 @@ export const getOrganizationByProfileId = async (profileId: string): Promise<Org
   }));
 };
 
-export const createOrganization = async (data: TNewOrganization) => {
-  const [organization] = await db.insert(schema.organization).values(data).returning();
+export const createOrganization = async (data: TNewOrganization, dbClient: DbOrTxClient = db) => {
+  const [organization] = await dbClient.insert(schema.organization).values(data).returning();
 
   return organization;
 };
 
-export const createOrganizationMember = async (data: TNewOrganizationmember) => {
-  const [member] = await db.insert(schema.organizationmember).values(data).returning();
+export const createOrganizationMember = async (data: TNewOrganizationmember, dbClient: DbOrTxClient = db) => {
+  const [member] = await dbClient.insert(schema.organizationmember).values(data).returning();
 
   return member;
 };
@@ -534,10 +534,14 @@ export const getOrganizationCount = async (): Promise<number> => {
 /**
  * Creates a new organization plan
  * @param data Organization plan creation data
+ * @param dbClient Optional DB or transaction client for use within transactions
  * @returns Created organization plan record
  */
-export const createOrganizationPlan = async (data: TNewOrganizationPlan): Promise<TOrganizationPlan> => {
-  const [plan] = await db.insert(schema.organizationPlan).values(data).returning();
+export const createOrganizationPlan = async (
+  data: TNewOrganizationPlan,
+  dbClient: DbOrTxClient = db
+): Promise<TOrganizationPlan> => {
+  const [plan] = await dbClient.insert(schema.organizationPlan).values(data).returning();
   return plan;
 };