diff --git a/.changeset/forty-trains-fail.md b/.changeset/forty-trains-fail.md
new file mode 100644
index 00000000000..f515944f6e3
--- /dev/null
+++ b/.changeset/forty-trains-fail.md
@@ -0,0 +1,20 @@
+---
+'@clerk/shared': patch
+---
+
+Bug fix: In `createCheckAuthorization` allow for old `org_role` format in JWT v1 where `org:` is missing.
+
+Example session claims:
+```json
+{
+  "org_id": "org_xxxx",
+  "org_permissions": [],
+  "org_role": "admin",
+  "org_slug": "test"
+}
+```
+Code
+```ts
+authObject.has({ role: 'org:admin' }) // -> true
+authObject.has({ role: 'admin' }) // -> true
+```
diff --git a/packages/backend/src/tokens/__tests__/authObjects.test.ts b/packages/backend/src/tokens/__tests__/authObjects.test.ts
index 02746b3f143..f79f9b17ddb 100644
--- a/packages/backend/src/tokens/__tests__/authObjects.test.ts
+++ b/packages/backend/src/tokens/__tests__/authObjects.test.ts
@@ -81,6 +81,34 @@ describe('signedInAuthObject', () => {
       expect(authObject.has({ feature: 'org:reservations' })).toBe(false);
       expect(authObject.has({ feature: 'org:impersonation' })).toBe(false);
     });
+
+    it('has() for orgs for old `admin` role', () => {
+      const mockAuthenticateContext = { sessionToken: 'authContextToken' } as AuthenticateContext;
+
+      const partialJwtPayload = {
+        ___raw: 'raw',
+        act: { sub: 'actor' },
+        sid: 'sessionId',
+        org_id: 'orgId',
+        org_role: 'admin',
+        org_slug: 'orgSlug',
+        org_permissions: ['org:f1:read', 'org:f2:manage'],
+        sub: 'userId',
+      } as Partial<JwtPayload>;
+
+      const authObject = signedInAuthObject(mockAuthenticateContext, 'token', partialJwtPayload as JwtPayload);
+
+      expect(authObject.has({ role: 'org:admin' })).toBe(true);
+      expect(authObject.has({ role: 'admin' })).toBe(true);
+      expect(authObject.has({ permission: 'org:f1:read' })).toBe(true);
+      expect(authObject.has({ permission: 'f1:read' })).toBe(true);
+      expect(authObject.has({ permission: 'org:f1' })).toBe(false);
+      expect(authObject.has({ permission: 'org:f2:manage' })).toBe(true);
+      expect(authObject.has({ permission: 'org:f2' })).toBe(false);
+
+      expect(authObject.has({ feature: 'org:reservations' })).toBe(false);
+      expect(authObject.has({ feature: 'org:impersonation' })).toBe(false);
+    });
   });
 
   describe('JWT v2', () => {
@@ -120,6 +148,33 @@ describe('signedInAuthObject', () => {
       expect(authObject.has({ feature: 'org:impersonation' })).toBe(true);
     });
 
+    // This state should not happen since the JWT v2 payload is normalized to remove the `org:` prefix from o.rol.
+    it('has() for orgs with `org:` prefix in role', () => {
+      const mockAuthenticateContext = { sessionToken: 'authContextToken' } as AuthenticateContext;
+
+      const partialJwtPayload = {
+        v: 2,
+        ___raw: 'raw',
+        act: { sub: 'actor' },
+        sid: 'sessionId',
+        fea: 'o:reservations,o:impersonation',
+        o: {
+          id: 'orgId',
+          rol: 'org:admin',
+          slg: 'orgSlug',
+          per: 'read,manage',
+          fpm: '3',
+        },
+
+        sub: 'userId',
+      } as Partial<JwtPayload>;
+
+      const authObject = signedInAuthObject(mockAuthenticateContext, 'token', partialJwtPayload as JwtPayload);
+
+      expect(authObject.has({ role: 'org:admin' })).toBe(true);
+      expect(authObject.has({ role: 'admin' })).toBe(true);
+    });
+
     it('has() for billing with scopes', () => {
       const mockAuthenticateContext = { sessionToken: 'authContextToken' } as AuthenticateContext;
 
diff --git a/packages/shared/src/authorization.ts b/packages/shared/src/authorization.ts
index e8f3bee080e..cb8c7e04428 100644
--- a/packages/shared/src/authorization.ts
+++ b/packages/shared/src/authorization.ts
@@ -70,7 +70,7 @@ const isValidMaxAge = (maxAge: any) => typeof maxAge === 'number' && maxAge > 0;
 const isValidLevel = (level: any) => ALLOWED_LEVELS.has(level);
 const isValidVerificationType = (type: any) => ALLOWED_TYPES.has(type);
 
-const prefixWithOrg = (value: string) => (value.startsWith('org:') ? value : `org:${value}`);
+const prefixWithOrg = (value: string) => value.replace(/^(org:)*/, 'org:');
 
 /**
  * Checks if a user has the required organization-level authorization.
@@ -92,7 +92,7 @@ const checkOrgAuthorization: CheckOrgAuthorization = (params, options) => {
   }
 
   if (params.role) {
-    return orgRole === prefixWithOrg(params.role);
+    return prefixWithOrg(orgRole) === prefixWithOrg(params.role);
   }
   return null;
 };
@@ -236,7 +236,7 @@ type AuthStateOptions = {
 
 /**
  * Shared utility function that centralizes auth state resolution logic,
- * preventing duplication across different packages
+ * preventing duplication across different packages.
  * @internal
  */
 const resolveAuthState = ({