diff --git a/packages/features/pbac/services/__tests__/permission-check.service.test.ts b/packages/features/pbac/services/__tests__/permission-check.service.test.ts
index c415a8dddd01e5..577d2221c4f4ad 100644
--- a/packages/features/pbac/services/__tests__/permission-check.service.test.ts
+++ b/packages/features/pbac/services/__tests__/permission-check.service.test.ts
@@ -147,6 +147,43 @@ describe("PermissionCheckService", () => {
       expect(result).toBe(false);
     });
 
+    it("should fallback to legacy roles when PBAC permission check fails (dogfood)", async () => {
+      const membership = {
+        id: 1,
+        teamId: 1,
+        userId: 1,
+        accepted: true,
+        role: "ADMIN" as MembershipRole,
+        customRoleId: "admin_role",
+        disableImpersonation: false,
+        createdAt: new Date(),
+        updatedAt: new Date(),
+      };
+
+      (MembershipRepository.findUniqueByUserIdAndTeamId as Mock).mockResolvedValueOnce(membership);
+      mockFeaturesRepository.checkIfTeamHasFeature.mockResolvedValueOnce(true);
+      mockRepository.getMembershipByMembershipId.mockResolvedValueOnce({
+        id: membership.id,
+        teamId: membership.teamId,
+        userId: membership.userId,
+        customRoleId: membership.customRoleId,
+        team: { parentId: null },
+      });
+      mockRepository.getOrgMembership.mockResolvedValueOnce(null);
+      mockRepository.checkRolePermission.mockResolvedValueOnce(false); // Permission check fails
+
+      const result = await service.checkPermission({
+        userId: 1,
+        teamId: 1,
+        permission: "eventType.create",
+        fallbackRoles: ["ADMIN", "OWNER"],
+      });
+
+      // Should fallback to role check and pass since user is ADMIN
+      expect(result).toBe(true);
+      expect(mockRepository.checkRolePermission).toHaveBeenCalled();
+    });
+
     it("should return false if PBAC enabled but no customRoleId", async () => {
       const membership = {
         id: 1,
@@ -252,7 +289,7 @@ describe("PermissionCheckService", () => {
       expect(mockRepository.checkRolePermissions).not.toHaveBeenCalled();
     });
 
-    it("should return false when permissions array is empty", async () => {
+    it("should fallback to legacy roles when PBAC permissions check fails (dogfood)", async () => {
       const membership = {
         id: 1,
         teamId: 1,
@@ -265,6 +302,43 @@ describe("PermissionCheckService", () => {
         updatedAt: new Date(),
       };
 
+      (MembershipRepository.findUniqueByUserIdAndTeamId as Mock).mockResolvedValueOnce(membership);
+      mockFeaturesRepository.checkIfTeamHasFeature.mockResolvedValueOnce(true);
+      mockRepository.getMembershipByMembershipId.mockResolvedValueOnce({
+        id: membership.id,
+        teamId: membership.teamId,
+        userId: membership.userId,
+        customRoleId: membership.customRoleId,
+        team: { parentId: null },
+      });
+      mockRepository.getOrgMembership.mockResolvedValueOnce(null);
+      mockRepository.checkRolePermissions.mockResolvedValueOnce(false); // Permissions check fails
+
+      const result = await service.checkPermissions({
+        userId: 1,
+        teamId: 1,
+        permissions: ["eventType.create", "team.invite"],
+        fallbackRoles: ["ADMIN", "OWNER"],
+      });
+
+      // Should fallback to role check and pass since user is ADMIN
+      expect(result).toBe(true);
+      expect(mockRepository.checkRolePermissions).toHaveBeenCalled();
+    });
+
+    it("should return false when permissions array is empty", async () => {
+      const membership = {
+        id: 1,
+        teamId: 1,
+        userId: 1,
+        accepted: true,
+        role: "MEMBER" as MembershipRole, // Change to MEMBER so fallback also fails
+        customRoleId: "admin_role",
+        disableImpersonation: false,
+        createdAt: new Date(),
+        updatedAt: new Date(),
+      };
+
       (MembershipRepository.findUniqueByUserIdAndTeamId as Mock).mockResolvedValueOnce(membership);
       mockFeaturesRepository.checkIfTeamHasFeature.mockResolvedValueOnce(true);
       mockRepository.getMembershipByMembershipId.mockResolvedValueOnce({
diff --git a/packages/features/pbac/services/permission-check.service.ts b/packages/features/pbac/services/permission-check.service.ts
index 8b9c67d2e54409..3c9ab0236d03d1 100644
--- a/packages/features/pbac/services/permission-check.service.ts
+++ b/packages/features/pbac/services/permission-check.service.ts
@@ -16,6 +16,8 @@ import type {
 import { PermissionRepository } from "../infrastructure/repositories/PermissionRepository";
 import { PermissionService } from "./permission.service";
 
+const DOGFOOD_PBAC_INTERNALLY = true;
+
 export class PermissionCheckService {
   private readonly PBAC_FEATURE_FLAG = "pbac" as const;
   private readonly logger = logger.getSubLogger({ prefix: ["PermissionCheckService"] });
@@ -126,7 +128,21 @@ export class PermissionCheckService {
           return false;
         }
 
-        return this.hasPermission({ membershipId: membership.id }, permission);
+        const hasPbacPermission = await this.hasPermission({ membershipId: membership.id }, permission);
+
+        if (DOGFOOD_PBAC_INTERNALLY && !hasPbacPermission) {
+          return this.dogfoodFallback({
+            userId,
+            teamId,
+            membershipId: membership.id,
+            permissions: [permission],
+            hasPbacPermission,
+            fallbackRoles,
+            membershipRole: membership.role,
+          });
+        }
+
+        return hasPbacPermission;
       }
 
       return this.checkFallbackRoles(membership.role, fallbackRoles);
@@ -175,7 +191,21 @@ export class PermissionCheckService {
           return false;
         }
 
-        return this.hasPermissions({ membershipId: membership.id }, permissions);
+        const hasPbacPermission = await this.hasPermissions({ membershipId: membership.id }, permissions);
+
+        if (DOGFOOD_PBAC_INTERNALLY && !hasPbacPermission) {
+          return this.dogfoodFallback({
+            userId,
+            teamId,
+            membershipId: membership.id,
+            permissions,
+            hasPbacPermission,
+            fallbackRoles,
+            membershipRole: membership.role,
+          });
+        }
+
+        return hasPbacPermission;
       }
 
       return this.checkFallbackRoles(membership.role, fallbackRoles);
@@ -252,6 +282,52 @@ export class PermissionCheckService {
     return allowedRoles.includes(userRole);
   }
 
+  /**
+   * Internal dogfooding fallback for PBAC permissions
+   *
+   * This method is used internally at Cal.com to help us transition to PBAC.
+   * When PBAC is enabled but a user doesn't have the necessary permission strings,
+   * we fall back to checking their legacy fallback roles to avoid breaking existing workflows.
+   *
+   * An alert is logged to Axiom when this fallback occurs so we can identify and fix
+   * missing permissions in our PBAC configuration.
+   *
+   * @private
+   * @param params - Object containing userId, teamId, membershipId, permissions, hasPbacPermission, fallbackRoles, and membershipRole
+   * @returns boolean - Whether the user has permission via fallback roles
+   */
+  private dogfoodFallback(params: {
+    userId: number;
+    teamId: number;
+    membershipId: number;
+    permissions: PermissionString[];
+    hasPbacPermission: boolean;
+    fallbackRoles: MembershipRole[];
+    membershipRole: MembershipRole;
+  }): boolean {
+    const { userId, teamId, membershipId, permissions, hasPbacPermission, fallbackRoles, membershipRole } =
+      params;
+
+    const debugInfo = {
+      userId,
+      teamId,
+      membershipId,
+      permissions,
+      hasPbacPermission,
+      fallbackRoles,
+    };
+
+    this.logger.warn(
+      `PBAC INTERNAL - Failed but user doesnt have permission string to carry out this action. Falling back to fallback roles. \n JSON${JSON.stringify(
+        debugInfo,
+        null,
+        2
+      )}`
+    );
+
+    return this.checkFallbackRoles(membershipRole, fallbackRoles);
+  }
+
   /**
    * Gets all team IDs where the user has a specific permission
    */