diff --git a/packages/api/src/app/permissions.spec.ts b/packages/api/src/app/permissions.spec.ts
index b3a6c8deb..e3816d401 100644
--- a/packages/api/src/app/permissions.spec.ts
+++ b/packages/api/src/app/permissions.spec.ts
@@ -1311,6 +1311,142 @@ describe('updateInterfacePermissions - permissions', () => {
     });
   });
 
+  it('should re-enable memory permissions when memory.disabled changes from true to false', async () => {
+    // Mock existing memory permissions that are disabled
+    mockGetRoleByName.mockResolvedValue({
+      permissions: {
+        [PermissionTypes.MEMORIES]: {
+          [Permissions.USE]: false,
+          [Permissions.CREATE]: false,
+          [Permissions.READ]: false,
+          [Permissions.UPDATE]: false,
+          [Permissions.OPT_OUT]: false,
+        },
+        // Other existing permissions
+        [PermissionTypes.PROMPTS]: { [Permissions.USE]: true },
+        [PermissionTypes.BOOKMARKS]: { [Permissions.USE]: true },
+      },
+    });
+
+    const config = {
+      interface: {
+        // Not explicitly configuring memories in interface
+        prompts: true,
+        bookmarks: true,
+      },
+      memory: {
+        disabled: false, // Memory is explicitly enabled (changed from true to false)
+        agent: {
+          id: 'test-agent-id',
+        },
+        personalize: true,
+      } as unknown as TCustomConfig['memory'],
+    };
+    const configDefaults = {
+      interface: {
+        memories: true,
+        prompts: true,
+        bookmarks: true,
+      },
+    } as TConfigDefaults;
+    const interfaceConfig = await loadDefaultInterface({ config, configDefaults });
+    const appConfig = { config, interfaceConfig } as unknown as AppConfig;
+
+    await updateInterfacePermissions({
+      appConfig,
+      getRoleByName: mockGetRoleByName,
+      updateAccessPermissions: mockUpdateAccessPermissions,
+    });
+
+    // Check USER role call
+    const userCall = mockUpdateAccessPermissions.mock.calls.find(
+      (call) => call[0] === SystemRoles.USER,
+    );
+    // Memory permissions should be re-enabled
+    expect(userCall[1][PermissionTypes.MEMORIES]).toEqual({
+      [Permissions.USE]: true,
+      [Permissions.CREATE]:
+        roleDefaults[SystemRoles.USER].permissions[PermissionTypes.MEMORIES]?.[Permissions.CREATE],
+      [Permissions.READ]:
+        roleDefaults[SystemRoles.USER].permissions[PermissionTypes.MEMORIES]?.[Permissions.READ],
+      [Permissions.UPDATE]:
+        roleDefaults[SystemRoles.USER].permissions[PermissionTypes.MEMORIES]?.[Permissions.UPDATE],
+      [Permissions.OPT_OUT]: true, // Should be true when personalize is enabled
+    });
+
+    // Check ADMIN role call
+    const adminCall = mockUpdateAccessPermissions.mock.calls.find(
+      (call) => call[0] === SystemRoles.ADMIN,
+    );
+    expect(adminCall[1][PermissionTypes.MEMORIES]).toEqual({
+      [Permissions.USE]: true,
+      [Permissions.CREATE]:
+        roleDefaults[SystemRoles.ADMIN].permissions[PermissionTypes.MEMORIES]?.[Permissions.CREATE],
+      [Permissions.READ]:
+        roleDefaults[SystemRoles.ADMIN].permissions[PermissionTypes.MEMORIES]?.[Permissions.READ],
+      [Permissions.UPDATE]:
+        roleDefaults[SystemRoles.ADMIN].permissions[PermissionTypes.MEMORIES]?.[Permissions.UPDATE],
+      [Permissions.OPT_OUT]: true, // Should be true when personalize is enabled
+    });
+
+    // Verify the existing role data was passed to updateAccessPermissions
+    expect(userCall[2]).toMatchObject({
+      permissions: expect.objectContaining({
+        [PermissionTypes.MEMORIES]: expect.any(Object),
+      }),
+    });
+  });
+
+  it('should re-enable memory permissions when valid memory config exists without disabled field', async () => {
+    // Mock existing memory permissions that are disabled
+    mockGetRoleByName.mockResolvedValue({
+      permissions: {
+        [PermissionTypes.MEMORIES]: {
+          [Permissions.USE]: false,
+          [Permissions.CREATE]: false,
+          [Permissions.READ]: false,
+          [Permissions.UPDATE]: false,
+          [Permissions.OPT_OUT]: false,
+        },
+      },
+    });
+
+    const config = {
+      memory: {
+        // No disabled field, but valid config
+        agent: {
+          id: 'test-agent-id',
+          provider: 'openai',
+        },
+        personalize: false,
+      } as unknown as TCustomConfig['memory'],
+    };
+    const configDefaults = { interface: {} } as TConfigDefaults;
+    const interfaceConfig = await loadDefaultInterface({ config, configDefaults });
+    const appConfig = { config, interfaceConfig } as unknown as AppConfig;
+
+    await updateInterfacePermissions({
+      appConfig,
+      getRoleByName: mockGetRoleByName,
+      updateAccessPermissions: mockUpdateAccessPermissions,
+    });
+
+    // Check USER role call - memory should be re-enabled
+    const userCall = mockUpdateAccessPermissions.mock.calls.find(
+      (call) => call[0] === SystemRoles.USER,
+    );
+    expect(userCall[1][PermissionTypes.MEMORIES]).toEqual({
+      [Permissions.USE]: true,
+      [Permissions.CREATE]:
+        roleDefaults[SystemRoles.USER].permissions[PermissionTypes.MEMORIES]?.[Permissions.CREATE],
+      [Permissions.READ]:
+        roleDefaults[SystemRoles.USER].permissions[PermissionTypes.MEMORIES]?.[Permissions.READ],
+      [Permissions.UPDATE]:
+        roleDefaults[SystemRoles.USER].permissions[PermissionTypes.MEMORIES]?.[Permissions.UPDATE],
+      [Permissions.OPT_OUT]: undefined, // Should be undefined when personalize is false
+    });
+  });
+
   it('should override existing memory permissions when memory.disabled is true', async () => {
     // Mock existing memory permissions that are enabled
     mockGetRoleByName.mockResolvedValue({
diff --git a/packages/api/src/app/permissions.ts b/packages/api/src/app/permissions.ts
index ac37025a2..a039a1503 100644
--- a/packages/api/src/app/permissions.ts
+++ b/packages/api/src/app/permissions.ts
@@ -69,8 +69,12 @@ export async function updateInterfacePermissions({
   const interfaceConfig = appConfig?.config?.interface;
   const memoryConfig = appConfig?.config?.memory;
   const memoryEnabled = isMemoryEnabled(memoryConfig);
-  /** Check if memory is explicitly disabled */
-  const isMemoryExplicitlyDisabled = memoryConfig && !memoryEnabled;
+  /** Check if memory is explicitly disabled (memory.disabled === true) */
+  const isMemoryExplicitlyDisabled = memoryConfig?.disabled === true;
+  /** Check if memory should be enabled (explicitly enabled or valid config) */
+  const shouldEnableMemory =
+    memoryConfig?.disabled === false ||
+    (memoryConfig && memoryEnabled && memoryConfig.disabled === undefined);
   /** Check if personalization is enabled (defaults to true if memory is configured and enabled) */
   const isPersonalizationEnabled =
     memoryConfig && memoryEnabled && memoryConfig.personalize !== false;
@@ -111,19 +115,24 @@ export async function updateInterfacePermissions({
       const permTypeExists = existingPermissions?.[permType];
       const isExplicitlyConfigured =
         interfaceConfig && hasExplicitConfig(interfaceConfig, permType);
-      const isMemoryDisabled =
-        permType === PermissionTypes.MEMORIES && isMemoryExplicitlyDisabled === true;
+      const isMemoryDisabled = permType === PermissionTypes.MEMORIES && isMemoryExplicitlyDisabled;
+      const isMemoryReenabling =
+        permType === PermissionTypes.MEMORIES &&
+        shouldEnableMemory &&
+        existingPermissions?.[PermissionTypes.MEMORIES]?.[Permissions.USE] === false;
 
-      // Only update if: doesn't exist OR explicitly configured
-      if (!permTypeExists || isExplicitlyConfigured || isMemoryDisabled) {
+      // Only update if: doesn't exist OR explicitly configured OR memory state change
+      if (!permTypeExists || isExplicitlyConfigured || isMemoryDisabled || isMemoryReenabling) {
         permissionsToUpdate[permType] = permissions;
         if (!permTypeExists) {
           logger.debug(`Role '${roleName}': Setting up default permissions for '${permType}'`);
         } else if (isExplicitlyConfigured) {
           logger.debug(`Role '${roleName}': Applying explicit config for '${permType}'`);
         } else if (isMemoryDisabled) {
+          logger.debug(`Role '${roleName}': Disabling memories as memory.disabled is true`);
+        } else if (isMemoryReenabling) {
           logger.debug(
-            `Role '${roleName}': Disabling memories as it is explicitly disabled in config`,
+            `Role '${roleName}': Re-enabling memories due to valid memory configuration`,
           );
         }
       } else {
@@ -147,13 +156,15 @@ export async function updateInterfacePermissions({
         ),
       },
       [PermissionTypes.MEMORIES]: {
-        [Permissions.USE]: isMemoryExplicitlyDisabled
-          ? false
-          : getPermissionValue(
-              loadedInterface.memories,
-              defaultPerms[PermissionTypes.MEMORIES]?.[Permissions.USE],
-              defaults.memories,
-            ),
+        [Permissions.USE]: (() => {
+          if (isMemoryExplicitlyDisabled) return false;
+          if (shouldEnableMemory) return true;
+          return getPermissionValue(
+            loadedInterface.memories,
+            defaultPerms[PermissionTypes.MEMORIES]?.[Permissions.USE],
+            defaults.memories,
+          );
+        })(),
         ...(defaultPerms[PermissionTypes.MEMORIES]?.[Permissions.CREATE] !== undefined && {
           [Permissions.CREATE]: isMemoryExplicitlyDisabled
             ? false
@@ -169,7 +180,9 @@ export async function updateInterfacePermissions({
             ? false
             : defaultPerms[PermissionTypes.MEMORIES][Permissions.UPDATE],
         }),
-        [Permissions.OPT_OUT]: isPersonalizationEnabled,
+        [Permissions.OPT_OUT]: isMemoryExplicitlyDisabled
+          ? false
+          : isPersonalizationEnabled || undefined,
       },
       [PermissionTypes.MULTI_CONVO]: {
         [Permissions.USE]: getPermissionValue(