diff --git a/src/modules/cards/application/useCases/commands/AddCardToCollectionUseCase.ts b/src/modules/cards/application/useCases/commands/AddCardToCollectionUseCase.ts
index 45623969..37277146 100644
--- a/src/modules/cards/application/useCases/commands/AddCardToCollectionUseCase.ts
+++ b/src/modules/cards/application/useCases/commands/AddCardToCollectionUseCase.ts
@@ -9,6 +9,7 @@ import { CardId } from '../../../domain/value-objects/CardId';
 import { CollectionId } from '../../../domain/value-objects/CollectionId';
 import { CuratorId } from '../../../domain/value-objects/CuratorId';
 import { CardCollectionService } from '../../../domain/services/CardCollectionService';
+import { AuthenticationError } from '../../../../../shared/core/AuthenticationError';
 
 export interface AddCardToCollectionDTO {
   cardId: string;
@@ -30,7 +31,7 @@ export class AddCardToCollectionUseCase extends BaseUseCase<
   AddCardToCollectionDTO,
   Result<
     AddCardToCollectionResponseDTO,
-    ValidationError | AppError.UnexpectedError
+    ValidationError | AuthenticationError | AppError.UnexpectedError
   >
 > {
   constructor(
@@ -46,7 +47,7 @@ export class AddCardToCollectionUseCase extends BaseUseCase<
   ): Promise<
     Result<
       AddCardToCollectionResponseDTO,
-      ValidationError | AppError.UnexpectedError
+      ValidationError | AuthenticationError | AppError.UnexpectedError
     >
   > {
     try {
@@ -104,6 +105,10 @@ export class AddCardToCollectionUseCase extends BaseUseCase<
           curatorId,
         );
       if (addToCollectionsResult.isErr()) {
+        // Propagate authentication errors
+        if (addToCollectionsResult.error instanceof AuthenticationError) {
+          return err(addToCollectionsResult.error);
+        }
         if (addToCollectionsResult.error instanceof AppError.UnexpectedError) {
           return err(addToCollectionsResult.error);
         }
diff --git a/src/modules/cards/application/useCases/commands/AddCardToLibraryUseCase.ts b/src/modules/cards/application/useCases/commands/AddCardToLibraryUseCase.ts
index 2fa040ef..3fa9332d 100644
--- a/src/modules/cards/application/useCases/commands/AddCardToLibraryUseCase.ts
+++ b/src/modules/cards/application/useCases/commands/AddCardToLibraryUseCase.ts
@@ -8,6 +8,7 @@ import { CollectionId } from '../../../domain/value-objects/CollectionId';
 import { CuratorId } from '../../../domain/value-objects/CuratorId';
 import { CardLibraryService } from '../../../domain/services/CardLibraryService';
 import { CardCollectionService } from '../../../domain/services/CardCollectionService';
+import { AuthenticationError } from '../../../../../shared/core/AuthenticationError';
 
 export interface AddCardToLibraryDTO {
   cardId: string;
@@ -31,7 +32,7 @@ export class AddCardToLibraryUseCase
       AddCardToLibraryDTO,
       Result<
         AddCardToLibraryResponseDTO,
-        ValidationError | AppError.UnexpectedError
+        ValidationError | AuthenticationError | AppError.UnexpectedError
       >
     >
 {
@@ -46,7 +47,7 @@ export class AddCardToLibraryUseCase
   ): Promise<
     Result<
       AddCardToLibraryResponseDTO,
-      ValidationError | AppError.UnexpectedError
+      ValidationError | AuthenticationError | AppError.UnexpectedError
     >
   > {
     try {
@@ -87,6 +88,10 @@ export class AddCardToLibraryUseCase
         curatorId,
       );
       if (addToLibraryResult.isErr()) {
+        // Propagate authentication errors
+        if (addToLibraryResult.error instanceof AuthenticationError) {
+          return err(addToLibraryResult.error);
+        }
         if (addToLibraryResult.error instanceof AppError.UnexpectedError) {
           return err(addToLibraryResult.error);
         }
@@ -118,6 +123,10 @@ export class AddCardToLibraryUseCase
             curatorId,
           );
         if (addToCollectionsResult.isErr()) {
+          // Propagate authentication errors
+          if (addToCollectionsResult.error instanceof AuthenticationError) {
+            return err(addToCollectionsResult.error);
+          }
           if (
             addToCollectionsResult.error instanceof AppError.UnexpectedError
           ) {
diff --git a/src/modules/cards/application/useCases/commands/UpdateUrlCardAssociationsUseCase.ts b/src/modules/cards/application/useCases/commands/UpdateUrlCardAssociationsUseCase.ts
index 37c00430..65c6955e 100644
--- a/src/modules/cards/application/useCases/commands/UpdateUrlCardAssociationsUseCase.ts
+++ b/src/modules/cards/application/useCases/commands/UpdateUrlCardAssociationsUseCase.ts
@@ -14,6 +14,7 @@ import { CardCollectionService } from '../../../domain/services/CardCollectionSe
 import { CardContent } from '../../../domain/value-objects/CardContent';
 import { CardFactory } from '../../../domain/CardFactory';
 import { CardLibraryService } from '../../../domain/services/CardLibraryService';
+import { AuthenticationError } from '../../../../../shared/core/AuthenticationError';
 
 export interface UpdateUrlCardAssociationsDTO {
   cardId: string;
@@ -40,7 +41,7 @@ export class UpdateUrlCardAssociationsUseCase extends BaseUseCase<
   UpdateUrlCardAssociationsDTO,
   Result<
     UpdateUrlCardAssociationsResponseDTO,
-    ValidationError | AppError.UnexpectedError
+    ValidationError | AuthenticationError | AppError.UnexpectedError
   >
 > {
   constructor(
@@ -57,7 +58,7 @@ export class UpdateUrlCardAssociationsUseCase extends BaseUseCase<
   ): Promise<
     Result<
       UpdateUrlCardAssociationsResponseDTO,
-      ValidationError | AppError.UnexpectedError
+      ValidationError | AuthenticationError | AppError.UnexpectedError
     >
   > {
     try {
@@ -190,6 +191,10 @@ export class UpdateUrlCardAssociationsUseCase extends BaseUseCase<
           const addNoteCardToLibraryResult =
             await this.cardLibraryService.addCardToLibrary(noteCard, curatorId);
           if (addNoteCardToLibraryResult.isErr()) {
+            // Propagate authentication errors
+            if (addNoteCardToLibraryResult.error instanceof AuthenticationError) {
+              return err(addNoteCardToLibraryResult.error);
+            }
             if (
               addNoteCardToLibraryResult.error instanceof
               AppError.UnexpectedError
@@ -232,6 +237,10 @@ export class UpdateUrlCardAssociationsUseCase extends BaseUseCase<
             curatorId,
           );
         if (addToCollectionsResult.isErr()) {
+          // Propagate authentication errors
+          if (addToCollectionsResult.error instanceof AuthenticationError) {
+            return err(addToCollectionsResult.error);
+          }
           if (
             addToCollectionsResult.error instanceof AppError.UnexpectedError
           ) {
@@ -282,6 +291,10 @@ export class UpdateUrlCardAssociationsUseCase extends BaseUseCase<
             curatorId,
           );
         if (removeFromCollectionsResult.isErr()) {
+          // Propagate authentication errors
+          if (removeFromCollectionsResult.error instanceof AuthenticationError) {
+            return err(removeFromCollectionsResult.error);
+          }
           if (
             removeFromCollectionsResult.error instanceof
             AppError.UnexpectedError
diff --git a/src/modules/cards/infrastructure/http/controllers/AddCardToCollectionController.ts b/src/modules/cards/infrastructure/http/controllers/AddCardToCollectionController.ts
index f9745863..c558b949 100644
--- a/src/modules/cards/infrastructure/http/controllers/AddCardToCollectionController.ts
+++ b/src/modules/cards/infrastructure/http/controllers/AddCardToCollectionController.ts
@@ -2,6 +2,7 @@ import { Controller } from '../../../../../shared/infrastructure/http/Controller
 import { Response } from 'express';
 import { AddCardToCollectionUseCase } from '../../../application/useCases/commands/AddCardToCollectionUseCase';
 import { AuthenticatedRequest } from '../../../../../shared/infrastructure/http/middleware/AuthMiddleware';
+import { AuthenticationError } from '../../../../../shared/core/AuthenticationError';
 
 export class AddCardToCollectionController extends Controller {
   constructor(private addCardToCollectionUseCase: AddCardToCollectionUseCase) {
@@ -32,12 +33,16 @@ export class AddCardToCollectionController extends Controller {
       });
 
       if (result.isErr()) {
+        // Check if the error is an authentication error
+        if (result.error instanceof AuthenticationError) {
+          return this.unauthorized(res, result.error.message);
+        }
         return this.fail(res, result.error);
       }
 
       return this.ok(res, result.value);
     } catch (error: any) {
-      return this.fail(res, error);
+      return this.handleError(res, error);
     }
   }
 }
diff --git a/src/modules/cards/infrastructure/http/controllers/AddCardToLibraryController.ts b/src/modules/cards/infrastructure/http/controllers/AddCardToLibraryController.ts
index befde33b..0999dd2d 100644
--- a/src/modules/cards/infrastructure/http/controllers/AddCardToLibraryController.ts
+++ b/src/modules/cards/infrastructure/http/controllers/AddCardToLibraryController.ts
@@ -2,6 +2,7 @@ import { Controller } from '../../../../../shared/infrastructure/http/Controller
 import { Response } from 'express';
 import { AddCardToLibraryUseCase } from '../../../application/useCases/commands/AddCardToLibraryUseCase';
 import { AuthenticatedRequest } from '../../../../../shared/infrastructure/http/middleware/AuthMiddleware';
+import { AuthenticationError } from '../../../../../shared/core/AuthenticationError';
 
 export class AddCardToLibraryController extends Controller {
   constructor(private addCardToLibraryUseCase: AddCardToLibraryUseCase) {
@@ -33,12 +34,16 @@ export class AddCardToLibraryController extends Controller {
       });
 
       if (result.isErr()) {
+        // Check if the error is an authentication error
+        if (result.error instanceof AuthenticationError) {
+          return this.unauthorized(res, result.error.message);
+        }
         return this.fail(res, result.error);
       }
 
       return this.ok(res, result.value);
     } catch (error: any) {
-      return this.fail(res, error);
+      return this.handleError(res, error);
     }
   }
 }
diff --git a/src/modules/cards/infrastructure/http/controllers/UpdateUrlCardAssociationsController.ts b/src/modules/cards/infrastructure/http/controllers/UpdateUrlCardAssociationsController.ts
index 8be4f155..bd48963f 100644
--- a/src/modules/cards/infrastructure/http/controllers/UpdateUrlCardAssociationsController.ts
+++ b/src/modules/cards/infrastructure/http/controllers/UpdateUrlCardAssociationsController.ts
@@ -2,6 +2,7 @@ import { Controller } from '../../../../../shared/infrastructure/http/Controller
 import { Response } from 'express';
 import { UpdateUrlCardAssociationsUseCase } from '../../../application/useCases/commands/UpdateUrlCardAssociationsUseCase';
 import { AuthenticatedRequest } from '../../../../../shared/infrastructure/http/middleware/AuthMiddleware';
+import { AuthenticationError } from '../../../../../shared/core/AuthenticationError';
 
 export class UpdateUrlCardAssociationsController extends Controller {
   constructor(
@@ -33,12 +34,16 @@ export class UpdateUrlCardAssociationsController extends Controller {
       });
 
       if (result.isErr()) {
+        // Check if the error is an authentication error
+        if (result.error instanceof AuthenticationError) {
+          return this.unauthorized(res, result.error.message);
+        }
         return this.fail(res, result.error);
       }
 
       return this.ok(res, result.value);
     } catch (error: any) {
-      return this.fail(res, error);
+      return this.handleError(res, error);
     }
   }
 }