diff --git a/src/app/directives/library-membership.directive.spec.ts b/src/app/directives/library-membership.directive.spec.ts
index d6c2abe8f..e6e2b44e4 100644
--- a/src/app/directives/library-membership.directive.spec.ts
+++ b/src/app/directives/library-membership.directive.spec.ts
@@ -35,6 +35,7 @@ import { AppTestingModule } from '../testing/app-testing.module';
 import { DirectivesModule } from './directives.module';
 import { LibraryMembershipDirective } from './library-membership.directive';
 import { NO_ERRORS_SCHEMA, SimpleChange } from '@angular/core';
+import { throwError } from 'rxjs';
 
 describe('LibraryMembershipDirective', () => {
   let alfrescoApiService: AlfrescoApiService;
@@ -165,5 +166,18 @@ describe('LibraryMembershipDirective', () => {
       expect(addMembershipSpy).toHaveBeenCalled();
       expect(deleteMembershipSpy).not.toHaveBeenCalled();
     }));
+
+    it('should emit error when the request to join a library fails', fakeAsync(() => {
+      spyOn(directive.error, 'emit');
+      addMembershipSpy.and.returnValue(throwError('err'));
+
+      const selection = { entry: { id: 'no-membership-requested' } };
+      const change = new SimpleChange(null, selection, true);
+      directive.ngOnChanges({ selection: change });
+      tick();
+      directive.toggleMembershipRequest();
+      tick();
+      expect(directive.error.emit).toHaveBeenCalled();
+    }));
   });
 });
diff --git a/src/app/directives/library-membership.directive.ts b/src/app/directives/library-membership.directive.ts
index 8f9c5710c..fda7569f2 100644
--- a/src/app/directives/library-membership.directive.ts
+++ b/src/app/directives/library-membership.directive.ts
@@ -130,6 +130,18 @@ export class LibraryMembershipDirective implements OnChanges {
             error,
             i18nKey: 'APP.MESSAGES.ERRORS.JOIN_REQUEST_FAILED'
           };
+
+          const senderEmailCheck = 'Failed to resolve sender mail address';
+          const receiverEmailCheck =
+            'All recipients for the mail action were invalid';
+          if (
+            error.message &&
+            (error.message.includes(senderEmailCheck) ||
+              error.message.includes(receiverEmailCheck))
+          ) {
+            errWithMessage.i18nKey = 'APP.MESSAGES.ERRORS.INVALID_EMAIL';
+          }
+
           this.error.emit(errWithMessage);
         }
       );
diff --git a/src/assets/i18n/en.json b/src/assets/i18n/en.json
index 1c3e6ccf3..3aa3db4fb 100644
--- a/src/assets/i18n/en.json
+++ b/src/assets/i18n/en.json
@@ -277,7 +277,8 @@
                 "DELETE_LIBRARY_FAILED": "Cannot delete the library",
                 "JOIN_REQUEST_FAILED": "Cannot join the library",
                 "JOIN_CANCEL_FAILED": "Cannot cancel the request to join the library",
-                "LEAVE_LIBRARY_FAILED": "Cannot leave this library"
+                "LEAVE_LIBRARY_FAILED": "Cannot leave this library",
+                "INVALID_EMAIL": "Sender or receiver email configured on server not valid, contact IT"
             },
             "UPLOAD": {
                 "ERROR": {