diff --git a/libs/common/src/vault/models/domain/cipher.spec.ts b/libs/common/src/vault/models/domain/cipher.spec.ts
index 1b97ad06bc3..ba83cf38ae4 100644
--- a/libs/common/src/vault/models/domain/cipher.spec.ts
+++ b/libs/common/src/vault/models/domain/cipher.spec.ts
@@ -68,6 +68,68 @@ describe("Cipher DTO", () => {
     });
   });
 
+  it("Decrypt should handle cipher key error", async () => {
+    const cipher = new Cipher();
+    cipher.id = "id";
+    cipher.organizationId = "orgId";
+    cipher.folderId = "folderId";
+    cipher.edit = true;
+    cipher.viewPassword = true;
+    cipher.organizationUseTotp = true;
+    cipher.favorite = false;
+    cipher.revisionDate = new Date("2022-01-31T12:00:00.000Z");
+    cipher.type = CipherType.Login;
+    cipher.name = mockEnc("EncryptedString");
+    cipher.notes = mockEnc("EncryptedString");
+    cipher.creationDate = new Date("2022-01-01T12:00:00.000Z");
+    cipher.deletedDate = null;
+    cipher.reprompt = CipherRepromptType.None;
+    cipher.key = mockEnc("EncKey");
+    cipher.permissions = new CipherPermissionsApi();
+
+    const loginView = new LoginView();
+    loginView.username = "username";
+    loginView.password = "password";
+
+    const login = mock<Login>();
+    login.decrypt.mockResolvedValue(loginView);
+    cipher.login = login;
+
+    const keyService = mock<KeyService>();
+    const encryptService = mock<EncryptService>();
+    const cipherService = mock<CipherService>();
+
+    encryptService.unwrapSymmetricKey.mockRejectedValue(new Error("Failed to unwrap key"));
+
+    (window as any).bitwardenContainerService = new ContainerService(keyService, encryptService);
+
+    const cipherView = await cipher.decrypt(
+      await cipherService.getKeyForCipherKeyDecryption(cipher, mockUserId),
+    );
+
+    expect(cipherView).toMatchObject({
+      id: "id",
+      organizationId: "orgId",
+      folderId: "folderId",
+      name: "[error: cannot decrypt]",
+      type: 1,
+      favorite: false,
+      organizationUseTotp: true,
+      edit: true,
+      viewPassword: true,
+      decryptionFailure: true,
+      collectionIds: undefined,
+      revisionDate: new Date("2022-01-31T12:00:00.000Z"),
+      creationDate: new Date("2022-01-01T12:00:00.000Z"),
+      deletedDate: null,
+      reprompt: 0,
+      localData: undefined,
+      permissions: new CipherPermissionsApi(),
+    });
+
+    expect(login.decrypt).not.toHaveBeenCalled();
+  });
+
   describe("LoginCipher", () => {
     let cipherData: CipherData;
 
diff --git a/libs/common/src/vault/models/domain/cipher.ts b/libs/common/src/vault/models/domain/cipher.ts
index d816ebb24ce..e6d11a82b69 100644
--- a/libs/common/src/vault/models/domain/cipher.ts
+++ b/libs/common/src/vault/models/domain/cipher.ts
@@ -145,14 +145,15 @@ export class Cipher extends Domain implements Decryptable<CipherView> {
     if (this.key != null) {
       const encryptService = Utils.getContainerService().getEncryptService();
 
-      const cipherKey = await encryptService.unwrapSymmetricKey(this.key, encKey);
-      if (cipherKey == null) {
+      try {
+        const cipherKey = await encryptService.unwrapSymmetricKey(this.key, encKey);
+        encKey = cipherKey;
+        bypassValidation = false;
+      } catch {
         model.name = "[error: cannot decrypt]";
         model.decryptionFailure = true;
         return model;
       }
-      encKey = cipherKey;
-      bypassValidation = false;
     }
 
     await this.decryptObj<Cipher, CipherView>(
diff --git a/libs/key-management/src/user-asymmetric-key-regeneration/services/default-user-asymmetric-key-regeneration.service.ts b/libs/key-management/src/user-asymmetric-key-regeneration/services/default-user-asymmetric-key-regeneration.service.ts
index 096e9236a30..dbdac6bfc99 100644
--- a/libs/key-management/src/user-asymmetric-key-regeneration/services/default-user-asymmetric-key-regeneration.service.ts
+++ b/libs/key-management/src/user-asymmetric-key-regeneration/services/default-user-asymmetric-key-regeneration.service.ts
@@ -162,17 +162,26 @@ export class DefaultUserAsymmetricKeysRegenerationService
     const ciphers = await this.cipherService.getAll(userId);
     const cipher = ciphers.find((cipher) => cipher.organizationId == null);
 
-    if (cipher != null) {
-      try {
-        await cipher.decrypt(userKey);
-        return true;
-      } catch (error) {
+    if (!cipher) {
+      return false;
+    }
+
+    try {
+      const cipherView = await cipher.decrypt(userKey);
+
+      if (cipherView.decryptionFailure) {
         this.logService.error(
-          "[UserAsymmetricKeyRegeneration] User Symmetric Key validation error: " + error,
+          "[UserAsymmetricKeyRegeneration] User Symmetric Key validation error: Cipher decryption failed",
         );
         return false;
       }
+
+      return true;
+    } catch (error) {
+      this.logService.error(
+        "[UserAsymmetricKeyRegeneration] User Symmetric Key validation error: " + error,
+      );
+      return false;
     }
-    return false;
   }
 }