[PM-16699] Improve decrypt failure logging

libs/common/src/auth/services/master-password/master-password.service.ts

@@ -180,10 +180,18 @@
     let decUserKey: Uint8Array;
 
     if (userKey.encryptionType === EncryptionType.AesCbc256_B64) {
-      decUserKey = await this.encryptService.decryptToBytes(userKey, masterKey);
+      decUserKey = await this.encryptService.decryptToBytes(
+        userKey,
+        masterKey,
+        "Content: User Key; Encrypting Key: Master Key",
+      );
     } else if (userKey.encryptionType === EncryptionType.AesCbc256_HmacSha256_B64) {
       const newKey = await this.keyGenerationService.stretchKey(masterKey);
-      decUserKey = await this.encryptService.decryptToBytes(userKey, newKey);
+      decUserKey = await this.encryptService.decryptToBytes(
+        userKey,
+        newKey,
+        "Content: User Key; Encrypting Key: Stretched Master Key",
+      );
     } else {
       throw new Error("Unsupported encryption type.");
     }

libs/common/src/platform/abstractions/encrypt.service.ts

@@ -8,12 +8,32 @@ import { SymmetricCryptoKey } from "../models/domain/symmetric-crypto-key";
 export abstract class EncryptService {
   abstract encrypt(plainValue: string | Uint8Array, key: SymmetricCryptoKey): Promise<EncString>;
   abstract encryptToBytes(plainValue: Uint8Array, key: SymmetricCryptoKey): Promise<EncArrayBuffer>;
+  /**
+   * Decrypts an EncString to a string
+   * @param encString - The EncString to decrypt
+   * @param key - The key to decrypt the EncString with
+   * @param decryptTrace - A string to identify the context of the object being decrypted. This can include: field name, encryption type, cipher id, key type, but should not include
+   * sensitive information like encryption keys or data. This is used for logging when decryption errors occur in order to identify what failed to decrypt
+   * @returns The decrypted string
+   */
   abstract decryptToUtf8(
     encString: EncString,
     key: SymmetricCryptoKey,
-    decryptContext?: string,
+    decryptTrace?: string,
   ): Promise<string>;
-  abstract decryptToBytes(encThing: Encrypted, key: SymmetricCryptoKey): Promise<Uint8Array>;
+  /**
+   * Decrypts an Encrypted object to a Uint8Array
+   * @param encThing - The Encrypted object to decrypt
+   * @param key - The key to decrypt the Encrypted object with
+   * @param decryptTrace - A string to identify the context of the object being decrypted. This can include: field name, encryption type, cipher id, key type, but should not include
+   * sensitive information like encryption keys or data. This is used for logging when decryption errors occur in order to identify what failed to decrypt
+   * @returns The decrypted Uint8Array
+   */
+  abstract decryptToBytes(
+    encThing: Encrypted,
+    key: SymmetricCryptoKey,
+    decryptTrace?: string,
+  ): Promise<Uint8Array>;
   abstract rsaEncrypt(data: Uint8Array, publicKey: Uint8Array): Promise<EncString>;
   abstract rsaDecrypt(data: EncString, privateKey: Uint8Array): Promise<Uint8Array>;
   abstract resolveLegacyKey(key: SymmetricCryptoKey, encThing: Encrypted): SymmetricCryptoKey;

libs/common/src/platform/models/domain/domain-base.ts

@@ -63,8 +63,8 @@ export default class Domain {
     map: any,
     orgId: string,
     key: SymmetricCryptoKey = null,
+    objectContext: string = "No Domain Context",
   ): Promise<T> {
-    const promises = [];
     const self: any = this;
 
     for (const prop in map) {
@@ -73,23 +73,15 @@ export default class Domain {
         continue;
       }
 
-      (function (theProp) {
-        const p = Promise.resolve()
-          .then(() => {
-            const mapProp = map[theProp] || theProp;
-            if (self[mapProp]) {
-              return self[mapProp].decrypt(orgId, key);
-            }
-            return null;
-          })
-          .then((val: any) => {
-            (viewModel as any)[theProp] = val;
-          });
-        promises.push(p);
-      })(prop);
+      const mapProp = map[prop] || prop;
+      if (self[mapProp]) {
+        (viewModel as any)[prop] = await self[mapProp].decrypt(
+          orgId,
+          key,
+          `Property: ${prop}; ObjectContext: ${objectContext}`,
+        );
+      }
     }
-
-    await Promise.all(promises);
     return viewModel;
   }
 
@@ -114,15 +106,22 @@ export default class Domain {
     key: SymmetricCryptoKey,
     encryptService: EncryptService,
     _: Constructor<TThis> = this.constructor as Constructor<TThis>,
+    objectContext: string = "No Domain Context",
   ): Promise<DecryptedObject<TThis, TEncryptedKeys>> {
-    const promises = [];
+    const decryptedObjects = [];
 
     for (const prop of encryptedProperties) {
       const value = (this as any)[prop] as EncString;
-      promises.push(this.decryptProperty(prop, value, key, encryptService));
+      const decrypted = await this.decryptProperty(
+        prop,
+        value,
+        key,
+        encryptService,
+        `Property: ${prop.toString()}; ObjectContext: ${objectContext}`,
+      );
+      decryptedObjects.push(decrypted);
     }
 
-    const decryptedObjects = await Promise.all(promises);
     const decryptedObject = decryptedObjects.reduce(
       (acc, obj) => {
         return { ...acc, ...obj };
@@ -137,10 +136,11 @@ export default class Domain {
     value: EncString,
     key: SymmetricCryptoKey,
     encryptService: EncryptService,
+    decryptTrace: string,
   ) {
     let decrypted: string = null;
     if (value) {
-      decrypted = await value.decryptWithKey(key, encryptService);
+      decrypted = await value.decryptWithKey(key, encryptService, decryptTrace);
     } else {
       decrypted = null;
     }

libs/common/src/platform/models/domain/enc-string.ts

@@ -156,21 +156,21 @@ export class EncString implements Encrypted {
     return EXPECTED_NUM_PARTS_BY_ENCRYPTION_TYPE[encType] === encPieces.length;
   }
 
-  async decrypt(orgId: string, key: SymmetricCryptoKey = null): Promise<string> {
+  async decrypt(orgId: string, key: SymmetricCryptoKey = null, context?: string): Promise<string> {
     if (this.decryptedValue != null) {
       return this.decryptedValue;
     }
 
-    let keyContext = "provided-key";
+    let decryptTrace = "provided-key";
     try {
       if (key == null) {
         key = await this.getKeyForDecryption(orgId);
-        keyContext = orgId == null ? `domain-orgkey-${orgId}` : "domain-userkey|masterkey";
+        decryptTrace = orgId == null ? `domain-orgkey-${orgId}` : "domain-userkey|masterkey";
         if (orgId != null) {
-          keyContext = `domain-orgkey-${orgId}`;
+          decryptTrace = `domain-orgkey-${orgId}`;
         } else {
           const cryptoService = Utils.getContainerService().getKeyService();
-          keyContext =
+          decryptTrace =
             (await cryptoService.getUserKey()) == null
               ? "domain-withlegacysupport-masterkey"
               : "domain-withlegacysupport-userkey";
@@ -181,20 +181,28 @@ export class EncString implements Encrypted {
       }
 
       const encryptService = Utils.getContainerService().getEncryptService();
-      this.decryptedValue = await encryptService.decryptToUtf8(this, key, keyContext);
+      this.decryptedValue = await encryptService.decryptToUtf8(
+        this,
+        key,
+        decryptTrace == null ? context : `${decryptTrace}${context || ""}`,
+      );
     } catch (e) {
       this.decryptedValue = DECRYPT_ERROR;
     }
     return this.decryptedValue;
   }
 
-  async decryptWithKey(key: SymmetricCryptoKey, encryptService: EncryptService) {
+  async decryptWithKey(
+    key: SymmetricCryptoKey,
+    encryptService: EncryptService,
+    decryptTrace: string = "domain-withkey",
+  ): Promise<string> {
     try {
       if (key == null) {
         throw new Error("No key to decrypt EncString");
       }
 
-      this.decryptedValue = await encryptService.decryptToUtf8(this, key, "domain-withkey");
+      this.decryptedValue = await encryptService.decryptToUtf8(this, key, decryptTrace);
     } catch (e) {
       this.decryptedValue = DECRYPT_ERROR;
     }

libs/common/src/platform/services/cryptography/encrypt.service.implementation.ts

@@ -114,7 +114,7 @@ export class EncryptServiceImplementation implements EncryptService {
       const macsEqual = await this.cryptoFunctionService.compareFast(fastParams.mac, computedMac);
       if (!macsEqual) {
         this.logMacFailed(
-          "[Encrypt service] MAC comparison failed. Key or payload has changed. Key type " +
+          "[Encrypt service] decryptToUtf8 MAC comparison failed. Key or payload has changed. Key type " +
             encryptionTypeName(key.encType) +
             "Payload type " +
             encryptionTypeName(encString.encryptionType) +
@@ -128,7 +128,11 @@ export class EncryptServiceImplementation implements EncryptService {
     return await this.cryptoFunctionService.aesDecryptFast(fastParams, "cbc");
   }
 
-  async decryptToBytes(encThing: Encrypted, key: SymmetricCryptoKey): Promise<Uint8Array> {
+  async decryptToBytes(
+    encThing: Encrypted,
+    key: SymmetricCryptoKey,
+    decryptContext: string = "no context",
+  ): Promise<Uint8Array> {
     if (key == null) {
       throw new Error("No encryption key provided.");
     }
@@ -145,7 +149,9 @@ export class EncryptServiceImplementation implements EncryptService {
         "[Encrypt service] Key has mac key but payload is missing mac bytes. Key type " +
           encryptionTypeName(key.encType) +
           " Payload type " +
-          encryptionTypeName(encThing.encryptionType),
+          encryptionTypeName(encThing.encryptionType) +
+          " Decrypt context: " +
+          decryptContext,
       );
       return null;
     }
@@ -155,7 +161,9 @@ export class EncryptServiceImplementation implements EncryptService {
         "[Encrypt service] Key encryption type does not match payload encryption type. Key type " +
           encryptionTypeName(key.encType) +
           " Payload type " +
-          encryptionTypeName(encThing.encryptionType),
+          encryptionTypeName(encThing.encryptionType) +
+          " Decrypt context: " +
+          decryptContext,
       );
       return null;
     }
@@ -167,23 +175,27 @@ export class EncryptServiceImplementation implements EncryptService {
       const computedMac = await this.cryptoFunctionService.hmac(macData, key.macKey, "sha256");
       if (computedMac === null) {
         this.logMacFailed(
-          "[Encrypt service] Failed to compute MAC." +
+          "[Encrypt service#decryptToBytes] Failed to compute MAC." +
             " Key type " +
             encryptionTypeName(key.encType) +
             " Payload type " +
-            encryptionTypeName(encThing.encryptionType),
+            encryptionTypeName(encThing.encryptionType) +
+            " Decrypt context: " +
+            decryptContext,
         );
         return null;
       }
 
       const macsMatch = await this.cryptoFunctionService.compare(encThing.macBytes, computedMac);
       if (!macsMatch) {
         this.logMacFailed(
-          "[Encrypt service] MAC comparison failed. Key or payload has changed." +
+          "[Encrypt service#decryptToBytes]: MAC comparison failed. Key or payload has changed." +
             " Key type " +
             encryptionTypeName(key.encType) +
             " Payload type " +
-            encryptionTypeName(encThing.encryptionType),
+            encryptionTypeName(encThing.encryptionType) +
+            " Decrypt context: " +
+            decryptContext,
         );
         return null;
       }

libs/common/src/tools/send/models/domain/send.spec.ts

@@ -123,7 +123,12 @@ describe("Send", () => {
     const view = await send.decrypt();
 
     expect(text.decrypt).toHaveBeenNthCalledWith(1, "cryptoKey");
-    expect(send.name.decrypt).toHaveBeenNthCalledWith(1, null, "cryptoKey");
+    expect(send.name.decrypt).toHaveBeenNthCalledWith(
+      1,
+      null,
+      "cryptoKey",
+      "Property: name; ObjectContext: No Domain Context",
+    );
 
     expect(view).toMatchObject({
       id: "id",

libs/common/src/vault/models/domain/attachment.spec.ts

@@ -101,7 +101,7 @@ describe("Attachment", () => {
       it("uses the provided key without depending on KeyService", async () => {
         const providedKey = mock<SymmetricCryptoKey>();
 
-        await attachment.decrypt(null, providedKey);
+        await attachment.decrypt(null, "", providedKey);
 
         expect(keyService.getUserKeyWithLegacySupport).not.toHaveBeenCalled();
         expect(encryptService.decryptToBytes).toHaveBeenCalledWith(attachment.key, providedKey);
@@ -111,7 +111,7 @@ describe("Attachment", () => {
         const orgKey = mock<OrgKey>();
         keyService.getOrgKey.calledWith("orgId").mockResolvedValue(orgKey);
 
-        await attachment.decrypt("orgId", null);
+        await attachment.decrypt("orgId", "", null);
 
         expect(keyService.getOrgKey).toHaveBeenCalledWith("orgId");
         expect(encryptService.decryptToBytes).toHaveBeenCalledWith(attachment.key, orgKey);
@@ -121,7 +121,7 @@ describe("Attachment", () => {
         const userKey = mock<UserKey>();
         keyService.getUserKeyWithLegacySupport.mockResolvedValue(userKey);
 
-        await attachment.decrypt(null, null);
+        await attachment.decrypt(null, "", null);
 
         expect(keyService.getUserKeyWithLegacySupport).toHaveBeenCalled();
         expect(encryptService.decryptToBytes).toHaveBeenCalledWith(attachment.key, userKey);

libs/common/src/vault/models/domain/attachment.ts

@@ -38,14 +38,19 @@ export class Attachment extends Domain {
     );
   }
 
-  async decrypt(orgId: string, encKey?: SymmetricCryptoKey): Promise<AttachmentView> {
+  async decrypt(
+    orgId: string,
+    context = "No Cipher Context",
+    encKey?: SymmetricCryptoKey,
+  ): Promise<AttachmentView> {
     const view = await this.decryptObj(
       new AttachmentView(this),
       {
         fileName: null,
       },
       orgId,
       encKey,
+      "DomainType: Attachment; " + context,
     );
 
     if (this.key != null) {

libs/common/src/vault/models/domain/card.ts

@@ -37,7 +37,11 @@ export class Card extends Domain {
     );
   }
 
-  decrypt(orgId: string, encKey?: SymmetricCryptoKey): Promise<CardView> {
+  async decrypt(
+    orgId: string,
+    context = "No Cipher Context",
+    encKey?: SymmetricCryptoKey,
+  ): Promise<CardView> {
     return this.decryptObj(
       new CardView(),
       {
@@ -50,6 +54,7 @@ export class Card extends Domain {
       },
       orgId,
       encKey,
+      "DomainType: Card; " + context,
     );
   }