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[apple/security.git] / keychain / ckks / tests / CKKSAESSIVEncryptionTests.m
diff --git a/keychain/ckks/tests/CKKSAESSIVEncryptionTests.m b/keychain/ckks/tests/CKKSAESSIVEncryptionTests.m
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+/*
+ * Copyright (c) 2016 Apple Inc. All Rights Reserved.
+ *
+ * @APPLE_LICENSE_HEADER_START@
+ *
+ * This file contains Original Code and/or Modifications of Original Code
+ * as defined in and that are subject to the Apple Public Source License
+ * Version 2.0 (the 'License'). You may not use this file except in
+ * compliance with the License. Please obtain a copy of the License at
+ * http://www.opensource.apple.com/apsl/ and read it before using this
+ * file.
+ *
+ * The Original Code and all software distributed under the License are
+ * distributed on an 'AS IS' basis, WITHOUT WARRANTY OF ANY KIND, EITHER
+ * EXPRESS OR IMPLIED, AND APPLE HEREBY DISCLAIMS ALL SUCH WARRANTIES,
+ * INCLUDING WITHOUT LIMITATION, ANY WARRANTIES OF MERCHANTABILITY,
+ * FITNESS FOR A PARTICULAR PURPOSE, QUIET ENJOYMENT OR NON-INFRINGEMENT.
+ * Please see the License for the specific language governing rights and
+ * limitations under the License.
+ *
+ * @APPLE_LICENSE_HEADER_END@
+ */
+
+#if OCTAGON
+
+#import <XCTest/XCTest.h>
+#import "CloudKitMockXCTest.h"
+
+#import "keychain/ckks/CKKS.h"
+#import "keychain/ckks/CKKSKey.h"
+#import "keychain/ckks/CKKSItem.h"
+#import "keychain/ckks/CKKSOutgoingQueueEntry.h"
+#import "keychain/ckks/CKKSIncomingQueueEntry.h"
+#import "keychain/ckks/CKKSItemEncrypter.h"
+
+#include <securityd/SecItemServer.h>
+#include <Security/SecItemPriv.h>
+
+@interface CloudKitKeychainAESSIVEncryptionTests : CloudKitMockXCTest
+@end
+
+@implementation CloudKitKeychainAESSIVEncryptionTests
+
++ (void)setUp {
+    // We don't really want to spin up the whole machinery for the encryption tests
+    SecCKKSDisable();
+
+    [super setUp];
+}
+
+- (void)setUp {
+    [super setUp];
+}
+
+- (void)tearDown {
+    [super tearDown];
+}
+
++ (void)tearDown {
+    [super tearDown];
+    SecCKKSResetSyncing();
+}
+
+- (void)testKeyGeneration {
+    CKKSAESSIVKey* key1 = [CKKSAESSIVKey randomKey];
+    CKKSAESSIVKey* key2 = [CKKSAESSIVKey randomKey];
+    CKKSAESSIVKey* fixedkey1 = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+    XCTAssertNotNil(fixedkey1, "fixedkey1 generated from base64");
+    CKKSAESSIVKey* fixedkey2 = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+    XCTAssertNotNil(fixedkey2, "fixedkey2 generated from base64");
+
+    XCTAssertEqualObjects(fixedkey1, fixedkey2, "matching fixed keys match");
+    XCTAssertNotEqualObjects(fixedkey1, key1, "fixed key and random key do not match");
+    XCTAssertNotEqualObjects(key1, key2, "two random keys do not match");
+
+    XCTAssertNil([[CKKSAESSIVKey alloc] initWithBase64: @"AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA------AAAAAAAAAAAAAAAAAAAAAAAAAAAAA=="], "Invalid base64 does not generate a key");
+}
+
+- (void)testBasicAESSIVEncryption {
+    NSString* plaintext = @"plaintext is plain";
+    NSData* plaintextData = [plaintext dataUsingEncoding: NSUTF8StringEncoding];
+
+    NSError* error = nil;
+
+    CKKSKey* key = [[CKKSKey alloc] initSelfWrappedWithAESKey: [[CKKSAESSIVKey alloc] initWithBase64: @"AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA=="]
+                                                         uuid:@"8b2aeb7f-4af3-43e9-b6e6-70d5c728ebf7"
+                                                     keyclass:SecCKKSKeyClassC
+                                                        state: SecCKKSProcessedStateLocal
+                                                       zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                                              encodedCKRecord: nil
+                                                   currentkey: true];
+
+    NSData* ciphertext = [key encryptData: plaintextData authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext, "Received a ciphertext");
+    NSData* roundtrip = [key decryptData: ciphertext authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(plaintextData, roundtrip, "roundtripped data matches input");
+
+    NSData* shortDecrypt = [key decryptData: [@"asdf" dataUsingEncoding:NSUTF8StringEncoding] authenticatedData:nil error:&error];
+    XCTAssertNotNil(error, "Decrypting a short plaintext returned an error");
+    XCTAssertNil(shortDecrypt, "Decrypting a short plaintext returned nil");
+    error = nil;
+
+    // Check that we're adding enough entropy
+    NSData* ciphertextAgain = [key encryptData: plaintextData authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertextAgain, "Received a ciphertext");
+    NSData* roundtripAgain = [key decryptData: ciphertextAgain authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtripAgain, "Received a plaintext");
+    XCTAssertEqualObjects(plaintextData, roundtripAgain, "roundtripped data matches input");
+
+    XCTAssertNotEqualObjects(ciphertext, ciphertextAgain, "two encryptions of same input produce different outputs");
+
+    // Do it all again
+    CKKSKey* key2 =  [[CKKSKey alloc] initSelfWrappedWithAESKey: [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="]
+                                                           uuid:@"f5e7f20f-0885-48f9-b75d-9f0cfd2171b6"
+                                                       keyclass:SecCKKSKeyClassC
+                                                          state: SecCKKSProcessedStateLocal
+                                                         zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                                                encodedCKRecord: nil
+                                                     currentkey: true];
+
+    NSData* ciphertext2 = [key2 encryptData: plaintextData authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext2, "Received a ciphertext");
+    NSData* roundtrip2 = [key decryptData: ciphertext authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip2, "Received a plaintext");
+    XCTAssertEqualObjects(plaintextData, roundtrip2, "roundtripped data matches input");
+
+    XCTAssertNotEqualObjects(ciphertext, ciphertext2, "ciphertexts with distinct keys are distinct");
+}
+
+- (void)testAuthEncryption {
+    NSString* plaintext = @"plaintext is plain";
+    NSData* plaintextData = [plaintext dataUsingEncoding: NSUTF8StringEncoding];
+
+    NSError* error = nil;
+
+    CKKSKey* key = [[CKKSKey alloc] initSelfWrappedWithAESKey: [[CKKSAESSIVKey alloc] initWithBase64: @"AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA=="]
+                                                         uuid:@"8b2aeb7f-4af3-43e9-b6e6-70d5c728ebf7"
+                                                     keyclass:SecCKKSKeyClassC
+                                                        state:SecCKKSProcessedStateLocal
+                                                       zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                                              encodedCKRecord:nil
+                                                   currentkey:true];
+    NSDictionary<NSString*, NSData*>* ad = @{ @"test": [@"data" dataUsingEncoding: NSUTF8StringEncoding] };
+
+    NSData* ciphertext = [key encryptData: plaintextData authenticatedData: ad error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext, "Received a ciphertext");
+    NSData* roundtrip = [key decryptData: ciphertext authenticatedData: ad error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(plaintextData, roundtrip, "roundtripped data matches input");
+
+    // Without AD, decryption should fail
+    roundtrip = [key decryptData: ciphertext authenticatedData: nil error: &error];
+    XCTAssertNotNil(error, "Not passing in the authenticated data causes break");
+    XCTAssertNil(roundtrip, "on error, don't receive plaintext");
+    error = nil;
+
+    roundtrip = [key decryptData: ciphertext authenticatedData: @{ @"test": [@"wrongdata" dataUsingEncoding: NSUTF8StringEncoding] } error: &error];
+    XCTAssertNotNil(error, "Wrong authenticated data causes break");
+    XCTAssertNil(roundtrip, "on error, don't receive plaintext");
+    error = nil;
+}
+
+- (void)testDictionaryEncryption {
+    NSDictionary<NSString*, NSData*>* plaintext = @{ @"test": [@"data" dataUsingEncoding: NSUTF8StringEncoding],
+                                                     @"more": [@"testdata" dataUsingEncoding: NSUTF8StringEncoding] };
+    NSDictionary<NSString*, NSData*>* roundtrip;
+
+    NSError* error = nil;
+
+    CKKSKey* key =  [[CKKSKey alloc] initSelfWrappedWithAESKey: [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="]
+                                                          uuid:@"f5e7f20f-0885-48f9-b75d-9f0cfd2171b6"
+                                                      keyclass:SecCKKSKeyClassC
+                                                         state: SecCKKSProcessedStateLocal
+                                                        zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                                               encodedCKRecord: nil
+                                                    currentkey: true];
+
+    NSData* ciphertext = [CKKSItemEncrypter encryptDictionary: plaintext key: key.aessivkey authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext, "Received a ciphertext");
+    roundtrip = [CKKSItemEncrypter decryptDictionary: ciphertext key: key.aessivkey authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(plaintext, roundtrip, "roundtripped dictionary matches input");
+
+    NSDictionary* authenticatedData = @{@"data": [@"auth" dataUsingEncoding: NSUTF8StringEncoding], @"moredata": [@"unauth" dataUsingEncoding: NSUTF8StringEncoding]};
+    NSDictionary* unauthenticatedData = @{@"data": [@"notequal" dataUsingEncoding: NSUTF8StringEncoding], @"moredata": [@"unauth" dataUsingEncoding: NSUTF8StringEncoding]};
+
+    NSData* authciphertext = [CKKSItemEncrypter encryptDictionary: plaintext key: key.aessivkey authenticatedData: authenticatedData error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext with authenticated data");
+    XCTAssertNotNil(authciphertext, "Received a ciphertext");
+    roundtrip = [CKKSItemEncrypter decryptDictionary: authciphertext key: key.aessivkey authenticatedData: authenticatedData error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip with authenticated data");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(plaintext, roundtrip, "roundtripped dictionary matches input");
+
+    roundtrip = [CKKSItemEncrypter decryptDictionary: authciphertext key: key.aessivkey authenticatedData: unauthenticatedData error: &error];
+    XCTAssertNotNil(error, "Error decrypting roundtrip with bad authenticated data");
+    XCTAssertNil(roundtrip, "Did not receive a plaintext when authenticated data is wrong");
+}
+
+- (void)testKeyWrapping {
+    CKKSAESSIVKey* key = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+
+    CKKSAESSIVKey* keyToWrap = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+
+    NSError* error = nil;
+
+    CKKSWrappedAESSIVKey* wrappedKey = [key wrapAESKey: keyToWrap error:&error];
+    XCTAssertNil(error, "no error wrapping key");
+    XCTAssertNotNil(wrappedKey, "wrapped key was returned");
+
+    XCTAssert(0 != memcmp(keyToWrap->key, (wrappedKey->key)+(CKKSWrappedKeySize - CKKSKeySize), CKKSKeySize), "wrapped key is different from original key");
+
+    CKKSAESSIVKey* unwrappedKey = [key unwrapAESKey: wrappedKey error:&error];
+    XCTAssertNil(error, "no error unwrapping key");
+    XCTAssertNotNil(unwrappedKey, "unwrapped key was returned");
+
+    XCTAssert(0 == memcmp(keyToWrap->key, unwrappedKey->key, CKKSKeySize), "unwrapped key matches original key");
+    XCTAssertEqualObjects(keyToWrap, unwrappedKey, "unwrapped key matches original key");
+}
+
+- (void)testKeyWrappingFailure {
+    CKKSAESSIVKey* key = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+
+    CKKSAESSIVKey* keyToWrap = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+
+    NSError* error = nil;
+
+    CKKSWrappedAESSIVKey* wrappedKey = [key wrapAESKey: keyToWrap error:&error];
+    XCTAssertNil(error, "no error wrapping key");
+    XCTAssertNotNil(wrappedKey, "wrapped key was returned");
+
+    XCTAssert(0 != memcmp(keyToWrap->key, (wrappedKey->key)+(CKKSWrappedKeySize - CKKSKeySize), CKKSKeySize), "wrapped key is different from original key");
+    wrappedKey->key[0] ^= 0x1;
+
+    CKKSAESSIVKey* unwrappedKey = [key unwrapAESKey: wrappedKey error:&error];
+    XCTAssertNotNil(error, "error unwrapping key");
+    XCTAssertNil(unwrappedKey, "unwrapped key was not returned in error case");
+}
+
+- (void)testKeyHierarchy {
+    NSError* error = nil;
+    NSData* testCKRecord = [@"nonsense" dataUsingEncoding:NSUTF8StringEncoding];
+    CKKSKey* tlk =  [self fakeTLK:self.testZoneID];
+
+    [tlk saveToDatabase:&error];
+    [tlk saveKeyMaterialToKeychain:&error];
+    XCTAssertNil(error, "tlk saved to database without error");
+
+    CKKSKey* level1 = [CKKSKey randomKeyWrappedByParent: tlk keyclass:SecCKKSKeyClassA error:&error];
+    level1.encodedCKRecord = testCKRecord;
+    XCTAssertNotNil(level1, "level 1 key created");
+    XCTAssertNil(error, "level 1 key created");
+
+    [level1 saveToDatabase:&error];
+    XCTAssertNil(error, "level 1 key saved to database without error");
+
+    CKKSKey* level2 = [CKKSKey randomKeyWrappedByParent: level1 error:&error];
+    level2.encodedCKRecord = testCKRecord;
+    XCTAssertNotNil(level2, "level 2 key created");
+    XCTAssertNil(error, "no error creating level 2 key");
+    [level2 saveToDatabase:&error];
+    XCTAssertNil(error, "level 2 key saved to database without error");
+
+    NSString* level2UUID = level2.uuid;
+
+    // Fetch the level2 key from the database.
+    CKKSKey* extractedkey = [CKKSKey fromDatabase:level2UUID zoneID:self.testZoneID error:&error];
+    [extractedkey unwrapViaKeyHierarchy: &error];
+    XCTAssertNotNil(extractedkey, "could fetch key again");
+    XCTAssertNil(error, "no error fetching key from database");
+
+    CKKSAESSIVKey* extracedaeskey = [extractedkey ensureKeyLoaded:&error];
+    XCTAssertNotNil(extractedkey, "fetched key could unwrap");
+    XCTAssertNil(error, "no error forcing unwrap on fetched key");
+
+    XCTAssertEqualObjects(level2.aessivkey, extracedaeskey, @"fetched aes key is equal to saved key");
+}
+
+- (void)ensureKeychainSaveLoad: (CKKSKey*) key {
+    NSError* error = nil;
+    [key saveToDatabase:&error];
+    XCTAssertNil(error, "no error saving to database");
+    [key saveKeyMaterialToKeychain:&error];
+    XCTAssertNil(error, "no error saving to keychain");
+
+    CKKSKey* loadedKey = [CKKSKey fromDatabase:key.uuid zoneID:self.testZoneID error:&error];
+    XCTAssertNil(error, "no error loading from database");
+    XCTAssertNotNil(loadedKey, "Received an item back from the database");
+
+    XCTAssert([loadedKey loadKeyMaterialFromKeychain:&error], "could load key material back from keychain");
+    XCTAssertNil(error, "no error loading key from keychain");
+
+    XCTAssertEqualObjects(loadedKey.aessivkey, key.aessivkey, "Loaded key is identical after save/load");
+}
+
+- (void)testKeychainSave {
+    NSError* error = nil;
+    NSData* testCKRecord = [@"nonsense" dataUsingEncoding:NSUTF8StringEncoding];
+    CKKSKey* tlk =  [self fakeTLK:self.testZoneID];
+    [self ensureKeychainSaveLoad: tlk];
+
+    // Ensure that Class A and Class C can do the same thing
+    CKKSKey* classA = [CKKSKey randomKeyWrappedByParent: tlk keyclass:SecCKKSKeyClassA error:&error];
+    classA.encodedCKRecord = testCKRecord;
+    XCTAssertNil(error, "No error creating random class A key");
+    [self ensureKeychainSaveLoad: classA];
+    CKKSKey* classC = [CKKSKey randomKeyWrappedByParent: tlk keyclass:SecCKKSKeyClassC error:&error];
+    classC.encodedCKRecord = testCKRecord;
+    XCTAssertNil(error, "No error creating random class C key");
+    [self ensureKeychainSaveLoad: classC];
+}
+
+- (void)testCKKSKeyProtobuf {
+    NSError* error = nil;
+    CKKSKey* tlk =  [self fakeTLK:self.testZoneID];
+
+    NSData* tlkPersisted = [tlk serializeAsProtobuf:&error];
+    XCTAssertNil(error, "Shouldn't have been an error serializing to protobuf");
+    XCTAssertNotNil(tlkPersisted, "Should have gotten some protobuf data back");
+
+    CKKSKey* otherKey = [CKKSKey loadFromProtobuf:tlkPersisted error:&error];
+    XCTAssertNil(error, "Shouldn't have been an error serializing from protobuf");
+    XCTAssertNotNil(otherKey, "Should have gotten some protobuf data back");
+
+    XCTAssertEqualObjects(tlk.uuid, otherKey.uuid, "Should have gotten the same UUID");
+    XCTAssertEqualObjects(tlk.keyclass, otherKey.keyclass, "Should have gotten the same key class");
+    XCTAssertEqualObjects(tlk.zoneID, otherKey.zoneID, "Should have gotten the same zoneID");
+    XCTAssertEqualObjects(tlk.aessivkey, otherKey.aessivkey, "Should have gotten the same underlying key back");
+    XCTAssertEqualObjects(tlk, otherKey, "Should have gotten the same key");
+}
+
+- (BOOL)tryDecryptWithProperAuthData:(CKKSItem*)ciphertext plaintext:(NSDictionary<NSString*, NSData*>*)plaintext {
+    NSDictionary<NSString*, NSData*>* roundtrip;
+    NSError *error = nil;
+    roundtrip = [CKKSItemEncrypter decryptItemToDictionary: (CKKSItem*) ciphertext error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(plaintext, roundtrip, "roundtripped dictionary matches input");
+    return error == nil && roundtrip != nil && [plaintext isEqualToDictionary:roundtrip];
+}
+
+- (BOOL)tryDecryptWithBrokenAuthData:(CKKSItem *)ciphertext {
+    NSDictionary<NSString*, NSData*>* brokenAuthentication;
+    NSError *error = nil;
+    brokenAuthentication = [CKKSItemEncrypter decryptItemToDictionary: (CKKSItem*) ciphertext error: &error];
+    XCTAssertNotNil(error, "Error exists decrypting ciphertext with bad authenticated data: %@", error);
+    XCTAssertNil(brokenAuthentication, "Did not receive a plaintext if authenticated data was mucked with");
+    return error != nil && brokenAuthentication == nil;
+}
+
+- (void)testItemDictionaryEncryption {
+    NSDictionary<NSString*, NSData*>* plaintext = @{ @"test": [@"data" dataUsingEncoding: NSUTF8StringEncoding],
+                                                     @"more": [@"testdata" dataUsingEncoding: NSUTF8StringEncoding] };
+    NSError* error = nil;
+    NSString *uuid = @"8b2aeb7f-4af3-43e9-b6e6-70d5c728ebf7";
+
+    CKKSKey* key = [self fakeTLK:self.testZoneID];
+    [key saveToDatabase: &error];
+    [key saveKeyMaterialToKeychain:&error];
+    XCTAssertNil(error, @"could save the fake TLK to the database");
+
+    CKKSItem* ciphertext = [CKKSItemEncrypter encryptCKKSItem: [[CKKSItem alloc] initWithUUID:uuid
+                                                                                parentKeyUUID:key.uuid
+                                                                                       zoneID:self.testZoneID]
+                                               dataDictionary:plaintext
+                                             updatingCKKSItem:nil
+                                                    parentkey:key
+                                                        error:&error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext, "Received a ciphertext");
+    XCTAssertEqual(ciphertext.encver, currentCKKSItemEncryptionVersion, "Encryption sets the current protocol version");
+
+    [self tryDecryptWithProperAuthData:ciphertext plaintext:plaintext];
+
+    // Make sure these fields are authenticated and that authentication works.
+    // Messing with them should make the item not decrypt.
+    ciphertext.generationCount = 100;
+    XCTAssertTrue([self tryDecryptWithBrokenAuthData:ciphertext], "Decryption with broken authentication data fails");
+    ciphertext.generationCount = 0;
+    XCTAssertTrue([self tryDecryptWithProperAuthData:ciphertext plaintext:plaintext], "Decryption with authentication data succeeds");
+
+    ciphertext.encver += 1;
+    XCTAssertTrue([self tryDecryptWithBrokenAuthData:ciphertext], "Decryption with broken authentication data fails");
+    ciphertext.encver -= 1;
+    XCTAssertTrue([self tryDecryptWithProperAuthData:ciphertext plaintext:plaintext], "Decryption with authentication data succeeds");
+
+    ciphertext.uuid = @"x";
+    XCTAssertTrue([self tryDecryptWithBrokenAuthData:ciphertext], "Decryption with broken authentication data fails");
+    ciphertext.uuid = uuid;
+    XCTAssertTrue([self tryDecryptWithProperAuthData:ciphertext plaintext:plaintext], "Decryption with authentication data succeeds");
+}
+
+- (void)testEncryptionVersions {
+    NSDictionary<NSString*, NSData*>* plaintext = @{ @"test": [@"data" dataUsingEncoding: NSUTF8StringEncoding],
+                                                     @"more": [@"testdata" dataUsingEncoding: NSUTF8StringEncoding] };
+    NSDictionary<NSString*, NSData*>* output;
+    NSError *error = nil;
+    NSData* data = [NSPropertyListSerialization dataWithPropertyList:plaintext
+                                                              format:NSPropertyListBinaryFormat_v1_0
+                                                             options:0
+                                                               error:&error];
+    XCTAssertNil(error);
+    CKKSKey* key = [self fakeTLK:self.testZoneID];
+    [key saveToDatabase: &error];
+    [key saveKeyMaterialToKeychain:&error];
+    XCTAssertNil(error, @"could save the fake TLK to the database");
+
+    CKKSAESSIVKey* keyToWrap = [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="];
+    CKKSWrappedAESSIVKey* wrappedKey = [key wrapAESKey: keyToWrap error:&error];
+    XCTAssertNil(error, "no error wrapping key");
+    XCTAssertNotNil(wrappedKey, "wrapped key was returned");
+    CKKSItem* baseitem = [[CKKSItem alloc] initWithUUID:@"abc"
+                                          parentKeyUUID:key.uuid
+                                                 zoneID:self.testZoneID
+                                                encItem:data
+                                             wrappedkey:wrappedKey
+                                        generationCount:0
+                                                 encver:CKKSItemEncryptionVersionNone];
+    XCTAssertNotNil(baseitem, "Constructed CKKSItem");
+
+    // First try versionNone. Should fail, we don't support unencrypted data
+    output = [CKKSItemEncrypter decryptItemToDictionary:baseitem error:&error];
+    XCTAssert(error, "Did not failed to decrypt v0 item");
+    XCTAssertNil(output, "Did not failed to decrypt v0 item");
+    error = nil;
+    output = nil;
+
+    // Then try version1. Should take actual decryption path and fail because there's no properly encrypted data.
+    baseitem.encver = CKKSItemEncryptionVersion1;
+    output = [CKKSItemEncrypter decryptItemToDictionary:baseitem error:&error];
+    XCTAssertNotNil(error, "Taking v1 codepath without encrypted item fails");
+    XCTAssertEqualObjects(error.localizedDescription, @"could not ccsiv_crypt", "Error specifically failure to ccsiv_crypt");
+    XCTAssertNil(output, "Did not receive output from failed decryption call");
+    error = nil;
+    output = nil;
+
+    // Finally, some unknown version should fail immediately
+    baseitem.encver = 100;
+    output = [CKKSItemEncrypter decryptItemToDictionary:baseitem error:&error];
+    XCTAssertNotNil(error);
+    NSString *errstr = [NSString stringWithFormat:@"%@", error.localizedDescription];
+    NSString *expected = @"Unrecognized encryption version: 100";
+    XCTAssertEqualObjects(expected, errstr, "Error is specific to unrecognized version failure");
+    XCTAssertNil(output);
+}
+
+- (void)testKeychainPersistence {
+
+    NSString* plaintext = @"plaintext is plain";
+    NSData* plaintextData = [plaintext dataUsingEncoding: NSUTF8StringEncoding];
+
+    NSError* error = nil;
+
+    NSString* uuid = @"f5e7f20f-0885-48f9-b75d-9f0cfd2171b6";
+
+    CKKSKey* key =  [[CKKSKey alloc] initSelfWrappedWithAESKey: [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="]
+                                                           uuid:uuid
+                                                       keyclass:SecCKKSKeyClassA
+                                                          state:SecCKKSProcessedStateLocal
+                                                         zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                                                encodedCKRecord: nil
+                                                     currentkey: true];
+
+    NSData* ciphertext = [key encryptData: plaintextData authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext, "Received a ciphertext");
+    NSData* roundtrip = [key decryptData: ciphertext authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(plaintextData, roundtrip, "roundtripped data matches input");
+
+    // Check that there is no key material in the keychain
+    CKKSKey* reloadedKey = [CKKSKey keyFromKeychain:uuid
+                                      parentKeyUUID:uuid
+                                           keyclass:SecCKKSKeyClassA
+                                              state:SecCKKSProcessedStateLocal
+                                             zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                                    encodedCKRecord:nil
+                                         currentkey:true
+                                              error:&error];
+
+    XCTAssertNotNil(error, "error exists when there's nothing in the keychain");
+    XCTAssertNil(reloadedKey, "no key object when there's nothing in the keychain");
+    error = nil;
+
+    [key saveKeyMaterialToKeychain:&error];
+    XCTAssertNil(error, "Could save key material to keychain");
+
+    // Reload the key material and check that it works
+    reloadedKey = [CKKSKey keyFromKeychain:uuid
+                             parentKeyUUID:uuid
+                                  keyclass:SecCKKSKeyClassA
+                                     state:SecCKKSProcessedStateLocal
+                                    zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                           encodedCKRecord:nil
+                                currentkey:true
+                                     error:&error];
+
+    XCTAssertNil(error, "No error loading key from keychain");
+    XCTAssertNotNil(reloadedKey, "Could load key from keychain");
+
+    NSData* ciphertext2 = [reloadedKey encryptData: plaintextData authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext2, "Received a ciphertext");
+    NSData* roundtrip2 = [reloadedKey decryptData: ciphertext2 authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip2, "Received a plaintext");
+    XCTAssertEqualObjects(plaintextData, roundtrip2, "roundtripped data matches input");
+
+    XCTAssertEqualObjects(key.aessivkey, reloadedKey.aessivkey, "reloaded AES key is equal to generated key");
+
+    [key deleteKeyMaterialFromKeychain: &error];
+    XCTAssertNil(error, "could delete key material from keychain");
+
+    // Check that there is no key material in the keychain
+    // Note that TLKs will be stashed (and deleteKeyMaterial won't delete the stash), and so this test would fail for a TLK
+
+    reloadedKey = [CKKSKey keyFromKeychain:uuid
+                             parentKeyUUID:uuid
+                                  keyclass:SecCKKSKeyClassA
+                                     state:SecCKKSProcessedStateLocal
+                                    zoneID:[[CKRecordZoneID alloc] initWithZoneName:@"testzone" ownerName:CKCurrentUserDefaultName]
+                           encodedCKRecord:nil
+                                currentkey:true
+                                     error:&error];
+
+    XCTAssertNotNil(error, "error exists when there's nothing in the keychain");
+    XCTAssertNil(reloadedKey, "no key object when there's nothing in the keychain");
+    error = nil;
+}
+
+- (void)testCKKSKeyTrialSelfWrapped {
+    NSError* error = nil;
+    CKKSKey* tlk =  [self fakeTLK:self.testZoneID];
+    XCTAssertTrue([tlk wrapsSelf], "TLKs should wrap themselves");
+
+    CKRecord* record = [tlk CKRecordWithZoneID:self.testZoneID];
+    XCTAssertNotNil(record, "TLKs should know how to turn themselves into CKRecords");
+    CKKSKey* receivedTLK = [[CKKSKey alloc] initWithCKRecord:record];
+    XCTAssertNotNil(receivedTLK, "Keys should know how to recover themselves from CKRecords");
+
+    XCTAssertTrue([receivedTLK wrapsSelf], "TLKs should wrap themselves, even when received from CloudKit");
+
+    XCTAssertFalse([receivedTLK ensureKeyLoaded:&error], "Received keys can't load themselves when there's no key data");
+    XCTAssertNotNil(error, "Error should exist when a key fails to load itself");
+    error = nil;
+
+    XCTAssertTrue([receivedTLK trySelfWrappedKeyCandidate:tlk.aessivkey error:&error], "Shouldn't be an error when we give a CKKSKey its key");
+    XCTAssertNil(error, "Shouldn't be an error giving a CKKSKey its key material");
+
+    XCTAssertTrue([receivedTLK ensureKeyLoaded:&error], "Once a CKKSKey has its key material, it doesn't need to load it again");
+    XCTAssertNil(error, "Shouldn't be an error loading a loaded CKKSKey");
+}
+
+- (void)testCKKSKeyTrialSelfWrappedFailure {
+    NSError* error = nil;
+    CKKSKey* tlk =  [self fakeTLK:self.testZoneID];
+    XCTAssertTrue([tlk wrapsSelf], "TLKs should wrap themselves");
+
+    CKRecord* record = [tlk CKRecordWithZoneID:self.testZoneID];
+    XCTAssertNotNil(record, "TLKs should know how to turn themselves into CKRecords");
+    CKKSKey* receivedTLK = [[CKKSKey alloc] initWithCKRecord:record];
+    XCTAssertNotNil(receivedTLK, "Keys should know how to recover themselves from CKRecords");
+
+    XCTAssertTrue([receivedTLK wrapsSelf], "TLKs should wrap themselves, even when received from CloudKit");
+
+    XCTAssertFalse([receivedTLK ensureKeyLoaded:&error], "Received keys can't load themselves when there's no key data");
+    XCTAssertNotNil(error, "Error should exist when a key fails to load itself");
+    error = nil;
+
+    XCTAssertFalse([receivedTLK trySelfWrappedKeyCandidate:[[CKKSAESSIVKey alloc] initWithBase64: @"aaaaaZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="] error:&error], "Should be an error when we give a CKKSKey the wrong key");
+    XCTAssertNotNil(error, "Should be an error giving a CKKSKey the wrong key material");
+
+    XCTAssertFalse([receivedTLK ensureKeyLoaded:&error], "Received keys can't load themselves when there's no key data");
+    XCTAssertNotNil(error, "Error should exist when a key fails to load itself");
+    error = nil;
+}
+
+- (void)testCKKSKeyTrialNotSelfWrappedFailure {
+    NSError* error = nil;
+    CKKSKey* tlk =  [self fakeTLK:self.testZoneID];
+    XCTAssertTrue([tlk wrapsSelf], "TLKs should wrap themselves");
+
+    CKKSKey* classC = [CKKSKey randomKeyWrappedByParent: tlk keyclass:SecCKKSKeyClassC error:&error];
+    XCTAssertFalse([classC wrapsSelf], "Wrapped keys should not wrap themselves");
+
+    XCTAssertTrue([classC ensureKeyLoaded:&error], "Once a CKKSKey has its key material, it doesn't need to load it again");
+    XCTAssertNil(error, "Shouldn't be an error loading a loaded CKKSKey");
+
+    XCTAssertFalse([classC trySelfWrappedKeyCandidate:classC.aessivkey error:&error], "Should be an error when we attempt to trial a key on a non-self-wrapped key");
+    XCTAssertNotNil(error, "Should be an error giving a CKKSKey the wrong key material");
+    XCTAssertEqual(error.code, CKKSKeyNotSelfWrapped, "Should have gotten CKKSKeyNotSelfWrapped as an error");
+    error = nil;
+
+    // But, since we didn't throw away its key, it's still loaded
+    XCTAssertTrue([classC ensureKeyLoaded:&error], "Once a CKKSKey has its key material, it doesn't need to load it again");
+    XCTAssertNil(error, "Shouldn't be an error loading a loaded CKKSKey");
+}
+
+- (BOOL)padAndUnpadDataWithLength:(NSUInteger)dataLength blockSize:(NSUInteger)blockSize extra:(BOOL)extra {
+    // Test it works
+    NSMutableData *data = [NSMutableData dataWithLength:dataLength];
+    memset((unsigned char *)[data mutableBytes], 0x55, dataLength);
+    NSMutableData *orig = [data mutableCopy];
+    NSData *padded = [CKKSItemEncrypter padData:data blockSize:blockSize additionalBlock:extra];
+    XCTAssertNotNil(padded, "Padding never returns nil");
+    XCTAssertEqualObjects(data, orig, "Input object unmodified");
+    XCTAssertTrue(padded.length % blockSize == 0, "Padded data aligns on %lu-byte blocksize", (unsigned long)blockSize);
+    XCTAssertTrue(padded.length > data.length, "At least one byte of padding has been added");
+    NSData *unpadded = [CKKSItemEncrypter removePaddingFromData:padded];
+    XCTAssertNotNil(unpadded, "Successfully removed padding again");
+
+    // Test it fails by poking some byte in the padding
+    NSMutableData *glitch = [NSMutableData dataWithData:padded];
+    NSUInteger offsetFromTop = glitch.length - arc4random_uniform((unsigned)(glitch.length - data.length)) - 1;
+    uint8_t poke = ((uint8_t)arc4random_uniform(0xFF) & 0x7E) + 1; // This gets most of the values while excluding 0 and 0x80
+    unsigned char *bytes = [glitch mutableBytes];
+    bytes[offsetFromTop] = poke;
+    XCTAssertNil([CKKSItemEncrypter removePaddingFromData:glitch], "Cannot remove broken padding (len %lu, dlen %lu, plen %lu glitchidx %lu, glitchval 0x%x)", (unsigned long)glitch.length, (unsigned long)data.length, (unsigned long)glitch.length - data.length, (unsigned long)offsetFromTop, poke);
+
+    return padded && unpadded && [unpadded isEqual:data];
+}
+
+- (void)testPadding {
+       [self runPaddingTest:NO];
+       [self runPaddingTest:YES];
+
+    NSData *data = nil;
+    XCTAssertNil([CKKSItemEncrypter removePaddingFromData:[NSData data]], "zero data valid ?");
+
+    data = [CKKSItemEncrypter removePaddingFromData:[NSData dataWithBytes:"\x80" length:1]];
+    XCTAssert(data && data.length == 0, "data wrong size");
+
+    data = [CKKSItemEncrypter removePaddingFromData:[NSData dataWithBytes:"\x80\x00" length:2]];
+    XCTAssert(data && data.length == 0, "data wrong size");
+    data = [CKKSItemEncrypter removePaddingFromData:[NSData dataWithBytes:"\x80\x00\x00" length:3]];
+    XCTAssert(data && data.length == 0, "data wrong size");
+    data = [CKKSItemEncrypter removePaddingFromData:[NSData dataWithBytes:"\x80\x80\x80" length:3]];
+    XCTAssert(data && data.length == 2, "data wrong size");
+    data = [CKKSItemEncrypter removePaddingFromData:[NSData dataWithBytes:"\x80\x80\x00" length:3]];
+    XCTAssert(data && data.length == 1, "data wrong size");
+    data = [CKKSItemEncrypter removePaddingFromData:[NSData dataWithBytes:"\x00\x80\x00" length:3]];
+    XCTAssert(data && data.length == 1, "data wrong size");
+
+}
+
+- (void)runPaddingTest:(BOOL)extra {
+
+       // Aligned, arbitrary lengths
+       for (int idx = 1; idx <= 128; ++idx) {
+               XCTAssertTrue([self padAndUnpadDataWithLength:idx blockSize:idx extra:extra], "Padding aligned data succeeds");
+       }
+
+       // Off-by-one, arbitrary lengths
+       for (int idx = 1; idx <= 128; ++idx) {
+               XCTAssertTrue([self padAndUnpadDataWithLength:idx - 1 blockSize:idx extra:extra], "Padding aligned data succeeds");
+               XCTAssertTrue([self padAndUnpadDataWithLength:idx + 1 blockSize:idx extra:extra], "Padding aligned data succeeds");
+       }
+
+       // Misaligned, arbitrary lengths
+       for (int idx = 1; idx <= 1000; ++idx) {
+               NSUInteger dataSize = arc4random_uniform(128) + 1;
+               NSUInteger blockSize = arc4random_uniform(128) + 1;
+               XCTAssertTrue([self padAndUnpadDataWithLength:dataSize blockSize:blockSize extra:extra], "Padding data lenght %lu to blockSize %lu succeeds", (unsigned long)dataSize, (unsigned long)blockSize);
+       }
+
+       // Special case: blocksize 0 results in 1 byte of padding always
+       NSMutableData *data = [NSMutableData dataWithLength:23];
+       memset((unsigned char *)[data mutableBytes], 0x55, 23);
+       NSData *padded = [CKKSItemEncrypter padData:data blockSize:0 additionalBlock:extra];
+       XCTAssertNotNil(padded, "Padding never returns nil");
+    XCTAssertTrue(padded.length == data.length + extra ? 2 : 1, "One byte of padding has been added, 2 if extra padding");
+       NSData *unpadded = [CKKSItemEncrypter removePaddingFromData:padded];
+       XCTAssertNotNil(unpadded, "Successfully removed padding again");
+       XCTAssertEqualObjects(data, unpadded, "Data effectively unmodified through padding-unpadding trip");
+
+       // Nonpadded data
+       unpadded = [CKKSItemEncrypter removePaddingFromData:data];
+       XCTAssertNil(unpadded, "Cannot remove padding where none exists");
+
+       // Feeding nil
+       padded = [CKKSItemEncrypter padData:nil blockSize:0 additionalBlock:extra];
+       XCTAssertNotNil(padded, "padData always returns a data object");
+    XCTAssertEqual(padded.length, extra ? 2ul : 1ul, "Length of padded nil object is padding byte only--two if extra");
+       unpadded = [CKKSItemEncrypter removePaddingFromData:nil];
+       XCTAssertNil(unpadded, "Removing padding from nil is senseless");
+}
+
+- (BOOL)encryptAndDecryptDictionary:(NSDictionary<NSString*, NSData*>*)data key:(CKKSKey *)key {
+    NSDictionary<NSString*, NSData*>* roundtrip;
+    NSError *error = nil;
+    NSData* ciphertext = [CKKSItemEncrypter encryptDictionary: data key: key.aessivkey authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error encrypting plaintext");
+    XCTAssertNotNil(ciphertext, "Received a ciphertext");
+    // AES-SIV adds 32 bytes, need to subtract them
+    XCTAssertTrue((ciphertext.length - 32) % SecCKKSItemPaddingBlockSize == 0, "Ciphertext aligned on %lu-byte boundary", (unsigned long)SecCKKSItemPaddingBlockSize);
+    roundtrip = [CKKSItemEncrypter decryptDictionary: ciphertext key: key.aessivkey authenticatedData: nil error: &error];
+    XCTAssertNil(error, "No error decrypting roundtrip");
+    XCTAssertNotNil(roundtrip, "Received a plaintext");
+    XCTAssertEqualObjects(data, roundtrip, "roundtripped dictionary matches input");
+    return (ciphertext.length  - 32) % SecCKKSItemPaddingBlockSize == 0 && roundtrip && error == nil && [data isEqualToDictionary:roundtrip];
+}
+
+- (void)testDictionaryPadding {
+    // Pad a bunch of bytes to nearest boundary
+    NSDictionary<NSString*, NSData*>* unaligned_74 = @{ @"test": [@"data" dataUsingEncoding: NSUTF8StringEncoding],
+                                                     @"more": [@"testdata" dataUsingEncoding: NSUTF8StringEncoding] };
+    // Pad precisely one byte
+    NSDictionary<NSString*, NSData*>* unaligned_79 = @{ @"test12345": [@"data" dataUsingEncoding: NSUTF8StringEncoding],
+                                                      @"more": [@"testdata" dataUsingEncoding: NSUTF8StringEncoding] };
+    // Already on boundary, pad until next boundary
+    NSDictionary<NSString*, NSData*>* aligned_80 = @{ @"test123456": [@"data" dataUsingEncoding: NSUTF8StringEncoding],
+                                                      @"more": [@"testdata" dataUsingEncoding: NSUTF8StringEncoding] };
+    CKKSKey* key =  [[CKKSKey alloc] initSelfWrappedWithAESKey: [[CKKSAESSIVKey alloc] initWithBase64: @"uImdbZ7Zg+6WJXScTnRBfNmoU1UiMkSYxWc+d1Vuq3IFn2RmTRkTdWTe3HmeWo1pAomqy+upK8KHg2PGiRGhqg=="]
+                                                          uuid:@"f5e7f20f-0885-48f9-b75d-9f0cfd2171b6"
+                                                      keyclass:SecCKKSKeyClassC
+                                                         state:SecCKKSProcessedStateLocal
+                                                        zoneID:nil
+                                               encodedCKRecord:nil
+                                                    currentkey:true];
+
+    XCTAssertTrue([self encryptAndDecryptDictionary:unaligned_74 key:key], "Roundtrip with unaligned data succeeds");
+    XCTAssertTrue([self encryptAndDecryptDictionary:unaligned_79 key:key], "Roundtrip with unaligned data succeeds");
+    XCTAssertTrue([self encryptAndDecryptDictionary:aligned_80 key:key], "Roundtrip with aligned data succeeds");
+}
+
+@end
+
+#endif // OCTAGON