Objective-C: eveluate server certificate signed by our own PKI (root CA) on TLS TCP connection

Question

*solved*

My problem is referencing to the following question:
Objective-C: How to verify SecCertificateRef with signer's public key?

We have an own PKI and so an own rootCA that we trust. With this rootCA we sign the certificates that are delivered to the personal servers. Now I want to connect with the iOS app and check if the cert that is delivered from the server is signed with our CA.

My app should be able to connect to n servers with this certificates (maybe found with zero-conf service) using a TCP-connection, established by GCDAsyncSocket. I have the public part of the certificate in my app that I would like to add to my "CertChain" so the app will trust them on connect.

I have tried a lot, but I'm still not able to pass SecTrustEvaluate(trust, &result); with a valid result. (I want to use this in productive, so please don't tell me anything about deactivating validation)

My certificates:
in app: rootCA, oldServerCA (cer)
on server (via trust): homeServer, oldServer

My certificate chain:
rootCA signed homeServer
oldServerCA signed oldServer

My code parts:
added updates

- (void)socket:(GCDAsyncSocket *)sock didConnectToHost:(NSString *)host port:(uint16_t)port;
{
// Configure SSL/TLS settings
NSMutableDictionary *settings = [NSMutableDictionary dictionaryWithCapacity:3];

// Allow self-signed certificates
[settings setObject:[NSNumber numberWithBool:YES]
             forKey:GCDAsyncSocketManuallyEvaluateTrust];

[sock startTLS:settings];

// get the certificates as data for further operations
NSString *certFilePath1 = [[NSBundle mainBundle] pathForResource:@"rootCA" ofType:@"cer"]; // also tried it with 'der', same result
NSData *certData1 = [NSData dataWithContentsOfFile:certFilePath1];

NSString *certFilePath2 = [[NSBundle mainBundle] pathForResource:@"oldServerCA" ofType:@"cer"];
NSData *certData2 = [NSData dataWithContentsOfFile:certFilePath2];

// if data exists, use it
if(certData1 && certData2)
{
    SecCertificateRef   cert1;
    cert1 = SecCertificateCreateWithData(NULL, (__bridge CFDataRef) certData1);

    SecCertificateRef   cert2;
    cert2 = SecCertificateCreateWithData(NULL, (__bridge CFDataRef) certData2);

    // only working for "cer"
    NSString *name = [NSString stringWithUTF8String:CFStringGetCStringPtr(SecCertificateCopySubjectSummary(cert1), kCFStringEncodingUTF8)];
    // maybe I understood the usage of "name" in "kSecAttrApplicationTag" wrong?
    OSStatus status = SecItemAdd((__bridge CFDictionaryRef)[NSDictionary dictionaryWithObjectsAndKeys:
                                                   (__bridge id)(kSecClassKey), kSecClass,
                                                   (__bridge id)kSecAttrKeyTypeRSA, kSecAttrKeyType,
                                                   (__bridge id)kSecAttrKeyClassPublic, kSecAttrKeyClass,
                                                   kCFBooleanTrue, kSecAttrIsPermanent,
                                                   [name dataUsingEncoding:NSUTF8StringEncoding], kSecAttrApplicationTag,
                                                   certData1, kSecValueData,
                                                   kCFBooleanTrue, kSecReturnPersistentRef,
                                                   nil],
                                 NULL);   //don't need public key ref

    // Setting "cer" is successfully and delivers "noErr" in first run, then "errKCDuplicateItem"

    NSLog(@"evaluate with status %d", (int)status);
    NSString *name2 = [NSString stringWithUTF8String:CFStringGetCStringPtr(SecCertificateCopySubjectSummary(cert2), kCFStringEncodingUTF8)];
    OSStatus status2 = SecItemAdd((__bridge CFDictionaryRef)[NSDictionary dictionaryWithObjectsAndKeys:
                                                            (__bridge id)(kSecClassKey), kSecClass,
                                                            (__bridge id)kSecAttrKeyTypeRSA, kSecAttrKeyType,
                                                            (__bridge id)kSecAttrKeyClassPublic, kSecAttrKeyClass,
                                                            kCFBooleanTrue, kSecAttrIsPermanent,
                                                            [name2 dataUsingEncoding:NSUTF8StringEncoding], kSecAttrApplicationTag,
                                                            certData2, kSecValueData,
                                                            kCFBooleanTrue, kSecReturnPersistentRef,
                                                            nil],
                                 NULL);   //don't need public key ref

    NSLog(@"evaluate with status %d", (int)status2);

    // log here -> certificates were loaded. Fine

    // create references of each to proof them seperatly
    const void *ref[] = {cert1};
    CFArrayRef aryRef = CFArrayCreate(NULL, ref, 1, NULL);

    const void *ref2[] = {cert2};
    CFArrayRef aryRef2 = CFArrayCreate(NULL, ref2, 1, NULL);

    // need this way to get sock.sslContext, otherways it's NULL (see implementation of GCDAsyncSocket)
    [sock performBlock:^{
        SSLContextRef sslContext = sock.sslContext;
        OSStatus status = SSLSetCertificate(sslContext, aryRef);

        // the status is everywhere always -909 -> badReqErr /*bad parameter or invalid state for operation*/

        if(status == noErr)
            NSLog(@"successfully set ssl certificates");
        else
            NSLog(@"setting ssl certificates failed");

        status = SSLSetCertificate(sock.sslContext, aryRef2);

        if(status == noErr)
            NSLog(@"successfully set ssl certificates");
        else
            NSLog(@"setting ssl certificates failed");

        status = SSLSetEncryptionCertificate(sock.sslContext, aryRef);

        if(status == noErr)
            NSLog(@"successfully set ssl certificates");
        else
            NSLog(@"setting ssl certificates failed");
    }];

}

@synchronized( self )
{
    if( isConnected == NO )
    {
        if(gcdAsyncSocket && [gcdAsyncSocket isConnected])
        {
            isConnected = YES;
            [gcdAsyncSocket readDataWithTimeout:READ_TIMEOUT tag:0];
            [NSThread detachNewThreadSelector:@selector(readDataToData:withTimeout:tag:) toTarget:gcdAsyncSocket withObject:nil];
            [gcdAsyncSocket readDataToData:[GCDAsyncSocket LFData] withTimeout:READ_TIMEOUT tag:0];
            [del onConnect];
        }
    }
} 
}

well... if not working here, then check manually...

- (void)socket:(GCDAsyncSocket *)sock didReceiveTrust:(SecTrustRef)trust
completionHandler:(void (^)(BOOL shouldTrustPeer))completionHandler
{
//    https://code.csdn.net/OS_Mirror/CocoaAsyncSocket/file_diff/a4b9c4981b3c022ca89d0cdaadecc70b825ad4f1...5d58af30d2d8a3e0f7219487e72f1b4b2c3b4894/GCD/Xcode/SimpleHTTPClient/Desktop/SimpleHTTPClient/SimpleHTTPClientAppDelegate.m
    dispatch_queue_t bgQueue = dispatch_get_global_queue(DISPATCH_QUEUE_PRIORITY_DEFAULT, 0);
    dispatch_async(bgQueue, ^{
    // This is where you would (eventually) invoke SecTrustEvaluate.
    // Presumably, if you're using manual trust evaluation, you're likely doing extra stuff here.
    // For example, allowing a specific self-signed certificate that is known to the app.
    NSString *certFilePath1 = [[NSBundle mainBundle] pathForResource:@"rootCA" ofType:@"cer"];
    NSData *certData1 = [NSData dataWithContentsOfFile:certFilePath1];

    NSString *certFilePath2 = [[NSBundle mainBundle] pathForResource:@"oldServerCA" ofType:@"cer"];
    NSData *certData2 = [NSData dataWithContentsOfFile:certFilePath2];

    if(certData1 && certData2)
    {
        CFArrayRef arrayRefTrust = SecTrustCopyProperties(trust);
        SecTrustResultType result = kSecTrustResultUnspecified;

        // usualy should work already here
        OSStatus status = SecTrustEvaluate(trust, &result);

        NSLog(@"evaluate with result %d and status %d", result, (int)status);
        NSLog(@"trust properties: %@", arrayRefTrust);

        /* log:
         evaluate with result 5 and status 0
         trust properties: (
         {
            type = error;
            value = "Root certificate is not trusted."; // expected, when top part was not working
         }
         */

        SecCertificateRef   cert1;
        cert1 = SecCertificateCreateWithData(NULL, (__bridge CFDataRef) certData1);

        SecCertificateRef   cert2;
        cert2 = SecCertificateCreateWithData(NULL, (__bridge CFDataRef) certData2);

        const void *ref[] = {cert1};

        CFIndex count = SecTrustGetCertificateCount(trust);
//            CFMutableArrayRef aryRef = CFArrayCreateMutable(NULL, count + 1, NULL);
//            CFArrayAppendValue(aryRef, ref);

        CFArrayCreate(NULL, ref, 2, NULL);

        // # # # #
        // so check one by one...

        BOOL isMatching = NO;

        for (int i = 0; i < count; i++)
        {
            SecCertificateRef certRef = SecTrustGetCertificateAtIndex(trust, i);
            NSString *name = [NSString stringWithUTF8String:CFStringGetCStringPtr(SecCertificateCopySubjectSummary(certRef), kCFStringEncodingUTF8)]; // only working for "cer"
            NSLog(@"remote cert at index %d is '%@'", i, name);
            /*
                first is 'homeserver', second is 'oldServer'

            */
//                const void *ref[] = {certRef, cert1, cert2};
//                CFArrayRef aryCheck = CFArrayCreate(NULL, ref, 3, NULL);
            // check against the new cert (rootCA)
            const void *ref[] = {certRef, cert1};
            CFArrayRef aryCheck = CFArrayCreate(NULL, ref, 2, NULL);

            SecTrustRef trustManual;
            OSStatus certStatus = SecTrustCreateWithCertificates(aryCheck, SecPolicyCreateBasicX509(), &trustManual);
            // certStatus always noErr
            NSLog(@"certStatus: %d", (int)certStatus);

            SecTrustResultType result;
            OSStatus status =  SecTrustEvaluate(trustManual, &result);
            CFArrayRef arrayRef = SecTrustCopyProperties(trustManual);

            NSLog(@"evaluate with result %d and status %d", result, (int)status);
            NSLog(@"trust properties: %@", arrayRef);
            /* log:
             evaluate with result 5 and status 0
             trust properties: (
             {
             type = error;
             value = "Root certificate is not trusted.";
             }
             */
            // always else-part because result is "kSecTrustResultRecoverableTrustFailure"
            if (status == noErr && (result == kSecTrustResultProceed || result == kSecTrustResultUnspecified))
            {
                isMatching = YES;
                NSLog(@"certificates matches");
            }
            else
            {
                NSLog(@"certificates differs");
            }
        }


        if (isMatching || (status == noErr && (result == kSecTrustResultProceed || result == kSecTrustResultUnspecified)))
        {
            completionHandler(YES);
        }
        else
        {
            completionHandler(NO);
        }
    }
    completionHandler(NO);
    });
}

UPDATE 1

removed

[settings setObject:[NSNumber numberWithBool:YES]
             forKey:GCDAsyncSocketManuallyEvaluateTrust];

using now

SecCertificateRef   cert1, cert2;

// init certs, see top part

// according to @SeanBaker "Certs[0] would be nil (you don't want to do client auth), and certs[1...] would be the root certificates you want to trust in establishing the connection"
const void *certs[] = {NULL, cert1, cert2};
// const void *certs[] = {nil, cert1, cert2};
    CFArrayRef aryCerts = CFArrayCreate(NULL, certs, 3, NULL);
[settings setObject:(__bridge NSArray*)aryCerts
                 forKey:(NSString *)kCFStreamSSLCertificates];

but getting OSStatus -50 (/*error in user parameter list*/) in

// 2. kCFStreamSSLCertificates

value = [tlsSettings objectForKey:(NSString *)kCFStreamSSLCertificates];
if ([value isKindOfClass:[NSArray class]])
{
    CFArrayRef certs = (__bridge CFArrayRef)value;

    status = SSLSetCertificate(sslContext, certs);
...

seems like I'm using it wrong, but I don't see the mistake :/ (not using often core foundation)

If you need further information, just ask. Every hint can rescue lifes :)

Answer 1

I myself use custom certificate to verify multiple servers used by our messaging application in development mode.

If you have access to p12(included private key and hence signed identity) file you can validate server certificate using kCFStreamSSLCertificates

Otherwise(in case of just public key) you have the option to validate through peer name kCFStreamSSLPeerName.

In your code snippet, one thing that you are doing incorrect is how you are supplying the certificates to GCDAsyncSocket module. and hence finding the error that you mentioned.

The correct way is like below:

    NSArray *myCerts = [[NSArray alloc] initWithObjects:(__bridge id)identity1, (__bridge id)myReturnedCertificate1, nil];
    [settings setObject:myCerts forKey:(NSString *)kCFStreamSSLCertificates];

As per the Apple documentation identity is mandatory while using kCFStreamSSLCertificates:

You must place in certRefs[0] a SecIdentityRef object that identifies the leaf certificate and its corresponding private key. Specifying a root certificate is optional;

---

Complete Details:

Below are the steps to follow if you use custom signed CA certificates. Please note: Example is based on GCDAsyncSocket

1. Keep your public part certificate in application resource bundle.
2. Read the above certificate and add certificate to keychain
3. Implement delegate function-

(void)socket:(GCDAsyncSocket *)sock didConnectToHost:(NSString *)host port:(uint16_t)port;

Within this function provide your certificate to GCDAsyncSocket

    NSArray *myCerts = [[NSArray alloc] initWithObjects:(__bridge id)identity1, (__bridge id)myReturnedCertificate1, nil];
    [settings setObject:myCerts forKey:(NSString *)kCFStreamSSLCertificates];

Use YES(Not recommended) or NO to below, based on weither you want to verify trust manually?

   [settings setObject:[NSNumber numberWithBool:YES]
                 forKey:GCDAsyncSocketManuallyEvaluateTrust];

4. If you elected to verify trust manually, override following delegate method.

(void)socket:(GCDAsyncSocket *)sock didReceiveTrust:(SecTrustRef)trust completionHandler:(void (^)(BOOL shouldTrustPeer))completionHandler

Within this function you should read all certificates from the trust and try to match along with certificate that you provided with the application.

Sample Code:

---

- (void)socket:(GCDAsyncSocket *)sock didConnectToHost:(NSString *)host port:(uint16_t)port;
{

    // Configure SSL/TLS settings
    NSMutableDictionary *settings = [NSMutableDictionary dictionaryWithCapacity:3];

    // get the certificates as data for further operations


    SecIdentityRef identity1 = nil;
    SecTrustRef trust1 = nil;

    NSData *certData1 = [[NSData alloc] initWithContentsOfFile:[[NSBundle mainBundle] pathForResource:@"[Dev] InHouse_Certificates" ofType:@"p12"]];
    CFDataRef myCertData1 = (__bridge_retained CFDataRef)(certData1);

    [self extractIdentityAndTrust:myCertData1 withIdentity:&identity1 withTrust:&trust1 withPassword:CFSTR("1234")];
    NSString* summaryString1 = [self copySummaryString:&identity1];


    SecIdentityRef identity2 = nil;
    SecTrustRef trust2 = nil;

    NSData *certData2 = [[NSData alloc] initWithContentsOfFile:[[NSBundle mainBundle] pathForResource:@"[Dis] InHouse_Certificates" ofType:@"p12"]];
    CFDataRef myCertData2 = (__bridge_retained CFDataRef)(certData2);

    [self extractIdentityAndTrust:myCertData2 withIdentity:&identity2 withTrust:&trust2 withPassword:CFSTR("1234")];
    NSString* summaryString2 = [self copySummaryString:&identity2];

    // if data exists, use it
    if(myCertData1 && myCertData2)
    {
        //Delete if already exist. Just temporary
        SecItemDelete((__bridge CFDictionaryRef)[NSDictionary dictionaryWithObjectsAndKeys:
                                                (__bridge id)(kSecClassKey), kSecClass,
                                                (__bridge id)kSecAttrKeyTypeRSA, kSecAttrKeyType,
                                                (__bridge id)kSecAttrKeyClassPublic, kSecAttrKeyClass,
                                                kCFBooleanTrue, kSecAttrIsPermanent,
                                                [summaryString1 dataUsingEncoding:NSUTF8StringEncoding], kSecAttrApplicationTag,
                                                certData1, kSecValueData,
                                                kCFBooleanTrue, kSecReturnPersistentRef,
                                                nil]);

        OSStatus status1 = SecItemAdd((__bridge CFDictionaryRef)[NSDictionary dictionaryWithObjectsAndKeys:
                                                                (__bridge id)(kSecClassKey), kSecClass,
                                                                (__bridge id)kSecAttrKeyTypeRSA, kSecAttrKeyType,
                                                                (__bridge id)kSecAttrKeyClassPublic, kSecAttrKeyClass,
                                                                kCFBooleanTrue, kSecAttrIsPermanent,
                                                                [summaryString1 dataUsingEncoding:NSUTF8StringEncoding], kSecAttrApplicationTag,
                                                                certData1, kSecValueData,
                                                                kCFBooleanTrue, kSecReturnPersistentRef,
                                                                nil],
                                     NULL);   //don't need public key ref

        // Setting "cer" is successfully and delivers "noErr" in first run, then "errKCDuplicateItem"

        NSLog(@"evaluate with status %d", (int)status1);

        //Delete if already exist. Just temporary
        SecItemDelete((__bridge CFDictionaryRef)[NSDictionary dictionaryWithObjectsAndKeys:
                                                 (__bridge id)(kSecClassKey), kSecClass,
                                                 (__bridge id)kSecAttrKeyTypeRSA, kSecAttrKeyType,
                                                 (__bridge id)kSecAttrKeyClassPublic, kSecAttrKeyClass,
                                                 kCFBooleanTrue, kSecAttrIsPermanent,
                                                 [summaryString2 dataUsingEncoding:NSUTF8StringEncoding], kSecAttrApplicationTag,
                                                 certData2, kSecValueData,
                                                 kCFBooleanTrue, kSecReturnPersistentRef,
                                                 nil]);

        //NSString *name2 = [NSString stringWithUTF8String:CFStringGetCStringPtr(SecCertificateCopySubjectSummary(cert2), kCFStringEncodingUTF8)];
        OSStatus status2 = SecItemAdd((__bridge CFDictionaryRef)[NSDictionary dictionaryWithObjectsAndKeys:
                                                                 (__bridge id)(kSecClassKey), kSecClass,
                                                                 (__bridge id)kSecAttrKeyTypeRSA, kSecAttrKeyType,
                                                                 (__bridge id)kSecAttrKeyClassPublic, kSecAttrKeyClass,
                                                                 kCFBooleanTrue, kSecAttrIsPermanent,
                                                                 [summaryString2 dataUsingEncoding:NSUTF8StringEncoding], kSecAttrApplicationTag,
                                                                 certData2, kSecValueData,
                                                                 kCFBooleanTrue, kSecReturnPersistentRef,
                                                                 nil],
                                      NULL);   //don't need public key ref

        NSLog(@"evaluate with status %d", (int)status2);


        SecCertificateRef myReturnedCertificate1 = NULL;
        OSStatus status3 = SecIdentityCopyCertificate (identity1, &myReturnedCertificate1);

        SecCertificateRef myReturnedCertificate2 = NULL;
        OSStatus status4 = SecIdentityCopyCertificate (identity2, &myReturnedCertificate2);

        NSArray *myCerts = [[NSArray alloc] initWithObjects:(__bridge id)identity1, (__bridge id)myReturnedCertificate1, nil];
        [settings setObject:myCerts forKey:(NSString *)kCFStreamSSLCertificates];

        // Allow self-signed certificates
        [settings setObject:[NSNumber numberWithBool:YES]
                     forKey:GCDAsyncSocketManuallyEvaluateTrust];

        [sock startTLS:settings];

    }

}

If for some reason you decided to evaluate trust manually.

- (void)socket:(GCDAsyncSocket *)sock didReceiveTrust:(SecTrustRef)trust completionHandler:(void (^)(BOOL shouldTrustPeer))completionHandler
{
    dispatch_queue_t bgQueue = dispatch_get_global_queue(DISPATCH_QUEUE_PRIORITY_DEFAULT, 0);
    dispatch_async(bgQueue, ^{
        // This is where you would (eventually) invoke SecTrustEvaluate.

        SecIdentityRef identity1 = nil;
        SecTrustRef trust1 = nil;

        NSData *certData1 = [[NSData alloc] initWithContentsOfFile:[[NSBundle mainBundle] pathForResource:@"[Dev] InHouse_Certificates" ofType:@"p12"]];
        CFDataRef myCertData1 = (__bridge_retained CFDataRef)(certData1);

        [self extractIdentityAndTrust:myCertData1 withIdentity:&identity1 withTrust:&trust1 withPassword:CFSTR("1234")];

        SecIdentityRef identity2 = nil;
        SecTrustRef trust2 = nil;

        NSData *certData2 = [[NSData alloc] initWithContentsOfFile:[[NSBundle mainBundle] pathForResource:@"[Dis] InHouse_Certificates" ofType:@"p12"]];
        CFDataRef myCertData2 = (__bridge_retained CFDataRef)(certData2);

        [self extractIdentityAndTrust:myCertData2 withIdentity:&identity2 withTrust:&trust2 withPassword:CFSTR("1234")];

        if(myCertData1 && myCertData2)
        {
            CFArrayRef arrayRefTrust = SecTrustCopyProperties(trust);
            SecTrustResultType result = kSecTrustResultUnspecified;

            // usualy should work already here
            OSStatus status = SecTrustEvaluate(trust, &result);

            NSLog(@"evaluate with result %d and status %d", result, (int)status);
            NSLog(@"trust properties: %@", arrayRefTrust);

            /* log:
             evaluate with result 5 and status 0
             trust properties: (
             {
             type = error;
             value = "Root certificate is not trusted."; // expected, when top part was not working
             }
             */

            SecCertificateRef myReturnedCertificate1 = NULL;
            OSStatus status3 = SecIdentityCopyCertificate (identity1, &myReturnedCertificate1);

            SecCertificateRef myReturnedCertificate2 = NULL;
            OSStatus status4 = SecIdentityCopyCertificate (identity2, &myReturnedCertificate2);


            const void *ref[] = {myReturnedCertificate1};

            CFIndex count = SecTrustGetCertificateCount(trust);
            //            CFMutableArrayRef aryRef = CFArrayCreateMutable(NULL, count + 1, NULL);
            //            CFArrayAppendValue(aryRef, ref);

            CFArrayCreate(NULL, ref, 2, NULL);

            // # # # #
            // so check one by one...

            BOOL isMatching = NO;

            for (int i = 0; i < count; i++)
            {
                SecCertificateRef certRef = SecTrustGetCertificateAtIndex(trust, i);
                NSString *name = [NSString stringWithUTF8String:CFStringGetCStringPtr(SecCertificateCopySubjectSummary(certRef), kCFStringEncodingUTF8)]; 
                NSLog(@"remote cert at index %d is '%@'", i, name);


                const void *ref[] = {certRef, myReturnedCertificate1};
                CFArrayRef aryCheck = CFArrayCreate(NULL, ref, 2, NULL);

                SecTrustRef trustManual;
                OSStatus certStatus = SecTrustCreateWithCertificates(aryCheck, SecPolicyCreateBasicX509(), &trustManual);
                // certStatus always noErr
                NSLog(@"certStatus: %d", (int)certStatus);

                SecTrustResultType result;
                OSStatus status =  SecTrustEvaluate(trustManual, &result);
                CFArrayRef arrayRef = SecTrustCopyProperties(trustManual);

                NSLog(@"evaluate with result %d and status %d", result, (int)status);
                NSLog(@"trust properties: %@", arrayRef);
                /* log:
                 evaluate with result 5 and status 0
                 trust properties: (
                 {
                 type = error;
                 value = "Root certificate is not trusted.";
                 }
                 */

                if (status == noErr && (result == kSecTrustResultProceed || result == kSecTrustResultUnspecified))
                {
                    isMatching = YES;
                    NSLog(@"certificates matches");
                }
                else
                {
                    NSLog(@"certificates differs");
                }
            }

            if (isMatching || (status == noErr && (result == kSecTrustResultProceed || result == kSecTrustResultUnspecified)))
            {
                completionHandler(YES);
            }
            else
            {
                completionHandler(NO);
            }
        }
        completionHandler(NO);
    });
}

Update:

As per the Apple documentation:

You must place in certRefs[0] a SecIdentityRef object that identifies the leaf certificate and its corresponding private key. Specifying a root certificate is optional;

As suggested by Apple, in case you are using certificate in.cer format, you should match both certificates using peer domain name(fully qualified domain name).

You can use this function to verify the common name field in the peer’s certificate. If you call this function and the common name in the certificate does not match the value you specify in the peerName parameter, then handshake fails and returns errSSLXCertChainInvalid. Use of this function is optional.