I figured it out, finally. Because our server has a dynamically-assigned IP 
address, and no hostname, we couldn't create a cert that matched. By default, 
iOS and OS X want to verify the hostname. The solution is to create a new 
SecTrustRef with a policy that does not check the hostname, and evaluate that. 
The final code is:

- (void)
connection: (NSURLConnection*) inConnection
    willSendRequestForAuthenticationChallenge: (NSURLAuthenticationChallenge*) 
inChallenge
{
    NSLogDebug(@"Connection challenged");
    
    //  Build a new trust based on the supplied trust, so that we can set the 
policy…
    
    NSURLProtectionSpace* protectionSpace = inChallenge.protectionSpace;
    SecTrustRef trust = protectionSpace.serverTrust;
    
    CFIndex numCerts = SecTrustGetCertificateCount(trust);
    NSMutableArray* certs = [NSMutableArray arrayWithCapacity: numCerts];
    for (CFIndex idx = 0; idx < numCerts; ++idx)
    {
        SecCertificateRef cert = SecTrustGetCertificateAtIndex(trust, idx);
        [certs addObject: CFBridgingRelease(cert)];
    }
    
    //  Create a policy that ignores the host name…
    
    SecPolicyRef policy = SecPolicyCreateSSL(true, NULL);
    OSStatus err = SecTrustCreateWithCertificates(CFBridgingRetain(certs), 
policy, &trust);
    CFRelease(policy);
    if (err != noErr)
    {
        NSLogDebug(@"Error creating trust: %d", err);
        [inChallenge.sender cancelAuthenticationChallenge: inChallenge];
        return;
    }
    
    //  Set the root cert and evaluate the trust…
    
    NSArray* rootCerts = @[ CFBridgingRelease(mRootCert) ];
    err = SecTrustSetAnchorCertificates(trust, CFBridgingRetain(rootCerts));
    if (err == noErr)
    {
        SecTrustResultType trustResult;
        err = SecTrustEvaluate(trust, &trustResult);
        CFRelease(trust);
        
        bool trusted = err == noErr;
        trusted = trusted && (trustResult == kSecTrustResultProceed || 
trustResult == kSecTrustResultUnspecified);
        if (trusted)
        {
            NSURLCredential* credential = [NSURLCredential credentialForTrust: 
trust];
            [inChallenge.sender useCredential: credential 
forAuthenticationChallenge: inChallenge];
            return;
        }
    }
    
    //  An error occurred, or we don't trust the cert, so disallow it…
    
    [inChallenge.sender cancelAuthenticationChallenge: inChallenge];
}

On May 16, 2013, at 12:46 , Jens Alfke <j...@mooseyard.com> wrote:

> 
> On May 15, 2013, at 9:13 PM, Rick Mann <rm...@latencyzero.com> wrote:
> 
>> I'm trying to validate our self-signed certificate in 
>> NSURLConnectionDelegate's 
>> -connection:willSendRequestForAuthenticationChallenge: using itself as the 
>> root cert. I'm not 100% sure I'm doing it right, but looking at the 
>> ridiculously, excessively complicated example code, I've come up with this:
> 
> Ugh, yeah, I’ve had trouble with this too, but it was long enough ago that I 
> don’t remember the details.
> One thing that might help is calling SecTrustGetResult to get detailed info 
> on the results of trust evaluation. The returned structure might have some 
> clues in it.
> 
> You can also ask for help on the apple-cdsa list (which is for 
> security/crypto related topics).
> 
> —Jens
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-- 
Rick




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