iOS connect with self-signed TLS/SSL certificate not working - ios

Question

I would like to encrypt and secure a network connection agains MITM attacks for an iOS application. Since the application will only connect to one server, there is no need to have the certificate signed by a CA like VeriSign. I want to self-sign the certificate and distribute it with the application.
I tried this but end up with kSecTrustResultRecoverableTrustFailure and can not figure out where I went wrong. Can someone look over it and identify the problem or point me into a direction on how to debug this? Is it a problem because I use/test on localhost?
I think it is a problem in the creation of the certificate or setup of the server but I don't know what it is. I tested it with openssl s_client and it seems to work but iOS does not accept it (see below). I could accept kSecTrustResultRecoverableTrustFailure as success but would rather avoid it.
Creation of certificate
My openssl.cnf. The last line specifies subjectAltName and should be the only important one.
[ req ]
default_bits = 2048 # Size of keys
default_keyfile = key.pem # name of generated keys
default_md = sha256 # message digest algorithm
string_mask = nombstr # permitted characters
distinguished_name = req_distinguished_name
[ req_distinguished_name ]
# Variable name Prompt string
# #---------------------- ----------------------------------
0.organizationName = Organization Name (company)
organizationalUnitName = Organizational Unit Name (department, division)
emailAddress = Email Address
emailAddress_max = 40
localityName = Locality Name (city, district)
stateOrProvinceName = State or Province Name (full name)
countryName = Country Name (2 letter code)
countryName_min = 2
countryName_max = 2
commonName = Common Name (hostname, IP, or your name)
commonName_max = 64
# Default values for the above, for consistency and less typing.
# Variable name Value
#------------------------------ ------------------------------
0.organizationName_default = The Sample Company
localityName_default = Metropolis
stateOrProvinceName_default = New York
countryName_default = US
[ server ]
basicConstraints = critical,CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
nsCertType = server
subjectAltName = IP:127.0.0.1,DNS:localhost
This is how I create the certificate. I use sha256 since md5 seems not supported. Afterwards I transform the certificate to DER format which iOS needs.
macbook:~/Documents/app/https-test/cert$ openssl req -x509 -sha256 -newkey rsa:2048 -keyout key.pem -out cert.pem -days 356 -nodes -config openssl.cnf
Generating a 2048 bit RSA private key
..+++
............................................................+++
writing new private key to 'key.pem'
-----
You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
-----
Country Name (2 letter code) [AU]:DE
State or Province Name (full name) [Some-State]:
Locality Name (eg, city) []:
Organization Name (eg, company) [Internet Widgits Pty Ltd]:com
Organizational Unit Name (eg, section) []:
Common Name (e.g. server FQDN or YOUR name) []:
Email Address []:
macbook:~/Documents/app/https-test/cert$ ls
cert.der cert.pem key.pem openssl.cnf
macbook:~/Documents/app/https-test/cert$ openssl x509 -in cert.pem -outform der -out cert.der
Server
The server is a node.js server that accepts https requests.
var https = require('https');
var fs = require('fs');
var options = {
key: fs.readFileSync('../cert/key.pem'),
cert: fs.readFileSync('../cert/cert.pem')
};
https.createServer(options, function (req, res) {
res.writeHead(200);
res.end("test return\n");
}).listen(8443);
I tested this server with the following output:
macbook:~/Documents/app/https-test/server$ openssl s_client -showcerts -host localhost -port 8443 -CAfile ../cert/cert.pem
CONNECTED(00000003)
depth=0 /O=The Sample Company/L=Metropolis/ST=New York/C=US
verify return:1
---
Certificate chain
0 s:/O=The Sample Company/L=Metropolis/ST=New York/C=US
i:/O=The Sample Company/L=Metropolis/ST=New York/C=US
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
---
Server certificate
subject=/O=The Sample Company/L=Metropolis/ST=New York/C=US
issuer=/O=The Sample Company/L=Metropolis/ST=New York/C=US
---
No client certificate CA names sent
---
SSL handshake has read 983 bytes and written 468 bytes
---
New, TLSv1/SSLv3, Cipher is AES256-SHA
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
SSL-Session:
Protocol : TLSv1
Cipher : AES256-SHA
Session-ID: C8901BBE04CB24444E0DDEA60EB7A72A64822E652973AD1D16E27D1E1F29F828
Session-ID-ctx:
Master-Key: D143A0F58C848B0E1BCA7BDF22EEBC326F811961CC10FF3A653715A8D8F96F5825AFC6D200F334D2E1581BFECA940111
Key-Arg : None
Start Time: 1393256956
Timeout : 300 (sec)
Verify return code: 0 (ok)
---
^C
iOS app
The app uses this NSURLConnectionDelegate https://gist.github.com/dhoerl/2051599

Answer 1

The iOS code you linked to expects the server's certificate to be in the device's trusted root certificate store, or at least signed by a trusted root certificate authority. The error you are getting suggests that this is not the case.
That error means the certificate is not trusted. By definition, a self-signed certificate is not trusted because it isn't signed by a trusted root certificate authority (so there's no way to verify that the signer of the certificate is who they say they are).
If you just want the benefits of SSL encryption without the protection from MITM attacks, you can bypass the server check by doing something like the following in the NSURLConnection delegate's didReceiveAuthenticationChallenge method:
- (void)connection:(NSURLConnection *)connection didReceiveAuthenticationChallenge:(NSURLAuthenticationChallenge *)challenge
{
if ([challenge.protectionSpace.authenticationMethod isEqualToString:NSURLAuthenticationMethodServerTrust])
[challenge.sender useCredential:[NSURLCredential credentialForTrust:challenge.protectionSpace.serverTrust] forAuthenticationChallenge:challenge];
[challenge.sender continueWithoutCredentialForAuthenticationChallenge:challenge];
}
Note that this will not prevent MITM attacks, since you are now allowing a connection to any SSL host, but if you truly want that kind of protection you shouldn't use a self-signed certificate. If you just want the encryption offered by SSL, a self-signed certificate is fine.
That said, you can do server authentication if you are bundling the server certificate in with your application - this is known as certificate pinning. You would need to add code in the didReceiveAuthenticationChallenge method above to compare the server's certificate with the one that's embedded in your application and have it trust ONLY that specific certificate and no other. This of course means that if the certificate on your server ever expires or changes, your clients will no longer be able to connect (until you rebuild and redistribute your application with the new certificate). It also means that if your server's private key is ever stolen or compromised, you won't be able to revoke it and issue a new one, and the Bad Guys will be able to impersonate your server to any clients that try to connect using the compromised key. Using a certificate issued by a trusted root CA avoids both problems, and is still the recommended way to go if you truly need server authentication. That way you can revoke the certificate if you ever need to, issue a new one, and everything will still work.

Answer 2

#1703536 's solution almost did it, I only had to implement another URLConnection's delegate message :
- (BOOL)connection:(NSURLConnection *)connection canAuthenticateAgainstProtectionSpace:(NSURLProtectionSpace *)protectionSpace
{
return [protectionSpace.authenticationMethod isEqualToString:NSURLAuthenticationMethodServerTrust];
}
- (void)connection:(NSURLConnection *)connection didReceiveAuthenticationChallenge:(NSURLAuthenticationChallenge *)challenge
{
if ([challenge.protectionSpace.authenticationMethod isEqualToString:NSURLAuthenticationMethodServerTrust])
[challenge.sender useCredential:[NSURLCredential credentialForTrust:challenge.protectionSpace.serverTrust] forAuthenticationChallenge:challenge];
[challenge.sender continueWithoutCredentialForAuthenticationChallenge:challenge];
}
Concerns about security doing that are well explained in the other answer ;-)