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I'm running Apache 2.2 on Windows, and have mod_ssl working fine for delivering a commercially signed server cert. (A wildcard cert, though I don't think it matters.)

I'm trying to get the server, on certain VirtualHosts, to require a client certificate, so I've built an SSLCACertificateFile containing PEMs; as I understand it, that list of signing DNs should be proffered for the client to respond during SSL establishment.

I have a StartSSL personal identity certificate, and if I put StartSSL's root cert into the SSLCACertificateFile, the browser (Chrome and IE tested) pops up "select a certificate" and shows me my StartSSL certificate.

However, my real use case is to use my own CA, and sign client certs, and that's what I can't get working. I self-sign a CA, then I create a client CSR and sign it with the CA cert and load it in my client cert store, then I put the CA PEM into my SSLCACertificateFile -- and the browser doesn't offer the client cert in the "select a certificate".

WTF.

Because it all works with the StartSSL CA and cert, I'm wondering if it's actually an issue with my CA cert or client cert -- but I can't figure out what the issue might be; the CA cert works for signing, and has CA:TRUE; the client certs have Client Authentication as a purpose... what's missing.

Not sure how to diagnose; thanks.

Here's my CA PEM, as pasted into the SSLCACertificateFile:

Certificate:
    Data:
        Version: 3 (0x2)
        Serial Number:
            bf:45:a7:db:f9:8e:8f:d0
        Signature Algorithm: sha1WithRSAEncryption
        Issuer: C=US, ST=California, L=San Diego, O=TestCA, OU=TestCA-OU, CN=TestCA-CN
        Validity
            Not Before: Mar  8 21:39:52 2013 GMT
            Not After : Apr  7 21:39:52 2013 GMT
        Subject: C=US, ST=California, L=San Diego, O=TestCA, OU=TestCA-OU, CN=TestCA-CN
        Subject Public Key Info:
            Public Key Algorithm: rsaEncryption
            RSA Public Key: (2048 bit)
                Modulus (2048 bit):
                    <snip>
                Exponent: 65537 (0x10001)
        X509v3 extensions:
            X509v3 Subject Key Identifier:
                5E:99:47:8A:52:D3:38:20:68:A5:91:D9:E1:2E:6B:50:0D:5C:98:CB
            X509v3 Authority Key Identifier:
                keyid:5E:99:47:8A:52:D3:38:20:68:A5:91:D9:E1:2E:6B:50:0D:5C:98:CB

            X509v3 Basic Constraints:
                CA:TRUE

Signature Algorithm: sha1WithRSAEncryption
<snip>

...and here's the client cert:

Certificate:
    Data:
        Version: 3 (0x2)
        Serial Number: 20481 (0x5001)
        Signature Algorithm: sha1WithRSAEncryption
        Issuer: C=US, ST=California, L=San Diego, O=TestCA, OU=TestCA-OU, CN=TestCA-CN
        Validity
            Not Before: Mar  8 23:46:55 2013 GMT
            Not After : Mar  8 23:46:55 2014 GMT
        Subject: C=US, ST=California, L=San Diego, O=TestClient, OU=TestClient-OU, CN=TestClient-CN
        Subject Public Key Info:
            Public Key Algorithm: rsaEncryption
            RSA Public Key: (2048 bit)
                Modulus (2048 bit):
                    <snip>
                Exponent: 65537 (0x10001)
        X509v3 extensions:
            X509v3 Basic Constraints:
                CA:FALSE
            X509v3 Key Usage:
                Key Encipherment
            X509v3 Extended Key Usage:
                TLS Web Client Authentication
    Signature Algorithm: sha1WithRSAEncryption
<snip>

/*******************************************************************/

Further info per Mike's request (took me a couple of tries to get 'openssl s_client' behaving.)

Here's the results: [...]

---
Acceptable client certificate CA names
/C=UK/O=Test Certificates/CN=Test CA
/C=US/ST=California/L=San Diego/O=TestCA/OU=TestCA-OU/CN=TestCA-CN
/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Certific
ation Authority
---

[...]

So, the server is saying

/C=US/ST=California/L=San Diego/O=TestCA/OU=TestCA-OU/CN=TestCA-CN

is an acceptable client certificate, and the client has

Issuer: C=US, ST=California, L=San Diego, O=TestCA, OU=TestCA-OU, CN=TestCA-CN

in it's store -- but the browser doesn't include that in the list I can pick from. The browser does offer the client certs signed by

/C=UK/O=Test Certificates/CN=Test CA

and

/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Certification Authority

...bringing me back to "WTF?"

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9
  • I've submitted an edit that runs your certs through a openssl x509 -text filter. Saves people the trouble of doing it themselves. (might take a moment to clear peer review)
    – Andrew B
    Commented Mar 9, 2013 at 0:26
  • Thanks; I almost did that, but in some of the threads I was reading, the style seemed to be to post the raw PEM.
    – lairdb
    Commented Mar 9, 2013 at 0:29
  • Hopefully I'm not stepping on any toes then. These will still be available in the revision history if needed.
    – Andrew B
    Commented Mar 9, 2013 at 0:31
  • I wouldn't think so -- I just figured without the "source code" people might wonder if that was an issue.
    – lairdb
    Commented Mar 9, 2013 at 0:33
  • Does the client trust your self-signed CA?
    – mpontillo
    Commented Mar 9, 2013 at 1:07

1 Answer 1

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1

Yes, I'm answering my own question.

Solved.

Turns out that KeyUsage keyEncipherment is NOT the correct keyUsage for an SSL/TLS client. The correct KeyUsage constraint is KeyUsage digitalSignature; useful info was found at this Mozilla article.

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2
  • Interesting; I just checked a cert I use for client SSL authentication, and its key usage field indeed matches this requirement. (It's using Digital Signature, Non Repudiation, Key Encipherment.)
    – mpontillo
    Commented Mar 18, 2013 at 5:00
  • One other note. The fact that the openssl returned 3 acceptable CAs raises a red flag for me. (You might want to double-check that this isn't a security risk?)
    – mpontillo
    Commented Mar 18, 2013 at 5:03

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