Can't get self-signed CA cert to request corresponding client cert; Apache

Question

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?"

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, Mar 09 '13 at 00:26
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, Mar 09 '13 at 00:29
Hopefully I'm not stepping on any toes then. These will still be available in the revision history if needed. — Andrew B, Mar 09 '13 at 00:31
I wouldn't think so -- I just figured without the "source code" people might wonder if that was an issue. — lairdb, Mar 09 '13 at 00:33
Mike: Yes; when I packaged the client cert and key into a pfx I included the CA cert, and certmgr imported it and trusted it. — lairdb, Mar 09 '13 at 01:15
Did you also create a server certificate from the same CA? In other words, does the output of `openssl s_client -connect :443 -showcerts < /dev/null` return a trust chain that is trusted by the same self-signed CA? Actually, it would be helpful if you post the full transcript from the `openssl s_client` command I mentioned. — mpontillo, Mar 09 '13 at 01:17
Not from the same CA; the server's cert is commercially issued. AFAIK, this is a legit setup; I should (I think) be able to accept client certs from different trust chains than the server's, and that appears to work with the commercially issued client certs -- just not with my self-issued client cert. — lairdb, Mar 11 '13 at 15:21

score 1 · Accepted Answer · answered Mar 12 '13 at 01:12

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.

answered Mar 12 '13 at 01:12

lairdb

131
7

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 Mar 18 '13 at 05:00
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 Mar 18 '13 at 05:03

Can't get self-signed CA cert to request corresponding client cert; Apache

1 Answers1