SSL – SSL23_WRITE: SSL Handshake Failure

opensslssl

I'm trying to use OpenSSL to connect to an SSL server.

When I run:

openssl s_client -connect myhost.com:443

The following SSL client configurations work just fine:

Windows (OpenSSL 0.9.83e 23 Feb 2007)
Linux (OpenSSL 0.9.8o 01 Jun 2010)
Linux (OpenSSL 1.0.0-fips 29 Mar 2010)

Output from any successful connection looks like this:

New, TLSv1/SSLv3, Cipher is DES-CBC3-SHA
Server public key is 2048 bit
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1
    Cipher    : DES-CBC3-SHA
    Session-ID: (hidden)
    Session-ID-ctx:
    Master-Key: (hidden)
    Key-Arg   : None
    Krb5 Principal: None
    PSK identity: None
    PSK identity hint: None
    Start Time: 1337266099
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)

However, when I use client with my Ubuntu 12.04 (w/ OpenSSL 1.0.1 14 Mar 2012) I get error:

CONNECTED(00000003)
...:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure:s23_lib.c:177:

How can I proceed on solving this?

All tips are much appreciated!

Best Answer

This looks to be a known issue with Ubuntu's 1.0.1 OpenSSL: https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/965371

It doesn't look like a fix is available. If possible you could downgrade to 1.0.0.

Try openssl s_client -tls1 -connect myhost.com:443

Related Solutions

Ssl error handshake failure alert

I edited my virtualhost configuration and deleted :

    SSLVerifyClient require
    SSLVerifyDepth 10

And now it is working for server-side authentication. The "SSLVerifyClient require" directive override the lines :

SSLCertificateFile /usr/lib/ssl/demoCA/servercert.pem
SSLCertificateKeyFile /usr/lib/ssl/demoCA/serverkey.pem
SSLCACertificateFile /usr/lib/ssl/demoCA/stcert.pem

And that was the problem. The "SSLVerifyClient require" directive is for client-Side authentication and it makes openSSL to always require a certificate from the client.

Openssl update 1.0.1f to 1.0.1g broke sendmail (SSL23_GET_SERVER_HELLO:tlsv1 alert decode error)

Circumstances forced me to compile openssl 1.0.1g from sources and I encountered behavior identical to that reported above. This is under Fedora 18 on a 64-bit Intel. Like the original poster reports, most mail went out OK but one mail destination suffered the same TLS handshake failures.

The openssl change log (brief CL here, detailed CL here) showed only three changes from 1.0.1f to 1.0.1g:

a security update
another security update
Add TLS padding extension workaround for broken servers.

Speculating that third change was responsible for the problem I commented out one line in ssl/tls1.h that appears to control presence of this "TLS padding" modification, like so:

/* #define TLSEXT_TYPE_padding 21 */

Compiled again, put the library .so files in place, restarted sendmail, and out went the queued mail with no problems. I hope I haven't opened up new issues as a result.

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