On Wed, May 08, 2013 at 06:54:01PM +0530, Vijay Rajah wrote: > I think this is an openssl bug... > > FYI: http://www.mail-archive.com/openssl-dev@openssl.org/msg28217.html
That bug is a bug in DTLS, which is quite different from regular TLS, so it need not be the same issue. > > May 8 00:30:04 albatross postfix/smtp[29327]: SSL_connect error to > > mail.vex.net[98.158.139.68]:25: 0 > > May 8 00:30:04 albatross postfix/smtp[29327]: warning: TLS library > > problem: 29327:error:1408C06F:SSL routines:SSL3_GET_FINISHED:bad digest > > length:s3_both.c:239: > > May 8 00:30:04 albatross postfix/smtp[29327]: 3b4wVg5fKkz7LkB: Cannot > > start TLS: handshake failure Does this happen consistently, or intermittently? Can you reproduce this with: openssl s_client \ -cipher $(postconf -xh tls_export_cipher_list) \ -sslv2 \ -starttls smtp -connect mail.vex.net:25 Can you report the output of "openssl version -a"? And any non-default postconf settings that tweak SSL protocol or cipher selection. If you capture a full packet dump and apply wireshark, it may shed light on the handshake details. The client thinks the TLS finished message has the wrong length, this feels like a problematic interaction with TLSv1.2, but you're running 1.0.0x I think, which has no TLSv1.2 support... -- Viktor.