libssl has a new "feature" implemented by: crypto/openssl/ssl/t1_lib.c 672 /* Add padding to workaround bugs in F5 terminators. 673 * See https://tools.ietf.org/html/draft-agl-tls-padding-03 674 * 675 * NB: because this code works out the length of all existing 676 * extensions it MUST always appear last. 677 */ 678 //if (s->options & SSL_OP_TLSEXT_PADDING) unfortunatly this makes sendmail incompatible with various email servers around the world, including (apparently (ironically (*))) Ironport email gateways. It fails in TLS handshake. These are commonly installed at companies and government departments. consequently if you are mailing an important documant to your bank, or maybe some tax information to your friendly tax department, youe emails sit in your queue for a week until they time out and get dropped. (you may r may not get notified depending on your spam filters) I had to make the following "fix" to libssl to get sendmail to be able to get my tax forms out. Index: crypto/openssl/ssl/t1_lib.c ==================================================================--- crypto/openssl/ssl/t1_lib.c (revision 279747) +++ crypto/openssl/ssl/t1_lib.c (working copy) @@ -675,7 +675,8 @@ * NB: because this code works out the length of all existing * extensions it MUST always appear last. */ - if (s->options & SSL_OP_TLSEXT_PADDING) + //if (s->options & SSL_OP_TLSEXT_PADDING) + if (0) { int hlen = ret - (unsigned char *)s->init_buf->data; /* The code in s23_clnt.c to build ClientHello messages I saw some hints that there is a change in send mail somewhere that gets around this but haven't been able to find the exact configuration change required to make it happen. Julian (*) Ironically because : 1/ Ironport runs on FreeBSD 2/ I used to work there.