Using OpenConnect v5.01. I upgraded a lot of stuff at once so I'm not sure the exact cause, but I: upgraded to OSX 10.8.5, upgraded to XCode 5, and upgraded the Command Line Utilities within xcode. I noticed that the OpenSSL version on OSX is now "OpenSSL 0.9.8y 5 Feb 2013". For my co-workers that haven't upgraded yet, their OpenSSL version is "OpenSSL 0.9.8x 10 May 2012". Now after I connect to my VPN server, I get this message twice (60 seconds apart): DTLS handshake failed: 2 Then after that, I get these 2 messages at the same time every 60 seconds: DTLS handshake failed: 1 2531:error:14102410:SSL routines:DTLS1_READ_BYTES:sslv3 alert handshake failure:/SourceCache/OpenSSL098/OpenSSL098-47.2/src/ssl/d1_pkt.c:1037:SSL alert number 40 I continuously get those messages until I disconnect from the VPN server. I can easily enough ignore it, but I wanted to bring it up. I am not noticing any particular issue with my connection, just that I'm getting that warning now. Do you need any other debug info from my to look into this?