SSL_connect SYSCALL returned=5 errno=0 state=SSLv2/v3 read server hello A

Question

I have a ruby client that connects to an exchange server using IMAP & SSL. I use the Ruby Net::IMAP library (which uses openssl under the covers) to connect. Its been wo

Answer 1

Well it turns out the root cause on this one was ms exchange was misconfigured. I would love to have learned more about ssl errors and how to troublshoot them, but I just didnt get much info on this.

I did try to just troublshoot this using open ssl, fyi, you can do: OpenSSL> s_client -connect myserver:993

When it was broken, I received this error: CONNECTED(00000003) 26831:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure:s23_lib.c:188:

Once we fixed I got a cert and handshake message etc.

Here is what my exchange admin said he did: "I just went to the IMAP protocol and went to the access tab. Then the certificates button. From there I chose to replace the cert and chose the new cert."