Connecting to Zimbra over SSL

If 143 works with Apple Mail then it should also work in MailMate. The problem seems to be the SSL handshake. Do you have SSL enabled in Apple Mail?

You should not use port 443 since this an https port and not for IMAP, but you can try to see if port 993 works.

You can try temporarily disabling SSL on port 143 in MailMate to see if this is the only problem.

Here is what my settings are like for Apple Mail: http://cl.ly/image/2V1t3h1j1m3I

I did come across this post: #1002 Force MailMate to use TLS 1.2 instead of SSL v3

When you say disabling SSL, do you mean just don't select the 'Require SSL' box? When I do that I get 'Error: Cannot log in since LOGINDISABLED (no plain text login allowed) is reported by the server.'

I have also tried port 993 but unfortunately it didn't work either.

Our server does support TLS 1, 1.1, 1.2 - does that make a difference?

Yes, then it's not the same issue. Could you provide me with the server address if it's accessible from the outside? I don't need to login I just need to be able to try connecting to the server. You can send it via “Help ▸ Send Feedback” (if you have a working SMTP server).

Okay. I sent it using Send Feedback.

@benny, just following up on this - did you receive my server address? I did see there was a new release and I have downloaded and installed it. I reviewed the release notes and it doesn't look like there was a fix for my specific problem, but it looks like things have been put in place to debug issues. Below are the logs from the activity viewer.

17:53:49 Running action
17:53:49 Sending request (7)
17:53:49 Handling request
17:53:49 Clearing connection to xxxx.xxx.xxx.xxx
17:53:49 Ready to run action
17:53:49 Clearing connection to xxxx.xxx.xxx.xxx
17:53:49 Trying to connect to xxxx.xxx.xxx.xxx on port 143
17:54:05 Error: Time limit (16s) reached while trying to write data (xxxx.xxx.xxx.xxx)
17:54:05 Error: Failed while trying to connect to “xxxx.xxx.xxx.xxx” on socket 49.
17:54:05 Clearing connection to xxxx.xxx.xxx.xxx
17:54:05 Trying to connect to xxxx.xxx.xxx.xxx on port 993
17:54:05 Successful connection on socket 49.
17:54:05 Initiating secure connection...
17:54:05 Error: Failed SSL handshake (-1/1).
    “error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure”
17:54:05 Error code: 9
17:54:05 Failed action (1000). Reset observed read/write timeouts: 8/8

17:54:05 Handling reply
17:54:05 Running action
17:54:05 Sending request (7)
17:54:05 Handling request
17:54:05 Clearing connection to xxxx.xxx.xxx.xxx
17:54:06 Ready to run action
17:54:06 Clearing connection to xxxx.xxx.xxx.xxx
17:54:06 Trying to connect to xxxx.xxx.xxx.xxx on port 143
17:54:22 Error: Time limit (16s) reached while trying to write data (xxxx.xxx.xxx.xxx)
17:54:22 Error: Failed while trying to connect to “xxxx.xxx.xxx.xxx” on socket 49.
17:54:22 Clearing connection to xxxx.xxx.xxx.xxx
17:54:22 Trying to connect to xxxx.xxx.xxx.xxx on port 993
17:54:22 Successful connection on socket 49.
17:54:22 Initiating secure connection...
17:54:22 Error: Failed SSL handshake (-1/1).
    “error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure”
17:54:22 Error code: 9
17:54:22 Failed action (1000). Reset observed read/write timeouts: 8/8

17:54:22 Handling reply
17:54:22 Running action
17:54:22 Sending request (8)
17:54:22 Handling request
17:54:22 Clearing connection to xxxx.xxx.xxx.xxx
17:54:24 Ready to run action
17:54:24 Clearing connection to xxxx.xxx.xxx.xxx
17:54:24 Trying to connect to xxxx.xxx.xxx.xxx on port 143
17:54:40 Error: Time limit (16s) reached while trying to write data (xxxx.xxx.xxx.xxx)
17:54:40 Error: Failed while trying to connect to “xxxx.xxx.xxx.xxx” on socket 49.
17:54:40 Clearing connection to xxxx.xxx.xxx.xxx
17:54:40 Trying to connect to xxxx.xxx.xxx.xxx on port 993
17:54:40 Successful connection on socket 49.
17:54:40 Initiating secure connection...
17:54:40 Error: Failed SSL handshake (-1/1).
    “error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure”
17:54:40 Error code: 9
17:54:40 Failed action (1000). Reset observed read/write timeouts: 8/8

17:54:40 Handling reply
17:54:40 Running action
17:54:40 Sending request (8)
17:54:40 Handling request
17:54:40 Clearing connection to xxxx.xxx.xxx.xxx
17:54:43 Ready to run action
17:54:43 Clearing connection to xxxx.xxx.xxx.xxx
17:54:43 Trying to connect to xxxx.xxx.xxx.xxx on port 143
17:54:59 Error: Time limit (16s) reached while trying to write data (xxxx.xxx.xxx.xxx)
17:54:59 Error: Failed while trying to connect to “xxxx.xxx.xxx.xxx” on socket 49.
17:54:59 Clearing connection to xxxx.xxx.xxx.xxx
17:54:59 Trying to connect to xxxx.xxx.xxx.xxx on port 993
17:54:59 Successful connection on socket 49.
17:54:59 Initiating secure connection...
17:54:59 Error: Failed SSL handshake (-1/1).
    “error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure”
17:54:59 Error code: 9
17:54:59 Failed action (1000). Reset observed read/write timeouts: 8/8

17:54:59 Handling reply
17:54:59 Error: Failed multiple retries (4). Final error code was 9.

Sorry about the late response. I get the same error if I try connecting to the server manually:

> openssl s_client -connect mail.xxx.edu:993
CONNECTED(00000003)
20296:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol:/SourceCache/OpenSSL098/OpenSSL098-52.40.1/src/ssl/s23_clnt.c:618:

I've tried various command line arguments for openssl, but with no luck. Since I'm using openssl within MailMate then it's unlikely I can make it work :-(

The best I can do is to notify you when/if I replace openssl (if that's part of the problem).

Hey Benny, I'm still bummed that I'm not able to use MailMate for this account. I continue to keep the app on my Mac and update hoping you've replaced openssl but, alas, this is not the case. Do you have recommendations for what I can do on the server level to allow MailMate to work with this account? Thanks in advance for your assistance.