I'm setting up FogBugz 7 to send mail through a mail server using SSL and it's not working
FogBugz On Demand
This article is for locally-installed FogBugz for your server. If you are on FogBugz On Demand, please see this post.
First, if you're not sure that SSL is to blame, here are thorough, general debugging steps for outgoing mail problems
If your mail server's certificate is self-signed, check out these instructions, but change
How SSL over SMTP works
There are two ways to do SMTP over SSL: Explicit and Implicit. Explicit means you connect to a normal SMTP port (usually 25 or 587) in plaintext, then issue the "starttls" command to switch to SSL-mode. Implicit means you connect to a port that expects everything to be SSL (usually 465).
In FogBugz 7, we support Explicit SSL automatically if you check the "Use SSL" box in Site Settings. This means that connecting to servers like Gmail is much easier: just put in the server, port, and check the box. If the server doesn't support Explicit SSL, then you still have to use Stunnel which is a bit more complicated.
For more info, see this MSDN article.
Setting it up in FogBugz 7 or 8
I. Determine if the server supports Explicit SSL
II. If the server supports Explicit SSL
II. If the server only supports Implicit SSL
If FogBugz gives you an error about your certificate when setting up SMTP, or in site diagnostics on the mail sending step, see this guide.