Question

We recently moved our Exchange server from an in-house solution to something online and we're having a bit of a problem changing mail servers.

I've used a couple of starter posts as guidelines like http://fogbugz.stackexchange.com/questions/593/why-is-my-self-signed-certificate-no-longer-working-in-fogbugz-7 (we don't use self-signed) or the holy grail http://fogbugz.stackexchange.com/questions/441/fogbugz-mailbox-problems with no luck.

Since this is secure we can't use telnet to check anything and that may be an indicator of part of the problem. I seem to remember most secure-pop starting in some form of plaintext or would at least spit out encrypted text when you connect to the port. When you connect to port 995 the only thing that happens is an almost immediate disconnect. Outlook Express setup as the FogBugz user perpetually whines about the certificate not being trusted, despite placing it in every store that has the word Trusted in it. What likely doesn't help is for that specific server, which is really just an OWA proxy, there is no Secure Email listed as one of the properties in the certificate. I can't tell that even if I did get the cert added right would if even work.

Our easiest and current course is to use Gmail to check their POP account and hopefully use that as our relay. I thought about email forwarding but it would likely be hard to tell who actually sent the ticket in. I don't know if much could be done but I wanted to at least ask this question in case someone else hits our problem too.

Answer 1

Figured out the problem to be implicit SSL, so stunnel is needed as an intermediary on the box. Just about whenever you see this message it means the SSL connection needs to be made first.

Here's the breadcrumb that started the discovery http://fogbugz.stackexchange.com/questions/876/smtp-secure-starttls-with-fogbugz-4 with the ultimate solution being http://www.fogcreek.com/blog/post/Using-Gmail-(or-any-other-secure-SMTP-server)-for-FogBugz.aspx.

Our solution to attempt to use gmail as an intermediary is what prompted this as they are also SSL only and wouldn't work. Since this directly applies to Google Apps or gmail itself, I'm baffled as to how I didn't stumble upon the fix before. Perhaps the link wasn't being made in my head. I just hope this question and answer are enough to point anyone else in the right direction.