Redmine

That one will be hard to tackle without a way to reproduce… Could you please post the output of RAILS_ENV=production script/about, and try with a fresh install if the problem still persists?

Thanks, that helped: a fresh install does not exhibit the email problem.

Now I have to get the freshly installed directory to use our current database.
I'll report back with the results when that's done.

Check that your Exchange allows to send mail from and to the configured addresses. Also make sure, you send the correct HELO (domain parameter in email.yml)

If you would have googled the error message you saw in the logs you would have seen the first hit is a Microsoft KB article explaining the issue: http://support.microsoft.com/kb/291828

The problem is not in MS exchange, although I have been barking up that wrong tree myself after googling for that error message (a bit unkind to assume I had not).

Of course our exchange server allows sending emails, it has done it for well over two years. Also with a fresh setup of redmine it works.
When I migrate our current database and reinstall the plugins we use, the problem reappears. OTOH removing the plugins doesn't solve the issue, so I don't assume it's a plugin related issue.

The problem as far as I can see is that redmine tries to send an email without a to: address (see the original ticket description above for more details)
I suspect it has something to do with permissions, but I can't find which ones would affect redmines ability to get the current user's email address.

I understand this is hard to repro as it may depend on issues specific to our installation, but I need more guidance to troubleshoot the problem.

i've got similar problem, and found, that old installation's server was running, instead of upgraded. after i have stopped old installation's server, and started upgraded, e-mail notifications were working again

Try using simple 'from' address in Redmine's administration settings: foo@zoo.com instead of foo <foo@zoo.com>. May be it has something to do with the new rails version.

Richard Pecl wrote:

Try using simple 'from' address in Redmine's administration settings: foo@zoo.com instead of foo <foo@zoo.com>. May be it has something to do with the new rails version.

That was exactly what we discovered just yesterday. Replacing the fancy email address of the form:
Name <name@domain.com>
by a simple email address solved the issue. We were wondering why this apparently wasn't a problem in earlier versions. Nice to know this has to do with the rails version which we had to update as well for the redmine update (8.4 => 9.5).
The ticket was already closed, else I would close it now.
Thanks