Tag Archives: SMTP

Another Ubuntu upgrade, Another dovecot+postfix breakage

It seems like every time I upgrade Ubuntu, dovecot+postfix breaks. Maybe its just my luck, but it has gotten fairly annoying to be the only service that breaks after any upgrade.

This time I spent hours last weekend reinstalling, uninstalling and reinstalling postfix and dovecot about 4 or 5 times. Sad to say here I don’t know quite what fixed it but I was able to receive mail.

Now today I found out I wasn’t able to send mail. So back into debug mode again to resolve that.

While doing some tests I realized that i couldn’t even log into my mail server under smtp (port 25). After some digging around I came across this little post:
http://www.howtoforge.com/ubuntu-11.10-saslauthd-sasl-plain-authentication-failed-no-mechanism-available

The most important part here was a new line and change to an existing one:

Which for me was that auxprop_plugin went from mysql to sql and I added the new line below. This after a proper service restart resolved that problem. However I still had a problem of connecting to mail across SMTP+SSL (ie SMTPS on 465).

First off, I discovered my SSL certs for dovecot where outdated (expired it seems). While this shouldn’t of been causing the problem, I reissued the certificates. A quick search turned up makecert.sh and I was quickly back in business after backing up, deleting and generating the new certificates. I did modify the file and generate longer certificates though so it wouldn’t expire as fast (default is 1 year).

In my research, I found out a helpful command would tell me if SSL was working:

It failed as you can see. I will also mention you can test just TLS here by using:

I ran this command on the server directly, and it did give me more output, which became my basis for google searches.

This problem here after many google searches not turning up too many results, I stumbled onto this blog post, which had my answer.http://abing.gotdns.com/posts/2008/getting-postfix-to-run-smtps-on-port-465/

I had the options commented out. So while the service was running on 465, the options where not set to enable TLS on that port. A few quick changes and service restart later, everything was working. Which leaves me with another note of being more careful doing file merging when using SSH during a upgrade. I most likely botched the file at that time.

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