I am still fighting a battle to get Roundcube to send emails on port 587. My setup is a Debian Lenny server configured using the Perfect Server tutorial here with ISPConfig3. In the tutorial, Squirrelmail is installed. I had successfully configured Squirrelmail to send emails on port 587. When I ran into problems with Roundcube, I decided to back up and confirm Squirrelmail was still working. It seems after the recent upgrade, the Squirrelmail settings reverted to using port 25. Perhaps this was part of the reconfiguration of services done as part of the ISPConfig3 upgrade to the most recent build. Anyhow, I changed the SMTP port in the Squirrelmail conf.pl file back to port 587 and now I get the following error when trying to send emails from Squirrelmail. Code: 530 5.7.0 Must issue a STARTTLS command first I have tried a variety of settings, but I can't get email to go out unless the port is set to 25.
roundcube connects on localhost, so there is really no need and no benefit to let it connect on port 587. Also letting it to use tls is not nescessary, as it connects on the server only internally.
I am open to suggestions on my approach. I am trying to treat Roundcube and/or Squirrelmail as any other email client that can be used by my users. In the case of Roundcube and/or Squirrelmail, they just happen to reside on the same server where you can get away using localhost. However, I am now using amavisd to perform DKIM signatures regardless of the email clients the end user utilizes. (I was using dkim proxy earlier.) Since I can't control whether a user connects with Outlook remotely one day and then uses a webmail program the next, I feel like I have to treat all the email client the same and have them connect on port 587. My initial hunch is that perhaps this was reconfigured as part of the recent upgrade performed on ISPConfig3. When I upgraded, it asked me if services should be reconfigured to which I answered yes. Postfix was configured previously to look for email submitted on port 587 to pass out to amavisd for the signature process. I have a virtualized environment. If it was really required, I could virtualize the webmail programs onto another virtual machine in an effort to force them to connect "remotely" rather than using localhost. But that seems like a lot of overhead and not the most ideal solution.
There is really no need for the complicated configuration you do. All outgoing email is passed to amavisd anyway so all emails are scanned. Just configure roundcube to connect to localhost on port 25.
