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Upgrading is always one of the most fearful things in the world. Big upgrades generally tend to break somewhere. That's why I have been putting off the upgrade from exim3 to exim4, even though the developers say that exim3 is deprecated and everyone should move over to exim4.
The last server I needed to upgrade was a server running Debian stable. Real email goes through the server and if the upgrade broke, then all sorts of email might be bouncing. Sunday morning, therefore, seemed to be a good time to do it.
apt-get update apt-get install exim4
But I was pleasantly surprised. The exim4 installer recognised that I was using a smarthost and seemed to read options from the existing exim3 configuration file. The new exim4 configuration file was properly set up. All email seems to be routed where it should be. So, don't be afraid of upgrading from exim3 to exim4 if you are using Debian stable.
Update: Of course there was one problem. There's always a problem. The installer decided that the server only wanted to listen on the local interface for email, that is on 127.0.0.1. No email coming from outside could therefore be delivered. I don't know why the installer wanted to do this, but it did. I had to fix the dc_local_interfaces option in /etc/update-exim4.conf.conf. Now, it seems to work.
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