I started running my own servers on an old PowerBook 5300 back in the late 1990s. By the early 2000s I was running a mail server on an old Mac running Yellow Dog Linux. I migrated that to Ubuntu eventually, all the while adding features — fax services, SMS, a document interface to my electronic medical record (EMR), voicemail for my phone system, and probably other things I’ve long forgotten. The mail system became deeply entwined with my digital life and was the central hub that coordinated my medical and IT businesses and my family. Email itself has become vastly more complicated over those years, largely due to the effort it takes to combat spam.
I ended up settling on a very early long-term support (LTS) version of Ubuntu Linux (probably 6.06). A new LTS version was released every two years, but they were guaranteed support for five years. I would upgrade every two years until…
In 2018 I tried to upgrade from Ubuntu 16.04lts to 18.04, and something went wrong. I was really busy: both my sons were teenagers, my business was growing fast and I was the supervising MD, the CEO, and the chief technology officer responsible for the EMR (which I’d written) and all the telecommunications systems. I couldn’t afford to be without email even for a couple of days, and I was too busy to figure out what was keeping the email from working on the new system. I reverted to a backup. After all, I had three more years of support.
I tried several times to accomplish the upgrade, but things were just too busy and the server had become a complex mess of interconnected bits and bobs I had added on over the years. It was all documented, sure, but so much documentation might as well be none at all. Then it was April 2020 and all Hell had broken loose in the medical field with Covid lockdowns. Canonical (the company that oversees Ubuntu) announced a program to add a couple of years of support. I took another stab at updating, but failed again and decided to take Canonical up on their offer. Then I was all tangled up with retirement and moving to the island, but support for servers was extended another couple of years, so ten total.
It all ends in a week. No more extensions. My server is now running on a ten year old system and has twenty years of cruft built up and is now becoming end-of-life. On the other hand, I no longer have a staff and hundreds of patients and a bunch of nonprofits relying on my system. There are a few people who use the email, but it’s mostly just me. So I’ve opted to re-build the server from scratch.
I’ve been chipping away at it, but today was the designated Big Day. It was pouring rain most of the day, and HA went to the sunny side of the island to give me the space to yell and swear at the new server with impunity. It went pretty well, though I got to one point where everything seemed to work fine, there were no error messages, but there was simply no mail. Ugh. It took some hammering at it, but I finally got it fixed (permissions problem, natch).
So the new mail server is up and running and tested. I haven’t thrown the Big Switch yet (that needs to happen on a weekend), but I’m confident the problems won’t be too challenging.
—2p