Back in 2014, most of my servers were using Ubuntu. In April of that year, a long-term support (LTS) version was released and I migrated the servers to it. LTS releases are supported for five years—it seemed an eternity at the time.

In April 2016, the next LTS release came out. By then, I probably had close to 50 servers running a handful of distributions. All the Ubuntu-based servers migrated successfully except for two (four, actually, as each of those servers had a hot backup). One of those handled the office phones (asterisk, hylafax, IAXmodem), the other mostly handled email (postfix, dovecot, spamassassin). Those machines died horribly when I attempted to upgrade to 16.04 (saved by backups!) and, since they handled critical services, I decided to leave them on 14.04. After all, I had until 2019 to upgrade.

Plenty of time.

But I have two 3/4-time jobs and am a single dad to two teenage boys whom I refuse to leave in child care. Since 2016, I’ve been grabbing time whenever I could to try to migrate, but (thanks largely to the abysmal error reporting in systemd), I couldn’t make the switch.

Then it was 2019, and I had only a few months. I dedicated evenings and weekends to ironing out the problem without disrupting my clients’ businesses with downtime. I missed the April deadline, and had to leave machines talking to the internet that didn’t have up-to-date software. That’s a scary place to be, even with other layers of security wrapped around them.

Earlier today, I migrated the last of the servers to 16.04. I retired the venerable beasts and and replaced them with much more efficient and compact boxes. I’ll be moving them to 18.04 just as soon as I get a chance, but for now they’re stable and supported, and I have until April 2021 to make the transition.

Plenty of time.