Upgrading twice FTW
You probaly know, CiviCRM has security update coming up next month.
So here's a crazy idea:
It might be smart to upgrade twice.
Yeah, I know. Upgrading is work, so why double that work?
But consider this:
When a security update is released, it's important to upgrade quickly.
The more versions your upgrade spans, the greater chance you'll have of hitting some surprising challenges to complete that upgrade.
So, if it's been a while since your last upgrade (say, you're running the most recent security release from version 5.65.0 or thereabouts), you’ll have a large upgrade (greater chance of surprises) at the same time as a time-sensitive security update.
Upgrading twice will allow you to split those problems and deal with them separately.
In this case, we know (per the announcement) that the security release will come on June 19, after version 5.74.0 is released around June 5.
So you could take the “upgrade twice” approach like so:
Soon after the release of 5.74.0 on June 5, upgrade to that version. This will give you a chance to deal with any surprises without the time pressure of a security upgrade.
On June 19, when the security update is released, upgrade to that version. Since the time between upgrades will be very small, you'll have a very small chance of hitting any challenging surprises, which means you'll be more likely to get that security upgrade done in a very timely manner.
The alternative is to do the whole thing at once on June 19. That's not impossible, but you're setting yourself up for the chance of hitting difficult upgrade challenges while you're under some serious time pressure.
You can avoid that — by upgrading twice.
All the best,
A.