When should I update to the latest version of my operating system (OS)?

21 May 2025
computer

TLDR: Updates to your current version of your OS should be done immediately, for major upgrades it would be advisable to wait a couple months.

This is more geared to Apple Mac users, as they get yearly major updates (ex: macOS 14 Sonoma to macOS 15 Sequoia). Windows users get lots of smaller updates, but fewer major releases (the current release, Windows 11, was released in 2021).

Guidance: Install any updates to your current version of your OS immediately. These updates usually contain bug fixes and security updates that are going to fix potential issues on your machine. For major OS upgrades, it's probably best to wait a couple of months; at least until the .1 or .2 updates (the first updates after the initial release). This allows fixes to any bugs that were discovered in the initial wide release to be rolled out.

Most enterprise level software and programs (ex: Microsoft Office) will have been upgraded in preparation for a major release, but waiting a couple months will avoid any issues with delays (sometimes UMB IT is more pragmatic about allowing security software to be upgraded, etc).

If you are not sure if your software is compatible with a new version of an OS, you can usually find it in their release notes. For example, if your work involves Microsoft Office for the Mac and you want to know if it will work in macOS 15 (Sequoia), you can do a search for "Microsoft office for mac compatibility macOS 15 sequoia". For me, the top result was from Microsoft's support documentation, reading: "Yes. macOS Sequoia is supported starting with the September 2024 update (16.89). " So, I would be comfortable upgrading based on those parameters.

FYI, I (Jeff) have been running Sequoia for a while without any issues.