Should I Update macOS? How to Decide Each Year

Every September, Apple ships a new macOS. Every September, the question repeats: install it now, wait, or skip entirely? The right answer depends on your Mac, your apps, and how much patience you have for early-version bugs.

Here’s a framework that holds up year to year, regardless of which macOS is currently new.

The four questions to answer

Before deciding, ask yourself:

1. Does my Mac officially support the new version?
2. Do my critical apps support it?
3. What does the new version add that I’d actually use?
4. How much downtime can I afford if the upgrade goes sideways?

Work through those four and the answer usually picks itself.

Question 1: hardware support

Apple drops a few Mac models from the supported list every year. Check the Apple support page for the new version’s compatibility list before you do anything else.

If your Mac is on the list:

• Performance will be at least passable on most supported models.
• Apple has tested it on your hardware.

If your Mac isn’t on the list:

• You’re staying on your current macOS.
• Skip the rest of this guide.
• Tools like OpenCore Legacy Patcher exist but they’re unsupported and can break unpredictably.

A model on the bottom of the supported list (the oldest year still included) often runs the new macOS measurably worse than the previous version. The Mac will technically work, but it’s the model Apple supported reluctantly.

Question 2: app support

Critical apps to verify before upgrading:

• Adobe Creative Cloud — Adobe is usually slow to certify new macOS versions. Check the Adobe Tech Support pages for your specific apps.
• Microsoft Office — Microsoft is usually fine on launch day, occasionally buggy.
• VPN clients — corporate VPNs (Cisco AnyConnect, GlobalProtect, Pulse Secure) often break with major macOS updates and don’t fix promptly.
• Pro audio software — Logic, Pro Tools, Ableton. Plugins are the bigger issue than the DAWs themselves.
• Pro video software — Final Cut, DaVinci Resolve, Premiere. Plugins same problem.
• Antivirus / endpoint security — frequently breaks on new macOS. Often blocks login on upgrade.
• Backup software — Carbon Copy Cloner, SuperDuper, ChronoSync usually update quickly but verify.

If you depend on any of those for daily work, check the vendor’s support page before upgrading. “It worked on my Mac” forum posts are not enough — you want the vendor’s official statement.

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Question 3: what’s new

Most macOS versions include a few features people will actually use, plus a long list of marketing bullet points nobody touches. Identify which category applies to you.

Genuinely-useful features from the last few macOS versions:

• Sequoia (15): iPhone Mirroring, window tiling
• Sonoma (14): desktop widgets, Game Mode, Continuity Camera
• Ventura (13): Stage Manager (mixed reception), Continuity Camera (introduced)
• Monterey (12): Universal Control, Live Text, Shortcuts on Mac
• Big Sur (11): visual redesign, Apple Silicon support

If a release doesn’t include anything you care about, the upgrade is just risk without reward. Apple will support your current version for at least 2–3 years.

Question 4: how much downtime can you afford?

Pick the right time:

• Don’t upgrade on a workday. If something breaks, you’ve lost a workday.
• Don’t upgrade right before a deadline. Apple ships new macOS the second or third week of September. If you have a project due that week, wait.
• Don’t upgrade right before travel. A broken Mac on a plane is worse than a working old version.
• Do upgrade on a Friday evening. If something goes wrong, you have the weekend to recover.

Plan for two hours of total downtime even on a smooth upgrade. Allow more if your Mac is older or you have a lot of installed software.

The four upgrade strategies

People generally fall into one of four patterns. Pick the one that matches your tolerance for issues:

Pattern 1: Day-one upgrader

Install on launch day. You’ll hit early bugs. You’ll get the new features first.

This is fine if:

• You’re on a current Mac (not the oldest supported model)
• You have a good Time Machine backup
• You don’t use specialized software (DAWs, video pipelines, corporate VPNs)
• You enjoy debugging

Pattern 2: One-month waiter

Install after the first .x.1 release. Major bugs are usually patched. Most third-party apps have caught up.

This is the right strategy for most people. You miss launch-week chaos but get current features within a month.

Pattern 3: Major-fix waiter

Install after the .x.2 or .x.3 release, typically January–March. Apple has shipped at least two rounds of bug fixes. Vendors have updated.

Good for people who depend on specialized software but still want to be current within the year.

Pattern 4: Year-late upgrader

Install only when the next macOS comes out, meaning your “old” version becomes the second-to-newest. You always run the most polished version of any given macOS.

Reasonable for risk-averse users with stable workflows. Downside: you’re typically a year behind on security patches for current vulnerabilities (though Apple does ship security updates to two prior versions).

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When to skip an entire version

Some macOS releases are worth skipping. Reasons:

• Major redesign release — Big Sur was a large visual change with associated bugs. Some users skipped it for Monterey.
• A version that targets Macs newer than yours — features you can’t use, performance cost you’ll pay.
• A version with a known long-term issue with your hardware — research before upgrading.

You can typically skip one major version without consequence. Apple supports at least two prior versions with security updates.

Pre-upgrade checklist

Whenever you decide to upgrade, do these in order:

1. Time Machine backup. Full backup, not just snapshots. Verify it completed successfully.
2. Clone backup if you can. Carbon Copy Cloner or SuperDuper to a separate drive. Belt and suspenders.
3. Check disk space. You need 30–35GB free, not 12GB. The upgrade stages everything.
4. Note your current macOS version. Apple menu → About This Mac. Useful if you need to roll back.
5. Disable third-party security software. Re-enable after.
6. Plug in. Don’t update on battery alone.
7. Set aside two hours minimum. Plan for more.

System Settings → General → Software Update → click Upgrade.

Post-upgrade checklist

After the upgrade completes:

1. First boot may take longer than normal. macOS finishes setup tasks.
2. Plug in and let it sit for an hour or two. Spotlight indexes, Photos analyzes faces, sync catches up.
3. Audit login items. System Settings → General → Login Items. Major upgrades sometimes re-enable disabled background helpers.
4. Check that your critical apps launch. If anything fails, vendors usually have a guidance page within days.
5. Revisit performance after a week. Some operations get faster as caches rebuild.

How to roll back if you regret upgrading

You have options:

1. Restore from Time Machine — easiest. Boot to Recovery, choose Restore from Time Machine Backup, point at your pre-upgrade backup.
2. Erase and reinstall the previous macOS — Recovery Mode → Reinstall macOS, then choose the older version if available.
3. Boot from an external installer — make a USB installer of your previous version, erase the internal drive, install fresh.

None of these are quick — plan for several hours. But you’re not stuck on a version you regret.

My honest framework

For most people:

• Take a Time Machine backup before upgrading. Always.
• Wait at least until the .x.1 release unless you have a specific feature you need.
• Check your critical apps’ compatibility before installing.
• Don’t upgrade right before something important.
• Skip a version entirely if you have specific reasons — Apple supports two prior versions with security patches.

The default cadence I’d recommend: upgrade on the .x.2 or .x.3 release, typically December–February. You’re current enough for security and features, late enough that the worst bugs are fixed.