Keep getting message that an update is required to connect my iPhone

Hey there kurtnmsuedu,

Let's rule out some possible causes, along with better understanding what's happening:

1. There could be a few things occurring, the first is that you're using outdated software on both devices. While iOS 15.7 is the latest for older iPhone models, for compatible models, the latest version would be iOS 16.0.3. Which iPhone model are you using? This can be found under Settings > General > About.
2. For compatible Mac models, the latest version is macOS 12.6. As you mentioned having macOS 10.15.7, this would be the latest for this macOS version, but it may not be the latest compatible version for your Mac model. Which Mac model are you using? This can be found by clicking on the Apple logo at the top left corner, then checking on the model/year under 'About This Mac'.
3. Do you have any pending updates for the currently installed macOS 10.15.7 version? While you may see the macOS 12.6 update available, we're asking if you see any updates other than that one.
4. Sometimes unexpected behavior can be resolved with a restart. Check out Restart your iPhone and the section 'Restart' here: Log out, sleep, wake, restart, or shut down your Mac

Cheers.

Hello kurtnmsuedu,

We completely understand how time consuming issues like this are.

There is one more thing we would like to suggest. If an issue does not occur in safe mode, but returns when the Mac is started up normally, we would suggest you go through these steps found at How to use safe mode on your Mac:

If the issue returns after leaving safe mode, startup items are probably at fault. Apps can install such items in numerous places, and they aren't always easy to find or recognize. For that reason, you should first make sure that you've installed any available updates for your Apple software and third-party apps.

If updating your software doesn't help, try any of these solutions:

• Test your login items.

• To learn whether software in your user account is causing the issue, set up a new user account, then log in to it and try to reproduce the issue in that account.

• Unplug all accessories from your Mac, including printers, drives, USB hubs, and other nonessential devices. You could have an issue with one or more of those devices or their cables.

• Reinstall macOS.

Cheers.

Kurtnmsuedu,

Thanks for keeping us updated. Moving forward, it may be helpful to contact Apple directly about this issue. Use the following link to get that conversation started when you have time. Contact - Official Apple Support

Take care!

Is the phone connected via cable to your Mac, or are you connecting using Wi-Fi to the Finder on the Mac?

Whichever it is, try the other type of connection as an experiment to see if the same error appears.

I recall seeing the message a few times when I was still using Catalina, but the same type of message has never appeared using Big Sur.

We're happy to hear your issue was resolved, kurtnmsuedu!

We hope you have a great rest of your day!