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Hi Nathan,

At least on genuine apple hardware with a real serial:

The iMessage thing is probably because certain root certificates expired in high sierra and others by now and they can be updated manually. [0]

https://osxchateau.com/articles/updating-ssl-certificates-on...

A bunch expired in 2019 and Apple pushed new installer versions for several OS releases going back to Yosemite. High Sierra made the cut but you don’t have to reinstall [1]

https://tidbits.com/2019/10/28/redownload-archived-macos-ins...

You’d see this if you booted off the CD or recovery partition. an Internet restore should be okay.

You can also get a newer macOS on that laptop altogether using something called OpenCore. I think I stopped somewhere around Monterey but my 2013 clunker would run Tahoe if you wanted it to. I had a newer m1 I just gave away but I had updated the Intel because it was still in mint condition and ran perfectly. I still preferred it to the new one. I just needed a functional browser. /rant

Interesting - thanks for this info. I'll have to look into the certificates. I wonder why it eventually worked though if the issue is expired root certificates?

Realistically the laptop is pretty old even to run Catalina. I don't expect it would handle a more modern OS very well.