This doesn’t necessarily mean that you have to update your 2014 iMac to High Sierra rather, just make sure to go to the App Store’s “Updates” tab to check for any incremental updates to Yosemite or whatever it’s running. Make sure both Macs are running the latest version of their operating systems.

Many things in tech are frustrating, but few are more upsetting than getting a new machine that then takes hours and hours to get set up.

I’m not sure whether this is an indication of a problem with High Sierra, necessarily, but I thought I’d take the opportunity to give you all some pointers on how to make sure Migration Assistant works properly (and what to do if it doesn’t). In all three cases, the old computers and the new ones were running High Sierra, and all three migrations failed and had to be redone. Over the last ten days, I have worked with three clients who attempted to migrate to new Macs using Migration Assistant, Apple’s built-in program for transferring applications, user documents, music, photos, and so on from an old Mac.