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Question: Migration Assistant Didn't Transfer Everything

I got a new MacBook Pro this past April and used Migration Assistant to transfer all my files from my time machine backup of my 3ish year old MacBook Pro. It worked like a charm, everything transferred without fail and my new computer looked and acted exactly like my old one (only better) without me having to adjust any settings. I was incredibly impressed.

Those were both work computers and I left that job for a new one in August. I backed up my files with Time Machine before I turned my computer in and just bought a brand new MacBook Pro. I logged in using my same Apple ID and used Migration Assistant from the same Time Machine backup: some things transferred but not everything. The most obvious losses so far is my personal email account did not transfer to Mail and none of my purchased fonts transferred. Also, I had to download all the apps that I used on my old computer when they loaded automatically last time.

Why did Migration Assistant work seamlessly in April and fall short today? Anything I can do to transfer these files (especially my fonts)?

MacBook Pro TouchBar and Touch ID, macOS High Sierra (10.13.2)

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Question: Migration Assistant Didn't Transfer Everything