Just in case somebody else has this problem:
After upgrading from TextPad 7 to 8 on Windows 10, I thought the start menu jump list was broken: no new files were being added.
The problem was that the file types weren't associated with TextPad 8: the jump list works on file associations, not on application used to open the file. I re-created the file associations both within TextPad and from Windows' "Choose the application you want to use to open this file" box, and the jump list is working again.
Jump list problem SOLVED
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Jump list problem SOLVED
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