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After the first installation I paused the cast and got the contents of a few directories.
You can see that after accepting the merge the first time, the merge prompt still occurs on the second attempt.
Is this supposed to trigger with each install or only if something has changed?
Experienced while installing MT 5.3.4 (abd3c5c3e15d89cfe55d2343663ff116f798ea8e)
Yes this is normal, the install process resets the docs everytime as in the general case a subsequent installation is for a new version. That in turns trigger the dialog (for testing purposes you can say no there if you don't want to wait, same dialog can be triggered again in macdoc with MD > Help)