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    It is impossible to answer this question with facts. You can have a hardware failure: power outage, broken harddisk, corrupted memory that can mess up an upgrade. All you can do is prepare for failure: make backups of personal files and know how to restore a backup. I would myself aim to setup your system such that you can erase your system partition/disk and re-install from scratch where you afterwards add your personal files/partition/disk and non-standard software. This also works if you want to move to better hardware. Commented 20 hours ago
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    Please confirm if Wine is installed from WineHQ. Commented 20 hours ago
  • This seems to be fully answered but let me just add the following: I have a rig with 20.04, 22.04 & 24.04 with a common 'home'. I have multiple WINE application that run the same common code (WINEPREFIX) from all three. The only problem between them is the desktop icon I use to evoke the programs which has to have small differences between each OS flavour. Hence I have a row of icons for each OS version. When running on a new OS WINE has to find the correct version and install it before it runs it. Commented 20 hours ago