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As of now, the installer uses the InstallDelete section to remove files. However, if a file that should be deleted is locked (which can happen for fonts), there is no error that a file can not be deleted and old files might remain active.
Maybe all entries in InstallDelete should be moved to a script based delete method that first uses the "normal" delete and if this doesn't work, use MoveFileEx (e.g. https://www.codeproject.com/Tips/1193043/Inno-Setup-Cleanup-Extra-Files) which will delete the file upon next restart.
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