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How should I make sure my Visual Studio installer updates DLLs when installing an older version?

I recently noticed that my installer (VS 2008) does not uninstall DLLs during uninstall. This doesn't bother me too much, but the following is worrying: when I install an older version of my software, it doesn't overwrite the DLL - it supports the newer version.

When I rollback my system to an older version , I would like it to be rolled back. What's the best way to do this? Do I need to create a custom action to remove DLLs on uninstall to be safe, or is there another way to remove them, or is there an option to force the installer to always write the DLL.

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First you have to ask yourself why the installer didn't delete the files, because it should, and if not, it's BUG (or that the installer is waiting for a reboot to delete the files).
You can run a logged MSI to see what's going on there:
msiexec.exe / i / l * v



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