How's that? Unless Evernote's application name changes or its file path changes, the "old" pinned item will still point to something. For those who manually pin Evernote to the taskbar, it is most likely pointing to C:\Program Files (x86)\Evernote\Evernote\Evernote.exe unless Evernote is intervening and doing something else and pointing to what, the registry? C:\Users\%user%\AppData\Local (or Roaming)? Because the MSI uninstall process cleans up the shortcut (during RemoveShortcuts). During an upgrade, the old product is uninstalled and then the new one is installed. (If you know MSI terminology, we schedule RemoveExistingProducts before InstallInitialize) When you pin the app, we do not intervene. The _only_ API Microsoft provides for interfacing with a pinned item is IStartMenuPinnedList::RemoveFromList. I think that name is descriptive enough that it's obvious what it does... The _only_ legal way to get the shortcut to stick on upgrade is to change the installer to first do an install and then uninstall the old product. This has it's own set of issues, especially in an already released product. Bottom line, this is not going to change unless Microsoft changes msiexec.