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Any new shortcuts I add to the start menu fail to show up in the start menu search results. I've tried rebuilding the index to no avail.

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[Credit to CraigsNotHere on reddit]

Turns out the issue was due to having UAC disabled. To re-enable, simply toggle User Account Control: Run all administrators in admin approval mode in your Group Policy Editor (gpedit), otherwise if you're running Windows Home, open up regedit and enable (set to 1) EnableLUA under HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Policies\System.

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