Windows 10 Start Menu can't have multiple shortcuts with the same target

As of Win 10 (1903) Aug 2019, it seems that the Start Menu will now allow duplicate shortcuts to the same .exe as long as the arguments are different. For this to work though, the "duplicate" shortcuts needs to be created by any method OTHER THAN making a copy of the already existing shortcut in the Start Menu and modifying it.

So, a shortcut created with the target as

C:\Windows\system32\cmd.exe /K "cd C:\"

will open up the command prompt at C:\, and a shortcut created with the target as

C:\Windows\system32\cmd.exe /K "cd C:\Users\"

will open up the command prompt at C:\Users\. Both shortcuts will be shown on the Start Menu, in addition to the default Command Prompt shortcut, even if they have the same name.

I was also able to create a duplicate shortcut to cmd.exe that will show up in the Start Menu and function identically by using ' as an argument. Target:

C:\Windows\system32\cmd.exe '

Which I can then modify to launch cmd with different properties (admin/compatability etc.). This may not be suitable for other executables.

A number of Windows 10 updates have caused issues with shortcuts, such as disabling the keyboard shortcuts to links and requiring links to be in specific locations, as well as this issue of allowing only a single target.

Though I know of no fix within Windows, some free third-party tools such as ClassicShell and Clavier+ provide a workaround. Because these tools' configurations can be saved or copied to new Windows installations and can easily be edited, I've come to prefer them to the native Window link files and keyboard shortcuts.

The method I used was to open up an Administrator: Command Prompt and create a symbolic link to cmd.exe and then create a shortcut to that symlink

(Administrator) C:\> cd \Windows\System32

(Administrator) C:\Windows\System32> mklink cmd_admin.exe cmd.exe
symbolic link created for cmd_admin.exe <<===>> cmd.exe

Once you have created the symbolic link, you can make a copy of the Command Prompt shortcut (in any folder) and name it whatever you want. Then follow these steps:

1. right click on the shortcut and click on Properties at the bottom of the pop-up menu
2. if it's not already selected, click on the Shortcut tab of the Properties window that just opened up
3. change the Target: from %windir%\system32\cmd.exe to %windir%\system32\cmd_admin.exe and click the OK button to save your change
4. (optional) you could make additional changes from the same Properties pop-up such as:
   • the Start in: location
   • make it an Administrator: Command Prompt by clicking on the Advanced button and then checking the Run as adminstrator checkbox