@Stanseas ,
You didn’t say which OS, or which precise version of Notepad++ you are using, both of which may be relevant; based on your screenshot, I’m guessing Win11. If it’s an older Notepad++ and Win11, then some older versions had some difficulties with the context menu for a while. (?-menu’s Debug Info would answer both.)
I am also wondering whether it’s the Edit with Notepad++ entry from the Shell Extension, as described in the User Manual, or whether it’s added as a registry entry.
If it’s the Shell Extension, maybe you could try to un-register then re-register the extension, as described further down in the User Manual link above. Or maybe un-register, then re-install Notepad++ (making sure to [install v8.7.1], which is the last confirmed-stable version). You can also reg query HKLM\SOFTWARE\Classes /s /f NppShell.dll: mine shows the following results:
HKEY_LOCAL_MACHINE\SOFTWARE\Classes\CLSID\{B298D29A-A6ED-11DE-BA8C-A68E55D89593}\InProcServer32
(Default) REG_SZ C:\Program Files\Notepad++\contextMenu\NppShell.dll
HKEY_LOCAL_MACHINE\SOFTWARE\Classes\PackagedCom\Package\NotepadPlusPlus_1.0.0.0_neutral__7njy0v32s6xk6\Class\{E6950302-61F0-4FEB-97DB-855E30D4A991}
DllPath REG_SZ NppShell.dll
End of search: 2 match(es) found.
If it’s an old-fashioned registry entry (less likely if you’re in Win11), you can run regedit.exe and search for notepad++.exe, looking for an entry named Edit with Notepad++ (it may be &Edit with Notepad++ or Edit with &Notepad++, which is why I suggested searching for the executable name, which won’t change) – there might be an entry pointing to an old location (maybe the Program Files (x86)\ when your active one is really in Program Files\)