I may have identified the cause of the missing context menu item.
What I found is that regardless of the UAC setting in the User Control Panel in Win2012r2 - if you have disabled admin mode manually either through the Security Settings or registry - the context menu item won't show.
If I turn on Admin mode (EnableLUA registry setting = 1) and reboot - then the Context item show up. If I go back and disable it (Set to 0 and reboot) - it then disappears.
I have several other programs that add similar context menu items that this doesn't happen with - so the problem would appear to be with how TextPad wrote their code.
Add shortcut to Context Menu button is grayed out?
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Possible Cause
Joseph Leathlean