N.B.: you could also use a quick step to do this. The advantage is that you can then combine the flagging with marking the item as read (and move to a folder optional - which I don't do because I prefer to hide completed emails automatically.). The drawback is, that you can not assign a hotkey to a Quick Step (afaik).
AutoHotkey Implementation
Code
This is implemented in OutlookShortcuts.ahk
The key part of the implementation relies upon opening the context menu with Shift+F10 and then trigger the proper action menu via the accelerator keys.
This only works for one last selected item.
Usage
VBA Implementation
Alternatively, you can implement this in VBA.
Code
The code is pretty simple.
You can get the code in this outlook-vba repository the Email.bas module. It also requires GetCurrentItems in Utils.bas.
Setup
You can set this macro as a button in the QAT (Quick Access Toolbar (QAT).
You can also trigger it with a hotkey. (If you press the Alt key they become highlighted.)
This works for multi-selection. (hold the Ctrl key)
(You could also remap this hotkey Alt+QAT # in your AutoHotkey script.)
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