How can I add an item to the context menu in Outlook from a Delphi application, while the Delphi application is running?
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You can write an com add-in for outlook to customize/create your context menu, and from there you can check if your delphi app is up then do the changes that you need.
To customize outlook (com add-in app), you can use a 3 party lib called add-in express, using that lib is very easy customize outlook/word/excel.
http://www.add-in-express.com/add-in-delphi/programming-outlook.php