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Is there any way I can create some popup message when I connect to my RDP session? I wanted to show some important information for my work colleague so we don't forget.

We share one account to login to the server and we never log off, so the message should appear right after connecting.

We're on windows server 2008 R2 and using the native RDP application to remote desktop.

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    I don't know how to do it natively, but what we do at our workplace (very similar setting to you), just before we log out and need to leave messages for the other user, we just open notepad and write our messages on the notepad, and make it full screen before closing the session (not logging out). So the next person logging in using the same account, that full-screen notepad will be the first thing they see and your message.
    – Darius
    Feb 11, 2014 at 1:09

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A Task Scheduler event can do that. Make a task that launches notepad with a text document listing notes you want to pass to each other. I would suggest three triggers so you cover when the server has rebooted or when one of you has logged off in addition to reconnecting. Example below is from a task to run BGInfo (a Sysinternals utility to put some information on the wallpaper) for ideas.

enter image description here

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