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I can set up an appointment to do this I guess, but would there be any way to pop up some sort of window with a text box in it every day at 4:30pm, allowing me to enter some notes, click ok and it would be saved to my calendar?

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If you are comfortable with a little bit of programming you can usethe included VBA to create a macro that can do this.

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There is no real way of doing this. The only way would be setting up an appointment to do with a reminder

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You could popup an outlook stickie using the outlook command line switches using a batch file and then get the tasksheduler to run the script at 4.30pm everyday e.g.

"C:\Program Files\Microsoft Office\Office12\outlook.exe" /c ipm.stickynote

I have not tested the above but there is more info here:

You can attach stickies to calendar entries - so you might be able to automate this too.

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