It sounds like you're encountering a common issue with the integration between Skype for Business and Outlook. Here are a few steps you can follow to troubleshoot and hopefully resolve the issue:
- Ensure Both Applications are Running:
- Make sure both Outlook and Skype for Business are running.
- Reconfigure Skype for Business Status Settings:
- Open Skype for Business.
- Go to
Tools
>Options
. - Click on the
Personal
category. - Make sure the options "Update my presence based on my calendar information" and "Show my Outlook Out of Office information to my contacts" are checked.
- Check Outlook Add-ins:
- In Outlook, go to
File
>Options
>Add-ins
. - At the bottom of the window, ensure "COM Add-ins" is selected and click
Go
. - Ensure that "Skype Meeting Add-in for Microsoft Office" (or a similarly named add-in) is checked.
- Restart Both Applications:
- Close both Outlook and Skype for Business completely. - Restart Skype for Business first, then Outlook.
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