Hello,
Sorry to hear you are having issues. Maybe something went wrong when you pinned Outlook. Try this, unpin Outlook from taskbar. Start Outlook from your Startpanel. Once Outlook is running, right click on taskbar button and select pin to taskbar. Once that is done. Close outlook and try click on that new pinned outlook button on taskbar.

Thank you,
Basj,
Stardock Community Assistant.

That issue was pinned to Start panel not Taskbar. Yours is on taskbar, how is that similar?

Please post a video on your issue so we understand it better.

Thank you,

Basj,
Stardock Community Assistant

I checked and something is look different in your Video. When I right click on Outlook I get this menu.

Which is, I believe is the correct one to be pinned. Not really sure why in your video it come as "Microsoft.OutlookforWindows". And, I checked deeper, its the way you pinned to taskbar while launching outlook via Windows 7/Modern style Start menu. And yes, I believe, this is related to that other issue you mentioned in your reply#2 on pinned item on Start panel. So, I have forward your problem to Stardock Support Team for their review. Please keep an eye on this thread for any updates. We appreciate your feedback and patience.

As a work around please change to any other Start11 style other than Windows 7/Modern style and Open up Outlook from there. Than pinned to taskbar while Outlook is open.

Thank you,

Basj,
Stardock Community Assistant