To be fair, is Stark the only one right now, but I guess it’s not about Stark.
The orange “update” button doesn’t work, neither Update All at the bottom right.
Yes, I tried restarting and the usual stuff.
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Oh noes 
You’re absolutely right, Leo. We’ll bring this to the team and see what they can find about the issue!
In the meantime, you can manually download the latest version of the plugin from this page, and drag-n-drop it in the Sketch window to update/install it!
As soon as we know more, we’ll update the thread!
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Update
Just reviewing the appcast.xml file (where the updates are specified), it seems that Stark does not have an entry for Stark 3.19.0 (the latest that shows on the file is 3.18.0).
We have opened an issue on their repository to report this!
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Same problem here with Stark Plugin Update: Sketch Version 98.2 (176424)
For me this happens with the Stark plugin every time it’s updated. The first time I try to update it the button doesn’t work and I need to restart Sketch in order to make it work.