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My wordpress (org) site is “experiencing a critical error” every time the site is connected to wordpress.com via Jetpack, disconnecting the site from wordpress.com (which works fine) will fix the issue. From what I’ve seen, the Jetpack debug panel did not find anything and removing and reinstalling the plugin will not fix the issue. Also it seems to only affect the account that is the “Jetpack owner”, working on the site from other accounts is possible.
I suspect the issue started when I tried to log in to the site via the wordpress.com Windows desktop program.