I figured out this latest issue. The problem was that as soon we tried to connect jetpack to the client’s wordpress.com ID the site would crash. Turning debug on didn’t yield an error message either.
Eventually the site emailed me the error message: Call to undefined function ctype_digit(). To get around this I had to add this to the php.ini: extension=ctype.so
Whenever Jetpack crashes a site I have found it to not be straight forward to figure out why. The fix almost always requires modifying the php.ini. I am fortunate to understand how to debug and tweak the php.ini, but I suspect a lot of folks aren’t as savvy.
Anyway, you would think the plugin could check for critical dependencies like this and advise ahead of time instead of crashing the site.