Thank you Rob for all this hard work!
I’m happy to help any time 
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But reading your amazingly written bug report, it sounds pretty bad. Race conditions are the worst (and so common).
Funny thing, my extension process just crashed moments ago, I think I’ve discovered a memory leak/infinite loop in my speed dial addon. So after a year, I have a new crash report …, it’s karma for bragging that I had none this year 
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So… I hate to ask this so soon, but what about the second issue?
(background script being terminated right after waking up)
And anything I can do to help?