This usually happens when I'm connected and then close the lid of my MacBook. When I open it back up, Cloak is gone and sometimes I don't notice that it never connected (I'm surfing unprotected).
I looked through Console.app and only saw some memory pool leak errors. Is there other info I can send to help debug this?
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This is the first we've heard of it -- we're not aware, nor have we encountered, any stability problems with the 0.9.20 build. (Is that the build you're on?)
Mind dropping an email to hello[at]getcloak[dot]com that contains the relevant console logs? Also helpful would be to include info about OS X version / hardware you're on...
...and finally, you're always welcome to drop by @seafreemob and get direct technical support! ;-)