How to create a kill-switched VPN on Mac OS X with Little Snitch

In this post, I describe why, after years of using the wonderful Mac/iOS VPN product, Cloak, I’m experimenting with an alternative approach, that combines Private Internet Access (PIA) and Little Snitch. (2015-08-28 — As mentioned in an update at the end of the article, I’ve actually now switched back to Cloak, but using Little Snitch as the kill-switch.)

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My iCloud Photo Library seems to be broken

iCloud Photo Library on my iPhone keeps reminding me that it’s been 10, 20, 30 days since I’ve last uploaded photos. But when I visit the Photos area of the Settings, here what I see:

It’s attempting, over and over again, to upload the first of 91 photos. As you can see, the upload fails, and starts over.

I have no idea how to resolve this, other than just disabling and re-enabling the whole thing and hoping for the best. But if I did that, would I end up re-uploading my entire photo library? Sigh…