Okay, so this was kind of just me being foolish and not thorough here:
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I'd set an exception breakpoint to get stack traces that was preventing me from see the actual exception error printout -- oops.
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Can't use version of uploadTaskWithRequest that has a completion callback for a backgroundSessionConfiguration (not surprising but still not well documented).
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Write your PNG data to /var/... and provide it to uploadTaskWithRequest with file:///var/... (this is just awkward because you don't often need to convert between the two for a single sequence of commands)
Happy to put up a NSUrlSessionUploadTask sample code here, since there seems to be zero of them on the entire interwebs. LMK if anyone wants that.






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