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I just poked around with this, and it's kind of funky in how it works. The 5v and GND alone will not make it charge, you need that Resistor in there on the third pin to Sense it. I used a 4.7k here, so anything between 4.7k and 5.6k should work. Here's the rub though, the order in which the pins make contact are where it gets picky. If you have the 5v and GND connected, then connect the Sense pin, it will not charge. If the Sense pin is connected first, then 5v and GND is connected it will charge. If you have all 3 of your pogo pins in a row you might get lucky half of the time and it would charge, but I'd make that Sense pin proud just a bit so that it makes contact before the 5v and GND pins do.
Ok , from what you say, i think its acting like a (DRP) USB-C 3.1, maybe resistor is needed 5.1k , and capacitor (100nF) on V+ to make a bit delay ?