I have recieved a new in box apple pencil 1st gen for my Ipad Pro 10.5 which was also recieved new in box for Christmas 2019, which is listed as supporting this pencil and have the exact same problem. I have returned my pencil and gotten a replacement and it also fails to pair long enough to use. I have gone through the forums and online and tried hard reset of Ipad, turning bluetooth on and off, making sure pencil is centered in charging port. having pencil fully charged. I was only able to get a partial pairing long enough to see that the battery app showed the pencil while plugged into the Ipad Pro 10.5 was at 100%, when I removed pencil to use the battery app quickly showed the pencil dropped to 1% land unpaired. That only happened once out of the two new pencils I have used. Plugging in most the time shows the pair window very quickly and then it dissappears, pushing pair does not work when you are able to catch it, to push . The about in settings does the same thing showing the pencil flashing in and out and if you are super quick you can push the > symbol and get a screen that flashes up fast and shows the version model and firmware version, which is easier to read if you have a phone camera ready to take a picture of it when is is up for a second. got to be quick. My wife also has a Ipad Pro 10.5 from 2017 and has a pencil 1 so I borrowed hers and it paired up with my Ipad Pro 10.5 no problem just as you would expect, not a problem, I then checked in Settings, General, About and found that her pencil 1 is version 02.61.00 , it had updated in her Ipad Pro while plugged in. I suspect that if one could update their new pencil 1 to the latest firmware it too would work with Ipad OS version 13.3. I called tech support and they suggested all the things I had done and finally suggested I either send in both my Ipad Pro 10.5 and my pencil 1 or take them to a Apple Support Center. Yes, I know what your thinking, why don't you update on your wifes Ipad Pro 10.5 , and I will do this soon , hopefully my new pencil will update the firmware on her Ipad to work on my Ipad. Pretty sure this is a issue of software, Ipad OS 13.3 and pencil firmware not being compatible.
