Pretty sure this is a issue of software, Ipad OS 13.3 and pencil firmware not being compatible. Now, with update, it does not show charge level of apple pencil, and also does not automatically connect to blue tooth when apple pencil is plugged into ipad pro lightning plug. 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. Before ipad pro updated to ios 11, my apple pencil would charge when plugged into ipad pro lightning plug. 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. 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. 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. 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. 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. That only happened once out of the two new pencils I have used. 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. After plugging in your pencil, quickly go back into Settings and turn on Bluetooth. With that done, go ahead and plug in your Apple Pencil. Then, make your way to Bluetooth and disable it. 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. To do this, follow the instructions given down below: First of all, open up the Settings app on your iPad. I have returned my pencil and gotten a replacement and it also fails to pair long enough to use. One of the possible causes why Apple Pencil Not Working Apple iPadOS is perhaps the Bluetooth is not turned ON. 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. The minimum battery percentage of your Apple Pencil is at least 30, if it falls below 30 your Apple Pencil might not work properly and may require you to recharge.
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