If you are using that drive then you must use the USB-C connection which is what is the charging pad is using. Or you need to find a way to connect a USB 3 hub to the passenger side and power that hub from somewhere besides that USB-A connector.
The USB-A side is only USB 2.0 last time I checked, which is limited to 0.5A of current. Those T5 drives need more current than 0.5A for reliable sustained writing of video files. While they may be USB 2.0 compatible, that is a loose definition, meaning you can connect via USB 2.0 and read files from them, and maybe write small files or create folders. Writing takes more power than reading, which is why when you try to write to them via USB 2.0 they do not work at all or they might write the first 1 second or so and then crap out, no more video, due to lack of power.
See page 22 of the user manual link below
https://images-na.ssl-images-amazon.com/images/I/91JYEAU9RIL.pdf
5V (USB 2.0 USB 3.x okay)
0.8A (USB 2.0 = no, USB 3.x ok if externally powered hub or USB 3.X connection from the car)
That drive will work just fine via USB 3, USB 3.1 connections like the USB-C on the driver's side. But trying to make it work reliably on the passenger's side USB-A is an exercise in futility.
If you do not want to give up the USB-C and wireless charging pad, then you need to do some research and find a drive that is fully compatible via USB 2.0, meaning it can do the minimum sustained write speed as required by Tesla (see owner's manual) and does not need more than 0.5A. When in doubt, keep it simple and small like normal flash drive, and not a SSD. Or just buy the same drive that Tesla is now selling for sentry mode. $20 on AMZ apparently last time I checked. There is a thread here that mentions that.