No longer able to upload to Nano BLE Sense

I have a BLE Sense and a "basic" BLE board. I'm working on getting them to communicate over BLE. Things were starting to go well, but now I've hit a point where:

  1. The sensor-less BLE board is taking uploaded sketches and operating just fine.
  2. The Sense board hangs on the Uploading... box and never advances (even though it compiles fine)

Maybe with restarts I can get a full upload process but then it hangs again or I'll get one of a few errors, including one about "Timeout. The IDE has not received the 'success' message from the monitor after successfully connecting to it. Could not connect to /dev/cu.usbmodem101 serial port."

I grabbed a fresh out of the box new Sense board and instantly had the same issues. So I don't think it's my specific board I was working with. And it's not a universal problem in some way because my basic Nano BLE board can take any sketch just fine. It's a problem with my Sense board. Or, Sense boards, plural, including the new one. I've tried to reinstall the Arduino Mbed OS Nano Boards package in the board manager, and I've hit the reset button. Restarted the IDE, restarted the laptop, nothing changes.

This was all working 15 minutes ago. I am not working with complex sketches, just some test things trying to get one sensor at a time working with BLE.

edit: I also grabbed my partner's laptop (these are both running the latest-ish OSX) and installed IDE (which had previously never been on this machine). Installed the Mbed OS Nano Boards, went to upload the Blink sketch.... nothing, still hangs at Uploading.

Cable, USB port ?

Using the same cable and USB port as the basic BLE board which is working perfectly. My laptop only has USB C ports and I'm connecting with a USB-A to USB-C converter. But like I said, the basic BLE connects and takes sketches perfectly fine, and up until an hour ago, so did the Sense boards.

Other users have had these problems when using Mac and USB C to other USB ports. A solution have been to use a hub. Why it have been working until now, if you just got an update is a guess since that's the only thing that could've changed.

I got a good quality hub hooked up but nothing has changed. BLE works, Sense does not.