Hardware:
1x SanDisk Fit 32GB USB 3.0 thumb/flash drive
1x SanDisk Ultra 512GB 3D SSD attached to 1x Apricorn USB 3.x (it's SuperSpeed with UAS for 2.5" Laptop/Notebook HDDs/SSDs) adapter.
1x freshly minted 8GB Raspberry Pi 4 Model B
1x 4GB Raspberry Pi 4 Model B
1x 2GB Raspberry Pi 4 Model B
1x Raspberry Pi 3 Model B (capable of USB booting)
Think I found something here. I used the Raspberry Pi Imager utility to wipe/clear the old data (bad config or otherwise borked for whatever reason) and wrote fresh images to both the SanDisk 512GB Ultra 3D SSD and the SanDisk 32GB FIT USB 3.0 drive.
One will receive an ERROR 44 with any attempted initial boot(s) of these freshly imaged drives when inserted into any Raspberry Pi 4B (my testing with the 2GB/4GB/8GB as I have one each of these models). Power cycling the Pi 4Bs with these freshly imaged USB drives yielded nothing until these USB drives are booted with the Pi 3B first. It's like the Pi 3B somehow sets a bit somewhere that the Pi 4Bs needs and won't boot until set otherwise -- or -- the other work around is to use the SD Copy utility to image the USB drive (seems fine this way from Pi 4B).
What clued me in? Tried moving the then working SSD to the 8GB model - No dice! Is it dead? Test booting with SD card - No issue booting the Pi 4B with the SD card. Checked a few things - realized I needed to update the 8GB Pi 4B's firmware when I saw the version and firmware status. Went back and forth a few times - several times actually - can't prove it now, but it seems the boot order was set to 0x1, but need 0xf41 for USB booting. Also had the "ah-ha light-bulb" moment and pulled up Christopher Barnett's video on USB booting the Raspberry Pi 4B (Jun 14, 2020). Err, oops, wrong video.. In his Jul 26th 2020 "Ultimate Raspberry Pi 4 Rig: M.2 SSD & ICE Tower" video (roughly the 9:30 mark - https://www.youtube.com/watch?v=HIYZwsc19CU), he states he had an issue when he used Etcher to write the image to the NVMe drive (in an USB adapter/enclosure, but the then used the SD Copy utility instead (just like I am doing here). I used the mid-June firmware (as is in his Jun 14th video) and finally got the 0xf41 boot order set; updated the firmware again to the latest and the boot order held ... so things look good.
As I have several Raspberry Pis - a B+ v1.2, 2B v1.1, several 3B v1.2, one of each Pi 4B @ 2GB, 4GB, & 8GB - I found using these freshly imaged devices in a Raspberry Pi 3B first is a work around to this issue. Otherwise, your other option is to boot from an SD card and transfer the information to the SSD with the SD Copy utility.
I got one USB drive to work, and then another, and then another (all those USB drives had prior Pi 3B usage) - but the SSD wasn't well - it somehow became borked. Saved the data needing saving, wiped it clean, and re-imaged it. Then I plugged in the SSD with the USB adapter ... and got ERROR 44 on the Pi 4B - so it wasn't booting. Tried it with the (borked) FIT drive as well .. same results. Place the FIT drive into the Pi 3B - booted, resized, rebooted, running well so far (updating as we speak on the Pi 3B). Likely need to do the same with the SSD .... boot it up once or twice in the Pi 3B, then move/transfer the drive over to the Pi 4B (with success).
So yeah, we have an annoying initial booting from freshly imaged USB devices on Pi 4B bug - it doesn't boot.
