Not necessarily. I've had the same symptoms once, and others have as well. Posts scattered around the forum. Basically, the system initially boots just fine but the config folder is completely empty except for freshly generated ssh files, so nothing works or works with default settings.
Could possibly be some race condition if the USB drive is slow to mount and the ssh files are created first, preventing mounting of the flash drive.
Perhaps DayDreamer could try another USB drive/port?
There were PCs interchanged. There's that.
Let's try another Drive. First one is a SanDisk Extreme 16GB USB 3.0
Weird stuff is going on.
Another stick. Fresh run, this time timed.
Thing is - there is a timeframe, about 5 seconds long between getting IP, and login prompt, when the webserver is working and accessible. But it works only on a first run, and not every first run.
I couldn't find out if it's time-dependent or login-dependent.
There are still no go file and i still have to run the webserv manually.
Added the config files there through putty and nano editor. on next reboot they were gone