Alright, so I've been having trouble with my Garmin 910XT and Garmin Express. Last Thursday I did a run, came home, and dropped the watch next to my PC, near the ANT stick as I normally do. I then went about my breakfast/shower routine, and checked Strava. No run. I got to my PC and found that the watch was sitting there, still on, and had never tried to sync. I hit the "Sync Now" in Garmin Express, and it acted like it was starting to sync, then it shut off.
After this, it wouldn't start back up. I plugged it in, and after a while, it booted up like normal, except that when I went in to the history on the device, the newest run it showed was several months old. So I tried syncing again, thinking maybe it would find the run for that day, and it showed like 191 unsynced files, which all errored out, and none synced.
Whatever, I reset the device, and figured it would probably (hopefully) be good from then on. Ran this morning, tried pairing, crashed again during sync. Took 3 tries to get it to boot, and today's workout is now gone from the device. That said, somehow, the run from THURSDAY is showing up. You know, the one that disappeared, and after which I did a reset on the device. Garmin Express now isn't finding the device at all, either.
I've tried to Google around a bit, but this seems to be a more complex issue than others have faced with syncing.