While echoing Bryce’s comment about reaching out to our Support team about the workout freezes, I wanted to look into this for you and see if we can get things moving forward for you as soon as possible:
It looks like the Garmin recording of your ride made it up to Strava first. Sometimes there’s a little bit of a processing lag from TR>Strava when uploading a workout, and if your Garmin or TR synced with your Garmin Connect account first, the workout could make it into Strava from GC before the TR version made it up.
In an effort to minimize unnecessary ride data, Strava will flag any ride upload as a “duplicate file” if it contains similar data and shares a start and finish time with another previously uploaded file.
What that means in this case is that if the ride file went Garmin/TR>Garmin Connect>Strava, it “blocked” the TR workout upload that came just after it.
The only workarounds I can think of for this are to turn off automatic upload from your Garmin to GC, or TR sync with GC, depending on which one pushed there. Or, you could turn off sync between Strava and GC. As you can see, things get complicated once a few different sync services start competing.
Regarding the freezes on Windows, I’d recommend closing any other apps you’re running, making sure you’re on “high performance” battery settings, and restarting your computer if you tend to leave it on for extended periods of time. Best of luck and happy holidays!