Not pushing outdoor workout to my Garmin

I am new to TR, only about 2-3 weeks into my formal training, and we finally have some decent weather this coming week and I was hoping to get back outside. I have synced Garmin up to TR, but no matter what I do, the Garmin connection always shows “re-authorize”. Is this normal? If so, how long does it typically take for the Garmin head unit to show the synced rides after authorizing?