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This query was also posted in this thread and received a reply. TLDR: Live segments don't always work when following routes on Garmin, this is an ongoing known issue. The solution is to unstar the old segments, resync your Garmin to Garmin Connect, then star them again and resync one more time.
I can imagine how tedious that must have been, I'm sorry it was so time consuming and understand it must be frustrating to have "lost" those starred segments. It doesn't seem ideal. I think that's a great idea that you should definitely share in the Ideas board! Be sure to check out our Ideas guidelines.
The idea has a few kudos now, but how many kudos does it need before it's being prioritized? It does not have hundreds of kudos, but I suspect it's a pretty simple thing to implement...
