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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.
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...
