ANOTHER SAD UPDATE: Today, my Longest Streak Badge reset itself again. Yesterday, my record stood at 2,199 days. Today, it stands at 35 days. I really hate this.
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Does your Watch show the same Longest Move Streak value as your iPhone?
I have found that some of the fitness statistics shown on my iPhone can be incorrect. For instance, for the monthly challenge I am always surprised by how the iPhone is off by a couple days but if I "force quit" and relaunch the fitness app things get caught up. Maybe you can try that?