Apple Watch
Do I need to re-set my calibration before or after my outside walk?
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If it's a new watch or you think it's not measuring accurately then yes and do it before your walk,but otherwise the watch learns your walking/running pace for a time and is not neccessary to calibrate too often.
The only time I recalibrate my watch is after a watch update and that's not because I have to do it,I do it just for maintenance purposes and I haven't had any problems in 5 years of owning watches.