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Using 'On the way, stop at' sometimes ignores the location.
You are using the same address more than once.
When using 'On the way, stop at' as a location on an order, you cannot use an address that has been used before. The address must be a unique address.
If you go from Location A to Location B, pick up orders and go back to Location B, ArcLogistics will not route to the second location because it has been there already. You must create a Location C or end the day at Location A, as follows:
Start at Location A. Make some pick-ups and 'On the way, stop at' Location B to drop them off. Continue with pickups and again, 'On the way, stop at' Location C to drop off the collected items, then end the day at Location A.