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Without some details on an example that is updating late I can't really say whether or not what you are experiencing is a "bug." I can say that we do not see any other reports of this occurring with other users.
Here are a few things to keep in mind when using the delayed notification feature in ShipStation:
1. Not all tracking events from USPS trigger the mail stream marketplace notification. Specifically any of the "Pre-shipment" or "Electronic Submission" events that appear on USPS' tracking site. What this means is that only actual scan events are monitored. Though if the Postman is scanning each box or a SCAN form that should trigger the event. BUT there is an important exception to note here. See 2.
2. ShipStation runs our mail stream monitoring service off the same external tracking portal that is shown to USPS customers: https://tools.usps.com/go/TrackConfirmAction_input USPS tracking does not update the tracking site immediately. This is to say that it could take a while for the initial tracking even to "update" on USPS's site even after a physical scan by the USPS driver. It's hard to find out exactly how often USPS updates their external tracking systems, but we find that it varies from 24 - 48 hours.
3. Our mail stream monitoring service used for the delayed notifications works in the background and will check a shipment's tracking actively about 5- 6 times a day starting off. This interval will drop off exponentially the further away the ShipDate was in comparison to the current date. What this looks like is if you ship something on Monday, then we will check it about 6 times before Tuesday. On Tuesday, we will check it about 5 times. Wednesday about 4 and by the time we get to Friday we are checking it only checking it once a day. We do this to maintain performance within the mail stream monitoring system.
So what does this all mean? Well, ShipStation has added what we feel like is a good wide sweeping net to catch any and all relevant mail stream events at time intervals that are performance efficient however we are still at the mercy of how often the tracking number is updated by USPS. With that 24 - 48 hour update time by USPS, it's easy to see how an order can be updated late in Amazon if it's shipped on the next to last possible expected ship date.
How do you make this all work within Amazon's terms? What I would recommend is to add an additional clause in the notification settings like this one:
What this will do is create a safety net for those cases when the tracking number doesn't update before a set time you control (in this case 6 hours after label creation.) That way, you are getting the best of both worlds and you are still able to make any adjustments within the allotted marketplace notification interval.