Automation Rules

We have automation rules set to "Require Signature" for items where declared value is more or equal to $250. We just noticed an order that went out Friday for $575 that left with no signature required. The actions are set to "Set Signature Confirmation" to "Indirect Signature Required" or "Signature Required". I assumed this would set it correctly for either USPS or FedEx.

Is there something we need to change in the settings maybe to make sure the automation works correctly? We just know that occasionally, someone may slip up and forget to change the shipment to signature required, so we added the automation to play it safe.

Thanks.