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Auto orders start processing on the platform at midnight EST. The platform continues processing them until finished which can vary depending upon the volume to process on any give day. The goal being that all of them are processed before 7AM when the first east coast fulfillment houses open to begin preparing shipments. 

How can I configure an auto order to trigger on a specific day of the month, regardless of when the auto order item is originally purchased?

The way this should be accomplished is to start off the auto order items auto order steps with a "pause" step and then set the delay until a future date. All new orders placed will pause rebilling until that date. As you ship for that month, just edit the item and set a new pause date. 

Related Documentation

Auto Order Processing Configuration screen (must be logged in to access)

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