There are two reasons possible:
1. In the Advanced tab of Pipemonk Settings, please check the setting "Sync Shopify Orders from the 1st day of the Webstore" is answered as "YES". If this is not selected; we will sync the orders that are created only after your chosen date.
2. If you have configured both the above settings correctly and the required orders didn't sync properly; please choose RETRY Failure to Yes and Sync.