Subscription Plan Requirement
This CSV upload feature is available for Bronze-level and higher subscription plans. It is not available for Starter plans. If you would like to use this feature but cannot access it as described here, you will need to upgrade your plan.
To upgrade your plan, go to Account Settings, then choose Account > Payment & Subscription. For more information, visit Manage Your Subscription.
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If importing by CSV, first prepare the CSV as follows.
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How to Import Orders With The Prepared CSV
Reference: https://help.shipstation.com/hc/en-us/articles/360036323571-Import-Orders-via-CSV