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Questions re: Workaround "sync" with Square (Non-Marketplace/ Manual Invoice Creation)

Hi Guys,
Is there anyway I can set-up an automation within Shipstation to import new orders from a particular csv file upon login? The csv would be on my local hard drive and be the only file in the folder all the time (let's say). I've used a few automation tools and I don'y see one that fits this need. I downloaded a SS desktop exe, so I assume this could be done. I'm new and wondering if this exists already.
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