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After using Shipworks for years, I have to recommend avoiding them as a company. It has been a bumpy several years filled with glitches and down time. Typically, the glitches are blamed on stamps.com (their parent company) and are almost always on critical shipping days. When you try to reach out to stamps, you get a follow up email a few days later stating they were too busy to handle your case. Without going into even a small portion of our issues with Shipworks, most recently we had the following issue. Shipworks stopped downloading the majority of our Walmart orders on 3/10. On 3/15 we had several late orders that had never been downloaded. When I reached out to Shipworks, they advised that they were aware of the issue for the past 5 days as Walmart had updated their API and they needed to update their systems (you know, their entire reason for existence?). Shipworks had advised me that they already had an update out that wasn't public. At no time did they advise their customers of 1) an issue or 2) the update. Reasons like this are why I absolutely recommend to build your shipping process on other software. As a note, Shipstation is also owned by the same company as Shipworks. We utilized Shipstation for a while and experienced the exact same inexcusable service.
Been using it for a few years now. It's been great, but been having issues with split orders. When splitting orders, it fulfills the order 100% in shopify with the first tracking number, then never updates shopfify when you fulfill further orders in shipworks. I contacted support and they said they had a previous feature request, but that request has been in the queue for over 3 years. Needless to say, I am looking for an alternative shipping solution.
Business model is get you to sign up so they can bill you even if you never use the product. Stay away.