thread Re: Digital File Upload in Payments Troubleshooting

Digital File Upload

theurbanemag — Sat, 20 Sep 2025 08:15:07 GMT

As a Digital Item, there's nowhere for me to upload the file, so my customers aren't able to download their issue after purchase although the "Change Item Type" page specifically says, "Digital - Lets you provide a digital file for download."

That is a big inconvenience if I'm not able to do either at any given time. This was not happening before the Weebly/Square merge. Will this inconvenience be corrected soon?

Re: Digital File Upload

VanKalkerFarms — Mon, 16 Oct 2023 16:38:05 GMT

It doesn't appear that you can have them download a file directly after a digital item purchase, you would have to send them an email with the link to the download. I was surprised when I looked into this as it isn't something we deal with but I sure would have thought would be automated.

https://squareup.com/help/us/en/article/6876-add-a-digital-item-to-square-online-store#:~:text=To%20add%20a%20digital%20item,section%20to%20set%20your%20price.

Re: Digital File Upload

Bitship — Wed, 03 Jan 2024 12:08:03 GMT

I know this can be a pain. If you are open to using a third-party tool to solve this issue, we have created an app called Bitship that can automate this process. There are dozens of Square Online merchants who already use this tool to automate the delivery of digital items to their sellers within seconds of a purchase being made.

Re: Digital File Upload

mattwells — Wed, 29 May 2024 19:20:28 GMT

Hi @theurbanemag

I noticed your post about wanting to setup a store to sell digital items. We just released SendOwl app in the Square Marketplace that makes selling digital products a breeze!

SendOwl is an all-in-one platform for selling digital products, memberships, and more. It integrates seamlessly with your existing website and provides secure, automated delivery of your digital files.

Here's how SendOwl can help you set up digital products with variations:

Install the SendOwl app in your Square account
Upload your digital files to SendOwl (supports various formats like PDF, EPUB, MP3, MP4, etc)
Connect your SendOwl products to your Square products
Start selling! SendOwl handles the automatic, secure delivery for you

The key benefits are:

Supports all file types and sizes
Secure file storage & delivery (expiring links, PDF stamping)
Built-in payment processing & checkout
Trusted by thousands of online sellers, with over $2 billion in sales powered by SendOwl

I hope this helps point you in the right direction! Let me know if you have any other questions.

Best regards,

Matt Wells