thread Unable to purchase multiple shipping labels in Online Store

Unable to purchase multiple shipping labels

scrappyhappy — Wed, 19 Nov 2025 17:20:24 GMT

For the past couple of weeks, I am unable to purchase shipping labels for multiple orders at a time.

From the orders page, I click the blue button "Create Shipping Labels". Then I get a list of pending orders with check boxes to "Select Orders". It seems to not matter whether I choose 1 or multiple orders, this interface fails to allow me to purchase labels. Note, I am using a custom defined box, if that matters. This is the error message I receive:

Something went wrong

We were unable to purchase labels for any of the orders you selected. You can try to purchase them again, or purchase each label individually.

From the orders page, I go individually to each order, I can purchase labels there.

What confuses me is this was working for me before, but not recently.

Re: Unable to purchase multiple shipping labels

JJ_ — Thu, 03 Aug 2023 17:11:27 GMT

Hey there @scrappyhappy

I am sorry to hear about your experience. I will recommend you reach out to our Square Online team so they can take a closer look at this situation.

They can be reached at 855-700-6000 between 6 am - 6 pm Pacific Time Monday-Friday. If you call outside of these hours, you will be required to enter your Customer Code to validate your account.

You can also get in touch with our Messaging and Email Support Teams here.

Re: bulk shipping labels

Apex86 — Fri, 13 Oct 2023 20:16:02 GMT

I am really frustrated with Square's choice to force us away from the "online" shipping label generator.

They advertised it as a "new and improved" function that we now have to access from the main dashboard. The reality is that it is missing basic functionality.

On the minor side: it won't remember which size label you want, forcing you to reselect 4x6 labels for every single order.

On the major side: it doesn't calculate package weight any more!

And like this thread confirms: No more bulk label creation

I can't be the only one who prints a label and packing list first and then takes that to pick and package the order. But, now we can't generate a shipping label without an accurate package weight. So even though square knows the weight of every single item and the boxes that I use, it won't add them up anymore. Are we really supposed to keep a list of these weights and manually add them up for every single package?

I can't see any way this has improved the user experience. It has ruined it.

If square won't fix these things, I am changing to another hosting company.

Re: Unable to purchase multiple shipping labels

Apex86 — Fri, 13 Oct 2023 20:22:07 GMT

I am really frustrated with Square's choice to force us away from the "online" shipping label generator.

They advertised it as a "new and improved" function that we now have to access from the main dashboard. The reality is that it is missing basic functionality.

On the minor side: it won't remember which size label you want, forcing you to reselect 4x6 labels for every single order.

On the major side: it doesn't calculate package weight any more!

Re: Unable to purchase multiple shipping labels

Ria — Sun, 15 Oct 2023 17:25:05 GMT

Hi @Apex86 - Thanks for reaching out!

Sorry to hear that you're experiencing some difficulty.

What you're experiencing sounds like something our engineers may be able to investigate and get to the root of so that you can have a better experience with Square Online.

Phone support is available Monday - Friday 6 AM - 6 PM PST. The telephone number is (855)700-6000.

Please know that we're committed to addressing these issues and restoring the features you found valuable.

We appreciate your patience and understanding as we work to make these improvements. Your feedback is invaluable to us, and it helps us refine our services to better meet your needs.