Share your perspective: What Square feature/function is your BIGGEST pain point?

[LeahK]

Hellloooooo!  For those who don't me, I'm Leah, I work on the community team here at Square. 👋

We've been heads down planning upcoming webinar events to bring to the seller community. One of the opportunities we are considering is bringing topics that ultimately help folks overcome common or frequent pain points using Square products.

Whether you are a restauranteur, own a hometown coffee shop, bakery, retail store, etc -- we'd love to hear from you! All are welcome & encouraged to participate!

👉 Question: What specific Square feature is your BIGGEST pain point? and why?

In other words, if you could name the one thing, that if you just knew how it worked (or the pain point was resolved) you'd be the happiest person in the entire world.

[DinaLRosenberg]

Another one- the ability to print labels from the item screen!

[TCSlaguna]

Yes!!!

[kelly67]

This kills me!!! It should be such an easy fix. We came from Quickbooks and it was sooooo much

easier to use for so many things. We keep trying to get Square to make some "simple" fixes but

they don't seem interested.

[DinaLRosenberg]

I I have been banging the drum on a notes field in inventory/items and orders for YEARS now,.. and I guess what makes me salty is that they redesigned this whole community.. but still no notes.

[kelly67]

ya i just don't understand why some of the simplest little tweaks never get fixed. I suppose what I assume is simple may not actually be simple for the people making the technical fixes but so many things could be so much less cumbersome and they just don't do them. We came from Quickbooks and everything was so user friendly and intuitive - had to leave because they weren't going to support their system anymore.  

Hoping that Square will get it together and make some of these changes!

[LeahK]

I see you submitted a feature request for this about a year ago too @DinaLRosenberg !

@kelly67 -- and anyone who comes across this thread, definitely encourage you to vote up and add your specific feedback via comments on the feature request here: Print labels from item screen

[Klahsa]

Hello,

 I am Kim who resides in Tennessee. My biggest pain points group texting, alerts, banners, invites etc.

[MudFire_Dex]

l'll start with the thanks 🙂 - our subscription option was tweaked to accommodate us - so grateful!!!! We still have to use an Acuity link to Square payments for our appointments though because multiple instructors teach a group of people at the same time and we want better class booking options. For now - the Acuity tie in works but adds an extra piece of the puzzle to reconcile and manage.

[VanKalkerFarms]

Honestly, for me and the absolute basic use we use square for, the only things I can think of that would make life a lot easier is having the ability to choose for the qty buttons to be at the top or bottom of the variations when choosing an item.  When there are 30 varriations having to scroll to the bottom every time is annoying (and introduces errors when scrolling sometimes it changes the variation chosen instead of scrolling).  And related I would love a way to increment an item already in the cart directly from the iPad home screen with a -/+ next to the items in the cart.  We don't use so many of the Square features and I'm sure if we did the list would grow longer.

[tonydow]

My biggest pain is not being able to message someone that hasn’t made a purchase etc. People could be potential customers but I can’t interact with them.

[Lovewell]

@LeahK Would absolutely love to see more customization within square website design. We are trying to make our square site flow better with our main website but there are so many limitations. I went to put white lettering onto the background and it won't let me because "it won't show up" but I know it will because it works on our main website and I copied the color code specifically. The black letter made our square site just look less happy. And it doesn't flow with our website. Very very frustrating for marketing and branding and having a website represent you well.

[OurCupCakery]

Ditto,

To be able to change fonts and colors within a text box.  Have the site fill the entire screen.  Having only 1/3 of the screen filled with content doesn't look as high end as we would like.

[PeterIstrate]

Stock counting / out of stock items.

And this is a very simple issue to fix.

So, if I create a new item, I can simply select a switch: to either have it in stock (unlimited stock) or not.

I can also specify the number of items in the stock, for that item, if I want.

But, once you set a number of items in the stock, the on/off switch option disappears forever, and you are no longer simply able to activate or deactivate the item with a switch. You always have to introduce the number of items in the stock, reason for re-stocking, etc, etc. And that's annoying, it takes way more clicks, and many times you may have unlimited number of items so no stock keeping is necessary.

Just allow the on/off switch as well, at all times, for all items, without the need to insert a stock number.

[OurCupCakery]

Event feature:

No event list of participants

No date listed for the event on the ticket.

We had to stop using the feature.

[TCSlaguna]

YES! We have been asking for event list of participants for SOOOO long! 

[SVLFever]

Hey @LeahK !   Just thinking out loud here, but I had a different thought.   I was coming here to add a post about wishing that we had the ability to take a reservation deposit in Square for Restaurants (that was seperate from using the gift card functionality.  After reading through this thread though, it feels like a LOT of these things in this thread have already been developed.

I'm wondering if you should make a new 2026 request for "pain points"???  

Again, just a thought but wanted to run this up the flagpole at least.   Have a great weekend!

[MagicToybox]

Basic Customer Service from REAL PEOPLE AT SQUARE. You're shooting yourselves in the foot but not having people who can just answer questions, or look into issues with workflow and updates. My company will be going through some expansion in the next year. I don't think Square will be going with me.