How Smarter Setup and Troubleshooting Tools Are Giving You More Control

As Head of Product at Square, I oversee our Point of Sale (POS) and commerce platform — the systems that power every checkout, manage orders, calculate carts, and report sales. These tools are at the very heart of your business. When they work smoothly, your business thrives. When they don’t, you risk losing sales. That’s why we’re deeply committed to reliability. Improving reliability isn’t just another initiative, it’s personal for me and for the entire team. Choosing Square means trusting us to help serve your customers without disruption, and we take that responsibility seriously.

As a result, we’ve increased our investment across product and engineering teams to bring you a more reliable experience. While there’s always the possibility for outages, we’re committed to reducing downtime and giving you the tools needed to keep running your business smoothly, take payments, and quickly diagnose and resolve issues when they arise. 

We’ve built new capabilities that help you monitor device statuses, manage printers, test your network, and respond to outages more confidently. Many of these improvements are already live in the Square Dashboard and POS, and more are on the way. These updates are all about giving you visibility into your setup and the control to fix issues, even when you’re not on site. This is an ongoing effort, and we’re devoted to doing the work to give you the confidence to grow your business with Square.

Let’s walk through what’s new.

Troubleshoot your system so it stays up and running

Running a business means balancing a lot at once. You’re serving customers, managing staff, keeping an eye on inventory — and in the background, your systems need to stay online and synced up. We’ve introduced several features to help you see what’s working, what’s not, and how to fix it, all from one place.

Manage all your Square devices from one central location

One of the biggest features we’ve added is Remote Device Monitoring and Management, available now in your Square Dashboard. Through the Device Hub, you can configure, monitor, and troubleshoot your hardware, printers, and accessories, without needing to be at your business location.

Think of the Device Hub as your command center. It gives you a real-time view of which devices are connected, which are misconfigured, and what might need attention. You can create settings and apply to devices across locations right from your laptop or phone.

Taziki’s Mediterranean Café uses this feature to track 183 devices spread across its 93 locations.

I don’t have to have a person that is reaching out to all locations making sure everybody is doing everything right… I can see everything right from the dashboard rather than having to call the manager. It’s made everything more efficient.”

Tommy Traynham → Director of Technology at Taziki’s Mediterranean Cafe

We also introduced remote settings, called modes, as part of Remote Device Management. A mode is a reusable set of configurations that you can apply to one or many devices. It’s an easier way to manage settings across multiple devices. For example, if you run a café and want all your POS devices to have tipping enabled and access to add-ons like gift cards, you can create a mode, save it, and apply it in just a few clicks. All updates to the mode get pushed automatically to all linked devices.

Whether you’re managing multiple locations or just looking to streamline setup, being able to control your devices remotely can make a big difference. 

Run a connectivity test on your device

Sometimes it’s not clear where a connection issue is coming from. Is it the device? The Wi-Fi? And when the network goes down, we know it can be during a frantic time for business operators. To help you pinpoint problems faster, we’ve added connectivity testing tools to your Square devices and Dashboard. 

You can now run a built-in connectivity test that checks: 

• Whether your device is connected properly
• Whether your internet or local network is the problem
• Whether Square’s services are reachable from your location

It’s more than just a “Is my Internet working?” test. It gives you a clear report so you understand what’s happening and can take the right action, without guessing or restarting everything. If there’s an issue, it provides a snapshot that will make sense to IT professionals or Square representatives, so they can help you resolve it quickly.

Continue taking payments when your business is offline

There’s always a chance disruption can happen. But they shouldn’t stop you from making sales. That’s the purpose of our offline payments feature. We’ve enhanced it so it kicks in more reliably and seamlessly — whether it’s a full internet outage or just a dropped connection to Square. And we continue to make the whole experience smoother, clearer, and more foolproof.

With offline payments, you can continue accepting card payments even when your internet or Square services are temporarily unavailable. If your POS goes offline, Square will securely store payment data on the device and process it once the connection is restored. You’ll need to reconnect to the internet within 24 hours of your first offline payment and open the Square Point of Sale app so your offline payments can be processed.

From your customer’s perspective, however, nothing changes. They tap or dip just like normal and core POS features continue working as usual. You can still accept cash or card, and carry on with your business.

Real-world use cases from Square businesses continue to show the impact. Take Offset Coffee, for example. Owner Vernon Lindholm shared how the offline payments feature saved the day during a network downtime. “We had an issue where a construction crew hit a fiber line and we were down for two days,” he explained. “The team was really having to figure it out and pivot, and we were all putting our heads together to find solutions. But the one thing we didn’t have to worry about was Square. We just ran it in the offline payments mode for a few days.”  

[Using offline payments] the customer experience was seamless. That piece of it has been a huge relief, especially when we see other businesses around us not being able to process things or trying to tether it to a cell phone or anything else.”

Vernon Lindholm → Offset Coffee Owner

We’ve gotten similar feedback from other Square businesses. Some even operate entire events (like concerts or outdoor markets) using offline payments and batch upload later.

To use offline payments, simply enable the feature in your Dashboard or POS settings. You’ll also get notified on your device when you’re accepting payments offline, so you’re always aware of what’s happening.

Turn on proactive alerts and notifications during downtime

Knowing about a service disruption as soon as it happens is key to staying in control. That’s why we’ve also made it easier to stay informed when something affects Square systems.

You can now sign up for real-time outage notifications via email or SMS. These alerts are tailored to the products you use, and you can add as many recipients as you need, so your entire team stays in the loop.

You can also visit the Square Status Page at any time to check for active incidents, system-wide issues, or scheduled maintenance. This visibility helps you adjust operations quickly and confidently, including offline payments.

Try out new features at your own schedule

If you use Square for Restaurants, you now have more flexibility over when new features appear on your devices. With Release Manager, you can opt into upcoming features early and test them on your schedule, without waiting for the full rollout.

You can enable features on a per-device basis, which is especially useful for training staff or testing new workflows before applying them to all your devices. Want to try out a new kitchen display update on just one station? You can do that. Prefer to wait and roll it out after a busy weekend? That’s your call.

And if a new feature doesn’t work for your team, you can revert to the previous experience during the introductory period. Once that period ends, updates will automatically roll out to all devices. This way, you’re always up to date, but still in control of the timeline.

Never lose a print job

Anyone who’s worked in a restaurant kitchen knows how much depends on the printer. It’s the heart of the operation. Orders flow through it. Kitchens rely on it. If it breaks or misprints, the whole flow gets disrupted, leading to delays, mistakes, and frustrations on both staff and customer sides.

We’ve made major improvements to how you set up, manage, and monitor your printers — so your back-of-house runs as reliably as your front-of-house.

Efficiently manage printer configuration using ‘Quick Setup’

Getting printers up and running is now easier with Quick Setup, which lets you apply default settings in just a couple of taps. Default settings are easily applied, so you don’t have to spend time customizing every detail unless you want to. It’s perfect for new businesses or smaller teams looking to simplify setup.

Quick Setup automatically configures commonly used settings like paper type, print format, and location-specific preferences, so you can start printing without delays or tech headaches.

Get visibility into printer connectivity in the Device Hub

From the Device Hub in Dashboard, you can now view and manage all your connected printer and device settings in one place. You can see which devices are online or offline, along with any warnings or error messages. This visibility lets you quickly spot issues — like a misconfigured receipt printer or a kitchen printer that’s gone offline — so you can stay on top of what’s working and what needs attention.

Troubleshoot printer issues faster

We’ve added more diagnostics to make troubleshooting easier and faster. One of the most common issues we see is a disconnected printer. It might be turned off, the USB cable could be loose, or it could be a network issue. In many cases, the solution is simple — often something you can fix yourself in just a few steps. So why should you have to call customer support just to be told to reboot your printer? That’s exactly what we set out to change.

Now, when a printer disconnects, you’ll be able to run a connectivity test to troubleshoot quickly. Click the Troubleshoot button to get the top four recommended fixes for a disconnected printer. Once you’ve tried the steps, use the Test Print button to confirm everything’s working again.

During early rollout, we saw Square businesses successfully resolve printer issues on their own roughly 20% of the time using these tools. That means less time spent troubleshooting and more time focused on your customers.

You can get more troubleshooting information in our Support Center.

Make sure you have the right printer

We’ve always supported a broad range of printers. Businesses running on Square could buy from us or bring their own. That flexibility was great, but it was also a double-edged sword. For example, you may choose Bluetooth printers, but these often run into connectivity issues in environments with too many competing signals — like those from common appliances.

That’s why we now offer specific printer recommendations based on real-world use cases. Whether you need a printer in the kitchen, receipt printer for front-of-house, sticky label printer for takeout, or a printer-cash drawer combo for the counter, you can now choose from a curated list of best-in-class POS printers from the world’s leading manufacturers. All recommended printers integrate seamlessly with Square. 

We’ve also improved the buying experience through our Square Shop, so you can select the right printer based on your workflow, without having to dig through technical specs on your own. If you’re replacing a printer or scaling up, you’ll know what works best for front-of-house, back-of-house, or to-go orders.

Stay ready, stay in control

These updates are all part of our broader work to make Square more reliable, more transparent, and more responsive to your needs. Whether you’re managing one location or several, we want you to have the visibility, tools, and control to keep the business running, even when things don’t go as planned.

Everything mentioned here is already live. You can log into your Square Dashboard today to explore the new tools, test your setup, and make sure your systems are battle-ready, so you never miss a sale.