Square Payments vs Cheddar Up

PayPal

Venmo

Stripe

PayPal provides an end-to-end suite of tools that can integrate with a business's existing systems and service providers. Its network of shoppers and businesses provides AI-driven data insights to help businesses reach new customers and drive results.

Venmo is a digital wallet and payment gateway that allows customers to send money and make purchases via mobile device, and share activity via the purchase feed

Stripe is a financial infrastructure platform that enables businesses to accept payments online and in person. It offers a suite of APIs for payment processing, subscription management, fraud prevention, and financial services integration Stripe provides both developer-focused tools with extensive documentation and no-code solutions for businesses without technical staff.

Owner

The resolution process was clumsy and communicating with customer service was nearly impossible.  

Sales Associate

It relies entirely on service and wi-fi, so large events with little service can be hard to make work well, especially with high customer volume.

Store Manager

Any issues, Square customer service helps us right away.

After you take the time to figure everything out it does work fairly seamlessly it can be very confusing though for a first time person trying to work with it but the customer support for Square is excellent

Accept every way your customers want to pay with Square Payments.

ACH Payment Processing

Activity Dashboard

Billing & Invoicing

Cash Management

Compliance Management

Contactless NFC

Credit Card Processing

Cryptocurrency Processing

Customer Database

Data Security

Debit/Credit Card Processing

Electronic Payments

Electronic Signature

Fraud Detection

Gift Card Management

In-Person Payments

Invoice Management

Mobile Access

Mobile Card Reader

Mobile Payments

Multiple Payment Options

Offline Access

Online Payments

Partial Payments

Payment Fraud Prevention

Payment Links

PCI Compliance

Point of Sale (POS)

Receipt Management

Recurring/Subscription Billing

Reminders

Reporting/Analytics

Reporting & Statistics

Sales Reports

SSL Security

Third-Party Integrations

Transaction History

Reviews for Square Payments come from a wide variety of industries, including retail (7% of reviewers), health, wellness and fitness (7%), and arts and crafts (4%). The most frequent use case for Square Payments cited by reviewers is payment processing (78% of reviewers).

Users and use cases

Reviewers indicate that Square Payments offers transparent, predictable pricing and no monthly fees, which they appreciate for small businesses. However, some users report that cumulative transaction fees and higher costs for advanced features can reduce overall value.

Value for money

The Square Payments integration most frequently cited by reviewers is ClinicSense, a massage therapy product rated 5.0 out of 5 for its integration with Square Payments.

Integrations

Square Payments is a payment processing program offering key features such as debit/credit card processing, data security, payment fraud prevention, mobile payments, and online payments, among others.

Square Payments

Web-based

iPad

Android

iPhone

Clover

PayPal Point of Sale

PayPal Commerce Platform

Square Point of Sale

SumUp

SpotOn

Cash App

Invoicely

ProPay

In person

Online

Invoices

Manually entered

Dependence on strong connectivity

Director 

Will not work without strong cell service/internet

78% of reviewers feel negative about Square Payments’ connection reliability. Users report frequent issues when Wi-Fi or cellular signals are weak, especially at events or in rural areas. They say transactions can be delayed or fail entirely if the connection drops, requiring restarts or troubleshooting. Reviewers mention that the need for a strong, stable internet connection can disrupt service and slow down business, making it challenging to process payments in certain locations.

Frequent swiping difficulties

40% of reviewers feel negative about Square Payments’ card swiping experience. Users report that the swipe reader often requires multiple attempts to process a card, which can be embarrassing or frustrating in front of customers. They mention that issues with device compatibility, orientation, and swipe technique can lead to delays or failed transactions. Reviewers also note that manual entry fees are higher if swiping fails, adding to their dissatisfaction.

Inconsistent card reader performance

Registered Dietitian

I only use the small card reader that Square provided at no charge and I find it has difficulty with various magnetic strips and won't complete the charge.

43% of reviewers feel negative about Square Payments’ card reader hardware. Users report that the card reader often struggles to read cards on the first attempt, requiring multiple swipes or manual entry. They mention compatibility issues with newer phones and cases, as well as problems with Bluetooth or battery life. Reviewers say these hardware challenges can slow down transactions and create inconvenience for both staff and customers.

Occasional glitches and crashes

58% of reviewers feel negative about Square Payments’ bugs and technical issues. Users say the software sometimes freezes, crashes, or loses sync with devices, disrupting transactions. They report difficulties with customer support when problems arise, including long response times and limited live assistance. Reviewers mention that technical glitches can slow down business operations, especially during busy periods, and that troubleshooting can be frustrating and time-consuming.

Processing fees add up

43% of reviewers feel negative about Square Payments’ pricing. Users express concern over transaction fees, especially for small businesses or high-value sales. They say fees can be difficult to calculate and may impact profit margins. Reviewers note that additional charges for certain features or manual entries can further increase costs, and some feel the overall fee structure is less competitive compared to other providers.

Fast and reliable processing

Account Manager

It is a fast process and they use great tech to make sure everything is sound.

business owner

I like that Square Payment Processing is rather simple to use.  

93% of reviewers feel positive about Square Payments’ processing. Users indicate that transactions are processed quickly and reliably, reducing wait times for customers. They appreciate the straightforward implementation and the immediate deduction of processing fees, which simplifies bookkeeping. Reviewers note that the platform is user-friendly for both in-person and mobile payments, and many highlight the system’s consistency and efficiency in daily business operations.

Flexible event payment tools

Project Manager

We loved the potential of being able to collect onsite payments at our fundraising events via credit card, etc., as opposed to our old process of collecting cash and checks that could be easily lost.

94% of reviewers feel positive about Square Payments’ event payment capabilities. Users report that the system allows them to process payments quickly and efficiently at markets, fundraisers, and remote events. They value the ability to accept card payments on the go, which increases sales and donations. Reviewers appreciate features like preset items, portable hardware, and multi-user support, making it easy for teams to handle busy events. Many say Square helps them reach more customers by eliminating cash-only limitations.

Versatile invoicing features

Producer/Director

Another plus is the ability to invoice customers for reoccurring payments, such as paying off a large invoice over two or three months, and the system is automatic.

91% of reviewers feel positive about Square Payments’ invoicing. Users say they can easily create, customize, and send invoices from anywhere, supporting both one-time and recurring payments. They appreciate features like automatic reminders, direct payment links, and detailed reporting. Reviewers find the invoicing system especially helpful for tracking payments, managing sales tax, and offering payment plans, which streamlines their business processes and improves cash flow.

Process Engineer

Square provides e-commerce and inventory capabilities, customer appointments, payroll processing, shift scheduling, and even access to banking and business loans.

Prodution manager

The system is straightforward to navigate, and the reporting tools provide helpful insights into sales and customer activity. While fees and occasional account reviews can be a drawback, the convenience, professionalism, and efficiency it brings to daily operations make it a valuable tool for business.

Managing Partneer

The ability to send payment links, use in our online store and even with our service technicians on the road has been a huge advantage.

Square allows these sellers to easily accept electronic forms of payments from buyers who they otherwise may not have been able to or would have historically may have only accepts cash or check for payment.

Provider and Practice Owner

As Square is an option through my ECR company, which provides a HIPPA compliant platform from which I process payments, I am forced to pay fees per transaction.

Licensed Massage Therapist

I really do like square payments, it helps me be able to get paid for my work at minimal cost as I just use the reader they sent me that connect to my phone, overall I’m pretty thankful for it

Owner and Founder

The Square reader magstripe (the small device) was a bit more difficult to use compare the other options that are contactless and can easily scan cards by just tapping on them.

What I like least about Square Payments is that the transaction fees can add up, especially for larger invoices or high-volume processing.

It’s a reliable and efficient solution for handling transactions, and it helps streamline the payment process without unnecessary complexity.

The search bar is necessary to find pretty much everything. When issuing a refund, processing fees are not refunded by Square so the business actually has to pay out of pocket for those anytime a refund is needed.

It is a standout choice for businesses that need to accept payments both in-person and online without dealing with complex contracts or specialized merchant accounts.

Customers can tap, dip, swipe, and use other options like CashApp Pay, Google Pay, and Apple Pay as well as deferment options like AfterPay.

Sometimes connectivity issues arise based on WIFI connection or issues with customer phones not having service to process apple pay or tap payments.

Fulfillment Manager

No real issues with Square, it does seem to be pretty heavily dependent on WiFi or Cellular access at the mobile level and that can sometimes be a hinderance during outages.

Fundraiser

I like the items list feature which allows for post-event analysis of what was sold.

Founder

It just takes too much time to get everything crafted and also the UI of manually creating orders for someone can be improved.

Staff Accountant

Square has helped us eliminate the need for physical money at our programing events, since attendees can easily pay with CC.

Property management

The processing fees can feel a bit high, especially for small-ticket transactions. But overall, these are minor compared to the convenience the system provides.

Co owner

The tricky part comes when fees start eating into smaller sales, and unexpected holds can leave funds out of reach for a while.

Being able to take payments in person, online, or through invoices all in one platform is incredibly convenient.

The reporting features allow me to pull data from a range of fields and pinpoint transactions.

We use Square's card readers for attendees to pay for admission to our program events.

owner

Square payments are up front with their processing fees and have affordable tiers for every business.

Managing Partner

The integration with other Square tools, like inventory management and analytics, also makes it a comprehensive solution for small businesses. Plus, the transparent pricing structure helps users avoid unexpected fees.

Equine Therapist

It allows me to create and send invoices on the go and trust that my clients will receive a detailed invoice and be able to pay me.

There’s also not a ton of flexibility in how those fees are structured, so you kind of just have to accept it as the cost of using the platform.

Office Manager

Allowing credit card payments opens up more potential customers from any type of business.

What i didn't like about square payments is that they dont take checks and alot of my customers pay by check

president

Ease of use, sending invoices and payment processing, having custom reminders for lack of payment from clients make the job much easier.

When our WiFi goes down, our store phone still works, and Square allows up to still be able to take payments or send over invoices to a customers email.

No one carries cash anymore and you can sell much more when you offer a credit card option to pay with.

The rapid posting of payments to business account has proved helpful in tracking earnings.

Manager

Used for a small bakery and also on a personal level to make purchases, create purchases, invoices, and process orders for caterings.

Owners

The mobile app is user-friendly, and being able to accept card payments anywhere is a huge plus.

One downside is the processing fees, which can add up over time, especially for small businesses with lower margins.

Digital asset manager

Overall, my experience has been fine, and seeing how restaurants offer Square as a payment option (or their only option) is familiar to me, so much so that I find the app synonymous with ordering food. Though I'm aware it can be used for other goods/services, Square has worked well for me when dealing with restaurants.

What I liked the least about Square Payments is how to add tax on the products and how to add a tipping option while gathering payments.

Financial Coach

You can't (as far as I could see) set an invoice to automatically charge the customer unless the customer selected it, and you can't enter a customer's payment information directly (as far as I could see).

I love being able to access customer data and transaction history with just a few taps—super handy for staying on top of things. Despite these small setbacks, Square has been a reliable sidekick in running my business, helping me keep everything streamlined and efficient."

As a consumer who has only used Square Payments for processing payments as a buyer, there is nothing that I can think of that I would consider a con of Square Payments.

I enjoyed the convenience of having a portable POS and way to accept card payments at events outside of physical business location.  

It’s great seeing the money in the bank and not having to send out an additional ten emails to our partners that always seem to forget.

Sometimes I feel like my Square Payments tends to run a little slow. But all in all, that is normal for most technology.

Takes payments on laptop, mobile and the Square terminal.  

Veterinary Technician

Overall I've been very satisfied with square payments customer service is great at works great payments are all kept in one spot and process when no problem

Writer

I use the app to send digital invoices and see real-time updates on my sales and inventory.

Payouts take way too long to happen and I need that cash in the bank for rent now.

Office manger

The fee are alot lower for use when customer pay with credit cards

I appreciate that I'm able to integrate Square into other services I use, such as Jotform, and also within webpages.

Payment Processing

Users report Square Payments’ payment processing is quick, intuitive, and works across multiple channels—mobile, online, and in-person. Reviewers say Square Payments enables instant or same-day transfers, clear receipts, and simple integration with other systems like EMRs. They find the payment processing aspect dependable, with transparent fees and easy setup. Some users mention delays in fund transfers or issues with customer service during disputes, but most feel Square Payments streamlines payment collection and improves business efficiency. Of the 163 Square Payments users who gave detailed accounts of their use of Payment Processing, 99% rated this feature as important or highly important.

Invoicing

Pricing

Inventory Management

Reporting

Card Reader

Connection Issues

Event Payments

Bank Account and Money

Card Swiping

Small Business

Large Enterprises

Mid-size Business

Freelancers

Square

Cheddar Up enables groups to process payments and information online – for free. Create custom forms to collect registrations, waivers with e-signatures, item variations, and more. Securely collect credit card or eCheck payments and track it all with streamlined reporting.

Square Payments vs Cheddar Up Comparison (2026)

Square Payments

Cheddar Up

Overview

Video & Screenshots

Pricing

User reviews

Key features

Integrations

Alternatives