What people complain about in Square

Capabilities people described needing that Square does not give them, taken from the highest-scoring problems first. These are individual accounts written in each person’s own terms, so two entries may describe the same underlying gap in different words.

• A single dashboard to manage and monitor multiple payment processors with automatic failover
• Automated low-balance alerts and payout scheduling to minimize funds at risk
• Integration with risk models to preemptively warn of trigger events
• POS app with guaranteed device compatibility and fast problem resolution for occasional use
• Third-party dispute resolution platform that provides transparent appeal process and human review for payment processor account closures
• Software that can self-recover from card reader connection errors without requiring a full reinstall
• Payment processor that properly underwrites event-based singles businesses instead of auto-rejecting based on keywords
• POS software that supports per-item modifiers within a bundle for fast food menus
• POS system that reliably accepts card payments without random failures or extra fees
• A POS app that maintains stable sessions without requiring reinstallation
• Self-repairing POS app that resolves errors without manual reinstallation
• Payment reader diagnostics that prevent tap and magstripe failures
• A payment processor that is explicitly compliant with CBD regulations and priced competitively for small businesses
• Durable POS hardware with longer warranty and easy replacement
• Customer support system that allows direct complaint filing and human contact
• App should maintain and restore card reader connection without requiring reinstall
• A POS system with reliable automatic bank transfers and no forced fee-based workarounds
• POS system with consistently working card reader and automatic tap-to-pay setup
• Reliable POS software that doesn't require manual reinstallation to restore functionality
• An automated patch or fix for app bugs that doesn't require manual reinstallation
• Automatic connection recovery without manual intervention
• A self-healing or persistent permissions management feature within the POS app
• A reliable tap-to-pay functionality that doesn't require daily reinstallation
• An automatic diagnostic and repair tool for common POS software glitches
• A mobile POS app with reliable offline phone-to-phone NFC tap payments

The manual processes people built around the gap. A long workaround list is the strongest evidence a problem is real: someone is already paying for it in time. Where several people described the same workaround, it is marked.

• Run two independent payment rails at all times
• Keep payouts frequent and on-platform balances low
• Get a real merchant account that underwrites upfront
• Document everything in writing for GDPR Article 22 appeal
• Cannot access POS to record purchases; 2-hour phone call unresolved
• Opened a new account after account was closed
• uninstalling and reinstalling app to fix card reader error
• Uses Square but feels unstable for their category
• Manually enters card payments
• reinstalls app every time before use
• uninstall the app 15 times a week to get it to work again
• Considering reverting to cash/check only for all transactions
• keeps buying new chip readers after warranty expires
• forced to troubleshoot via app with no option to log a complaint or speak to support
• uninstalls and reinstalls the app daily
• Uses Square's alternative options to access money (e.g., instant transfer with fee)
• enters card numbers by hand manually every transaction
• uninstalling and re-installing the app to fix crashes
• reinstalling Square POS app every few days
• uninstalls and reinstalls the app to fix tap-to-pay connection

The problems themselves

Highest opportunity score first.

• A growing pop-up retail business had their Square merchant account restricted and funds withheld after a bad customer service interaction, with no formal notice or resolution.

  5Critical
  Retail·Payment Processing·FundGuard

• Merchants and businesses face sudden account freezes and fund holds by payment facilitators with no warning, which can cripple operations.

  5Critical
  E-commerce·Operational Problem·FreezeGuard Multi-Rail

• Point-of-sale tablet app suddenly stopped working on a compatible device, preventing sale recording after hours of unsuccessful support.

  4High
  Retail·Point-of-Sale (POS) Management·EventPOS Go

• Square POS pauses first payment for verification, rejecting uploaded documents repeatedly with no clear resolution.

  4High
  General Business Services·Payment Processing·VerifyFast

• Square permanently closed business account after large transaction despite providing requested proof, with no effective appeal process.

  4High
  General Business Services·Account Management & Deactivation·AccountGuard Escalation

• POS system became incompatible with the user's Android tablet, threatening an upcoming sales event.

  5Critical
  Retail·Software Integration & Compatibility·Compatibility Guard

• Frequent card reader startup errors require reinstalling the app to resume payment processing, causing delays and frustration with customers waiting.

  5Critical
  Retail·Software Reliability & Performance·ReliPay POS

• Struggling to find a payment processor that won't flag the business as a high-risk dating service, despite not operating like one, due to keyword-based auto-rejection.

  4High
  Event Services·Payment Processing·EventPay Secure

• Square POS cannot handle fast food bundles with modifiable items, forcing manual order management.

  3Medium
  Restaurants & Food Service·Point-of-Sale (POS) Management·BundleBuilder POS

• Square POS randomly won't take card payments, forcing manual entry at a higher fee.

  4High
  Retail·Point-of-Sale (POS) Management·ReliablePay POS

• Square POS app requires reinstallation before every use due to persistent crashes or login issues.

  4High
  General Business Services·Software Reliability & Performance·StablePay POS

• The Square POS app crashes repeatedly during checkout, requiring frequent uninstalls, and tap-to-pay and magstripe readers are unreliable.

  4High
  Point-of-Sale (POS) Management·Software Reliability & Performance·StablePay POS

• A small CBD business is losing its payment processor (Square) due to industry restrictions and must either find a compliant, affordable replacement or revert to cash/check only, harming revenue.

  4High
  E-commerce·Payment Processing·CBD PayFlow

• Square POS hardware fails during events, support is inaccessible for complaints, and recurring failures force repeated repurchases.

  4High
  General Business Services·Software Reliability & Performance·EventPOS Reliable Payment Terminal

• Square POS app requires daily uninstall/reinstall to connect to card reader, causing lost payments and frustration for low-volume merchant.

  4High
  Retail·Software Reliability & Performance·CardConnect Reliable

• Square POS's fund transfer option frequently fails, preventing automatic transfers to the user's bank account and forcing them to use alternative, likely higher-fee access methods.

  4High
  Point-of-Sale (POS) Management·Payment Processing·FundFlow POS

• After every transaction, Square POS requires account verification which can take several days, blocking access to funds and disrupting business operations.

  4High
  Point-of-Sale (POS) Management·Account Reconciliation / Discrepancy Resolution·InstantVerify POS

• Card reader and tap-to-pay functionality never work, forcing manual card entry that slows down customer checkout.

  4High
  Retail·Point-of-Sale (POS) Management·TapFlow POS

• Square POS updates cause glitches and prevent the user from taking payments, disrupting their business.

  4High
  Retail·Software Performance·Reliable POS Pro

• Square POS app crashes daily, requiring constant reinstallation to restore functionality.

  4High
  Retail·Software Reliability & Performance·ReliPay POS