Oliver POS doesn't have a partnership with Square. It supports Square the same way any WooCommerce store does — through Square's official WooCommerce plugin, opened inside Oliver's in-POS browser view at the counter. The merchant's existing Square account does the processing, WooCommerce records the order, and Oliver is the till. This is for stores that want WooCommerce as the source of truth and Square as the processor — without giving up either.
What Square Online is, exactly
Square is best known as a US-founded card processor and small-business POS, with millions of sellers across the US, Canada, UK, Australia, Japan, France, Ireland, and Spain. Square Online is Square's hosted checkout — a Square-owned page where the customer enters card details (or taps Cash App Pay), Square authorises the charge, and the result is posted back to the integrating store. Square processes the funds and settles to the merchant's Square balance on Square's standard payout schedule.
For a WooCommerce merchant, that means the same Square account that runs their Square Reader transactions can run their WooCommerce online transactions and, through Oliver, their counter transactions — without rekeying anything between systems.
How Oliver POS opens Square at the counter
The Square WooCommerce POS flow inside Oliver is straightforward:
- The cashier rings the sale on the Oliver register and taps Charge.
- Oliver writes a pending WooCommerce order against the Square gateway.
- Oliver opens the Square-hosted checkout in the in-POS browser view — a full-screen webview locked to that one sale.
- The cashier rotates the tablet to the customer. The customer pays with card or Cash App Pay.
- Square authorises the charge and notifies WooCommerce. The order flips to processing.
- Oliver picks up the confirmation, closes the browser view, and prints the receipt.
A Square register sale through Oliver typically clears in 15 to 25 seconds. Funds settle from Square to the merchant's Square account on Square's normal next-business-day cadence; Oliver never sits in the funds path.
The Square WooCommerce plugin — what Oliver rides on
The plugin Oliver rides on is the official Square for WooCommerce, published by WooCommerce and Square together and listed at wordpress.org/plugins/woocommerce-square. It connects WooCommerce to a Square account via OAuth, syncs products and inventory two-ways if you enable it, and exposes Square as a checkout gateway. Cash App Pay is bundled — no separate plugin needed.
Configuration is the same regardless of channel: install the plugin, authorise your Square account through the in-plugin OAuth flow, and enable the Square gateway under WooCommerce → Settings → Payments. Oliver auto-detects any enabled gateway in WooCommerce and lists it on the register as a tender option. If Square works on the online store, it works on the POS for Square at the counter.
Why a Square merchant might use Oliver instead of Square POS
The interesting question is not why a generic merchant would use Square — Square's pricing and ubiquity speak for themselves — but why a merchant who already has a Square account would put Oliver in front of it rather than just running Square POS. A few reasons we hear:
- WooCommerce is the source of truth. If the catalogue, customers, inventory, and order history all live in WooCommerce — and the website is the marketing surface — running the counter through Square POS forces a sync. Running through Oliver keeps WooCommerce authoritative and uses Square only for the card processing step.
- Single backoffice. Reports, end-of-day, and inventory live in one place (WooCommerce + Oliver) rather than split across Square Dashboard and WooCommerce.
- Hardware flexibility. Oliver runs on existing iPads, Android tablets, and PCs, with receipt printers and barcode scanners over Bluetooth or USB.
- Cash App Pay at the counter. Cash App Pay is enabled by the Square WooCommerce plugin and appears on the hosted checkout Oliver opens. That puts a wallet that 50M+ US accounts already use in front of in-store shoppers.
None of which is a knock on Square POS — for a single-location store with no website, Square POS is excellent. It's specifically the WooCommerce-first merchant for whom a Square register inside Oliver makes sense.
What this is NOT
Oliver POS is not a Square partner. There is no co-marketing agreement, no revenue share, and no special Square rates for Oliver merchants. Oliver does not charge a markup on Square transactions; the merchant pays Square's published rates directly to Square. Square is the merchant of record on the transaction, funds settle to the merchant's Square account on Square's own schedule, and the Square Dashboard, refunds, disputes, and 1099-K reporting are all unchanged. Oliver is the POS software on top.
Setup in 4 steps
- Install the Square for WooCommerce plugin from wordpress.org/plugins/woocommerce-square.
- Connect to your Square account through the plugin's OAuth flow and enable the Square gateway (with Cash App Pay if you want it) under WooCommerce → Settings → Payments.
- Install Oliver POS, sign in on the counter tablet, and pick the Square gateway from the tender list — Oliver auto-detects it from WooCommerce.
- Run a small live test sale at the counter and confirm the order appears in WooCommerce, in your Square Dashboard, and on the printed receipt.
FAQ
Does Oliver POS partner with Square?
No. Oliver POS is not a Square partner. Square is supported because Square ships an official WooCommerce plugin that any WooCommerce store can install, and Oliver opens that gateway in our in-POS browser view at the counter.
Does Oliver charge a markup on Square?
No. Your Square rate is your Square rate. You pay Square directly on Square's published pricing. Oliver's pricing is a flat monthly POS software fee that does not change based on which gateway you use.
Does Cash App Pay work on the register?
Yes. Cash App Pay is enabled by the Square for WooCommerce plugin and appears as a button on the Square-hosted checkout that Oliver opens in the in-POS browser view. The customer scans the QR code with their Cash App or taps the button on the same device.
Can I still use Square Reader hardware?
Square's physical readers use Square POS or Square's mobile SDK. Oliver POS for Square uses the Square WooCommerce hosted-checkout path described here, not the reader SDK. If you want a physical card reader at the counter, see our integrations page for hardware options that pair with Oliver.
Try Oliver POS free for 30 days at /demo/ — bring your existing WooCommerce store and your existing Square account.