Switching point-of-sale systems is nerve-wracking because your menu, your prices, your regulars, and their loyalty balances all live inside the system you’re leaving. A Toast-to-Square move is very doable for a café — but it has one wrinkle that a Clover or Lightspeed move doesn’t: your Toast contract. Get that part wrong and the switch costs you thousands before you’ve imported a single item.
This guide is the plan. It’s written for an independent café or coffee shop owner moving a single location (or a few) from Toast to Square, and it’s upfront about the contract math, what data carries over, and what you rebuild by hand.
If you’re still deciding whether to switch, start with our side-by-side on Toast vs Square for a café. This post assumes you’ve decided and want to do it without a bad morning.
Step 0: read your Toast contract before anything else
This is the step people skip, and it’s the one that hurts. Toast is typically sold on a fixed-term software agreement — commonly two years, and some promotions require three — and the payment processor is locked to Toast Payments, so leaving means ending the agreement, not just switching a setting.
Third-party reviews report that canceling a Toast contract early can trigger fees covering the remaining software subscription balance plus any financed hardware, with early-termination charges that have been reported in the $1,000 to $5,000+ range depending on the plan and how much time is left. Those figures come from resellers and review sites, not a public Toast rate card, so treat them as directional and confirm your own number — the only source of truth is the agreement you signed.
Do this before you pick a switch date:
- Find your contract end date. If you’re within a few months of it, the cleanest move is often to time your switch to the renewal so you owe nothing extra.
- Ask Toast, in writing, for your exact early-termination cost. Get the number, not a verbal estimate.
- Separate hardware from software. Financed Toast hardware may have its own balance. You’ll be buying Square hardware anyway, so factor both into the comparison.
None of this means don’t switch. It means switch with the number in front of you, so the savings math is honest.
Step 1: know what transfers (and what doesn’t)
Set expectations before you touch anything. The pattern is the same as any POS migration: catalog and contact data move; money-and-balance data does not.
| Data | Transfers to Square? | How |
|---|---|---|
| Menu items, prices, categories | ✅ Yes | CSV export from Toast → Square item-import template |
| Item variations & modifiers | ⚠️ Partly | Re-map into Square’s modifier structure; complex modifier groups may need rebuilding |
| Item photos | ❌ No | Re-upload in Square |
| Customer names, emails, phones | ✅ Yes | Export from Toast → import to Square Customer Directory |
| Saved cards on file | ❌ No | Cannot move between processors (PCI rules); customers re-enter |
| Loyalty point balances | ❌ No | Export balances; honour manually or reissue in Square Loyalty |
| Gift card balances | ❌ No | Export balances; reissue as Square eGift cards or honour manually |
| Past sales reports | ⚠️ Export only | Keep Toast reports as records; they don’t import into Square analytics |
The two rows that cause real customer pain are loyalty and gift cards, because those are money your regulars are owed. Protect them deliberately (Step 4).
Step 2: rebuild your menu with a CSV import
Square imports your catalog from a spreadsheet, not from Toast directly. The flow:
- Export your item library from Toast. Pull your menu, prices, categories, and modifier groups out of the Toast dashboard as a spreadsheet or report.
- Download Square’s item-import template. In the Square Dashboard, go to Items → Actions → Import Library and download the blank Excel/CSV template so you’re mapping into the exact columns Square expects.
- Map your data into Square’s columns. Item name, price, category, and variations line up cleanly. Modifiers are where Toast and Square differ most — Square groups them as modifier sets, so plan to re-shape complex Toast modifier logic by hand.
- Upload and review before publishing. Import the file, then spot-check ten items across categories for correct price, tax, and modifiers before you rely on it.
- Re-add photos and fine details. Item images, colour/tile settings, and any Toast-specific course or prep-station logic don’t come across in a CSV. Re-add them in Square.
For a café with a tight menu, this is a half-day of focused work. The bigger your modifier complexity (build-your-own drinks, size/milk/syrup matrices), the more of it is manual.
Step 3: import your customers
Your customer relationships are worth protecting. Export your customer list — names, emails, phone numbers — from Toast, then import it into the Square Customer Directory (Dashboard → Customers → Import Customers, using Square’s CSV template).
What you can’t carry over is card-on-file data. For PCI and security reasons, saved card details never transfer between processors. Customers who had a card stored in Toast will simply re-enter it the first time they pay or order on Square. That’s normal and expected — just don’t promise anyone their saved card “will still be there.”
Step 4: handle loyalty and gift cards (the risky part)
This is where a rushed cutover burns goodwill. Both balances are money your customers already hold.
- Loyalty balances. Export every active customer’s current point balance from Toast before you cancel. Set up Square Loyalty for your café, then either credit regulars their equivalent points manually or honour a printed list at the counter during a transition window. Communicate the change so nobody feels their stars vanished.
- Gift card balances. Export outstanding gift card balances from Toast. You can’t move the cards, but you can reissue equivalent value as Square eGift cards or keep a redemption list and honour balances manually until they’re drawn down.
Give yourself a short overlap window — even a week — where you can look up an old balance. That single precaution prevents the most common post-switch complaint: “I had a gift card and now it’s gone.”
Step 5: set up hardware and cut over on a slow shift
Order your Square hardware before you cancel Toast so you’re never without a working till. Square’s café setups range from a phone with Tap to Pay on iPhone to a Square Terminal or Register — see our Square hardware guide for what fits a coffee bar.
Then cut over the boring, safe way:
- Run parallel for one slow shift. Keep Toast live and ring a few real orders through Square on a quiet afternoon. Confirm items, prices, tax, and receipts are correct.
- Test a full order end to end. Place an order, take payment, confirm it prints to the kitchen or shows on your display, and check the sale lands in Square reporting.
- Cut over fully, then cancel Toast on your planned date. Don’t cancel Toast until Square has handled a real service cleanly — and until your contract timing makes canceling the cheapest it’s going to be.
What does the switch actually save? Do this math
The savings come from three places, and you should size all three before you commit:
- Software fee. Toast’s Point of Sale plan is published at around $69/month per terminal (its Starter Kit is $0/month but carries higher processing). Square’s basic POS is free to use; you can add paid plans only if you need them.
- Processing. Toast rates are often custom-quoted and can be raised with notice; Square’s café rates are flat and public. Compare your effective rate — total fees ÷ total sales — not the sticker number. Our Square fees for restaurants guide shows how to calculate it.
- Contract flexibility. Square has no multi-year lock-in. The value of never facing a five-figure exit fee again is real, even if it doesn’t show up on one month’s statement.
Put your real Toast statement next to Square’s published rates and a $0 base plan, and subtract any early-termination cost from year one’s savings. If the number is still positive — and for many small cafés it is — the switch pays for itself.
Where a branded app fits after you switch
Once you’re on Square, you own a clean POS with your menu, customers, and loyalty in one place. The next lever most cafés reach for is a customer-facing ordering channel that’s unmistakably theirs.
That’s where Tany fits: a branded order-ahead app for iOS and Android plus web ordering, with self-running loyalty, eGift cards, and push notifications, built directly on your Square POS and live in about a day for $99 CAD/month per location. It’s not part of the migration — it’s the growth step that gets easier once your café’s data lives in Square instead of a locked contract.
Switch with your contract number in hand, protect your loyalty and gift card balances, and cut over on a slow shift. Do those three things and a Toast-to-Square move is calm, not chaotic.