Square Online Shipping Insurance
Square includes $50 on its labels. Your customers still cannot choose insurance at checkout. Here is the fix.
See all integrationsReviewed by Kyle Gibson, Compliance Auditor · Updated October 2026
Key takeaways
- InsureShip is integrated with Square Online (integration built with our fulfillment partner RapidFulfillment). Contact us to turn it on for your store.
- Square dashboard labels include $50 of insurance, and you can buy more by entering an insured value.
- That is seller-side label coverage, not a checkout choice for your customer.
- Automatic service charges cover pickup, delivery, QR-code and online-ordering-profile orders, not shipped orders.
- The workaround community members use is an optional insurance item. Keep it opt-in.
- A line named "insurance" needs a real insurer behind it.
Does Square Online include shipping insurance?
"There isn't a feature to add on shipping insurance cost in Square Online Store."— Square Community moderator, September 2025, Square Community thread
What Square does include is label coverage. Shipping labels bought in the Square dashboard include $50 of insurance, and you can add more by entering an insured value. Labels run through Shippo-connected carriers.
InsureShip is integrated with Square Online (integration built with our fulfillment partner RapidFulfillment). Contact us to turn it on for your store.
Label insurance or checkout insurance: what is the difference?
| Square label insurance | Checkout shipping insurance | |
|---|---|---|
| Who chooses it | You, when buying a label | Your customer, at checkout |
| Default amount | $50 included | Set by the policy (InsureShip: up to $5,000 per shipment) |
| Who pays | You, for any extra insured value | Usually the customer, when they opt in |
| Labels bought elsewhere | Not covered by Square's label insurance | Depends on the policy, not the label source |
Why don't Square service charges work for shipped orders?
Square Online's automatic service charges apply only to pickup, delivery, QR-code and online-ordering-profile orders. Shipped orders are left out. So the usual "add a fee" route is not available for the orders that need insurance most.
How do you add shipping insurance to Square Online?
- Contact InsureShip. Tell us about your Square Online store.
- We enable the integration for your store. The Square Online integration was built with our fulfillment partner RapidFulfillment, so there is no API build on your side.
- Choose an opt-in checkout presentation. Pick how the offer appears in your Square Online checkout. InsureShip recommends, and configures by default, an opt-in (unchecked) offer.
- Customers file claims at /pages/file-claim. InsureShip handles every claim.
Background: how an opt-in offer fits Square Online
For reference, because service charges skip shipped orders, an opt-in offer on Square Online usually takes the form of an optional "Shipping insurance" item the shopper adds on purpose, described honestly: what it covers, who insures it, and a link to the terms. Square's Orders API webhook order.fulfillment.updated (beta) reports old_state and new_state for each fulfillment, which helps confirm insured orders actually shipped. You can keep using Square's label insurance too. It protects you as the shipper; checkout insurance protects your customer's purchase.
How do claims work with InsureShip?
When a Square Online order goes missing or arrives broken, the claim goes to InsureShip, not to the platform.
- File online. Customers or merchants file at /pages/file-claim.
- InsureShip handles the claim. Your support team does not have to adjudicate it.
- Coverage up to $5,000 per shipment.
- Established in 2012. InsureShip is backed by Navigators (The Hartford), rated A+ by AM Best.
- Loss, damage and theft are covered, including porch piracy.
What are the checkout best practices on Square Online?
- Never pre-add the insurance item. InsureShip recommends, and configures by default, an opt-in (unchecked) offer. Several class actions allege pre-selected shipping protection charged shoppers without clear consent. See our lawsuits tracker.
- Know who insures. An item or fee you configure is not by itself insurance. See fake shipping insurance risks.
- Use the word "insurance" only for real insurance, and link terms near the item.
- Train staff to send claims to InsureShip, and read our scams resource center.
Frequently Asked Questions
Can I add a shipping insurance fee in Square Online?
Not natively. A Square Community moderator said in September 2025 that there is no feature to add shipping insurance cost in Square Online Store, and automatic service charges do not apply to shipped orders.
Does Square include insurance on shipping labels?
Yes. Labels bought in the Square dashboard include $50 of insurance, and you can buy more by entering an insured value. That is seller-side label coverage.
Is InsureShip integrated with Square Online?
Yes. InsureShip is integrated with Square Online (integration built with our fulfillment partner RapidFulfillment). Contact us to turn it on for your store.
Should the insurance item be in the cart by default?
No. We recommend opt-in only. Several class actions allege pre-selected shipping protection was charged without clear consent. This is general information, not legal advice.
How are claims handled?
Online through the InsureShip file-claim page. InsureShip handles the claim, with coverage up to $5,000 per shipment for loss, damage and theft, including porch piracy.
Related resources
Give Square Online shoppers a real choice
We will turn on the integration and help you set up a clear, opt-in offer for your Square Online store.
InsureShip: Established in 2012. Licensed by the California Department of Insurance, license #0G55434, and licensed in all 50 states. Underwritten by Navigators, a Hartford company, rated A+ by AM Best (Navigators Insurance Company, as of 2024).
Talk to InsureShipSources
Last checked October 9, 2026. General information, not legal advice. Square Community: insurance on shipped orders · Square: shipping labels · Square: service charges · Square order.fulfillment.updated webhook · The Hartford: Navigators fact sheet (April 2025)