ShipStation vs. Easyship vs. Pirate Ship: Shipping Software Pricing, Worked to the Label

Pirate Ship charges no monthly fee at any volume. ShipStation's cheapest plan starts at $14.99 a month. Easyship starts free and tops out at $99 to $199 a month. That is the whole pricing story — and a trap: the platform fee is the only comparable number, because postage is a pass-through on all three. The real decision is what the free platform leaves out, and whether your operation needs it.

This playbook is for the operator who prints labels every week. It prices the platform fee only: postage is the same underlying carrier rate on every platform, bought through different discount arrangements, so no postage figure appears in this guide.

The three offers, in one table

ShipStation sells three plans priced by monthly shipment volume. The Starter plan covers 50 shipments a month at $14.99, 100 at $29.99, 500 at $39.99, 1,000 at $79.99, 2,000 at $119.99 and 5,000 at $174.99. Standard, marked most popular, runs $29.99 at 50, $89.99 at 500 and $3,599.99 at 100,000. Premium starts at $349.99 a month for 50 shipments and climbs to $7,499.99 at 100,000. Every plan carries a $0.000 per-label fee: the subscription is the whole platform cost. Annual billing takes 20 percent off — Starter at 50 a month is $143.90 a year instead of $179.88 — and the first 30 days are free, no credit card required.

Easyship sells four plans by monthly shipment volume. Free is $0 for 50 shipments a month. Plus is $29 a month, or $276 a year, for 500 shipments. Premier is $69 a month, or $660 a year, for 2,500 shipments. Scale is $99 a month, or $948 a year, for 5,000 to 10,000 shipments, listed at $99 to $199 a month. Easyship advertises up to 91 percent off retail rates across 550 or more couriers; the paid plans carry a 14-day free trial plus $30 of free shipping credits.

Pirate Ship sells nothing: no monthly fee, no per-label fee, no paid tier. It gives shippers pre-negotiated USPS and UPS discounts — up to 89 percent off retail, by the vendor's own statement — with no minimum volume and no commitment, and reports $705,000,000 saved since 2014. The catch is scope: two carriers against ShipStation's 200-plus and Easyship's 550-plus.

The monthly cost math

The platform fee is the whole comparison — here it is at the five volumes that matter. Monthly cost is the plan price for the tier covering your volume; annual cost is that price times twelve, or times 9.6 with the 20 percent annual discount.

At 50 labels a month, ShipStation Starter costs $14.99 and both free options cost $0 — $179.88 a year saved against monthly billing, $143.90 against annual.

At 100 labels a month, ShipStation Starter costs $29.99 and Easyship Free no longer covers the volume — its cap is 50 — so the buyer moves to Plus at $29. Pirate Ship still costs $0, saving $359.88 a year against ShipStation, $348.00 against Easyship. Easyship and ShipStation are nearly tied here: $29 against $29.99, a $0.99 a month difference.

At 500 labels a month, ShipStation Starter costs $39.99, Easyship Plus $29, Pirate Ship $0. Pirate Ship saves $479.88 a year against ShipStation, $348.00 against Easyship. Easyship saves $10.99 a month against ShipStation — $131.88 a year.

At 2,500 labels a month, ShipStation needs its 5,000 tier at $174.99 — the 2,000 tier at $119.99 does not cover 2,500 — Easyship Premier costs $69, Pirate Ship $0. Pirate Ship saves $2,099.88 a year against ShipStation, $828.00 against Easyship. Easyship saves $1,271.88 a year against ShipStation.

At 5,000 labels a month, ShipStation Starter costs $174.99, Easyship Scale $99, Pirate Ship $0. Pirate Ship saves $2,099.88 a year against ShipStation, $1,188.00 against Easyship. Easyship saves $911.88 a year against ShipStation.

The per-label view shows the same shape. ShipStation Starter costs $0.2998 per label at 50 a month, $0.0800 at 500, $0.0350 at 5,000. Easyship Plus costs $0.0580 at 500, Premier $0.0276 at 2,500, Scale $0.0198 at 5,000. Pirate Ship costs $0.0000 per label at every volume.

ShipStation Starter at 500 a month is $383.90 a year on annual billing against $479.88 monthly-billed, a $95.98 saving. Easyship Plus is $276 against $348, a $72 saving (20.7 percent; the listing rounds it to 21 percent). Premier is $660 against $828, a $168 saving; Scale is $948 against $1,188, a $240 saving. Pirate Ship has no annual price — there is nothing to discount.

The discount-percentage trap

Every vendor leads with a discount percentage, and none can be compared head to head. ShipStation claims 80 to 90 percent off every major carrier, Easyship up to 91 percent off retail rates, Pirate Ship up to 89 percent off USPS and UPS rates. These are maximums against retail rates on different carriers and services. A maximum is not a rate: it is the best case on the vendor's best lane, and your lane is almost certainly not it.

The arithmetic shows why the percentages mislead even when they look close. Suppose they did apply to the same $10.00 retail label: at 91 percent off you pay $0.90; at 89 percent off you pay $1.10. The gap is $0.20 a label, $100.00 a month at 500 labels — larger than the $10.99 platform-fee gap between ShipStation Starter and Easyship Plus at the same volume. But the percentages do not apply to the same label, so that $100.00 is arithmetic, not a saving you can bank. The two-point gap could be worth $100 a month or nothing at all, depending on which services carry your parcels.

One discount difference is real: Pirate Ship gives access to Priority Mail Cubic pricing, which most small sellers cannot reach alone, and it rate-shops automatically between weight-based and cubic Ground Advantage rates so the cheaper of the two is always printed. Ground Advantage is the cheapest, slowest USPS service — the Postal Service merged First-Class Package and Parcel Select into it in July 2023. Cubic pricing rewards small, heavy parcels: a dense box ships at its cubic tier rather than its weight. If your parcels are small and heavy, that single feature can be worth more than the whole platform-fee comparison.

What the fee buys

The platform fee buys features — and the feature line is where the three platforms separate. ShipStation is the operations platform: unlimited store connections on every plan, automation rules that batch, route and print labels, an API and phone support from Standard up, and a dedicated account manager on Premium. Premium adds advanced inventory and warehouse management — scan to receive, purchase orders, forecasting, pick to tote — and custom analytics. Its entry price is the giveaway: Premium starts at $349.99 a month for 50 shipments, 23.3 times Starter's $14.99. Nobody buys Premium for the labels. They buy it for the warehouse.

Easyship is the cross-border platform: live tax and duty calculation at checkout, with delivered-duty-paid and delivered-duty-unpaid options, from Premier up. It connects 550 or more couriers, supports multi-box and split shipments from Premier up, and offers a global fulfillment network as an add-on on Scale. Branded tracking arrives from Plus up, and the shipping API from Premier up.

Pirate Ship is the label printer: single labels, spreadsheet imports, and ecommerce store connections for batch shipping. It offers customizable tracking emails, pay-on-use return labels, and international shipping through its exclusive Simple Export Rate. It lists no shipping API on its features page and offers no branded tracking page — its tracking surface is the email, not a page on your domain.

ShipStation Starter is email support only; phone support starts at Standard — $89.99 a month at 500 labels against Starter's $39.99, a $600.00 a year premium for the phone, the API, unlimited automations and ten users. Easyship's Free plan is email support only; 24-7 live chat arrives at Plus and 24-7 phone at Premier. Pirate Ship states no support tier on the pages fetched for this guide, so this guide claims none.

Who each platform is for

Pirate Ship is for the seller whose operation is domestic USPS and UPS labels and nothing else. A marketplace seller shipping 50 to 500 parcels a month from one location, with no API, no branded tracking page, and no duty calculation, pays nothing and loses nothing. The moment the operation needs a third carrier, a branded tracking page, or duties at checkout, Pirate Ship stops being an option — the feature does not exist.

Easyship is for the seller whose orders cross borders. The free plan covers 50 shipments a month with import tax and duty calculation included — enough to test international demand without paying. Plus at $29 is the workhorse at 500 shipments; Premier at $69 is where the cross-border operation lives: live tax and duty at checkout, the shipping API, and returns management. Scale is the volume tier, $99 to $199 a month for 5,000 to 10,000 shipments, with the fulfillment network as an add-on.

ShipStation is for the operation, not the seller. Starter at $14.99 is the cheapest way into unlimited store connections and automation rules — the buy for a multi-channel seller whose stores outnumber their staff. Standard is the buy for a team that needs the API, phone support, and unlimited automations; Premium is the buy for a warehouse — advanced inventory, pick to tote, custom analytics, and a dedicated manager, from $349.99 a month.

Execution checklist

1. Count your labels for the last three months and take the highest — the tier must cover your peak.
2. List your carriers. Any parcel on a carrier other than USPS or UPS rules Pirate Ship out.
3. List your international share. Above a fifth of orders crossing a border, price Easyship Premier against duty refunds and abandoned carts.
4. List your integrations. Anything calling a shipping API sets the floor at ShipStation Standard or Easyship Premier.
5. Run your five most common lanes through each platform's rate tool and compare postage totals, not discount percentages.
6. Price the support tier at the volume you actually ship: email only, or phone.
7. Run the winner alongside your current platform for two weeks on live orders before moving the rest.
8. Move the branded tracking page and returns portal first — they are customer-facing and break silently.
9. Rebuild automation rules one at a time and print a test batch before each goes live.
10. Re-count labels after 30 days and confirm the tier still covers your volume before the next billing cycle.

Related reading on Ibravra: Stripe vs Square vs PayPal: Payment Processing Fees prices the payment fee that sits next to every shipping label; Shopify vs WooCommerce vs BigCommerce: Ecommerce Platform Fees prices the storefront the labels ship from; IRS Form 1099-K: Payment App Reporting Threshold covers the reporting threshold that marketplace sellers cross as volume grows; Pricing Calculator runs the margin math that turns a shipping cost into a product price.