Payment links and checkout for indie software makers in 2026

Q: Can Gumroad sell software subscriptions?

Gumroad says it supports memberships . It offers one-time, recurring or fixed-length payments in the currency you choose . Its page lists video lessons and monthly subscriptions as examples of what you can sell . For a software product, check how its subscription handling and renewal messages work, since this page does not describe those details.

Compare payment links and checkout for indie software makers across Lemon Squeezy, Stripe, Gumroad, Square and Connections Pay.

By Uncommon Comforts · 2026-10-14

Uncommon Comforts is published by the team behind Connections, whose products are compared here alongside other tools.

Indie software makers usually need a way to take a payment, deliver a licensed product, charge repeat subscribers, and deal with sales tax. Tools differ in which of these they handle, what they charge, and whether you keep your own payment account. The options below are described from the facts each one publishes, and where a fee is not published, the table says so.

Option	Own fee	Card fee	Sales tax
Lemon Squeezy	not published	not published	Handled as merchant of record ^[1]
Stripe	Per-transaction pricing with no hidden fees, rate not stated here ^[2]	not published	not published
Gumroad	10% plus $0.50 per transaction on sales through your profile or direct links ^[3]	not published	Handled by Gumroad as merchant of record ^[3]
Square	not published	not published	not published
Connections Pay	not published	not published	Automated sales tax can be switched on, and Stripe calculates and collects it at checkout ^[4]

What indie software makers need from payment links and checkout

A payment link is a web address that opens a payment page for one product, and a checkout is the page where the buyer enters card details and confirms the purchase. For someone who builds software alone, taking the money is only part of the job. A buyer who pays once for a license often needs a key or another way to activate the product. A buyer who pays every month needs a subscription that renews, a way to change plans, and a clear response when a card fails. Each of these is a job a tool either covers or leaves to the seller. Sales tax is the job that trips up many solo sellers, because buyers in different places can face different tax rules, and the seller usually has to collect what is owed and pass it on. Some tools take that work on as part of the sale, while others offer a setting that calculates tax and leaves the rest to the seller. This page does not give tax advice. Small teams also watch how quickly a setup can be finished, which countries and currencies a buyer can pay from, and how much of each sale goes to fees. Those details change, so check current terms on each tool's own pages before deciding.

Lemon Squeezy for indie software makers

Lemon Squeezy says it is your merchant of record, and that it handles payments, merchant fees, fraud and sales tax ^[1]. It says you can accept payments from 135+ countries with zero setup ^[1], and that you can accept up to 21 payment methods, including PayPal, under one roof ^[1]. For software, it says it issues license keys automatically after each sale ^[1]. For subscriptions, it offers usage-based billing, where the charge follows how much a customer uses ^[1], and a system for recovering failed subscription payments ^[1]. It also says it securely signs download links ^[1].

Stripe for indie software makers

Stripe, the card payment service, says its pricing is integrated per transaction, with no hidden fees ^[2]. It says you can get up and running in as little as 10 minutes ^[2], and you can set up billing or share a payment link from its site without writing code ^[2]. It says it supports 135+ currencies and payment methods ^[2] and reports 99.999% historical uptime for its services ^[2]. Stripe also offers tools a developer can use to build payments into your own software ^[2]. Support is offered through tiered plans based on your needs ^[2].

Gumroad for indie software makers

Gumroad says you can sell anything, and lists video lessons and monthly subscriptions as examples ^[5]. It says it supports memberships ^[3], and offers one-time, recurring or fixed-length payments in the currency you choose ^[5]. Buyers can pay in their own currency ^[5]. It charges 10% plus $0.50 per transaction for sales through your profile or direct links ^[3], and 30% per transaction when new customers find and buy through its discover marketplace ^[3]. It says it does not charge a monthly fee ^[3]. Gumroad says it is a merchant of record that handles sales tax collection worldwide and passes the tax on to tax authorities ^[3].

Square for indie software makers

Square says it provides a point of sale platform for selling in person and online ^[6]. It offers a free 30-day trial on its Plus and Premium plans, which you can cancel or switch at any time ^[7]. It says it has no hidden fees or locked-in contracts ^[6]. Its hardware includes a Reader for contactless and chip payments, listed at $59 ^[6]. It says businesses that process over $250,000 per year can ask about custom pricing and processing fees ^[7]. Square also says it partners with hundreds of apps ^[6].

Connections Pay for indie software makers

Connections Pay is made by the team that publishes this site, Uncommon Comforts. You can connect your own Stripe account through Stripe's sign-in ^[4]. Each checkout page is served at its own web address ^[4], and buyers can enter discount codes at checkout ^[4]. You can also use an embeddable checkout page on your own site ^[4]. Subscribers get a manage page ^[4], and when a customer changes plans, the price difference is previewed ^[4]. Automated sales tax can be switched on, so Stripe calculates and collects it at checkout ^[4]. The product is live on the web ^[4]. You keep your own Stripe account for the sale ^[4], and each checkout page is served at its own web address ^[4]. This page does not state the product's fees, so check them before you choose.

Matching the tool to the job

If the job is a license sale where the buyer gets a key after paying, Lemon Squeezy says it issues license keys automatically after each sale ^[1]. For a plain payment link, Stripe's Dashboard can share one with no code required ^[2], and Connections Pay gives each checkout page its own web address ^[4]. For monthly subscriptions, Gumroad says it supports memberships ^[3], and Lemon Squeezy describes a system for recovering failed subscription payments ^[1]. Connections Pay gives subscribers a manage page ^[4] and previews the price difference when a customer changes plans ^[4]. The facts on this page do not say how Gumroad or Stripe handle failed renewals, so ask them directly. For sales tax, Lemon Squeezy says it handles sales tax as merchant of record ^[1]. Gumroad says it handles sales tax collection worldwide ^[3]. Connections Pay offers a setting where Stripe calculates and collects sales tax at checkout ^[4]. For discount codes, Connections Pay lets buyers enter them at checkout ^[4]. For buyers in many countries, Lemon Squeezy cites payments from 135+ countries ^[1], and Gumroad lets them pay in their own currency ^[5]. If you also sell in person, Square describes a point of sale platform for in-person and online selling ^[6].

Questions to ask before you choose

Which sales tax work does the tool take on, and which does it only calculate for you to handle? Does the fee apply to sales through your own link, through a profile page, or through a marketplace, and is it charged on top of a card rate set by another service? Do you keep your own payment account, and who holds the money between a sale and your bank? How are failed subscription payments retried, and how are refunds and disputed charges handled? Which currencies and payment methods do your buyers use, and does the tool support them? Do you need in-person selling as well as online, and does one tool cover both? How much time do you need to finish setup before a launch date, and what does the setup ask for? Which rates, terms and plan limits are current on each tool's own pages?

Frequently asked questions

Does Lemon Squeezy handle sales tax for software sellers?

Lemon Squeezy says it is your merchant of record, and that it handles payments, merchant fees, fraud and sales tax ^[1]. Read its current terms for the places your buyers live, and check how they apply to your own sales. This page does not give tax advice, so a tax professional is the right person for questions about your own obligations.

Can Gumroad sell software subscriptions?

Gumroad says it supports memberships ^[3]. It offers one-time, recurring or fixed-length payments in the currency you choose ^[5]. Its page lists video lessons and monthly subscriptions as examples of what you can sell ^[5]. For a software product, check how its subscription handling and renewal messages work, since this page does not describe those details.

Does Connections Pay work with Stripe?

Yes, you can connect your own Stripe account through Stripe's sign-in ^[4]. Each checkout page has its own web address ^[4]. This page does not state the product's fees or any fee Stripe charges, so check both before you choose.

Does Square have a free trial for online selling?

Square says it offers a free 30-day trial on its Plus and Premium plans, and that you can cancel or switch plans at any time ^[7]. It describes a point of sale platform for in-person and online selling ^[6]. Check which features each plan includes for a software sale, since this page does not compare them.

How long does it take to set up Stripe?

Stripe says it can get a business up and running in as little as 10 minutes ^[2]. That is the company's own figure, so plan with some margin before a launch date. Check the setup steps on Stripe's own site, since this page does not describe them.

Connections Free costs $0, and going over a limit stops the feature rather than billing you. ^[4] Connections Pro, the first paid plan, is $39.99 a month and adds premium features across every Connections product. ^[4]

Try Connections Pay