You're standing there. The dinner bill is a nightmare of split appetizers and that one friend who "forgot" their wallet. Or maybe you're a freelancer waiting on a client who swears they sent the check. It’s annoying. Honestly, chasing people for money is the worst part of any social or professional interaction. But if you’re an iPhone user, you basically have a debt collector in your pocket. Knowing how to request Apple Pay—specifically through the Apple Cash feature—is the fastest way to get your money without the back-and-forth of "what's your handle?" or "did you get my email?"
Most people think Apple Pay is just for tapping your phone at Starbucks. It's not.
Apple integrated peer-to-peer payments directly into iMessage years ago. Since then, it has become the cleanest way to settle up. No third-party apps to download. No separate accounts to link if you've already got a debit card in your Wallet. It just works. Well, it works if you know where the buttons are hiding.
The iMessage Method: Where Most People Start
Open your messages. That’s step one. Find the person who owes you money. You’ll see a row of icons right above the keyboard. Look for the black Apple logo that says "Cash." It’s usually right there next to the App Store icon and the photos button. Tap it.
Now, this is where people get tripped up. You’ll see a dollar amount and two buttons: Pay and Request. Obviously, you want Request. Dial in the amount. Maybe it’s $15.50 for that burrito. Maybe it’s $200 for your share of the Airbnb. Hit that request button.
The request pops into the text field like a little bubble. You can even type a message with it. "Hey, here's for the pizza!" or "Rent is due, thanks!" Send it. On their end, they get a notification that looks like a standard message. All they have to do is tap it and authenticate with FaceID or TouchID. It is embarrassingly simple.
Why does this matter? Friction.
In the world of UX design—the stuff people like Don Norman talk about in The Design of Everyday Things—friction is the enemy. If you send a Venmo request, the person has to open a different app. They might have to transfer funds. They might see a feed of what their ex-girlfriend bought for lunch. With Apple Cash, it stays in the conversation. It’s immediate.
What if the Apple Cash Icon is Missing?
It happens. You go to request money and the icon is just... gone. Don't panic. Usually, this means one of two things. Either you haven't turned on Apple Cash in your settings, or you’re trying to message someone who isn’t on an iPhone.
Yes, the green bubble struggle is real.
If you’re messaging an Android user, you cannot use the iMessage Apple Cash feature. Apple’s ecosystem is a walled garden, and this is one of the tallest walls. In that case, you’re stuck using a link or a third-party service. But for fellow iPhone users, if the icon is missing, go to Settings > Wallet & Apple Pay and make sure the "Apple Cash" toggle is green. You might need to verify your identity with your social security number if you're moving large amounts of money. Federal regulations like the Patriot Act require this for "Know Your Customer" (KYC) compliance. Banks have to do it. Apple has to do it.
Siri Can Do the Dirty Work
"Hey Siri, request twenty dollars from Mom."
Seriously. Try it. If you have the contact saved and Apple Cash set up, Siri handles the backend. It’ll ask you to confirm the request before it sends. This is actually the "pro" way to do it when you're driving or cooking and just remembered that your roommate still hasn't paid for the utilities. It's hands-free debt collection.
How to Request Apple Pay for Your Small Business
If you’re running a business, "Request" looks a little different. You aren't usually texting your customers from your personal iMessage—or maybe you are, if you're a local landscaper or a hair stylist.
For businesses, Apple introduced Apple Pay Later and more robust Apple Pay on the Web integrations. But for simple requests, many small business owners use invoices. If you use an accounting platform like QuickBooks, FreshBooks, or even Shopify, you can enable Apple Pay as a payment method.
When you send that invoice via email, the customer sees a "Check out with Apple Pay" button. They tap it, double-click the side button on their phone, and you're paid. No typing in 16-digit card numbers. No errors.
The psychology here is huge. According to various conversion rate optimization studies, the fewer steps a customer takes, the more likely they are to finish the transaction. Apple Pay removes almost every step. It’s a "one-tap" world. If you aren't offering this, you're literally leaving money on the table because someone was too lazy to get their purse from the other room.
The Wallet App Shortcuts
Sometimes you don't want to go through iMessage. Maybe you’re already in the Wallet app looking at your balance.
- Open the Wallet App.
- Tap on your Apple Cash card.
- Right there, front and center: Request and Send.
- Tap Request.
- Choose a contact from your recent list or type in a name.
This is arguably faster if you have to request money from multiple people in a row. It feels more like a financial app and less like a chat.
Limits You Need to Know
You can’t just request a million dollars. Apple has limits. For most people, you can send or receive up to $10,000 per message and up to $10,000 within a seven-day period. If you’re trying to buy a car via Apple Cash, you might hit a wall. Also, your Apple Cash balance itself has a cap—usually $20,000 for individual accounts.
If you’re a teenager using Apple Cash Family, your parents can set limits on who you can send money to and how much you can request. It’s a great way to teach kids about digital money without giving them a wide-open credit card.
Security and the "Is This a Scam?" Factor
Let's talk about the elephant in the room. When you request Apple Pay, is it safe?
Apple Cash is essentially a digital debit card issued by Green Dot Bank, Member FDIC. When you request money, the transaction is encrypted. Unlike a check, there’s no routing number or account number exposed.
However, scammers love "instant" payment methods.
Never request money from someone you don't know for a "deposit" on an apartment you haven't seen. Never "refund" someone who claims they accidentally sent you too much money. That’s a classic scam where they send money from a stolen card, you "refund" them your real money, and then the original transaction gets reversed by the bank. You’re left in the hole.
Stick to people you know. Friends, family, the guy who mows your lawn.
Why Apple Cash Beats Venmo and CashApp
Honestly? It's the integration.
Venmo is a social network disguised as a payment app. Do I really need to know that my cousin paid his landlord? No. CashApp is great, but it’s another thing to manage.
Apple Cash is part of the OS. When you receive money from a request, it sits in your Wallet. You can use it instantly to buy groceries at Trader Joe’s or gas at Shell. You don't have to "transfer to bank" and wait 1-3 days (unless you want to). It’s just... money. Available everywhere Apple Pay is accepted.
And if you do want it in your bank? The "Instant Transfer" feature works via your debit card for a small fee (usually 1.5%), or you can do the ACH transfer for free, which takes a couple of days.
Troubleshooting Common Issues
"I sent the request but they didn't get it."
Check your internet. Check theirs. If they have "Filter Unknown Senders" turned on in their message settings, and you aren't in their contacts, your request might be sitting in a junk folder they never look at.
Another weird glitch: Apple Cash is only available in the U.S. for now. If you're trying to request money from your friend in London or Toronto, it won't work. You’ll need to use something like Wise or Revolut for international stuff.
Also, make sure your iOS is updated. If you're running some ancient version of iOS from 2019, the buttons might not be where I said they are. Apple likes to move things around in their annual updates.
👉 See also: How to Make a Table in Desmos: What Most People Get Wrong
Actionable Steps to Get Paid Today
Stop waiting for people to "remember." People are busy and forgetful.
First, go into your Wallet app and ensure your Apple Cash card is active. If it asks you to "Set Up," follow the prompts—it takes about thirty seconds.
Next, find that person who owes you money. Don't send a long, apologizing text. Just open the iMessage, hit the Apple Cash icon, type the amount, and hit Request.
If they ask how to pay it, tell them to just tap the bubble in the chat. Most people find it easier than logging into a separate banking app anyway.
If you are a merchant, look into Tap to Pay on iPhone. This allows you to accept Apple Pay (and other contactless payments) directly on your iPhone without any extra hardware. No Square reader needed. You just enter the amount, show them your phone, and they tap their card or phone against yours. It’s the ultimate way to request and receive payment on the fly.
The money goes to your Apple Cash card. From there, you can pay your own bills or sweep it into your savings account. Simple. Clean. Done.