The biggest mistake I see developers make is treating these three as alternatives when they're actually complementary pieces of a payment infrastructure. After integrating all three in production systems, here's what each one actually does when the rubber meets the road.
Stripe: When You Need Money to Actually Move
Stripe processes credit card payments and doesn't fuck around about it. With $1.4 trillion processed in 2025, they've earned their spot as the least-broken payment processor on the planet.
Their Optimized Checkout Suite actually works. The fraud detection catches real fraud instead of flagging your biggest customer as suspicious. Apple Pay integration doesn't randomly break in Safari. And when something does go wrong, their error messages tell you what's actually broken instead of generic "please try again" bullshit.
What breaks: Rate limits. During our Black Friday sale, we hit 2.3x normal traffic and got throttled. Stripe's ML fraud detection occasionally flags legitimate B2B transactions as suspicious because apparently buying $50K of enterprise software looks sketchy. Their Connect 7-day rolling reserve can freeze significant cash during growth spurts without warning - we had $73K tied up during a product launch.
Timeline reality: Basic checkout in 2-3 days. Marketplace payments with Connect? 2-3 months, not 2-3 weeks like their docs suggest. The "simple" payment feature took us 6 weeks to build and still randomly fails on Fridays.
Plaid: The Necessary Evil of Bank Connections
Plaid connects your app to over 12,000 banks when those banks aren't having one of their surprise maintenance windows. They handle OAuth flows that would otherwise make you quit fintech entirely.
Their August 2025 updates include faster OAuth onboarding and DMV-backed identity verification. The new progress bars in Link actually reduce drop-off rates by showing users how many steps are left. Small improvements, but they matter when 20% of your users abandon the flow.
What breaks: Everything, but predictably. Chase and Wells Fargo connections fail 40% of the time in production. iOS Safari OAuth redirects break randomly - 15-20% of iOS users can't complete Link flows because Safari decides to block the redirect. Bank maintenance windows happen every Friday at 5pm, dropping your connection success rate to 40%.
The Friday Problem: Never demo payment flows on Fridays. Some major bank always decides to do maintenance, your user onboarding drops to shit, and you spend the weekend explaining to customers why "the app is broken" when it's actually First National Bank of Nowhere doing their weekly server restart.
We built manual sync capabilities because Plaid's webhook delivery stops during bank maintenance with no notification. Just silence. 20% of connections need re-authentication within 90 days, and users blame your app when their transaction data stops syncing.
Dwolla: ACH Done Right (Eventually)
Dwolla specializes in account-to-account transfers and they're actually good at it. Their FedNow integration from July 2025 adds instant payment capabilities alongside existing RTP support. Processing times went from "whenever ACH feels like it" to "within seconds" for supported institutions.
ACH is cheap but slow as fuck - customers expect Venmo speed but get 1970s banking reality. Same-day ACH helps but costs more and has cutoff times. Regular ACH takes 1-3 business days, and ACH returns can screw you up to 60 days after you thought the payment worked.
What breaks: Everything takes longer than expected. Integration complexity is brutal - their compliance requirements mean 2-4 weeks minimum setup time. Their webhook system had delivery issues that took our team 3 months to work around. ACH transfers fail mysteriously on Fridays because banks are allergic to weekends.
Hidden gotcha: ACH return codes are a special kind of hell. R01 "Insufficient Funds" can show up weeks later. R03 "No Account" means you validated an account that was closed between verification and transfer. Always build retry logic or prepare for angry support tickets.
The June 2024 Open Banking integration with Visa and MX helps with instant account verification, but the setup process still requires enterprise sales calls and custom pricing negotiations.