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Things I learnt about passkeys when building passkeybot

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A few weeks ago I had a bug with bitwarden where every passkey wanted to load from the macbook instead of bitwarden. I ended up being locked out of a few accounts that didn't have OTPs as a fallback. Mostly inconsequential stuff like Twitter.

I love passkeys, but they're still kinda hard to use. There's several sites that wont let you enroll multiple ones and it's easy for systems to step on each other like the aforementioned experience.

The problem is fallback. All my banking apps have SMS OTP fallbacks and that's no better than having only SMS OTP. If you're building these systems make sure you have good fallbacks. What matters in design is not so much how well it works when things go right but how well it works when things go wrong. With security you really cannot ignore edge cases

2 days agoby godelski

If I'm being honest, I regret every passkey I ever made. With my old flow, I knew when to use my Yubikey, when to use my OTP, and when to use SMS 2FA. With the new flow, these things say "use your passkey" and I don't know where in god's name I did this. If I did this on my iPhone in a WebUI that popped up when I followed a link to buy something, then it's never going to be on Chrome or Bitwarden.

I've decided to stop adding new ones. I'll just OTP 2FA. It's simple, reliable, and I can keep it in Bitwarden safely.

2 days agoby arjie

The scariest thing is the casual mention of the Digital Credentials API[1]. Forget passkeys, when you need government issued credentials to surf the net, the good times are over.

[1] https://developer.chrome.com/blog/digital-credentials-api-sh...

2 days agoby quantummagic

One thing I ran into recently when I played around with passkeys is the problem of orphaned keys. Basically if I log into a website using the passkey and then go to my account settings and remove that passkey then log out I have a problem. Now I can’t sign in but when I go to recover my account iOS/macOS will refuse to create a new passkey because one already exists for this website. So I have to go to my passwords list and manually remove it. I believe I was correctly using the JS API for signaling orphaned keys but the OS still wouldn’t remove it so it was a situation of having to educate the user to remove the orphaned key manually (and hoping the user doesn’t get confused and remove the wrong key). You also apparently can’t create more than one passkey for the same username and the same website. So if I initially create an account from my MacBook and the passkey gets listed as “MacBook”, I then go to log in from my iPhone and it still uses the “MacBook” passkey because of iCloud sync. But this is confusing because I cannot have an iPhone key.

Overall it’s not terrible but I think these edge cases are going to keep biting people and need to be addressed in some way. And yes I understand that I could use a Yubikey or Bitwarden or some such but the point was that I wanted to see how this flow works for “normal” users who just use the iCloud Keychain and the experience leaves something to be desired.

2 days agoby IgorPartola

Love these "lessons learned" posts, keep the coming!

My only feedback is about the Quickstart of passkeybot, "feed this example into a good LLM with these instructions". I undeerstand the idea, but I was a bit shocked that the first time I see these sort of instructions is for an auth framework.

3 days agoby BoppreH

Thanks for that!

I am in the middle of writing a passkey-driven server dashboard app (native SwiftUI app, with a small server component).

In the future, I would like to use passkeys as much as possible, but they do present a bit more friction to users than Sign in with Apple. When I was initially learning them I wrote this up: https://littlegreenviper.com/series/passkeys/

3 days agoby ChrisMarshallNY

The passkey spec authors think websites should be able to ban clients which allow users to manage their own data[1,2]. It makes me really hesitant to adopt passkeys if my client could get banned because it's open source and lets me control my client how I want to. It appears to be more useful for vendor lock-in than anything else[3]. A shame, since it could've been a cool tech if they had built it to be resilient to this kind of abuse, but it's clear they think vendor lock-in is actually a core feature of the protocol.

[1] Spec author quote: "To be very honest here, you risk having KeePassXC blocked by relying parties." https://github.com/keepassxreboot/keepassxc/issues/10407#iss...

[2] https://www.smokingonabike.com/2025/01/04/passkey-marketing-...

[3] https://fy.blackhats.net.au/blog/2024-04-26-passkeys-a-shatt...

3 days agoby coldpie

> generateKey is a JS API that allows you to create new key pairs, where the private key cannot be extracted similar to passkeys.

Is that "cannot be extracted" from JS only, or is this an actual device-locked, TPM/SEP-bound key like passkeys?

If it is, it seems kind of like the buried lede to me that there is a browser API that lets any website built its own completely unstandardized quasi-passkey system and lock the key to the current device.

3 days agoby xg15

In oauth2: when I /1 associate a random uuidv4 for each new flow with my user (server side), /2 stick that uuid into the state parameter, and then /3 look up my user with this on callback-endpoint execution. Isn't PKCE in that case redundant?

3 days agoby smallnix

How to add passkeybot support to your site, according to their official guide:

start

(1) Copy / paste example_http_server into your LLM of choice (use a paid/good model). (2) Prompt: Implement the HTTP handlers here for my project,..

Um, no? How about you give me real instructions on how to do it? I’m not going to delegate a security-critical task to an LLM. And since I need to review it carefully myself anyway, I might as well write it all by hand, right? Like, the whole premise is I just need to implement a couple of webhooks.

3 days agoby loloquwowndueo

> But much of the recommendations say to use the counter as a heuristic rather than evidence of a cloned authenticator because there are many legitimate reasons the counter can be wrong.

I'm curious on why there would be any legitimate reason for that. Security wise it should not happen, it's just some implementations being crappy or some bad practice like reusing same passkey with different devices ?

2 days agoby PunchyHamster

BTW, if you're looking for something minimal that you can self host, say for a home lab environment, I landed on Pocket ID:

https://pocket-id.org/

2 days agoby js2

Learning and building an outsourced security system at the same time ..... urgh.

2 days agoby wewewedxfgdf

i wish passkeys could replace passwords, not suppliment them

3 days agoby boombapoom

The authenticator GUI only shows “sign in to your_domain.com”. It never allows a more general “sign this content for your_domain.com”. E.g. “sign this transaction request to move £50 to Bob's account”.

That is why you should ship a pristine HTML+CSS+JS environment that can use subtle web crypto. YOU show what is being signed. And then the device can sign its hash using the secure enclave.

And you CAN do attestation even on consumer devices, by using the Device or AppAttest framework (I think that’s what it’s called). I did it myself in our app. It does show up 100% of the time but when it does it’s useful.

PS: being the web3 / blockchain geek that I am, I will tell you stuff that triggers anticryptobros on HN.

The Web3 ecosystem already has a standard called EIP712 for signing structured data. If you want to stick to standards, use that!

The secure enclaves all use P-256 (sometimes called R-256) while Bitcoin / Web3 uses K-256 (the Koeblitz curve, they distrust the NIST curve or whatever).

So that means you’re going to have to use Abstract Accounts and the new precompiled smart contracts to verify P256 signatures, which only Binance Smart Chain and a handful of other chains have deployed. Luckily BSC is the most widely used chain by volume and has plenty of money sloshing around so you can build your trustless programs there. If you want to be totally trustless — LET THE SMART CONTRACTS GENERATE THE CHALLENGE TO BE SIGNED BY THE AUTHENTICATOR. Then have it sign the temporary k256 public key (from the keypair) to use, as long as your session is open you can then add use your private key to sign transactions. As usual, do this for small amounts per day, transactions that move larger amounts should still require use of multisig keys etc.)

3 days agoby EGreg

Computerphile added a passkey video today https://www.youtube.com/watch?v=xYfiOnufBSk

3 days agoby QGQBGdeZREunxLe

Regarding PKCE, the way I remember it is that OAuth2 was deliberately designed to eliminate as much actual cryptography as possible, relying instead on same-origin and TLS security; PKCE is one of the few things that introduces an actual cryptography primitive.

3 days agoby tptacek