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jesseendahl

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i don't speak for my current or prior employer(s) - all posts are my own personal opinions.

https://twitter.com/jesseendahl

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www.wyden.senate.gov 4mo ago

The Government Surveillance Reform Act of 2026 [pdf]

jesseendahl
9pts2
blog.millerti.me 1y ago

Password managers aren't replacements for passkeys

jesseendahl
4pts1
developer.apple.com 4y ago

Meet passkeys

jesseendahl
1pts0
devd.me 4y ago

Early Security for Startups

jesseendahl
3pts0
www.wsj.com 6y ago

VC-funded startups may not qualify for Covid-19 “CARES Act” small business loans

jesseendahl
1pts0
medium.com 7y ago

On DEP, MDM, device identity, and authentication

jesseendahl
10pts0
blog.fleetsmith.com 9y ago

Introducing Fleetsmith Free and New Security and DevOps Catalog Apps

jesseendahl
10pts1
blog.fleetsmith.com 9y ago

Introducing Fleetsmith: Mac fleet management for everyone

jesseendahl
16pts0
www.washingtonpost.com 10y ago

Apple and Dropbox state they're against CISA bill ahead of crucial vote

jesseendahl
4pts0
www.apple.com 11y ago

iOS Security White Paper [pdf]

jesseendahl
3pts0
action.eff.org 13y ago

EFF Action Form -- Tell Congress: Stop Mass Surveillance

jesseendahl
4pts0
www.subfurther.com 14y ago

App Rejections Are a Lousy Way to Communicate Policy Changes

jesseendahl
2pts0
bittorrent.org 14y ago

Merkle Tree Hashing & BitTorrent

jesseendahl
1pts0
www.macrumors.com 14y ago

iPad 3 LCD Under Microscope Reveals 2048x1536 Retina Display

jesseendahl
20pts2
www.wired.com 14y ago

Apple’s Secret Plan to Steal Your Doctor’s Heart

jesseendahl
2pts0
bullishcross.com 14y ago

Apple: The Most Undervalued Large-Cap Stock in America

jesseendahl
3pts0
www.youtube.com 14y ago

Time-lapse Video from Space: Earth at Night [HD]

jesseendahl
1pts0
sunlightfoundation.com 14y ago

Save the Data In the Senate

jesseendahl
1pts0
digitaldueprocess.org 14y ago

Digital Due Process: Modernizing Surveillance Laws for the Internet Age

jesseendahl
1pts0
www.nytimes.com 14y ago

The New Generation of Microbe Hunters

jesseendahl
1pts0
glassboard.com 14y ago

Glassboard: Private Sharing for Groups

jesseendahl
9pts1
boingboing.net 14y ago

BART police officers website hacked, database released

jesseendahl
1pts0
ssd.eff.org 15y ago

EFF: Surveillance Self-Defense (SSD)

jesseendahl
36pts8
www.nytimes.com 15y ago

Debit Card Fees Prompt a Push Near Deadline

jesseendahl
1pts0
www.nytimes.com 15y ago

Rivals to the iPad Say This Is the Year

jesseendahl
1pts0
io9.com 15y ago

2000 Vs. 2010: How the world has changed

jesseendahl
2pts0
www.apple.com 15y ago

iPad + Velcro

jesseendahl
1pts0
mediadecoder.blogs.nytimes.com 15y ago

F.C.C. Approves Net Rules And Braces For Fight

jesseendahl
2pts0
www.nytimes.com 15y ago

Quantum Computing Reaches for True Power

jesseendahl
4pts0
www.nytimes.com 15y ago

Fed Will Buy $600 Billion in Debt, Hoping to Spur Growth

jesseendahl
3pts2

I don’t see hardware tokens (like Yubikey) in the list. Those are the only ones that provide a true second factor

passkeys are not meant to be a second factor; they are meant to replace the password as a primary factor.

to protect against the theft or compromise of your primary device.

I love Yubikeys, but the only additional protection you get by making the passkey hardware-bound is preventing an attacker who has already compromised your operating system from stealing the credential.

But! Unless you are also doing hardware binding of the session (aka cookie) after sign-in, then doing hardware binding of your credential is mostly security theater, because the attacker can just wait for you to sign in and then steal your session.

And there is standards work happening separately for hardening session security, such as DBSC: https://w3c.github.io/webappsec-dbsc/

I have no idea if Yubico is involved with DBSC, but I would hope that they are, because it would help them make Yubikeys live up to the security guarantees that I personally feel are heavily implied by their marketing.

There are some parts of this that are correct and other parts that are incorrect:

1. The idea was to provide a phishing resistant authentication method for enterprise users (companies loose quite a lot of money to phishing).

This is incorrect. The idea was to provide a phishing resistant primary factor that could compete with the usability of passwords to the point that consumers would actually want to adopt it.

2. Majority of industry players shared the vision of a credential which is available across the platforms and browsers

This is correct/accurate.

3. The vision for collaboration never materialized so everyone went their own way to implement it. Examples would be google rolling out browser (Chrome) managed authentication which led to this situation where even on the same machine you have to remember which browser you used to create the Passkey credential.

IIRC at least Chrome's default on Apple platforms is to save to the Passwords app by default. There are then multiple fallback options in the case that the user isn't using the default credential provider -- ultimately falling back all the way to cross-device passkey sign-in (the QR-code initiated sign in) or Security Key.

The security engineering behind the QR-code cross-device sign-in stuff is interesting: https://www.corbado.com/blog/webauthn-passkey-qr-code#4-pass...

That said, I strongly agree that fragmentation of where passkeys get saved is super confusing and I wish there:

(a) was stronger guidance from the FIDO alliance on both educating users that it's totally fine to have multiple passkeys across different ecosystems (e.g. one in Apple, one in Google), and;

(b) that all the credential managers could figure out a better way to place nice together and make it super clear to the end-user where a passkey is getting stored, what context it's for (e.g. personal vs. work), and actively help them store it in the right place (which might be different credential manager app for personal vs. work!).

4. Interestingly enough the earlier popular name was WebAuthn, Apple started calling it Passkey on fly, given Apple's popularity everyone just caved in.

This is incorrect -- passkeys are not just another name for WebAuthn. If you go back and look at the original definition Apple gave for the word passkey, you'll find that it was meant to be a discoverable WebAuthn credential that syncs across a user's devices with end-to-end encryption. There was a bunch of industry thrash around the definition, but it seems like the original Apple definition has largely stuck/settled now, and when passkeys don't sync they're typically called "device-bound passkeys" rather than just "passkeys".

5. My personal interpretation is that in some sense Apple wanted to be the default password manager on Apple devices.

If you go back and watch the original passkeys announcement from Apple, their stated goal was to create something that is both a better user experience and more secure than passwords. By "better user experience", they meant the act of creating credentials and then repeatedly using those credentials (logging in).

Part of actually achieving that goal means there needs to be something that "just works automatically out of the box" which means there needs to be a built-in credential manager. That said, Apple credential manager had already existed for many many years by the time passkeys came around. The only thing that changed was instead of being solely accessible from inside System Settings (which was hard for the average user to find), the functionality moved into a standalone Passwords app.

6. This is when all password manager companies jumped in strongly to save their business and the protocol went into a direction where you can use your existing password manager to store the credential/Passkey as well

I think it's a huge positive that all the password managers jumped on board, and that they could jump on board (since WebAuthn is an open standard). I think this is a good thing for consumer choice and for overall adoption and perception of passkeys. A lot of folks (including on this thread) have big tech lock-in conspiracy theories about passkeys, and the conspiracy theories would be even more prevalent without a wide spectrum of consumer choice for credential managers.

If you are using it with security in mind then my recommendation would be to use a hardware backed security key with NFC enabled. Everything else is pretty much lipstick on pig, they are worse than passwords in some sense from usage perspective.

Passkeys protect against phishing attacks, and you get that protection regardless of whether the credential is hardware-bound or not. That protection comes from the cryptographic binding of the credential to the domain at the time of credential creation.

The only additional protection you get by making the passkey hardware-bound is preventing an attacker who has already compromised your operating system from stealing the credential. But! Unless you are also doing hardware binding of the session (aka cookie) after sign-in, then doing hardware binding of your credential is mostly security theater, because the attacker can just wait for you to sign in and then steal your session.

And there is standards work happening separately for hardening session security, such as DBSC: https://w3c.github.io/webappsec-dbsc/

This is the #1 most common misconception I see about passkeys. They do not make it more likely that you will lose access to your accounts. They actually have nothing to do with account recovery. They are just a stronger primary factor than a password.

Most providers continue to offer email-based recovery in the case that the end-user loses access to their primary factor, regardless of whether the primary factor is a password or a passkey.

And email based account recovery does not make the security advantages of passkeys disappear, which are:

- credential that's guaranteed to be unique

- credential that's guaranteed to be strong

- credential that cannot be phished (due to cryptographic binding to the domain at the time of credential creation)

- changes the incentives for compromising servers (there's nothing worth stealing from the server -- only public keys)

- if/when an app/website transitions to retiring password-based authN, then it will entirely eliminates credential stuffing attacks

And if the account recovery scenario in question is your Gmail or Apple account, then you would need to go through their account recovery flows regardless of whether you were using a password or a passkey:

https://support.google.com/accounts/answer/7682439?hl=en https://support.apple.com/en-us/118574

Passkeys and 2FA are a usability nightmare if you need to recover, or all the security vanishes if you put usable recovery mechanisms for the passkey or the second factor.

Most providers continue to offer email-based recovery in the case that the end-user loses access to their primary factor, regardless of whether the primary factor is a password or a passkey.

And email based account recovery does not make the security advantages of passkeys disappear, which are:

- credential that's guaranteed to be unique

- credential that's guaranteed to be strong

- credential that cannot be phished (due to cryptographic binding to the domain at the time of credential creation)

- changes the incentives for compromising servers (they're nothing worth stealing from the server -- only public keys)

- if/when an app/website transitions to retiring password-based authN, then it will entirely eliminates credential stuffing attacks

Which defeats part of the point of passkeys in the first place in that they are supposed to be device-bound

If you watch the original Apple WWDC talk presenting passkeys, you will find that they were always intended to sync, at least for the consumer use-case.

What you are describing is how the WebAuthn standard had been implemented by Yubico and Google up until the point of the introduction of “passkeys” by Apple.

The reason passkeys have their own name and definition is because they are meant to be a phishing-resistant primary factor that competes with the UX of passwords. And a great usability trait of passwords is that they’re convenient to use across all your devices. With a technology involving public/private keypairs, the only possible way to compete with that UX is to sync the private key across the user’s devices.

This part of their requirements for how PCC is architected directly addresses your concern:

“Verifiable transparency. Security researchers need to be able to verify, with a high degree of confidence, that our privacy and security guarantees for Private Cloud Compute match our public promises. We already have an earlier requirement for our guarantees to be enforceable. Hypothetically, then, if security researchers had sufficient access to the system, they would be able to verify the guarantees. But this last requirement, verifiable transparency, goes one step further and does away with the hypothetical: security researchers must be able to verify the security and privacy guarantees of Private Cloud Compute, and they must be able to verify that the software that’s running in the PCC production environment is the same as the software they inspected when verifying the guarantees.”

This story was recently on first page of HN:

https://techcrunch.com/2026/03/18/fbi-is-buying-location-dat...

This is the bill referenced at the end of the TechCrunch article:

Last week, Wyden and several other lawmakers introduced a bipartisan, bicameral bill called the Government Surveillance Reform Act, which among other things would require a court-authorized warrant before federal agencies can buy Americans’ information from data brokers.

Previous HN discussion about the TechCrunch story: https://news.ycombinator.com/item?id=47430797

Passwords are terrible UX for old people in my experience. They try use the same password everywhere, but then password complexity requirements mean they can't use the exact same password everywhere, and then they forget which variant they used on which service, so they just end up going through the reset password flow every time they sign in. I am not convinced that's a better UX than them just using their fingerprint or face to login.

They bind you to your device/iCloud/Gaia account so if it gets stolen/banned you're out of luck

This is the biggest myth/misconception I see repeated about passkeys all the time. It's a credential just like your password. If you forget it, you go through a reset flow where a link is sent to your email and you just setup a new one.

And if it happens to be your Gmail account that you're locked out of, you need to go through the same Google Account Recovery flow regardless of whether you're using a password or a passkey.

I am not sure if you missed my earlier comment, but it's directly applicable to this point you've repeatedly made:

If Apple believes this class of attack is no longer viable, that’s worth stating.

To say it more directly this time: they do explicitly speak to this class of attack in the keynote that I linked you to in my previous comment. It's a very interesting talk and I encourage you to watch it:

https://www.youtube.com/watch?v=Du8BbJg2Pj4

Both of the major smartphone companies (Google and Apple) have pretty robust account recovery processes. Are you familiar with all the options they have? Your comment gives me the impression that you are making assumptions about what would happen, instead of doing research on how it actually works.

I experienced Google's recently and it was very robust.

Even before passkeys, the average user would have major problems if Apple and Google didn't have good account recovery processes.

There's nothing different about using a password vs. a passkey that makes it easier or harder for vendors to lock you out. I am not sure where this misconception comes from.

Whatever process a vendor requires someone to go through in order to gain access to someone's account when they pass away remains the same whether the user previously used a password or a passkey to login.

Are you aware of any vendor that actually does have differing policies based on the account's login credential type? I'm not aware of any.

(1) is already true today. There is no way for services to enforce whether a passkey is stored in software or hardware.

(2) I understand you don't like the user experience. But to make a technical clarification: requiring a user action to prove there's a human involved in the login action (e.g. by clicking a button in UI or requiring Touch ID) does not necessarily mean there's another factor involved at all (MFA). What you are describing is more of a "liveness check" than a separate factor/separate credential.

In theory any code could be written at any time that does something good or bad. Sure.

But in reality, the people who actually work on these standards within the FIDO alliance do not want a world where every website/service makes arbitrary decisions on which password managers are allowed. That would be a nightmare.

The primary credential a user relies on for logging in (whether it's a password or a passkey) is pretty unrelated to the the "lockout issue". The lockout issue is really the age old question of: what happens if I can't do a normal email-based account recovery flow (aka "I forgot/lost my password/passkey").

The answer to that is stuff like this:

https://blog.google/technology/safety-security/recovery-cont...

https://support.apple.com/en-us/102641

I legitimately wish there was an option for: "I show up for my appointments 100% of the time and I'll agree in advance to pay a giant fee if I ever don't show up, if you promise not to bother me with appointment confirmations every time".

all the encryption in the world does not matter if either end of the conversation is confiscated or pwned by adversaries.

Yes of course, but it's not so simple to bypass the hardware-enforced protections that exist both device side and server side. As far as I can tell, it seems effort was made to design/architect everything in such a way such that the protections can't be retroactively circumvented even under legal compulsion.

Disclosure: I previously worked for Apple, but not on the design/implementation of any of this stuff and this is all my own opinions, not those of Apple.

No it doesn't — that's a totally different threat model.

Advanced Data Protection is mostly concerned with protecting data from attackers on the server and in transit.

If you're interested in protections when an attacker has physical access to your device, you should read the "Encryption and Data Protection" section of Apple's Platform Security Guide.

Web: https://support.apple.com/guide/security/welcome/web

PDF: https://help.apple.com/pdf/security/en_US/apple-platform-sec...

This is not just encryption in transit or simplistic client-side encryption.

It is end-to-end encryption, where each device's key generation is handled by your phone's Secure Enclave.

This article is a decent starting point in terms of what Advanced Data Protection is:

https://support.apple.com/en-us/102651

If you want a deeper dive into the security engineering of iCloud Keychain, the second half of this Blackhat talk by Apple's head of Security Engineering & Architecture (SEAR) is really great:

Synchronizing secrets: https://youtu.be/BLGFriOKz6U?si=cY94TYo28bRj4G7y&t=1357

except for MDM devices where the MDM profile can allow attestation for RP domains on an opt-in basis.

And even then, the attestation you get in that scenario is just an attestation that the passkey was created on a managed device. It is not a hardware/device attestation.