I think the “multiple devices on different platforms” question is the most confusing user-facing part of the whole passkey design. Different software will “compete” to hold & serve passkeys:
- Your password manager(s)
- Your web browser, especially Google Chrome
- Your operating system, via its own sync mechanism (like iCloud Keychain or Windows Hello)
- Your operating system, delegating to a separate hardware device like a USB YubiKey
Even worse, each of these can decide how well they work with the other handlers… your password manager, for example, may or may not decide to ask you “Do you want to use the passkey I have, or check the web browser or OS one on your own?” (then passes it on)
If you don’t really remember where you saved it, there is no easy way to find it again either, except to keep passing through from one layer to the next in the hopes that one of them answers with “Oh yeah, I have a passkey for this site!” before the prompt times out. If you forget to unlock your password manager, for example, it might not even show you that and the OS will just go “nope, no idea” and make it look like you have no passkey for that site at all.
These different vendors are incentivized to not play nice with the other ones, because each one creates an opportunity to strengthen vendor lock-in. Apple wants you to keep using iCloud Keychain, because it works well between Macs and iPhones and iPads and such, especially if you’re in Safari. Once you add other companies into the mix… it gets a whole lot more fiddly and unpredictable. I use 1password between Android, Windows, and Mac, and my passkeys are something like 70% reliable. But every week or so, I need to fall back to passwords because the setup just didn’t work right for some app or site.
Different websites can also choose whether they accept the syncable kind of passkey, or only the hardware-tied ones, or only the USB security-key ones. So even if you like your password manager or Windows Hello, you might not be allowed to use it for some specific passkeys, even if it works for most of them.
I wasn’t sure about any of this, myself, and I did eventually ask AI for an explainer: Claude’s Passkey Field Guide
Honestly, it’s all really confusing… good for the companies (website owners) who want stronger security, but horrible user experience for any normal person who isn’t all-in on a single-vendor ecosystem (e.g. all Apple).