My work switched our passwords from minimum 8 digits of upper, lower, numeric and special (requires all 3 present) to a passphrase.

Now its 21 minimum but requires upper, lower and numeric. I guess at least I don't have to stick an exclamation on the end.

One major flaw in this approach is the one-way channel (keyboard input) prevents the password manager from knowing if it is supplying credentials to the correct recipient. Phishing attacks are relatively common and users expect a password manager to know these things, even in situations like you have described where it’s clearly impossible. I think this is why this approach hasn’t succeeded in the marketplace and FIDO2/WebAuthn support seem to be table stakes.