Same problem here. Here are my observations, which match the behavior
already described.

- To reproduce: Insert YubiKey, start Chromium, attempt login (nothing happens 
when tapping on YubiKey), replug YubiKey, attempt login (now it works).
- It works when done in this order: Start Chromium, go to 2FA login page (where 
Chromium asks user to tap on YubiKey), plug in YubiKey, confirm login (by 
tapping on YubiKey).
- Emitting the udev event instead of replugging works too.
- It seems to be important that Chromium already attempted to use YubiKey 
before YubiKey is actually plugged in. (Inserting YubiKey after Chromium is 
started but 2FA login page has not yet been visited gives the same result as 
when YubiKey is inserted before Chromium is started.)
- After first login it works reliably until Chromium is restarted.
- After installing Ubuntu 20.10 (clean install) I could not reproduce the 
problem for a few days, then it broke again. There was an update of the 
Chromium snap at this time, I suspect that that is what broke it again.
- dmesg shows several apparmor denied messages when accessing a site that 
attempts to use YubiKey:

[Sun Nov 22 10:10:11 2020] audit: type=1400 audit(1606036212.912:264): 
apparmor="DENIED" operation="open" profile="snap.chromium.chromium" 
name="/run/udev/data/+thunderbolt:domain0" pid=45717 comm="ThreadPoolForeg" 
requested_mask="r" denied_mask="r" fsuid=1000 ouid=0
[Sun Nov 22 10:10:11 2020] audit: type=1400 audit(1606036212.912:265): 
apparmor="DENIED" operation="open" profile="snap.chromium.chromium" 
name="/run/udev/data/+thunderbolt:0-0" pid=45717 comm="ThreadPoolForeg" 
requested_mask="r" denied_mask="r" fsuid=1000 ouid=0
[Sun Nov 22 10:10:11 2020] audit: type=1400 audit(1606036212.912:266): 
apparmor="DENIED" operation="open" profile="snap.chromium.chromium" 
name="/run/udev/data/+thunderbolt:0-101" pid=45717 comm="ThreadPoolForeg" 
requested_mask="r" denied_mask="r" fsuid=1000 ouid=0
[Sun Nov 22 10:10:11 2020] audit: type=1400 audit(1606036212.912:267): 
apparmor="DENIED" operation="open" profile="snap.chromium.chromium" 
name="/run/udev/data/+thunderbolt:0-1" pid=45717 comm="ThreadPoolForeg" 
requested_mask="r" denied_mask="r" fsuid=1000 ouid=0
[Sun Nov 22 10:10:11 2020] audit: type=1400 audit(1606036212.968:268): 
apparmor="DENIED" operation="open" profile="snap.chromium.chromium" 
name="/run/udev/data/c511:0" pid=45717 comm="ThreadPoolForeg" 
requested_mask="r" denied_mask="r" fsuid=1000 ouid=0

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Packages, which is subscribed to chromium-browser in Ubuntu.
https://bugs.launchpad.net/bugs/1884759

Title:
  U2f yubikey stopped working in chromium snap

Status in chromium-browser package in Ubuntu:
  Confirmed

Bug description:
  I was previously using u2f from yubikey in chromium snap, but now it doesn't 
work.
  No apparmor deny in dmesg (except accessing bluez), u2f slot is conneced.
  U2f still works in firefox installed as deb.

  # snap connections chromium | grep u2f
  u2f-devices               chromium:u2f-devices               :u2f-devices     
               manual

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