Sorry for the delay. It does not look like you enabled the debug.conf
override, which I need to see more detail about what wait-online is
doing. However, testing a similar setup locally, it seems that the
override is doing what you want it to do (i.e. add additional wait for
ipv6). Note, for the record, that your drop-in adds an additional
invocation of systemd-networkd-wait-online -- it does not override the
existing one (maybe you already know that).

I am wondering if networkd is reporting the link as configured after
*one* of the addresses is configured, but not both. That could create
the slight race we are seeing here. I will keep looking.

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https://bugs.launchpad.net/bugs/2081645

Title:
  (during boot) failed: Cannot assign requested address

Status in systemd package in Ubuntu:
  Incomplete

Bug description:
  Not sure where to post this, but since systemd controls boot
  precedence this section seems appropriate.

  I am testing oracular / 24.10 , and I bind some services to specific
  IPv6 addresses. In order to wait until the IP addresses are up before
  binding to them during boot, I use systemd-networkd-wait-online,
  modified to wait for IPv6.

  The problem is, despite systemd-networkd reporting the IPv6 addresses
  are up, binding to them still fails when the daemons attempt to
  launch. If I manually start the daemons after boot, they launch fine.

  It would appear the system is reporting IPv6 addresses as available
  before they are ready to be bound to by applications, therefore
  causing those application to fail during boot.

  Log attached.

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