There still doesn't appear to be a pattern to this, but I can definitely
tell the difference between when it works and when it doesn't.

When sudo 'works', I put in the incorrect password (which I do a lot
because I have many different passwords), it tells me;

Sorry, try again.

When sudo doesn't 'work', I put in the password, and it doesn't give any
error or message, simply drops to the next line and asks for the
password again.  It will do this twice (i.e. I type my password 3 times)
it will then give me the;

Sorry, try again.

Message.

I have Winbind installed and configured on this machine, to authenticate
on a Domain, although when this happens I'm authenticating locally.
Maybe that could be causing this issue?

-- 
sudo will not authenticate when trying to apt-get
https://bugs.launchpad.net/bugs/104787
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