I have been experiencing similar problems in pattern lists but only
noticed because I could not get the negating function to work - in the
man page it says:

"Patterns within pattern-lists may be negated by preceding them with an
exclamation mark (`!')"

So I was trying to do this sort of thing:

Host "!20.*.*.*"
    ProxyCommand nc -X connect -x 20.44.34.33:8118 %h %p

This should use the proxy for anything not on my 20 network but it just
gets ignored.

When are we likely to see this in a Ubuntu distro? Now that a huge
number of people in big corporates are working behind proxy servers and
using the Cloud via ssh I would suggest this is a critical issue that
will hurt Ubuntu takeup.

-- 
~/.ssh/config does not handle multiple hosts correctly
https://bugs.launchpad.net/bugs/306430
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