I replied on email list:

Hello Merlijn,

I can replicate the problem and I can work around it by using a faster
internet connection.

At some point, tcp connections have to time out. I can only replicate
the issue when that timeout is reached. If you have the means to
relocate to a faster internet connection temporarily for pushing to
charmstore, please do. You might also try recompressing any items in the
charm using a higher compression level. xz -9 instead of gzip -3 or
whatever things may be using now.

We are aware this is a poor longterm solution. We are investigating
better solutions for uploads. As you've mentioned, resources will also
help the situation.

I am sorry that I do not have a better solution.

-------

The timeout is apache setting `Timeout` which defaults to 300. It is
likely squid and/or haproxy also have a similar timeout. We cannot
support arbitrary large file uploads at arbitrary low speeds without
exhausting TCP connections. It seems we may wish to state 200MB as a
practical charm size limit.

** Changed in: charm (Ubuntu)
       Status: New => Confirmed

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https://bugs.launchpad.net/bugs/1592822

Title:
  Charm push crashes when pushing 'big' charm.

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