@mfonville, I can't figure this out really well. Could you try removing the read deadline from watchdogConn:

func (c *watchdogConn) Read(b []byte) (n int, err error) {
-	c.SetReadDeadline(time.Now().Add(c.timeout))
	return c.Conn.Read(b)
}

the, issue go install, and see if that works for you?

Even if that works, that doesn't mean we're done, we have to figure out why this is going wrong. The read/write deadline should be 1 minute. Can you time that this is the case? (Does it take ~1 minute or more for the program to fail?)

Sorry for my slow response, a bit short on time.

I don't know really how long it did take to fail, because all calls to github-release are done through some shell scripts on a server.

I think the best approach would be to set-up a script that does do some testing.

Make a test repository, create some relatively large files, and try to repeatedly upload them to spot for if any errors occur.
A bit like:

export GITHUB_TOKEN="xxxxxxxxxxx"
export GITHUB_USER="testuser"
while github-release upload -r "testrepo")" -t "testtag" -n "bigfile.zip" -f "bigfile.zip" -R; do
   # print some timestamps or other useful debug context
   sleep 60
done