I managed to get the rdesktop resize to fail by reszing again as it was handling the first resize. It reconnected properly, but it screwed up the authentication cookie somewhere along the line. I got this on stderr: > WARNING: Automatic reconnect using cookie, failed. One guess is that we disconnect for a resize even if we haven't yet gotten a new cookie since the last connection. Might need to add a delay there to handle the race.
Note that this only applies when connecting to Windows Server 2008 R2 or older. For newer Windows Server versions we now use a new protocol that allows for "online" resize. This means that the cookie isn't used for resize.
We added some tweaks to avoid rapid reconnects recently, so this shouldn't be a problem anymore.