Thanks everyone for the replies. Here are some more details and answers to some of the questions people have responded with 1. It's hanging on the same file every time, but it will transfer a bit more each time if I let the rsync timeout and then start it over (I'm using rsync's partial file support). The strange thing is that the "delta" of data is different each time; that is, it's not like it hangs after sending 2MB each time. Sometimes it send 8MB before hanging, sometimes it hangs after 1MB. The really strange thing is that if I compare the file size the rsync reports sending vs what the file system on the remote side reports they don't match up. Some of that may be unflushed buffers... 2. There are other files that are the same size or slightly larger that transfer fine 3. I've tested the integrity of the file. These are Dar (backup utility) archives and when I run the archive integrity check this file is passing. 4. The remote side has large file support enabled. In any case, the transfer starts hanging around the 200MB mark One of the interesting things to me is that I see the same behavior when I use SCP and rsync; as far as I can gather, the only thing these two have in common is that they use an SSH channel for data transfer. Mark's comment about an older version of OpenSSL and OpenSSH is interesting. If I have time I'll try to build older versions to see if that makes it work. Is there any way to get SSH to log packets or do some other low level debug logging? Thanks, Derek