I have a issue copying the file using scp between two hosts over VPN. One host is Ubuntu Linux Server(v9.10) which is a physical machine, and another is also Ubuntu Linux Server but which is virtual machine on the vSphere ESXi 4.0. Those two hosts are connected over VPN which can be connected with a private network address such as 192.168.0.4 and 192.168.10.10. In addition, those two hosts have global IP address too respectively.

In the above situation, when I try to copy the file between those two hosts using global IP address, I can finish the command successfully. However, when I try to copy the file using private address like

tahko@192.168.10.10> scp test.pdf 192.168.0.4:/tmp/

the scp starts, but it doesn't finish successfully. everytime, the scp status becomes 100% but does not finish. (the remote host waiting for the FIN packet, but it seemed to be timeout..)

all the other TCP protocols such as SMTP, POP, IMAP, DNS, WEB work well between two hosts and ssh command also works well. only scp does not work well...

Strangely, when I try the copy with very small file less than 1KB, the SCP will finish successfully.

In addition, between two physical machine(not virtual machine), the scp will finish successfully over the VPN even if the file is much larger over 10MB, which means that the VPN accept to transmit the large file. I think I should do something to the Virtual Machine on ESXi or ESXi itself. I need some help for this issue. Thank you in advance.

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Maybe related to MTU: unix.stackexchange.com/questions/14187/… – quanta Aug 13 '11 at 8:13
I second the MTU possibility. You should grab some packet captures on the source and dest and see if that is the issue. – polynomial Aug 21 '11 at 20:09
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migrated from stackoverflow.com Aug 12 '11 at 18:47

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