Cannot connect via SSH (Failed to connect: Session operation has timed out)


Hello everyone, I have started using Duplicati after CrashPlan’s end of life notice and have run into a problem connecting to a server via SSH.

I have Computer A (Windows 7, 64 bit) and Computer B (Windows 7, 32 bit) that I would like to back up to each other. Both have OpenSSH installed (Install Win32 OpenSSH · PowerShell/Win32-OpenSSH Wiki · GitHub) and I have been able to successfully connect to A (from B) and B (from A) via WinSCP. In WinSCP, I’m able to read/write files with no issues.

Using Duplicati, Computer A can connect to Computer B via SSH and backup fine. Unfortunately, Computer B cannot establish a connection to Computer A – the error message given at configuration is “Failed to connect: Session operation has timed out.”

I have checked my settings in Duplicati and Windows Firewall and everything appears to be the same on both Computers with the exception of the destination/credentials for each server. I can’t figure out what I’m doing wrong, so your feedback/suggestions are greatly appreciated. Thank you!


Hello @DL38, welcome to the forum!

While it is unfortunate that Duplicati doesn’t have a built in point-to-point backup feature like CrashPlan did, it sounds like you’re going about putting together your own solution correctly.

Are computers A and B on the same network or is this going over the internet?

Depending on your Duplicati version you could try adding --verbose=true to your job and try running it from the command line. Or using --log-file=<path> and --log-file-log-level=profiling to get a file full of detail…

Oh, and do your firewalls and ssh servers have their own logs you could check just to see if they register an incoming connection?

I realize OpenSSH is not the same as WinSSHD, but when you set up your OpenSSH servers, did you use any of the info from this #howto topic?