I'm not sure you have answered my question. Can you connect to that WinSRV2003 using any other SFTP/SSH client from the same machine, where you are trying WinSCP? If you can, post both WinSCP and the other client's log files.

Hey, thanks for the response.

Yes I can, got multiple Linux distros and newer Win Servers 2016 and 2019. And ofc to other Win10 workstations.

I haven't worked with Win SRV 2003 so it's too old school for me. Got gpedit.msc configured that 22 port is open, but with no changes so far.

And I've tried also transferring files with simple copy paster with Remote Desktop Connection, but with no avail. I can perform this task from my work PC to other servers.

P.S. newbie administrator here.

Can you connect with any other client using the same protocol?

Hello.

I've got an issue, I can't connect to a Windows Server 2003 (VirtualMachine) trough WinSCP

Network error: Connection to xx.xx.xx.xx timed out

The target WinSRV2003 is online, I can connect via Windows Remote Desktop, I need to transfer files out from this server.

What should I check?