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We need to transfer thousands of small htm files up to a web server running IIS7.5 on Windows Server 2008R2. The files are grouped in folders, each folder containing from 200 to 500 files. Remote Desktop Connection's drag-drop isn't working very well for this. Often it gets stuck at "calculating" and never seems to progress. So we would like to enable SSH file transfer on the server.

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There is no native feature to "enable SSH file transfer." IIS includes an FTP server, which has an FTPS feature, but nothing for SFTP (which, as you're aware, is a sub-protocol of SSH.)

You'll have to find a 3rd-party SSH server that supports SFTP; there are free ones and commercial ones for Windows. This site isn't a good one to ask for product recommendations, please read the FAQ.

You could also enable WebDAV over HTTPS, and then you don't even need anything on the client more specialized than a browser, or even a mapped drive from a Windows machine to the WebDAV server.

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Thanks. Removed the phrase mentioning client software. – Tim Apr 12 '13 at 19:13
Is WebDAV more robust than Remote Desktop? – Tim Apr 12 '13 at 19:14
WebDAV is an extension to the HTTP protocol for more extensive file transfer capabilities. Remote Desktop is for remote viewing of Graphical User Session... So Apples and Oranges? – Chris S Apr 12 '13 at 19:28
Remote Desktop happens to have a channel that allows for file transfers, and you know that it's not very robust. WebDAV using HTTP GET and PUT (or maybe POST, not sure), and those seem to work pretty good. – mfinni Apr 12 '13 at 19:42

Any protocol is going hurt because you are initiating thousands of connections over a network link, and each one will have network-delays as it starts up. Also WebDAV is a nice idea, but has proved a very temperamental thing for me before - this post and comment illustrate some example annoyances.

The simple workaround is compress the files up, copy the zip over RDP in one operation, then extract it on the server.

Regarding SSH servers, I've used before, but I don't know it well enough to leave it running long-term, and as the client. They will also do for a one-off sort of copy.

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