How do I transfer a file to my server using PuTTY?

Have you tried something like

pscp -l user1 c:\ftp\picture.jpg slacker1:/home/user1/pics

The manual for Putty suggests

To send (a) file(s) to a remote server:

pscp [options] source [source...] [user@]host:target

So to copy the local file c:\documents\foo.txt to the server example.com as user fred to the file /tmp/foo you would type:

pscp c:\documents\foo.txt [email protected]:/tmp/foo

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Postscript

The Putty download page lets you download putty.zip - a complete set of Putty tools or you can just download the tools you need (in which case you might have downloaded putty.exe but not yet have downloaded pscp.exe)

A solution that doesn't use PuTTY: Connect to server with FileZilla using SFTP to transfer files.

There's no way to initiate a file transfer back to/from local Windows from a SSH session opened in PuTTY window.

Though the recent versions of PuTTY support connection-sharing.

While you still need to run a compatible file transfer client (the pscp or the psftp), no new login is required, it automatically (if enabled) makes use of an existing PuTTY session.

To enable the sharing see:
Sharing an SSH connection between PuTTY tools.

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Alternative way, is to use WinSCP, a GUI SFTP/SCP client. While you browse the remote site, you can anytime open an SSH terminal to the same site using the Open in PuTTY command.

See Opening Session in PuTTY.

With an additional setup, you can even make PuTTY automatically navigate to the same directory you are browsing with WinSCP.

See Opening PuTTY in the Same Directory.

(I'm the author of WinSCP)