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To transfer files from my Win7 desktop to the Ubuntu 18 droplet with the Putty pscp program I used the following command from the PuTTY directory:
//prompt
braunj@BRAUNJ-DESKTOP C:\usr\PuTTY
// command
# pscp -i id_rsa.ppk c:\usr\PuTTY\README.txt root@167.71.###.###:/tmp
// reply
README.txt | 1 kB | 1.5 kB/s | ETA: 00:00:00 | 100%
My stumbling point was the login for the transfer. I finally found that I needed to include my key file (-i id_rsa.ppk) to authenticate myself to the server.