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I'm looking for a TFTP server that is:

  1. Free and legal to use at my workplace (i.e. "free for personal use" won't work)
  2. Runs on Windows, including 8.1

I'll use this server at work to transfer boot images to and from Cisco switches.

I already found this question but the accepted (and only) answer recommends a PXE Server solution. I also have tried FileZilla but apparently it's a strictly FTP server, not TFTP.

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Tftpd32 meets your specifications. According to the program description:

Tftpd32 is a free, opensource IPv6 ready application which includes DHCP, TFTP, DNS, SNTP and Syslog servers as well as a TFTP client.

32-bit and 64-bit versions are available here. There is a standalone program or a version that can be run as a Windows service.

The license is free for use in all circumstances:

The Licensor hereby grants You a world-wide, royalty-free, non-exclusive, sub-licensable licence [sic] to do the following...use the [software] in any circumstance and for all usage.

I have successfully used Tftpd32.exe on Windows 8.1 Pro to transfer files via TFTP to Cisco switches.

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