Latest value = "Not Downloaded"

I was able to remap the directory to fix my issue. To do this, I

• selected (right-clicked) the branch that included all of my code, and selected "Remove Mapping..."
• renamed the folder I was mapped to within TFS (you can delete it as well, but I renamed just to keep it during this experimental process)
• created a new folder with the original name of the branch I was mapped to in the beginning, and
• selected (right-clicked) the branch that included all of my code, and selected "Map to Local Folder".

This process forces a complete re-download of the entire branch. Luckily for me, my branch was only 2GB, so I was able to re-download in about 5-10 minutes.

The reason for getting "All files are up to date" - is that the information on the TFS server and the files on your disk is out of sync. If you delete the files on your disk with file explorer - the TFS server still thinks you have the file on disk. To re-sync you have to force an update like this:

Check the two checkbox on this dialog - and click Get: