Issues with Custom Segments

I have been attempting to add a custom segment in "My Audiences" from a list of 24,000 email addresses. I believe I have followed all of the documentation https://help.apple.com/iadworkbench/mac/2.0/#slv63f7ff57d on how to set them up to the letter. After multiple days, the segments have zero matches, and the "last updated" date remains blank.

Has anyone experience similar issues? I am running OS X 10.9.5 and Safari Version 7.1.7 (9537.85.16.12)