Anyone else experiencing a campaign failure when tag that supposed to fire it, doesn't?

Had an interesting situation develop. I made a video for my client while I was debugging the issue (so it’s all here and live) - but here’s the recap. I’m hoping someone at InfusionSoft can review the video (from about 3 or 4 minutes in) and help me debug what happened. Client wants to know, and I can’t answer. Bottom line? Tag was added, but the next step in the campaign didn’t fire. Customer never got the first email and didn’t enter the important part of the campaign!

https://www.screencast.com/t/OpuAVnSrTdi

Appreciate anyone willing to review and make suggestions or provide feedback.