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!

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