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Hi Rachel, this is sort of outside of the standard use of an engagement campaign, but do you think you could set up your reminders system in an engagement stream?
Sounds like what you could do is create a new engagement program and the smart list would be anyone you want to target for the webinar. Once their program status changes they're paused, but until then, they could continue to receive the emails that you set up on a regular cadence. You could limit the availability of the emails until the date of the webinar, so that you wouldn't have people receiving the emails after the webinar.
I haven't thought through this 100%, but it could be an alternate method to ensure that people only receive the emails at the right time, and they only receive the email once.