I found this topic and it was closed so I am reporting because this same behavior is occurring for me.
I have recurring series for credit card payments from my checking to the cards set up, all set to $1 and I pay my cards off on Friday of every week (I do not wait till the due dates) at that point, I set the actual value once statements come in. The issue is, the future transactions will completely disappear from the reminder list before the due date on the reminder. When I check the series, its start date is a week ahead of the missing transaction. I am not doing anything to cause this, it just happens on its own.
Reading through various threads I see recommendations to delete the transaction and start over. I did this a few weeks ago and it worked for one week and now I am back where I started. This weeks reminders are gone and the dates are set to next week.
Help.
Old thread: https://community.simplifimoney.com/discussion/comment/42984#Comment_42984?utm_source=community-search&utm_medium=organic-search&utm_term=Reminder+skip