Please allow me to chime in on this issue as I had the same problem. Just to clarify the issue I was experiencing was that I had approximately 40 Memorized transactions, some were scheduled for weekly, some monthly and some quarterly. The Memorized Transaction Pop Up box was functioning exactly how I wanted it to for years, as it would remind me per the schedule I had set up in memorized transaction list. At some point approximately 5 months ago for whatever reason, I must have not utilized the "Enter Transactions" button when the Pop Up came up and those transactions were never automatically entered. After which the Pop up, continued to Pop Up with those transaction in the window every day even though it was months later, and now that window is useless as I have to click "Enter all later", every time I open QBD. 

My Solution:  I first had to screen shot the window and print it out all of the transactions. As the window only showed 10 of the transaction at a time, I had use the scroll bar and make multiple screen shots, so that I captured all of the transactions that QBD was reminding me of to enter.  I then went to the Memorized Transaction List and rather than deleting all 40 memorized transactions, I simply right clicked each on individually, beginning with the first one on the print outs, and selected Edit Memorized Transaction, then clicked the Do Not Remind Me. Note they all still appeared in Memorized Transaction List just now at the top and under the Frequency Column it listed "Never". I then closed out of QBD and reopen it to discover that the Pop Up Window was no longer showing up, as all of those transactions no longer were set to be reminded. 

I then simply using the Print Out went back to all of those transactions that were set to never in the reminder list and gave them the next actual date to be reminded by Right Clicking each, selecting Add to my Reminders List, Under How Often I clicked the Correct Date by using the Lists that I had printed, and calculating what the next current reminder transaction date should be. This SOLVED MY PROBLEM.  Now I know some of you may have many more transactions than I, but after reading all of the comments in this thread, this has been the only viable solution I have found to rectify the issue. 

I hope that this helps at least one person, as I know how frustrated I was with this issue. 

QB User Since 2008