Thank you for reaching out to the Community regarding your issue, though I am sorry to hear that you are experiencing this.
With the issue you're having it may be best to have an agent view the issue alongside you, as such we would recommend contacting Quicken Support directly for the best assistance. I will leave our hours down below so you can find a time that works best for you.
Click here to review Quicken Support's hours of operation. Thanks, Quicken Francisco
Thank you for taking the time to visit the Community and adding to this discussion, though I apologize for the trouble.
What you two are experiencing is not the expected behavior of the software. We are not seeing a large number of customers experiencing this, nor are we seeing it happen in our own software. This tells me that it is most likely specific to your data files. That being said, there is something you can try, but it will take some extra work on your end.
This suggestion is meant to be applied to the Quicken for Windows software. You can copy the data in your current data file, this will give you a new file to work in. This way you can see if the reminders behave the same way there. If you don't see the same issue then it confirms that what you have been going through is file specific.
To do this;
1. Click on File.
2. Click on Copy or Backup File.
3. Click on Create a copy or template.
4. Click Save Copy.
5. Select New Copy and click Ok.
Now you are in the new file. If you decide to stay in this file you will need to reconnect all of your previously connected accounts. Be aware that this can cause duplicate transactions as well as other minor inconveniences.
In order to get back to your original file, go back up and click on "File" again. At the bottom of the menu options, right above "Exit", click on #2. This should take you back to the original file.
Let us know if you have any questions or concerns. I do hope you find this useful.
Quicken Alyssa