Describe the bug
We don't have a good way of tracking whether or not reminder emails are delivered. Anecdotally, some users have reported that they have not gotten these types of emails.
From Natalie Iwasa:
I used to get automatic updates when the 10-day period expired. I didn't get one for my last request (street sweeping). I happened to check about the time it expired and sent a reminder notice.

Example Affected Request: https://uipa.org/request/street-sweeping-schedule-oahu/
Expected behavior
Automatic reminder emails are always delivered.