I am creating an automated appointment reminder email system for our company's clients using Constant Contact’s API library, and am unsure if my setup here is the best approach for accomplishing the task. I think the main issue is that I am trying to send single emails to specific contacts, which seems to be the exact opposite of what this service was designed for... anyway here is as brief an outline as I could write to describe the system: Every morning via a cron job on our site, custom php code pulls data from our CRM’s calendar and sends the relevant info to Constant Contact via API calls to create or update each client contact that has an appointment coming up. Each contact is then added to one of many lists that trigger different Automation Paths which will then send a single appointment reminder email to each contact. Additionally, Custom Fields are used to store specific information about each appointment such as the date & time of the meeting. There are multiple lists set up since our company has many types of appointments and different information is needed to be sent in the reminder emails for each one. Finally, there are 2 reminders for each appointment - 7 days and 24 hours prior to the scheduled time, so there are 2 versions of every reminder email to accommodate for this. This all works just fine despite some inefficiencies that I need to polish up, and contacts receive the triggered email as soon as the API call puts them in the specific list for their appointment type. However, my main concern and the core issue we are having is this:   We need to send duplicate emails from these Automation Paths to the same contact if they come in for another meeting of the same type (the date & time gets updated by custom fields for the new appointment). From my tests, removing and re-adding a contact to that list does not trigger the automated email to be sent again, and it only appears to be sent the very first time the contact is added to the list. Is there any way to resend an automated email this way when a contact is removed and then added to the same list again?   Let me know if any further explanation is needed, the main need here is to send the same email to a specific contact again and again as they come back for more appointments. An automated process would be much better than manually sending dozens of emails each day by hand. ... View more