Pineapple Doesn’t Pay Promised Benefits and Ignores Repeated Follow-Ups

I have had an extremely poor experience with Pineapple Insurance.

My Drive Less benefit payments have repeatedly not been paid on time, despite the amounts being confirmed and despite multiple assurances that payment would be made. I was even promised proof of payment, which never arrived.

The July benefit remains outstanding, while the next month's payment is already becoming due. This means I have had to repeatedly follow up and waste my own time chasing Pineapple for a benefit that forms part of the product they actively market and sell.

What makes this worse is the complete lack of accountability. Promises are made, deadlines pass, and nothing happens unless the customer keeps following up.

This has seriously damaged my confidence in Pineapple. If a relatively straightforward benefit payment is handled this poorly, it raises a very real concern about what the experience would be like when dealing with an actual insurance claim involving a significant amount of money.

Customers should not have to fight for benefits that have already been verified and are contractually due.

Based on my experience, the service has been unreliable, frustrating and completely below the standard I would expect from an insurance company.

I would strongly caution anyone considering Pineapple to take this into account before moving their insurance to them.