Very Disappointed with Pineapple Insurance and Their Tracker Arrangement

When I first joined Pineapple Insurance, everything seemed great, easy sign-up, reasonable premiums, and smooth service for the first few months. However, my experience took a sharp turn for the worse when I decided to cancel my policy.

I had agreed to install their telematics device to track my vehicle mileage for discounts, and at the time I was told it was simply part of the insurance setup. What I wasn’t clearly informed of is that the device is actually managed through Tracker, and that I’d be locked into a 36-month contract with them — completely separate from my Pineapple policy. After cancelling my insurance, I was suddenly told I would need to pay a cancellation fee to Tracker, even though I had no direct agreement with them or prior warning about being tied to such a long-term contract.

To make matters worse, getting hold of Pineapple for assistance is nearly impossible. They have no phone line, and all communication must go through WhatsApp or email. Responses take hours or even days, which makes resolving urgent issues incredibly frustrating.

I cancelled my policy because it didn’t offer comprehensive enough coverage (specifically for vehicle theft), and I’ve since switched to Discovery — a much better experience overall.

I just want to warn others: be very careful with Pineapple’s telematics tracker setup. It feels misleading and ********* to be tied to a third-party contract without proper disclosure. Make sure you understand exactly what you’re agreeing to before signing up.