Deeply Disappointed with Pineapple Insurance – Avoid if You Value Customer Service

As a claim-free customer for over two years, I expected much better from Pineapple Insurance. Sadly, my recent experience has been nothing short of exasperating. While I acknowledge an initial delay on my part (due to incorrect IMEI blocking information from my network provider), what followed was a frustrating display of poor communication, broken promises, and a complete lack of customer care. It feels as though Pineapple has embraced a fami**** insurance industry playbook of delays and administrative roadblocks rather than delivering on the prompt service their marketing proudly promises.

1. Zero Guidance When I proactively asked if anything else would be needed beyond the outstanding IMEI block, there was no mention of requiring a physical police statement. This critical detail was only revealed days later, wasting valuable time and delaying the process unnecessarily ( note that after 4 days there was no response I had to call in and ask what the procedure is) 2. Silent Treatment After submitting documentation or seeking feedback, I’ve repeatedly been met with silence. In one instance, I waited days without an update, only to call and be told my case had been reassigned. The first person I spoke to didn’t even bother to follow up or escalate the issue, leaving me to make a second call before I got any response ( someone tells me their on the case only to never hear from them again) This has happened about 3/4 times now. 3. Broken Promises I’ve called their office on multiple occasions to request updates and was repeatedly assured of a callback , with promises to review my documents. Each time, I was told that the individual handling my case was unavailable and that someone else would personally manage it. Unsurprisingly, these promised callbacks never materialised, leaving me no other choice to make this post.

Pineapple has failed to provide any meaningful updates or clarity on the status of my claim. Each email I’ve sent has required a follow-up call to even confirm receipt. For a customer without a phone and relying solely on email as a communication method (which I made clear to them), their excuse of “attempting to call” me is unacceptable.

The most frustrating aspect is Pineapple’s consistent pattern of going silent, forcing me to chase after them for basic updates. Insurance is supposed to alleviate stress during difficult times, not amplify it. Days of radio silence on an active theft claim is entirely unacceptable, especially after repeated assurances that I would be contacted.

As someone who has faithfully paid premiums for years without filing a single claim, I expected at least the bare minimum: responsiveness, transparency, and some semblance of professionalism. Pineapple has failed on all counts.

To anyone considering Pineapple Insurance: think twice. Their inability to follow through on commitments, provide clear communication, or offer basic customer service makes them wholly unreliable when it matters most.