To say I was not happy with Healthy Paws is an understatement. They refused to cover a condition of a puppy I had that their policy specifically says is covered. I insured her at 9 weeks old, when I brought her home, and filed a claim for the problem when she was 10 months old. They said they wouldn't cover it because the policy hadn't been in force for 12 months. Ridiculous! She wasn't 12 months old, and I insured her as soon as I got her! Nowhere on their website or in their material does it say that policies have to be in force for a year. No way would I use them.
My experience with Trupanion has been the opposite. Again, Flurry's skin issue started before she was a year old. After my initial claim and contacting my vet, they reimbursed me within a week. Every claim since then (and we've had many, since this is ongoing) has been paid within 48 hours of my filing it. Filing claims is super easy online, and their customer service is terrific. They've covered 90 percent of everything. I can't recommend them highly enough.