We've been with Trupanion for a little over a year with both our Yellow Lab (1 yr old) and Kitten (1 yr old). Our vet recommended them when we were getting their first checkups. We did some research and read the good reviews and decided to give it a go. We're glad we did. Our Lab had kennel cough (much to our efforts to prevent it) and the ER tests on a holiday was covered. Our Kitten recently swallowed an object and we were not prepared for the $3k+ ER visit and surgery for that, we lucked out and the surgery was not needed but the tests, etc cost several hundred. After submitting the claim request we quickly received a response that it was being reviewed then followed up communication on its progress. We promptly received our reimbursement check (minus of course our deductible and coinsurance). It's come in handy already and we're only a year in.
Only bummer is sometimes large claim files get lost in FAX neverland - although they cleared that up quickly after we resubmitted which was great.