It started innocently enough. I booked a rental car using an authorized discount code through my alma mater's rental program. When booking through Enterprise's website, the Loss Damage Waiver (LDW) was automatically included and couldn't be unchecked. Good deal, I thought.

At pickup, everything was routine. The counter rep didn't mention anything about business vs. personal use restrictions. The rental agreement clearly showed the damage waiver as included in the charges.

Then came the fender bender. Not great, but I had coverage, right? I promptly reported it and filed all the required paperwork. That's when things took a turn.

Enterprise's damage recovery unit dropped a bomb: they were denying my LDW coverage and hitting me with a damage bill of nearly $10,000. Their justification was that LDWs only apply to business trips, not personal ones. Essentially, Enterprise was trying to stick me with a bill because of a screw-up on their end: the booking system force-included the LDW on a leisure trip.

Instead of panicking, I fed all my documentation into Claude - the rental agreement, correspondence, terms and conditions, everything. While I was feeling emotional about the situation, Claude stayed purely factual. Together, we analyzed everything methodically and found what mattered: there were zero restrictions on personal vs. business use in the coverage terms.

Claude helped me craft a detailed dispute letter laying out the evidence: the LDW was automatically included by their system, no terms restricted it to business use, and the code was explicitly authorized for personal use. The dispute that Claude drafted was honestly a thing of beauty.

I also got my school's Risk Management office involved. The combination of my comprehensive evidence (thanks to Claude's analysis) and institutional backing proved powerful.

The result? Enterprise dropped the entire claim and honored the coverage. The $10k bill vanished.

Document everything. These companies often count on people just paying up rather than fighting back. Having an AI assistant to analyze complex documents and spot important details was a game-changer.

Props to Claude for helping turn a $10k bill into $0.