Your Roof Is Leaking Right Now — What a Former Insurance Adjuster Says to Do

Q: Jonathan, you’ve held an adjuster license and you work as a roofing specialist. What does that combination tell you about how homeowners typically handle a roof emergency?
Jonathan: It tells me that most homeowners are making the same preventable mistakes — not because they’re careless, but because nobody has ever explained how the insurance side of this process works. When I was doing adjuster work I saw claims get complicated, delayed, or partially denied because of things the homeowner did in the first 24 hours that they thought were helpful. Things like making repairs before documenting the damage thoroughly, or waiting too long to report the claim, or letting a storm chaser operation put a tarp on the roof without any documentation of the original damage. Those early decisions create problems that are very hard to undo later. Having been on that side of the table, I approach every emergency call knowing what the adjuster is going to be looking for and making sure we set the homeowner up correctly from the start.

Q: Walk me through the first 30 minutes. Homeowner discovers their roof is leaking during a storm. What should they actually do?
Jonathan: First — do not go on the roof. I can’t say that firmly enough. A wet roof in Florida during a storm is genuinely dangerous. The pitch, the wet surface, the wind — every year people get seriously injured going on their own roofs during or right after a storm. That’s step zero. Stay off the roof.
After that, protect the interior. Move electronics, valuables, and furniture away from the leak. Put buckets down. If you see a bulge forming in the drywall ceiling, carefully pierce a small hole in the center of it with a screwdriver or pencil and let the water drain into a bucket below — a ceiling that’s holding a significant amount of water will collapse under its own weight, and a controlled drain is far less damaging than a ceiling coming down.
Then start documenting. Take photos and video of everything — the ceiling, the wet areas, any visible damage you can see from the attic if it’s safe to access. Time-stamp it if your phone doesn’t do that automatically. That documentation is what your insurance claim is built on. The more thorough it is, the smoother the process goes.

Q: You mentioned documentation. What does good documentation look like from an adjuster’s perspective — what are they actually looking for?
Jonathan: An adjuster is building a timeline. They want to see the damage as it existed at the time of the event — not after repairs have been made, not after someone’s moved things around. So the photos need to show the full scope: wide shots that establish the context, close-ups of the specific damage points, photos from the attic if accessible showing where water is penetrating, and photos of the interior water damage. The timestamp matters because it connects the damage to a specific weather event, which is what triggers coverage.
One thing I always tell homeowners: photograph the damage before you put any buckets down or move anything. I know that feels backwards when you’re in crisis mode and your instinct is to start protecting things. But take five minutes and document what you’re walking into first. You can’t un-photograph a ceiling that’s already been cleaned up.

Q: Who should a homeowner call first — the roofer or the insurance company?
Jonathan: Call the roofer first — but not just any roofer. Call someone who can stop the active damage and document it properly, in that order. The reason you call the roofer before the insurance company is that your immediate obligation as a homeowner is to mitigate further damage. If you can get someone out to put a proper temporary dry-in on the roof, you’ve protected the property and you’ve demonstrated to the insurer that you acted responsibly. Then you notify the insurer with full documentation in hand. That sequence works in your favor.
What doesn’t work in your favor is calling the insurance company first, waiting for them to schedule an adjuster visit — which can take days — while water continues to enter the home. Insurers expect you to mitigate. If you don’t act and the damage gets significantly worse while you wait, that can create coverage complications for the additional damage.

Q: Northeast Florida gets a lot of storm activity — St. Augustine, Jacksonville, the coastal areas. Are there specific emergency scenarios you see repeatedly in this market?
Jonathan: Three situations come up over and over in our area. The first is wind-driven rain penetration at the ridge and around roof penetrations — plumbing boots, HVAC units, any point where something comes through the roof. Northeast Florida gets storms that drive rain horizontally, and those penetration points are where water finds its way in even on roofs that are otherwise in decent shape. Second is damage that happens during the shoulder season — March, April, October, November — when people have let their guard down after hurricane season. A strong cold front moving through can generate wind damage that surprises homeowners who think storm season is over. Third is the older home situation. St. Augustine and Jacksonville have a lot of housing stock from the 1970s and 80s where the roofs are aging and every major storm event reveals another vulnerability. Those homeowners are in a cycle of emergency repairs when what they actually need is a replacement conversation.

Q: Storm chasers are a real problem in Florida after major events. How does a homeowner in the middle of a stressful situation identify a legitimate contractor versus someone who’s going to take advantage of them?
Jonathan: A few things that are non-negotiable. First, verify their Florida roofing license number before anyone gets on your roof. You can look it up on the Florida DBPR website in about 30 seconds — myfloridalicense.com. If they can’t give you a license number or if the number doesn’t come up valid, stop right there. Second, local presence. A contractor who has a physical address in St. Augustine or Jacksonville, who can show you past local projects and local Google reviews, is a fundamentally different risk than someone who drove in from another state after seeing news coverage of the storm. Third, anything that involves signing over your insurance claim rights to the contractor — what’s called an Assignment of Benefits — walk away. AOB arrangements in Florida have been the source of enormous abuse in the roofing industry and they remove your control over your own insurance claim. You want to stay in the driver’s seat on your claim.

Q: What does a legitimate emergency roof repair actually look like? What should a homeowner expect when J&M shows up?
Jonathan: The first thing we do is a thorough inspection of the damage — not a quick look and a quote, a real inspection with photos and documentation that the homeowner gets a copy of. Then we explain exactly what we found, what the temporary repair involves, and what the path to permanent repair or replacement looks like. A proper emergency temporary repair in Florida typically means a roofing-grade tarp secured correctly over the damaged area — not a home improvement store tarp thrown over the edge, but properly secured material that will actually hold through additional rain while the permanent repair is scheduled. For more significant damage we may do a partial or full dry-in using underlayment material. Whatever we do, the homeowner knows what it is, why we’re doing it, and what it’s going to cost before we start. No surprises.

Q: When you’re on site assessing emergency damage, how do you decide whether a repair will solve the problem or whether the homeowner needs a full replacement?
Jonathan: Honestly, I look at three things. First, how localized is the damage? Storm damage to a specific section of a roof that’s otherwise in good condition is a repair conversation. Widespread granule loss, widespread shingle deterioration, or damage that’s revealing an underlayment that was already compromised — that’s a replacement conversation. Second, what’s the age and overall condition of the roof? If a roof is 18 years old, has been through multiple Florida storm seasons, and it’s showing its age in multiple areas, putting money into a repair is throwing good after bad. We’ll fix the emergency, but I’m going to be honest with the homeowner about what they’re dealing with long-term. Third, what does Florida’s 25% rule mean for this situation? In St. Johns and Duval Counties, if emergency repairs are going to affect more than 25% of the roof surface, we’re into replacement permit territory under Florida Building Code. I factor that into the conversation from the start.

Q: What happens with the insurance claim from the point a roofer is involved? How does that process work?
Jonathan: Once we’ve done the emergency repair and documented everything, I help the homeowner put together what they need to file the claim — photos, our written assessment, the timeline of events. Then we communicate directly with the adjuster when they come out. Having been an adjuster myself, I know exactly what they’re looking at and exactly how to present the damage accurately. I’m not trying to inflate a claim — that creates problems down the road and it’s not how we operate. But I am going to make sure the adjuster sees everything that needs to be seen, and that legitimate damage isn’t missed or minimized. Homeowners on their own often don’t know what to point out or how to articulate what they’re seeing. That’s where having someone who understands the process from both sides makes a real difference.

Q: Last question — what’s the single most expensive mistake you see homeowners make when their roof is leaking?
Jonathan: Waiting. And I understand why it happens — it’s stressful, it’s expensive, people hope the problem is smaller than it is or that it won’t happen again. But water damage in Florida compounds fast. The humidity here means that moisture that gets into your decking, your insulation, or your drywall starts developing mold within 24 to 48 hours under the right conditions. What would have been a straightforward roof repair becomes a roof repair plus mold remediation plus interior damage restoration. I’ve seen jobs where a homeowner waited two weeks after noticing a water stain, hoping it would dry out, and by the time we got there the decking beneath that section was soft, the insulation was saturated, and there was visible mold growth in the attic. The repair cost was three times what it would have been if they’d called the day they first noticed it. Act fast. That’s the single most important thing.