Thomas RoofingBy Thomas Construction (opens in a new tab)

For Connecticut homeowners with an insurance letter

Your insurer sent a letter about your roof. Here’s what it means and what to do before the deadline.

It reads like an ultimatum, and sometimes it is one. The good news is that most of these letters ask for something specific, and you can know your options and your number this week.

Zach Thomas Caldwell, OwnerYann Luc Sylvester, Head of Sales & MarketingFrom the Thomas Roofing team · October 2026

Why we ask: your address lets us find your roof in aerial imagery and town records and measure it. No one comes to your house unless you ask, and we never sell your information.

Rather talk to someone first? Call (860) 710-5862

If you’re reading this, it probably sounds like this

  • “I didn’t even know anything was wrong with my roof.”
  • “There’s a date in this letter and I have no idea if that’s enough time.”
  • “Do I really have to replace it, or will something else satisfy them?”
  • “I can’t risk losing my coverage.”

Take a breath. The steps are straightforward: find out exactly what they’re asking for, get a real number, and pick a week that meets the date.

Do these first

  1. 1Find the deadline and the exact requirement in the letter: replacement, repair, or proof of the roof’s condition.
  2. 2Call your agent and ask what will satisfy the insurer, and whether a signed contract or a scheduled install date counts.
  3. 3Get a replacement price for your actual roof, so you know the number before you decide anything.
  4. 4Questions about timing? Call us at (860) 710-5862.
Call (860) 710-5862

5 things these letters usually mean

  1. Your roof is past an age they track

    Many insurers review asphalt roofs at around 15 to 20 years, regardless of how they look from the street.

    Look for: A mention of the roof’s age or the year it was installed.

  2. They want it replaced by a date

    Some letters ask for a new roof before renewal. The deadline is usually firm, though your agent can sometimes help with timing.

    Look for: A specific date, often tied to your renewal.

  3. They want proof of its condition

    Some insurers will accept documentation that the roof is sound, such as an insurer’s inspection or a contractor’s report, instead of a replacement.

    Look for: Words like certification or condition report, or a request for photos.

    Ready to see your number?

    See what a new roof costs on your house, from aerial measurement, before anyone comes out.

    Get My Roofing Estimate

  4. Your coverage may change

    Some policies switch the roof to depreciated value, paying what the old roof is worth rather than what a new one costs.

    Look for: Terms like actual cash value or a roof payment schedule.

  5. Non-renewal is on the table

    If nothing changes, the insurer may decline to renew. That’s the outcome worth planning around early.

    Look for: The word non-renewal, or a renewal date paired with a condition.

More on insurance roof-age letters →

Why not to sit on it

  • Weeks near your deadline fill first

    Our week prices follow how full the crew calendar is, and the weeks just before a deadline are the ones everyone with a deadline wants. Reserving early leaves room if weather moves the start.

  • Your agent needs time too

    If the insurer will accept a signed contract or a scheduled date, your agent needs it before the deadline, not on it.

  • Coverage gaps leave you exposed

    A lapse in coverage, or a roof covered only at depreciated value, leaves you carrying the risk if something happens in the meantime.

  • Winter weather needs slack

    Shingles need workable temperatures to seal, so winter installs are scheduled around the weather. Leave room for that.

Seeing your price takes minutes, and gives you something concrete to take to your agent.

How it works

How we help you meet the date

  1. 1

    See your price this week

    Enter your address and see three replacement options with real price ranges for your actual roof, in minutes.

  2. 2

    Pick a week that meets the date

    Reserve an install week online with a deposit that’s refundable until the day a technician comes out.

  3. 3

    A technician confirms the final price

    If you go ahead, a technician checks what aerial imagery can’t see, like the decking, the flashing and how many layers are up there, and confirms your final price before you sign anything.

  4. 4

    The paperwork insurers ask for

    When the job is done you get your Roof Record, with photos of the finished roof and the work underneath it, along with the town’s permit sign-off.

Who you’ll be dealing with

The people behind your roof

Thomas Roofing is run by Thomas Construction, a veteran-owned Connecticut contractor. These are the people behind it.

  • Zach Thomas Caldwell, Owner

    Zach Thomas Caldwell

    Owner

    A veteran and lifelong builder, Zach founded Thomas Construction and sets the standard for every roof we put on: done correctly, communicated honestly, and finished clean.

  • Yann Luc Sylvester, Head of Sales & Marketing

    Yann Luc Sylvester

    Head of Sales & Marketing

    Yann answers homeowners’ questions by phone and email and makes sure your price, your options and your next step are clear, so nobody has to come to your house to explain them.

Rather talk to someone first? Call (860) 710-5862

Questions people ask

Can I get more time from my insurer?+

Sometimes. Ask your agent, because a signed contract or a scheduled install week can help. Only your insurer can extend a deadline.

Do I have to replace it, or can it be repaired?+

That depends on what the letter asks for and what your agent says will satisfy it. Some insurers accept repairs or proof of condition. We replace roofs, and we’ll tell you plainly if a replacement doesn’t sound like what your letter is asking for.

Is the online price the real price?+

It’s a range based on your actual roof, measured from aerial imagery and town records. What aerial data can’t see, like a second layer of shingles or damaged decking, is why it’s a range. A technician confirms the final price before you sign.

Know your number before the deadline does the deciding.

Your roof, three options and an install week you can reserve online, in minutes.

Rather talk to someone first? Call (860) 710-5862

Not quite your situation?

Get My Roofing Estimate