Why You Should Hire a Roofing Company That's Also Licensed in Masonry

Here’s a scenario that plays out constantly in Chicago: a homeowner calls a roofer about a leak near the chimney. The roofer inspects, replaces some flashing, and calls it done. Three months later, the leak is back — because the actual problem was deteriorating mortar joints in the chimney itself, not the roofing material around it. Now the homeowner needs a second contractor, a second inspection, and a second invoice, for a problem that could have been diagnosed and fixed in one visit.

This is the exact gap that comes from treating roofing and masonry as separate, unrelated trades — when on many Chicago homes, they’re deeply intertwined.

Where Roofing and Masonry Physically Meet

Look at almost any older Chicago home and you’ll find several places where roofing materials meet masonry: chimneys rising through the roofline, parapet walls on flat-roofed buildings and courtyard apartments, decorative masonry details along rooflines common in the city’s older housing stock, and chimney crickets — the small triangular structures built behind a chimney to divert water and snow around it.

Every one of these intersections is a common leak point, and every one of them requires both roofing expertise (flashing, shingle integration, waterproofing) and masonry expertise (mortar condition, brick and stone integrity, structural soundness) to diagnose correctly. Treat only one half of that equation, and you’ve only solved half the problem — even if the repair looks complete from the ground.

Why a Roofing-Only Contractor Can Miss the Real Problem

A roofer who isn’t trained in masonry will naturally focus on what they know: shingles, flashing, underlayment. If a leak near a chimney is actually caused by cracked or spalling mortar joints letting water into the masonry itself, a roofing-only repair might stop the immediate symptom temporarily, without addressing the underlying cause. The leak returns, often in a different spot, and the homeowner is left thinking they hired “the wrong roofer” when really they needed two different specialists working together from the start.

This isn’t a knock on roofing-only contractors — most are genuinely skilled at what they do. The issue is scope. A roofer diagnosing a leak is trained to look for roofing causes, the same way a plumber diagnosing a wet ceiling looks for pipe issues before considering whether the roof above is the actual source. Neither is wrong to look where their training points them; the problem is what happens when nobody on the job is looking at the whole picture.

Chimney Cricket Repair: A Perfect Example

A chimney cricket is a small, peaked structure built on the uphill side of a chimney to redirect water and snow melt around it rather than letting it pool against the brick. When crickets fail — usually due to flashing deterioration or masonry cracking — water gets directed straight into vulnerable mortar joints instead of away from them.

Fixing this properly requires both roofing skill (rebuilding the flashing and waterproof membrane) and masonry skill (repairing or rebuilding the cricket structure and any damaged brick or mortar around it). This is one of the more common combined roofing-masonry repairs we handle, and it’s a textbook example of why the two trades shouldn’t be separated. A roofer without masonry training can rebuild the flashing correctly and still leave a homeowner with a chimney that keeps shedding water into cracked mortar — because that part of the job was never theirs to assess in the first place.

Parapet Walls and Commercial Buildings

On commercial and multi-unit flat-roof buildings, parapet walls — the low walls that extend above the roofline — are another frequent trouble spot. Masonry cracking, deteriorating coping stones on top of the wall, and flashing failure where the wall meets the roof membrane can all contribute to water intrusion. A contractor who only handles roofing membranes may not be equipped to properly assess or repair the masonry component of that same wall.

This matters even more on larger commercial properties, where a parapet wall failure can affect a much larger interior footprint than a single residential chimney leak — and where the cost of a second inspection, a second mobilization, and a second contract negotiation adds up quickly for a property manager already juggling multiple maintenance priorities.

One Contractor Means One Diagnosis, Not Two Guesses

When roofing and masonry issues are intertwined, having a single licensed contractor handle both means the diagnosis accounts for the whole problem from day one. There’s no back-and-forth between separate companies pointing at each other’s work, no duplicated inspection fees, and no gap in accountability if a repair doesn’t hold.

Super Roofer holds a Mason license (#MC6690) in addition to our residential and commercial roofing licenses, specifically because our team — with backgrounds in welding, steelwork, and masonry alongside roofing — kept running into these combined problems on Chicago homes and buildings, and wanted to be able to solve them completely, in one visit, rather than referring clients elsewhere.

The Hidden Cost of Hiring Two Separate Trades

It’s worth putting a number on what “hiring separately” actually costs, because it’s rarely just the price of a second invoice. Two separate contractors typically means two separate inspection visits, each with its own scheduling delay. It means explaining the same problem twice, sometimes to a mason who has never seen the roofing side of the issue and a roofer who has never assessed the masonry. And it often means a gap in accountability: if the leak returns, each contractor can reasonably point to the other’s work as the likely cause, leaving the homeowner stuck mediating a dispute between two companies instead of getting a straight answer.

There’s also a real cost in elapsed time. A homeowner dealing with an active leak doesn’t just want it fixed — they want it fixed before more water damage happens to drywall, insulation, or framing. Every week spent coordinating between two separate companies is a week the underlying moisture problem keeps doing damage, often in places that won’t become visible until the repair bill is already much larger than it needed to be.

Signs You Likely Need Both a Roofer and a Mason

• A leak near a chimney that has already been “fixed” once by a roofing-only repair and has come back
• Visible cracking, spalling, or crumbling mortar on a chimney or parapet wall near the roofline
• Water stains that appear specifically where roofing meets a masonry structure, rather than in the middle of an open roof field
• Standing water or debris collecting behind a chimney after rain, a common sign of a failed or missing cricket
• Any roofline detail on a pre-1960s Chicago home where the original masonry hasn’t been inspected in years

Chicago’s Older Housing Stock: Why This Matters More Here

This combined-trade problem isn’t unique to Chicago, but it’s more common here than in newer housing markets simply because of how much of the city’s housing stock is older. Brick two-flats, courtyard buildings, and bungalows built in the early-to-mid twentieth century were constructed with masonry chimneys and parapet details that have now been through eighty, ninety, or more years of Chicago freeze-thaw cycles. Mortar has a real lifespan — typically 25 to 50 years before it needs repointing — and roofing materials get replaced multiple times over a building’s life without anyone necessarily checking whether the masonry it meets has kept pace.

The result is a lot of Chicago rooflines where the roofing has been updated more recently than the masonry it’s sealed against — which is exactly the mismatch that produces chronic, hard-to-diagnose leaks. A contractor who only ever looks at the roofing side of that equation is working with half the information needed to actually solve it.

What to Ask a Contractor Before Hiring for a Chimney or Roofline Issue

If you’re dealing with a leak or visible damage near a chimney, parapet wall, or other masonry-roofing intersection, it’s worth asking directly: are you licensed for masonry work as well as roofing? Can you assess whether this is a roofing issue, a masonry issue, or both? Will one team handle the full repair, or will I need a separate mason? These questions can save you from a repair cycle that never quite solves the problem, and a contractor confident in their scope of work will answer them without hesitation.

The Bigger Picture: Fewer Contractors, Fewer Headaches

Beyond just chimneys and parapet walls, having a contractor licensed in both trades simplifies larger projects too — a full roof replacement on a home with an aging chimney, for example, can be planned and executed as one coordinated project rather than two separately scheduled ones with their own timelines and potential scheduling conflicts. It also means a single point of contact and a single warranty conversation if something needs attention down the line, instead of two companies each covering only their piece of the job.

For Chicago’s older housing stock in particular, where masonry chimneys and roofing systems have often been aging side by side for decades, this combined expertise isn’t a nice-to-have. It’s often the difference between a repair that actually holds and one that quietly fails again next season.