How to Spot a Cedar Shake Contractor Who Doesn't Actually Do Cedar Work
Cedar shake projects on Chicagoland estate homes attract contractor proposals from every general roofer in the market. The crews that do cedar consistently are different from the crews that do mostly asphalt and occasionally take on cedar — and you can tell the difference by asking specific questions.
Why this matters for estate homeowners
Cedar shake roofing is fundamentally different from asphalt shingle roofing. Different fasteners, different exposure, different ventilation, different flashing, different installation techniques, different crew skills. A general roofing contractor whose primary work is asphalt suburban replacement and who takes on a cedar project once or twice a year doesn't develop the specific judgment that cedar requires — and the consequences show up over the decade following the installation, not on installation day. For estate homeowners investing $80,000-$200,000+ in a cedar shake roof, the differential between a contractor who does cedar consistently and a contractor who does cedar occasionally is the difference between a 30-year roof performing to specification and a 12-year roof failing prematurely.
Red flag #1: fastener spec that doesn't specify stainless or copper
Cedar's natural acidity is incompatible with plain steel fasteners — the fasteners corrode within a few years, the cedar around them stains rust-color, and the cedar around the corroded fastener begins to fail. Quality cedar installation uses stainless steel ring-shank nails or copper nails specifically — not plain steel, not galvanized steel (which corrodes in cedar acid even with the zinc coating), not aluminum (which dissolves in cedar acid). When evaluating a cedar contractor's proposal, look for explicit fastener specification: 'stainless steel ring-shank nails, hand-driven' or 'copper nails for premium specification.' If the proposal doesn't specify the fastener type — or specifies 'galvanized roofing nails' or 'standard roofing nails' — the contractor doesn't understand cedar's basic compatibility requirements. This is the single fastest red flag.
Red flag #2: no mention of ventilation in the proposal
Cedar shake's longevity depends on ventilation more than on any other single factor. The cedar breathes from underneath; it requires continuous airflow through the assembly to dry between weather events. Without adequate ventilation, the cedar fails from the underside well before the visible face shows wear. Quality cedar installation includes spaced sheathing, breathable underlayment products like Cedar Breather, continuous soffit venting, and ridge venting. Quality cedar proposals include ventilation in the scope — assessing existing ventilation, correcting deficiencies, installing the breathable assembly that cedar requires. Proposals that focus only on the visible surface (cedar grade, exposure, color) without addressing ventilation are missing the most important determinant of cedar's actual service life. Ask: 'How are you handling ventilation under the cedar?' If the answer is anything vague or non-specific, the contractor isn't doing it right.
Red flag #3: 'standard exposure' instead of project-specific exposure
Cedar shake exposure — the visible portion of each shake row — varies with cedar length and project specifications. 18-inch cedar shake typically installs at 7.5 inch exposure; 24-inch cedar at 10 inch exposure. These exposures aren't arbitrary; they're calculated to provide the appropriate triple-ply layering across the roof field. A contractor who specifies 'standard exposure' or 'manufacturer-recommended exposure' without engaging with the specific cedar length and grade being installed is using a default that may or may not be appropriate. Quality cedar contractors specify exposure explicitly based on the project's specific cedar specification. Ask: 'What's the exposure on this cedar?' The answer should be a specific number tied to the cedar length and grade. Vague answers indicate vague specifications.
Red flag #4: no mention of fire treatment or wrong fire treatment claims
Cedar shake fire treatment matters in modern Illinois roofing — Class A or Class B fire-treated cedar is increasingly the appropriate specification for new installations. Quality cedar contractors specify the fire treatment level explicitly (Class A vs Class B), provide manufacturer treatment certifications with the project documentation, and explain when each rating is appropriate for the specific project. Red flags: proposals that don't mention fire treatment at all (probably proposing untreated cedar without disclosing it), proposals claiming 'fire-resistant' without specifying Class A or Class B (vague language that may indicate a non-compliant specification), or proposals that make impossible fire-rating claims for natural cedar. Ask: 'What's the fire rating on this cedar, and can you provide manufacturer certification?' Quality contractors answer this immediately with specific product line and rating details.
Red flag #5: aluminum or galvanized flashing on a cedar project
Cedar shake's natural acidity is incompatible with aluminum (dissolves) and most galvanized steel (corrodes faster than appropriate for the cedar's life). Copper is the right flashing material on cedar shake projects — its acidity-driven patina is protective rather than destructive, its service life matches or exceeds cedar's, and visible copper accents on cedar architecture are aesthetically appropriate. Contractors proposing aluminum or galvanized flashing on a cedar shake project are demonstrating either ignorance of cedar's chemistry or willingness to substitute lower-cost materials inappropriate to the specification. Quality cedar contractors specify copper flashing as the default and explain when alternatives might be appropriate (almost never on cedar shake estate work). Ask: 'What flashing material are you specifying?' If the answer isn't copper for a cedar shake project, the contractor isn't doing cedar correctly.
Red flag #6: very fast project timing claims
Cedar shake installation is slower than asphalt installation. Each shake is hand-applied, fastened individually, and integrated with the course pattern around it. A typical 4,000-5,000 sqft estate home cedar replacement takes 3-6 weeks of crew time depending on complexity, weather, and crew size — not the 1-week timeline that's normal for an asphalt replacement on the same home. Contractors proposing cedar projects on aggressive timelines (1-2 weeks for a substantial estate home) are either planning to rush the work in ways that compromise installation quality or estimating based on asphalt timing without understanding cedar's actual requirements. Ask: 'How long will the installation take, and how many crew members will be on site?' Cedar projects with realistic timing have larger crews working over longer periods than asphalt projects on equivalent homes.
Red flag #7: no questions about architectural review or HOA jurisdiction
Many estate communities have architectural review committees with jurisdiction over visible exterior changes including roofing materials. Lake Forest Historic Preservation Commission, Highland Park Sherwood Forest, parts of Kenilworth, certain Winnetka and Glencoe HOA districts — all require application and approval before visible cedar shake replacement work. A contractor experienced in cedar work in these communities asks early in the inspection: 'Is your home in a historic district or under HOA architectural review?' A contractor who skips this question and provides a proposal without addressing review process is either unaware that review is required (and you'll face issues later) or planning to leave the application work to the homeowner (much harder to navigate without contractor support). Ask early: 'How will you handle architectural review on this project?' Quality contractors describe a specific application preparation, sample submission, and meeting attendance scope.
Red flag #8: cedar samples that aren't the cedar being installed
Quality cedar contractors bring physical samples of the actual cedar grade, manufacturer, and treatment level being proposed for the project. The samples should be the same product line (Watkins Hand-Split, Waldun premium, Anbrook Number 1 Blue Label, etc.) and the same fire treatment level (Class A, Class B, or untreated) that will be installed on the home. Red flags: 'sample-only' cedar that's higher-grade than the cedar that will actually arrive on the truck, generic 'representative' cedar samples, no physical samples at all (just photographs in the proposal). Ask: 'Can I see the actual cedar product line and grade you're proposing?' Quality contractors can produce the samples; contractors who can't are working from generic specifications without project-specific sourcing.
What questions actually identify a quality cedar contractor
(1) 'What's the fastener specification?' Answer should be: stainless steel ring-shank or copper, hand-driven. (2) 'How are you handling ventilation under the cedar?' Answer should describe spaced sheathing, breathable underlayment, soffit venting, ridge venting. (3) 'What's the cedar grade, manufacturer, and fire treatment, and can I see physical samples?' Answer should be specific product line and rating with samples. (4) 'What flashing material are you specifying?' Answer should be copper for any estate-class cedar project. (5) 'How will you handle architectural review on this project?' Answer should describe a specific application preparation scope. (6) 'How long is the installation timeline?' Answer should reflect cedar's actual installation pace, not asphalt timing. (7) 'What's the workmanship warranty?' Answer should be at least 5 years, ideally 10. (8) 'Can I see references from cedar projects you've completed in the last 3 years in my community?' Answer should be specific names and project addresses you can verify.
Get a cedar shake assessment from contractors who actually do cedar work
Leaders Roofing Corp has installed cedar shake on Chicagoland estate homes since 1996, including projects under Lake Forest Historic Preservation Commission jurisdiction, Highland Park Sherwood Forest review, Kenilworth's tightly-controlled architectural inventory, and Winnetka and Glencoe HOA committees. We work with stainless and copper fasteners, soldered copper flashing, fire-treated Class A and Class B cedar from premium mills, proper ventilation assemblies, and the architectural review process when required. The proposals are detailed, the timelines are realistic, and the references are available. See our dedicated cedar shake roofing service page for full system specifications. Leaders Roofing Corp, founded 1996 by Jan Koszyk, IL Roofing Unlimited License #104.010248. Call (847) 312-2727 or use the contact form.