What Questions Should I Ask My Roofer?

A roof inspection is not just about shingles. A proper evaluation looks at the entire system, including ventilation, attic conditions, flashing details, and installation quality.

Many of the most expensive roofing issues start small and go unnoticed until they become visible inside the home.

That’s why homeowners should always approach inspections with the right questions — not just accept surface-level answers. 

Ventilation is one of the most overlooked but critical components of a roofing system.

Many homes in Old Saybrook and surrounding shoreline communities — especially older or antique-style homes — were built before modern ventilation standards existed.

A proper inspector should check:

• Soffit intake ventilation (air entering the attic) 
• Ridge or exhaust ventilation (air exiting the attic) 
• Airflow balance throughout the attic space 

Poor ventilation can lead to:

• Premature shingle aging 
• Excess heat buildup in summer 
• Moisture and condensation in winter 
• Mold or rot in attic structures 

In many cases, ventilation issues shorten roof lifespan significantly even when shingles are still in decent condition.

One of the most common problems seen in Connecticut roofing systems is improper installation from past work.

Roofing standards have changed significantly over the last 5–10years, meaning older or improperly installed roofs may not meet today’s best practices.

Common issues include:

• Improper flashing installation 
• Incorrect nail placement or over-driven nails 
• Incomplete sealing around penetrations 
• Bathroom vents improperly vented into soffits 

These small details can lead to long-term moisture and structural issues if not addressed.

This is one of the most important questions homeowners should ask.

A proper inspector should give you an honest breakdown based on:

• Roof age 
• Condition of shingles 
• Attic findings 
• Number of layers on the roof 
• Extent of existing damage 

Sometimes a repair may make sense for short-term protection. However, on older roofs (15–20+ years), repeated repairs can become more costly over time than a full replacement.

A trustworthy recommendation should always consider long-term value — not just short-term fixes.

Many roofing issues are not visible from the ground.

A thorough inspection should include checking:

• Roof decking (plywood condition) 
• Chimney flashing 
• Pipe boots and penetrations 
• Valley transitions 
• Signs of moisture in the attic 

Homeowners often only notice problems once leaks appear inside the home — but by then, damage may already be advanced.

During a recent inspection, a homeowner was concerned about winter condensation around their attic access and bedroom windows.

At first glance, it seemed like a minor ventilation issue.

However, a full inspection revealed:

• Insufficient attic insulation 
• Two bathroom vents improperly exhausting into soffit areas 
• Moisture buildup inside the attic space 
• Damaged roof decking caused by long-term condensation 

As a result, the roof required full decking replacement in several areas, along with corrected ventilation and insulation upgrades.

After the work was completed, the homeowner reported no further condensation issues during the following winter season.

This is a perfect example of why attic inspections matter just as much as roof surface evaluations.

A proper roof inspection should always include:

• Shingle condition and granule loss 
• Flashing around chimneys and walls 
• Pipe boots and roof penetrations 
• Gutter performance and debris 
• Signs of wind or storm damage 

• Ventilation airflow and balance 
• Moisture or staining on plywood or rafters 
• Insulation levels and placement 
• Bathroom vent termination points 

• Documentation with photos 
• Clear explanation of findings 
• Honest repair vs replacement recommendation