This is most common in homes built before about 1940. Old chimneys lose mortar from the joints, and the concrete or mortar cap on top, the crown, cracks. Both let water into the masonry, and the flashing around the chimney depends on sound mortar joints to hold.

1Why the timing matters
- Counter flashing sits in the mortar. It’s set into the mortar joints. Repointing after the new roof means disturbing new flashing.
- Access is already there. Scaffolding, ladders and roof protection are in place during a reroof.
- One sequence, fewer leaks. Masonry first, then flashing, then shingles is the order that keeps the joints tight.
2How to check it yourself
- Look with binocularsRecessed, crumbling or missing mortar between bricks, loose or spalling bricks, and cracks in the crown on top are the signs.
- Look at the baseRust streaks below the flashing or thick sealant smeared around the base suggest earlier leaks.
- Look insideDamp or stained walls or ceilings near the chimney, or crumbling mortar in the attic, point the same way.
- Put it in the planIf you’re getting roof quotes, tell each contractor about the chimney so the masonry is scheduled before the flashing goes on.
Your job here is spotting and scheduling, from the ground and the attic. Don’t climb onto the roof to inspect the chimney.
3How to sequence the work
What you handle
- Spot the mortar and crown problems
- Ask whether your roofer does masonry or works with someone who does
- Make sure the masonry is done before the new flashing
- Get the order of work in writing
What the crew does
- Tuckpoint failing joints
- Repair or replace the crown
- Install new step and counter flashing
- Shingle around the finished chimney
4What drives the cost
The price depends on the height of the chimney, how much mortar has failed, whether the crown needs repair or replacement, and access. Doing it while the roof crew and access are already there avoids paying for setup twice and avoids disturbing new flashing.
5Questions
Can I wait and do the chimney later?
You can, but it costs more and means disturbing the new flashing. If the chimney needs work, do it with the roof.
Does my roofer do masonry?
Some do; others bring in a mason. Ask, and get the order of work in writing so the masonry is finished before the flashing goes on.
Written by Jaylan Jones. I Like To Exterior Services earns a referral fee when a call connects to a contractor. See our business-model disclosure.