Look for damage to the caulking, and reapply caulk where necessary.
Remove damaged or deteriorated caulking so the new application can bond to the roof or flashing surface.
Use a putty knife to remove the loosened old caulk.
Clean and dry the area.
Cut the tip off the caulk tube and spread a bead along the same line, working it into the crack with an applicator. Let it dry.

Inspect areas where surfaces connect, such as a chimney or vent pipe.
Larger-scale repairs will be necessary if there is damage to the flashing around the chimney or the boots around vents, as these features may need to be replaced.
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