Bad Chimney Flashing
Good chimney flashing includes sections of “step flashing” that run up the sides of the chimney, and “counterflashing.” Counterflashing fits into grooves cut into the chimney and covers the step flashing. Cutting, fitting and installing all those parts takes time, so sloppy roofers take shortcuts.
Improperly flashed chimneys (top photo) cause lots of rotting roof sheathing and framing members. Chimneys need to be properly step-flashed and counterflashed so that water can't run down the face of the chimney and into the attic. You can't rely on caulk or roof cement to keep water out. If you suspect your flashing is shoddy, crawl into the attic after a heavy rain. Look for signs of water around the chimney and downhill from it.