Believe it or not, malfunctioning gutters can ruin a perfectly good paint job. Check your exterior siding for any paint that has bubbled up or peeled away due to excess moisture. Wherever you find a section of compromised paint, be sure to check the condition of the nearest gutter. If even your painted gutters are peeling, then you very likely have a leak. In cases where peeling paint extends beyond one or a couple of areas, think seriously about gutter replacement, not repair.