Whether you should repair or replace your leaky roof likely depends on the extent of the damage, the age of the roof and your budget. Some repairs may be very minor, and the total repair costs may be below your home insurance deductible. In that case, it may be worthwhile to either fix the repair yourself or hire a roofer. However, if the leak is extensive, you may be better off filing a claim through your insurance agency. Scheduling a roof inspection or consulting a local roofer may be the best way to assess the level of damage and potential repair costs for your roof.