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In the Christmas days of yore, people braved winter weather to staple or tack their Christmas lights onto their rooftops or nearby surfaces like the fascia boards. Problems quickly emerged with that approach. Damage to the roof, even small marks from staples, provides entryways for moisture and similar issues that can hasten roof rot, wear, and associated leaks. Plus, some homes had tough fiber cement boards or other materials where staples and screws didn’t work.

How many string lights can be on one outlet depends on a number of varying factors, including the total wattage of your circuit, the type of lights, the energy needs of the lights, and cord specifications. It’s better to play it safe here to protect your circuit, so figure out the max wattage of your circuit, compare that to the lights, and move on from there. Generally speaking, LED string lights require less energy than incandescent bulbs, translating to a higher number of lights per circuit. 

It's safe to hang Christmas lights from gutters with a few considerations. First, when installing the lights, follow safe ladder-use guidelines and avoid getting onto the roof. Second, for best results and the integrity of your lights, use clips to keep the bulbs away from inside the gutters where they could run into trouble with water or ice. 

Yes, you must use an extension cord specifically rated for outdoor use to power outdoor lights, such as Christmas lights. Extension cords intended for indoor use lack the protective properties to withstand exposure to outdoor elements. To safely hang and power lights outside your house or in your yard, always connect them to an outdoor power source using an outdoor-rated extension cord.