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I'm installing an underground fence for my dog, which requires putting the receiver inside the garage (plugged into an outlet) and running the insulated fencing wire to the outside where it will be buried. Using a suggestion from the manual, my plan is to simply drill a hole through the exterior wall, then caulk around it after installation. Is this the best way, functionally and aesthetically?

My exterior is vinyl siding.

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I would drill a slightly larger hole and run the wire thru pvc conduit. It will protect the wire from accidental damage from a weedwacker, lawnmower etc. I think look cleaner and more professional.

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Use a PVC elbow at the least or a "pull elbow" so the wire can easily turn the corner. – Jack May 26 '14 at 0:25

The way you suggested will be fine. On the exterior, make sure to leave a drip loop in the wire in order to prevent water from running down the cable. Drill the hole high enough so that standing water next to the foundation won't leak into the hole.

Drip Loop

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yep, the rain loop is the key. +1 – shirlock homes May 24 '14 at 19:22
This answer is not right on spot with what the poster has asked. @AceHarding is wanting to have a wire come out that goes down and then under ground around his dog confinement area. The above picture and comments apply to a wire that comes down from above and then enters the building. However with a wire that comes out and then goes down there is little or no point in stressing the importance of a rain drip loop. – Michael Karas May 24 '14 at 20:06
You can still leave a service loop that would act as a drip loop for a wire that drops i – Steven May 24 '14 at 22:47

I would peel back a piece of siding and then drill a whole that comes out near its bottom edge. I would then notch out the bottom lip so that the wire comes out and the siding can snap back on. If you go low enough, you might be able to come out behind the bottom piece of siding then then just go out the bottom of it.

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