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My house came with plastic faux shutters which were attached with plastic shutter anchors.  The idea is that you drill a 1/4" and shove the anchor in and your job is done.  Unfortunately, with a little wind the anchors pull out or they snap off, leaving your shutters barely clinging to the side of the house or flying down the street in a storm.

Over the years I've tried several approaches to reinstalling the shutters, many of which required getting the remnants of the previous plastic anchor out of the hole.  It is tough to get leverage to drill into the wall while perched atop a 25 foot ladder and can be dangerous if you push too hard and tip the ladder over.  The fastening methods I've tried previously didn't last, were too expensive or were too permanent.  (If the shutter itself breaks, you need to be able to get the anchors out!)  I've finally found a method that meets all my criteria and is easy to perform at high altitudes.

Step 1: Supplies

What I eventually found is pocket hole screws.   These are self-tapping screws with sharp points and intended to bite into wood and pull themselves in.  They have thin shafts and wide thread pitch in order to keep wood from splitting and this accommodates a wide range of play between the existing hole and remainder of the previous plastic anchor.  You can even improvise and use a sliver of wood or old shutter anchor as a shim, in the event you find a hole where the previous anchor has pulled all the way out.  Pocket hole screws have square heads so you can get torque to drive them in without pushing so hard that you almost tip the ladder off the wall.  Finally, the pocket hole screws are long because of the nature of pocket holes so it is easy to find them in lengths to fit any thickness of shutter and have enough left over for the anchor holes.  Because the pocket screw heads are small, I also used some fender washers.

Supply list:

1) Pocket hole screws
2) Fender washers
3) Spray paint to match the shutters (not pictured)

Step 2: Mounting the Shutter

The hard part of this process is figuring out what type of fastener to use.  After that, mounting the shutters is easy.

1) Check all the holes to make sure the previous anchors broke off.  If any holes are empty, cut a plastic anchor to size and insert it, or make your own shim.  It needs to be soft enough to allow the screw deep enough to snug up the shutter, rigid enough to hold the screw against high wind and thick enough to stay in while you are wrestling the shutter, screws, washers and tools.

2) Orient the shutter correctly and get at least one screw in far enough to hold it up without your help.

3) Go to town on the other screws. 

They should be snug enough to deform the shutter a bit but be careful not to crack the shutter by going too far.  Pocket hole screws practically pull themselves in and with the square drive all you need to do is hold the bit against the screw head.

Step 3: Paint, Then Check This Item Off the Honey-do List

I had no problem finding a paint to match my flat black shutters.  A quick shot of paint over the screw heads and washers and it is hard to tell the difference between these and the originals.  More important, they get the wife's stamp of approval and the honey-do list is vanquished for another weekend.
<p>My wife has asked me a few times about putting the one shutter that came off in a storm back on the house but each time I tried with the plastic bolts I failed. I will give this a try and see what happens, my only issue will be finding paint to match as the shutters are so discolored from the sun. Thanks</p>
<p>Thanks for the tips here. I was struggling to figure out how to re-attach my black plastic shutters to the house. I did exactly what you said and this worked very well. One thing I added is that I found the plastic shutter bolts that broke off and cut the head of them off with a razor knife and glued them to the head of the pocket hole screws with liquid nails, giving them a more finished look.</p>

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