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Could you make an upside down "U" that follows the profile of the railing (with a flat spot on top for the flower baskets?
Of course you'd need to saw the "U" in half, hold it tight to the railing and then screw it back together.
Dumber than I appear
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I would make brackets that would allow the boxes to hang on the outside of the railing so water could drain to the ground and not on the deck. A hard rain could scatter dirt from the boxes onto the deck as well if they sit on top of the railing.
Al
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Here's a few ideas. First, I don't think that rail system will resist even a little twisting force (certainly not long term). so I suggest they be centered on the top. If you make the sides so they're lower than usual, say 1-1/2" below the bottom, you could mill strips, coped to fit the cove on the rail, which could be screwed to the bottom. At least one of these strips would have to be attached after the box was in place, and obviously the ends would have to be cut to fit the upper portion of the rail. The flower boxes would not be easily removable to update plantings, but they may not need as many updates seeing they won't be accidentally knocked off as often.
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Commercially there is this style:
However, if I were to make one, I would make a "saddle" from pressure-treated lumber that straddles the railing. On the outside of the railing I would attach the flower pot or flower box.
On the inside, I would make a 6" or 8" deep shelf for drinks.
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Make an H shaped planter box that straddles the railing far enough to go below the bottom of the railing. Then use a dowel, scrape wood pieces or screws to lock it on the underneath the railing, capping off the bottom of the H. Avoid screwing in to the railing itself.
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Thanks for the input, guys. I separately contacted AZEK (manufacturer of the rail and deck materials). They recommended anchoring the box to the extended posts and not to the rail. I will mock up something based on your ideas and AZEKs recommendation and see how stable it is. Thanks!