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There's lots of little things like that that can break the SmartyPants algorithm. I've given up chasing them down. There is no one-size-fits-all turnkey solution that will handle every scenario with one pass. I'm to the point where every tweak to accommodate one scenario will often expose another.
It is what it is. Have a few regular expressions saved in your arsenal to handle the edge cases like this after you've run the plugin.
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