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Make braising liquid. Pour your water into a large pot, then squeeze in the juice from your citrus. And in the rest of your aromatics and seasonings.
Boil octopus. Add your octopus to the braise and bring to a boil, reduce heat to low, and simmer for around 30 minutes, until octopus is opaque and tentacles have curled.
Preheat grill and season octopus. Set your grill up for high heat around 400 degrees. Transfer your octopus from the braise to a baking sheet, then season with Kosher salt and black pepper.
Grill octopus. Place your seasoned octopus directly on the grill grates, close the lid, and cook 4-5 minutes per side. The braise cooks your octopus, so grilling just adds char and flavor.
Make chimichurri sauce. While your octopus is grilling, add all the ingredients for your sauce and stir to combine.
Serve and enjoy. Once your octopus is charred to your liking, transfer it to a serving platter, slice it, and top with your chimichurri sauce to serve.