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Bring a pot of water to a boil. Prep a separate bowl with ice water and set aside.
Slice the orange into ⅛” thick slices. A mandoline will help you keep the slices even.
Boil the oranges slices for 2 minutes, then immediately transfer them to the ice water. Once cooled, remove from water and pat dry.
Return the pot to the heat (heavy stainless steel works best here). Add the sugar and water to the pot over medium heat and attach a thermometer to the pot. Stir until the sugar is dissolved, and bring the mixture up to about 220˚F. Add in the orange slices and stir gently, making sure they are all submerged in the syrup.
Bring the syrup up to 250˚F, stirring occasionally. This will take longer than you think – it takes us an average of 20-30 minutes. Once they reach 250˚F, remove from heat and immediately transfer to a silicone baking mat. Parchment paper is fine too, but they may stick slightly. Let cool completely (you can speed this up by moving them to the fridge). For best results, let them dry out at room temperature overnight.
Melt chocolate in a double boiler or in the microwave. Dip each slice in chocolate, then sprinkle with a bit of flaky salt (optional) and let set. If stored properly, they can last for a month at room temperature, or several months in the fridge or freezer.