Toss strawberries with 1 ounce of the olive oil and place into a 250°F oven for 1 1/2 hours until they gain some color, dehydrate, and get jammy.
Cool completely, place inside a wide-mouth pint-size Mason jar, and cover with 2 ounces of olive oil. Infuse for at least 12 hours.
Add bourbon and agitate gently. Infuse at room temperature for 12–24 hours. Strain out the berries, put the bourbon into the freezer, and freeze overnight; the fat will solidify and be easily removed from the top. Fine strain through cheesecloth until your liqueur is clear of fruit sediment and chilled oil. Bottle and store in the fridge.