Preheat the oven to 375°F. Line two baking sheets with parchment paper.
In a large bowl whisk the nut butter, date sugar, maple syrup, non-dairy milk, ground flaxseeds, and vanilla extract.
Add in the oat flour, baking soda, and salt. Mix until a dough forms and all the flour is incorporated.
Transfer to a cutting board sprinkled with flour or cocoa powder. Use a rolling pin or drinking glass to roll the dough flat (about ⅛" thickness). You can do this in two batches. Use a cookie cutter to cut out circles. Re-roll any remaining dough and continue until all the dough has been portioned.
Transfer the circles to the prepared baking sheets. Bake for 10-12 minutes. Let sit on the pan for 2 minutes, then transfer to a wire rack to let the cookies cool completely.
When the cookies are cool, melt the chocolate. Place the chocolate in a small microwave-safe bowl (ideally a bowl with high sides). Heat in the microwave on 50% power, stirring every 30 seconds, until the chocolate is smooth.
Dip each cookie halfway into the chocolate. Set on a parchment-lined pan or wire rack. Before the chocolate is fully solid, sprinkle with candy canes. Allow the chocolate to solidify before serving.