Combine the 1/2 cup sugar and 1/2 cup water in a small sauce pan on medium-high heat until sugar is dissolved (about 3 to 4 minutes).
Remove the sauce pan from heat and add the cranberries. Stir gently to coat cranberries and remove cranberries immediately with a slotted spoon and transfer to a wire rack to let dry. (The cranberries may start popping if left too long in the hot simple syrup.)
After the berries have cooled and dried (about 25-30 minutes), they will be nice and sticky. Roll them in the additional granulated sugar. Let them sit in sugar until ready to use. Use as garnish for your pie. Store in fridge for 2 weeks.
Shortbread Crust (9 or 10-inch tart pan)
Heat oven to 375 F.
Use cooking spray to coat a 9 or 10-inch tart pan with a removable bottom.
In a medium sized bowl, stir in the dry ingredients.
Cut in the butter with a large fork until very crumbly.
Add the egg yolk and stir until the mixture forms a ball.
Press with fingers and smooth out with the back of a measure cup to help press out corners of tart pan.
Bake for 15 minutes. Remove from oven, if any bubbles appear gently press them down by hand while warm. Let cool while preparing remainer of tart.
Cranberry Orange Jam
Place all ingredients in a sauce pan over medium-high heat until all cranberries have popped, about 7 to 9 minutes.
Set aside, let cool, and use immersion blender or pulse in other blender to break up the berries. Place in fridge until ready to use.
Lemon Filling and Assembly
Preheat oven to 350 F.
In a large bowl, use a whisk and beat egg yolks until fairly smooth.
Add sweetened condensed milk and whisk in thoroughly with egg yolks.
Carefully whisk in lemon juice until completely combined and pour into prepared tart shell.
Place prepared tart pan on a parchment lined baking sheet.
Drop spoonfuls of cranberry jam on top of filling and use a knife to swirl in, pushing down on some of the jam as you swirl. (You will have about 1/2 cup of jam leftover.)
Bake for 15 minutes, remove from oven and let cool. Place in refrigerator until completely cooled, about 1 to 2 hours before serving. Serve with powdered sugar and sugared cranberries.