Preheat the oven to 350°F. Line a jelly roll pan or large cookie sheet with parchment paper.
In a large bowl, mix together the flour, cocoa, sugar, baking powder and salt and mix well. Add the cabernet, eggs, oil and vanilla and mix until all the ingredients have mixed together. Add the chocolate chips and mix again to evenly distribute the chips. I like to knead them in with my hands to best distribute them.
Divide the dough in half and shape each half into a log, about 10 to 12 inches long and place on the prepared pan at least 3 inches apart. Flatten each loaf slightly.
Bake for 30 to 35 minutes, or until the loaves feel pretty solid on top. Remove from the oven and let cool for 15 minutes. Slide the parchment and loaves off the pan. Slice each loaf crosswise into ½ to 3/4-inch-thick slices.
Place a new piece of parchment on the pan and place the sliced cookies on the parchment cut-side down. Place the pan in the oven and bake 5 minutes more, for cookies that are a bit soft. For crispier cookies, bake for 7 to 10 minutes. Slide the parchment off the cookie sheet onto a cooling rack and let the cookies cool.
To make the glaze, place the confectioners’ sugar into a bowl and add 4 teaspoons of the Cabernet. Whisk well. Add more wine, a teaspoon at a time, until you have a thick glaze you can drizzle. Drizzle the glaze over the cookies.
Place in an airtight container or freezer bags and store at room temperature for up to five days or freeze up to three months.