Heat oven to 375 degrees F. To roast the garlic, remove any extra skin around the head and slice off the top. You want the top of each clove to be exposed, but make sure to not separate the cloves. Place the garlic in aluminum foil and drizzle with 2 tsp of olive oil, a pinch of salt, and black pepper. Wrap foil around the garlic and place inside a ramekin. Roast in the oven for 1 hour. Once the tops are golden, remove from the oven and let cool on the counter.

To prepare the tomatoes, line a baking sheet with parchment paper or a reusable mat. Combine the cherry tomatoes, capers, 1 Tbsp of olive oil, salt and black pepper in a medium bowl. Spead tomato mixture on to the prepared baking sheet in a single layer. When garlic has 10 minutes remaining, add the tomatoes to the oven. Roast for 25 minutes, giving the pan a shake halfway through. 

Meanwhile, make the lentils. In a medium-sized saucepan, add lentils and 4 cups of water. Simmer lentils over medium-low heat for 20 minutes or until tender. Strain in a fine mesh strainer and set aside.

Once the garlic has cooled and you can handle it, squeeze out each softened clove of garlic into a food processor or high-powered blender. Add to the blender the remaining 2 Tbsp's of olive oil, dijon mustard, red wine vinegar, caper brine, agave, water, 1/4 tsp of salt, and black pepper. Blend until smooth. Season to taste- add salt or more vinegar, if needed. 

In a large bowl, combine the lentils, the roasted tomatoes, capers, and the juices from the pan, and about 1/2 the dressing. Toss to combine. Stir in half the fresh basil. 

To serve, spread lentil salad out on a serving platter or divide into bowls and top with remaining fresh basil leaves. Serve the remaining dressing on the side.