Preheat oven to 325 degrees.  Line rimmed cookie sheets with parchment or foil for easy clean up.

Remove cores from tomatoes and cut in half.  You want all of your pieces similar in size.  If you’re using small tomatoes, just cut them in half. Anything larger, quarter them.  If using cherry or grape tomatoes, I like to leave those whole and put them on their own baking sheet.

As you cut tomatoes, use clean hands to gently remove excess pulp and place tomatoes on rimmed baking sheet in a big pile.

Drizzle tomatoes generously with olive oil, enough to coat everything well.  Sprinkle with salt and pepper. Sprinkle 4-5 minced garlic cloves on top.Toss together so everything is coated.

Arrange tomatoes in a single layer, skins down, on your sheet.  I try to make sure most of the garlic is on top of the tomatoes and not on the baking sheet. Your tomatoes should be in a single layer, if they are not, pull out another pan and use 2 so you can spread them out!

Place pan in oven and cook for about 2.5 hours.  Important note about baking time: all ovens are different and tomatoes will vary on baking time due to a variety of factors (size, amount of pulp removed, desired level of doneness etc).  I suggest setting your timer for 1.5 hours and taking a peek through the oven window about every 30 minutes from then on, until they are finished.  Small tomatoes will be done early, larger pieces take closer to 2.5- 3 hours. I personally like my tomatoes to get a little chewy and browned so I leave them in longer.  Up to you!