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Bring a pot of water to a boil.
Cut a shallow x into the bottom of each tomato.
Drop them into the boiling water for 15 seconds.
Remove and cool.
Preheat the oven to 150C with the rack in the middle.
Peel and core the tomatoes.
Cut them in half crosswise and remove the seeds.
Arrange the tomatoes on a baking sheet cut side up.
In a small bowl, whisk together the vinegar and sugar.
Slowly drizzle in 3 Tbsp of oil while whisking.
Divide this mixture evenly between tomato halves.
Sprinkle tomatoes with salt.
Flip and salt the other side.
Pour another ¼ cup of oil all over the tomatoes.
Add the garlic and the herb sprigs to the baking dish.
Place in the middle of the oven for 1.5 hours or just until tomatoes are showing a hint of browning.
Remove the garlic and reserve.
Flip the tomatoes and put back in the oven for 30-60 minutes or until tomatoes are brown.
Cool to room temp and store tomatoes and oil in the fridge for up to 10 days.