Roughly chop the Summer Squash (2 cup). Heat a soup pot over medium-low. Add Olive Oil (1 tablespoon). Add squash and Salt (to taste). Cook for 5 minutes, stirring occasionally.
Add Chili Pepper (1/2) and cook for 2 minutes. Add Garlic (3 clove) and cook for 1 minute more. Add Canned Crushed Tomatoes (2 cup), Water (3 cup), and Maple Syrup (1 tablespoon). Bring to a boil, then reduce to a simmer and cook for about 10 minutes.
Remove from heat and add Fresh Basil (1/2 cup).
Blend with a hand blender (or in batches in a regular blender, with the lid's plug removed and the hole covered with a clean tea towel) for 1 minute. Taste and adjust seasoning if needed.