Heat the oven to 200°C/400°F. Put the tomatoes and half a chilli in a blender with most of the oregano (reserve a few leaves for serving), the red wine vinegar, a splash of water and a pinch of salt. Blend until smooth then add to the couscous in a large bowl, stir though and set aside for 1 hour to rehydrate.
Put the squash wedges in a roasting tray with plenty of olive oil, salt and pepper, crushed garlic and the smoked paprika. Toss everything together then place the feta in the centre of the tray and put in the oven, roast for 40-45 minutes until soft.
Fluff the couscous with a fork then add the squash and olives. Slice the remaining chillies and put in with the couscous. Toss everything together. Either crumble the feta and add to the bowl or serve in a block on top of the finished salad.
Notes
Nutrition information is an estimate and will vary depending on the exact ingredients used.