The Same Subject in Different Light

We were asked to take photographs of the same subject in different lights. I took several in the morning light coming into our porch. The sun was behind the subject and most of the pictures came out too dark. When I used the flash it washed out her face and made the image flat.

These were both shot at 500 ISO 1/80 f/8. On a cloudy morning.

Later in the day the sun came out, so I tried several shots from different angles with the light.

The first image is the subject facing the sun. Besides squinting a lot, the light also makes her look washed out and gives a flattened appearance to the photo. There are harsh shadows on the left side of her face. This type of lighting makes the photo seem harsher. The photo on the right was taken with the sun to her right and behind with a bit of shadow from the building. The photo has more dimension  and an overall softer feeling. 

I love the light in this shot. The sun was behind her and gave her face the dimension and highlights for a softer look and defined features without harsh shadows. The only issue is the circle, I don't know why that happened. These photos were all taken at 400 ISO 1/400 f/8.

Here are a few more shots where I had her wear a hat. Adding something else that gives off shadows is another challenge. I think that adding some fill light might have illuminated under the brim of the hat and lifted the shadows.