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However, the background is not behaving how I would like it to. First of all, I want it to be flush with the white header. Second, I would like the background to “start” at the bottom of the white header, and when I scroll, it would move up to the top of the window, filling the page.

There some conflicting things going on here.

The image is bg of your content div which sits below the header and the nav so you have to find some way of pulling it up.

Is the menu supposed to have that grey background (which is actually the body background color)?

I think it’s possible that we could lose the ‘bubble’ div altogether and replace it with a pseudo element..that might make things a little easier.