I have a listbox filled with different items. For each item in the list it will visit a site in the web browser, the user using the software fills out text on the page, then it moves down the list.

How can I make it so it iterates down the list to an item, waits for the user to enter the data and for them to click a button on the GUI of the program, then continue the iteration again doing the previous things of stopping continuing?

I would suggest that for each existing item in the list, you show a new form in dialog mode to navigate to the web page.
when the user closes this form, the calling will go to the next item in the list.

Hope this helps

Does the user click a button on the actual windows form or the website form before moving to the next item in the listbox?

If the user clicks a button on the winform, that's simple, use a button click event to move down the listbox to the next item, if there is no next item, move to the first one again (if that's what you want).

If it's a button on the website form they click to advance...I'm not sure, I never use the browser control.

See the ListBox.SelectedItem property and the ListBox.SelectedIndexChanged event.

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