White space beneath in-line image when at top of page

I am working on multiple word documents that all have the same issue. The document is a checklist type procedure, and the image I am having issues with is a square check box that is inserted at the end of the sentence. 

The problem is that when the text line is at the top of the page, the square check box does not stay on the same line as the text. This is not a problem when the text is not at the top of the page. It is also only a problem for paragraphs with more than 1 line. See attached image.

I noticed this wasn't a problem for other Heading Styles, so I was able to isolate the issue to the following settings:

1. Issue goes away if the "Don't add space between paragraphs of the same style" box is selected in the Paragraph menu.
2. Issue goes away if I select "Remove space before paragraph" in the line spacing options.

However, this isn't viable for me, because I want there to be white space between paragraphs for ease of reading the checklist, and having spaces between paragraphs is an easy way to implement this feature. The documents is hundreds of pages long, there are around 30 other documents with the same issue, and the documents change every few months, so it would be too time consuming to manage every paragraph at the top of every page.

Is this a bug of some sort? If so, is there a work around, or will I just have to live with it?

EDIT: Just noticed the highlighting of the text shows a different height. First is a new paragraph and is not affected, but the second picture shows a the list breaking across the next page and having the issue. Some setting I'm missing?