Pages don't maintain the style after implementing custom Style sheet

I am using the custom style sheet in the designer. When I open a page in the designer it automatically applies the style sheet to the page. However, when I navigate away from it, or update the style sheet all of the styling gets stripped away and I have to close and reopen the view in the designer to see the styles applied again. Everything looking good in an actual client. It's a real pain for developing. Has anyone else experienced this? I am using 8.1.37.

Have you tried just toggling the "Play" button in designer? Most of the time I find this refreshes the CSS

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No, unfortunately that doesn't want to work either.