Dashboard block not getting view.css

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I created a custom block to go on the News/Home page of the dashboard. (5.5.0) Everything works fine most of the time, but when I first log in and it checks for updates before showing the news feed, it doesn't get the view.css file from my block.

Because of ccm.app.css, styles are applied to elements depending on which section they're in, regardless of block. (such as div#ccm-dashboard-welcome-back h1) This is bad practice for an editable area in my opinion, but regardless, I should be able to use view.css whether loading the page from the dashboard or automatically upon logging in.

I can add a style tag inline as a workaround, but I believe this is a bug that needs to be addressed.

ZeusExMachina