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I think the answer is no OS does not automatically detect custom css files.

You will have to create a custom os_FrontOfficePageHeader razor file in your portal theme folder so that you can add the new link to your css.

Double check that path too... You want to place the custom os_FrontOfficePageHeader.cshtml in /Portals/0/Themes/ClassicAjax/default/ I am not seeing the portal number in your example. Your css should likewise be in /Portals/0/Themes/ClassicAjax/css/

Once you do that you should be able to add links to the razor, see your css changes and be upgrade proof.

I use custom css links exactly like this in a custom os_FrontOfficePageHeader.cshtml file :

<link href="/DesktopModules/NB…

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@james7342
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