• simple-css loads its custom styles at wp_head:10:

    
    add_action( 'wp_head', 'simple_css_generate' );
    

    (10 is the default priority.)

    This causes race conditions when plugins or themes load inline styles with the same priority, so that sometimes the custom styles override, and sometimes they don’t. I saw this issue specifically with the Arras theme, but there are lots of plugins that load stuff at wp_head, so I’m sure it’s a more common issue.

    Anyway, I’d suggest that simple-css styles should always be among the last to load. For my client site, I’ve done the following:

    
    add_action( 'plugins_loaded', function() {
        remove_action( 'wp_head', 'simple_css_generate' );
        add_action( 'wp_head', 'simple_css_generate', 999999 );
    } );
    

    For the plugin, I would suggest moving to a higher priority:

    
    add_action( 'wp_head', 'simple_css_generate', 999 );
    
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