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  1. For every enqueue action, there is a corresponding print_styles action:

    • wp_enqueue_scripts → wp_print_styles
    • admin_enqueue_scripts → admin_print_styles
    • customize_controls_enqueue_scripts → customize_controls_print_styles

    Not for the login page. There is no login_print_styles action or function, so your stylesheets are thrown out on do_action( 'login_footer' );.

    But there is a simple fix:

    if ( ! has_action( 'login_enqueue_scripts', 'wp_print_styles' ) )
        add_action( 'login_enqueue_scripts', 'wp_print_styles', 11 );
    

    WordPress will now print all link elements registered for that page at the proper place, the head element, right after the built-in stylesheets.

    Result:

    <link rel='stylesheet' id='dashicons-css'  href='http://git.wp/wp-includes/css/dashicons.min.css?ver=3.9-alpha' type='text/css' media='all' />
    <link rel='stylesheet' id='wp-admin-css'  href='http://git.wp/wp-admin/css/wp-admin.min.css?ver=3.9-alpha' type='text/css' media='all' />
    <link rel='stylesheet' id='buttons-css'  href='http://git.wp/wp-includes/css/buttons.min.css?ver=3.9-alpha' type='text/css' media='all' />
    <link rel='stylesheet' id='colors-fresh-css'  href='http://git.wp/wp-admin/css/colors.min.css?ver=3.9-alpha' type='text/css' media='all' />
    <!--[if lte IE 7]>
    <link rel='stylesheet' id='ie-css'  href='http://git.wp/wp-admin/css/ie.min.css?ver=3.9-alpha' type='text/css' media='all' />
    <![endif]-->
    <link rel='stylesheet' id='TEST-css'  href='http://themes.wp/t5-theme-base/css/login.css?ver=3.9-alpha' type='text/css' media='all' />
    

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