Issue with Custom Post Type Tags

You need to use 'taxonomies' => array( 'post_tag' ) to add tags support for a custom post type, like this:

function Work() {
    $labels = array(
        'name'               => _x( 'Work', 'post type general name' ),
        'singular_name'      => _x( 'Work', 'post type singular name' ),
        'add_new'            => _x( 'Add New', 'Work' ),
        'edit_item'          => __( 'Edit Work' ),
        'new_item'           => __( 'New Work' ),
        'all_items'          => __( 'All Work' ),
        'view_item'          => __( 'View Work' ),
        'search_items'       => __( 'Search Work' ),
        'not_found'          => __( 'No Work Found' ),
        'not_found_in_trash' => __( 'No Work Found In The Trash' ), 
        'parent_item_colon'  => '',
        'menu_name'          => 'Work'
    );
    $args = array(
        'labels'        => $labels,
        'description'   => 'Holds our Work and Work specific data',
        'public'        => true,
        'menu_position' => 5,
        'supports'      => array( 'title', 'editor', 'thumbnail', 'excerpt', 'comments' ),
        'has_archive'   => true,
        'taxonomies' => array('category', 'post_tag'),

    );
    register_post_type( 'Work', $args );
}