Caulfield starred in the independent feature film TiMER, released May 2009. She starred as the lead role in the Funny or Die short film, Don't Panic, It's Organic. In 2012, she received critical acclaim for her guest appearance on the ABC fantasy series Once Upon a Time, as the Blind Witch from the fairy tale Hansel & Gretel. She guest starred in the second season of the Jane Espenson scripted romantic comedy web series, Husbands.