Hi Hallie,
You could try one thing that I do . I have posted it before but am not sure that it works for anyone else. Sometimes I need to let my little son settle with a dummy. (He is allowed it for day sleeps but not for night). If I really need to at night he can have it to quiet down with. Once he is asleep I pull it out myself. He hasnt even gotten upset by this and will either stay asleep or can resettle from there. It tends to work better than letting it fall out as he then will wake up. Why dont you try it and let me know if you have any success? I find that babies with dummys dont tend to have a deep sleep. I use it when he has late afternoon sleeps because I can then wake him for a top up before bed. If he doesnt have the dummy he has a normal sleep and I cant get him to feed.