Krauss told the story of how she came to sing this Castleman song to The Boot: "We recorded in July and August and I said, 'We don't have it, we've got to stop and let me go look for some more things.' So we took a break, and I went looking for stuff. I called R.L. and said, 'Where are you?' I had known that he was in a place of being uninspired. I was lost. Sidney Cox [another frequent contributor to Alison's albums] was lost. We kept having these conversations of, 'I just can't find it. Nothing is sad enough. Nothing is resounding. I'm not able to connect with these things I'm singing about,' which is a very empty feeling. If you're not connecting with what you're singing, it doesn't mean the material is bad or that they aren't beautiful songs. They just weren't speaking to me yet.
When I called R.L., who's been a center of our recordings for the past 12 to 15 years, he said, 'I've been going to the ocean, going to the places I used to go when I was heartbroken and I just can't find it.' After a long conversation, he said, 'Just come over and sit here and talk to me.' So, I drove over there. When I walked in the door, he had a melody and it was 'Paper Airplane.' It was beautiful. I said, 'Well, what are you gonna do now?' He said, 'I'll wait.' I said, 'Wait for what?' [laughs] He said, 'It'll be here about midnight.' It's like a download for him. Completely inspired. He doesn't mess around with it, he just waits. And there it was, 'Paper Airplane.' I just loved it."