Songfacts®:

• This Jim Brickman song features the Contemporary Christian singer Kristy Starling on vocals. She sings about sending a care package to a loved on who is away on Christmas. In a Songfacts interview with Brickman, he said: "When I wrote that, we were actually thinking more about kids not coming home from college, because the concept of that song was what you might send somebody. If you could send Christmas in a box, what would it be?
  
  It's what I call a 'list' song. You start with all the things you might put in this box that represent the relationship that you have with someone else. In that case, a candy cane, some gingerbread, a stocking I made that has your name on it. You start making a list of all the things you might put in a box to send somebody. Then it was sort of appropriated by the USO and Operation Care Package because of the message."
• Billy Mann and Victoria Shaw wrote this song with Brickman. Mann has done a lot of work with Pink, co-writing four songs on her Funhouse album; Shaw is a recording artist who co-wrote Garth Brooks' hit "The River."
• Like his songs "The Gift" and "Christmas Where You Are," this song takes place at Christmas time, but isn't specifically about the holiday. "Every time I write a song like one of those, I think to myself, 'Why is it that it's only at this time of year that it's time to say, 'I miss you'?,' he told Songfacts. "It's because the emotional awareness of people and nostalgia is so amplified, so we tend to think that this is the time of year to write those things."
• Johnny Mathis sang this with Brickman on Brickman's 2013 album The Magic of Christmas. Brickman was very keen to work with Mathis, and sent him a number of original songs to consider. But the one Mathis wanted to record was "Sending You A Little Christmas," a song written a decade earlier.
• This went to #1 on the Adult Contemporary chart, giving Brickman his second chart-topper on that tally, following "Simple Things."