"When It Rains, It Pours" is the second episode of the fifth season of the American television comedy series 30 Rock, and the 82nd overall episode of the series. It was written by co-show runner and executive producer Robert Carlock and directed by series producer Don Scardino. "When It Rains, It Pours" originally aired on NBC in the United States on September 30, 2010. Guest stars in this episode include Joanna Adler, Ben Bailey, Elizabeth Banks, Craig Castaldo, Paul Giamatti, Andrea Mitchell, Chris Parnell, Sherri Shepherd, and Brian Williams.

The fifth season of 30 Rock, an American television comedy series on the NBC network in the United States, began airing on September 23, 2010. NBC announced on March 5, 2010, that 30 Rock would be returning for a fifth season in the 2010–2011 television season. Beginning with episode 11, 30 Rock was moved to the 10:00 PM timeslot, but, as a consolation, was renewed earlier than the other NBC sitcoms. During this time, Tracy Morgan underwent an emergency operation, causing his character to be written out for several episodes.