In 2009, The Lance was divided into two community newspapers to better cover the expanding and developing Winnipeg South area, and The Sou'wester was born.
Two niche publications, Uptown Magazine, an alternative news-and-entertainment weekly, and The Prime Times, a seniors' paper, were purchased from Rosebud Communications in 2005.
The Prime Times ceased publication in November 2011 and Canstar and FP Canadian Newspapers launched a bi-monthly magazine, Winnipeg Boomer, on Nov. 26, 2011.
Beginning in 2022, Canstar reduced the number of titles it operates from six to two with the creation of the East and West editions of the Free Press Community Review.
Coverage areas of the new publications are divided by the Red River, which flows south to north through the city of Winnipeg.