WKAF was seen by industry analyst Scott Fybush as a way for WAAF to finally achieve signal parity with WBCN; Fybush considered the combination of WAAF's new Boylston signal and WKAF's signal as "the biggest FM coverage of any single Boston facility." In 2007, the station was nominated for the Radio & Records magazine active rock station of the year in a top 25 market award; other nominees included WIYY in Baltimore, KBPI in Denver, WRIF in Detroit, WMMR in Philadelphia, and KISW in Seattle. WAAF became the longest-running rock radio station in the Boston market on August 12, 2009, after a complicated series of simultaneous format changes by CBS Radio, where WBCN's call sign changed to WBMX and format from rock to hot adult contemporary; WBMX's call sign changed to WBZ-FM and format from hot AC to sports radio as "The Sports Hub"; and WBCN's rock format was moved to the "new" WBZ-FM's second digital subchannel. WKAF broke away from the WAAF simulcast on January 5, 2017, when Entercom debuted a separate urban adult contemporary format; a press release sent out by Entercom stated that WKAF "delivered little appreciable audience beyond (WAAF's) booming signal". With the switch, WAAF added simulcasts on the second digital subchannel of WKAF and the third digital subchannel of WEEI-FM. One month later, Entercom entered into an agreement to merge with CBS Radio via a Reverse Morris Trust. Entercom, the surviving entity, retained WAAF and divested WKAF (along with several other stations) to iHeartMedia, Inc. Departure of Greg Hill The final Hill-man Morning Show aired on WAAF on July 19, 2019. Greg Hill and co-host Danielle Murr were transferred from WAAF to the morning-drive timeslot on WEEI-FM (and by extension, WVEI, due to it being a full-time affiliate of WEEI-FM's regional network) in the wake of Gerry Callahan's dismissal from WEEI-FM over declining ratings. Callahan's co-host, Mike Mutnansky, was reassigned to weeknights on WEEI-FM, while Hill's other co-host Lyndon Byers and producer Mike Hsu were moved to afternoon drive on WAAF. Byers abruptly quit on air in the middle of a show less than two months later. This left Hsu and Mistress Carrie as the lone remaining on air personalities on the station, along with The Mens Room in evenings, despite a "national search" for Hill's replacement announced by WAAF management when he left. In November 2019, the station announced a 50th anniversary concert for