CISS was acquired by Rogers Communications on February 26, 1999, and was rebranded first as Power 92, then Kiss 92.5 as a Top 40 station, but the station was renamed to 92.5 Jack FM on June 4, 2003, with the call letters CJAQ-FM under a jockless adult hits format before abandoning the concept in 2006, and played classic rock music.

[7] Some reports at the time indicated the staff had been taken out to a meal at a restaurant nearby, then returned to the station to find they were no longer allowed in.

In its early days, the station also aired imaging material in which an announcer pronounced the name of the city "Toe-ron-toe", widely considered a mispronunciation of Toronto.

Thanks to former CRTC content regulations on FM radio, CISS was the first, and remained the only Top 40 station on FM licensed to the City of Toronto in the late 1990s and early 2000s (the closest formatted station in the market, CIDC-FM, which airs a rhythmic contemporary format, is licensed to Orangeville, and is a rimshot from the northwestern portion of the market).

The station rode a wave of popularity for pop music acts like Backstreet Boys and 'NSYNC, and often seemed to supertarget a primary market of young teenage or preteen girls.

Station personalities included Jay Michaels, first paired with Daryn Jones as "Mad Dog and Daryn" and then with Billie Holiday in mornings as Mad Dog and Billie (frequently accompanied by voice actress Stephanie Beard as "Suga BayBee"), Kris James (a re-hired veteran of the country format, and temporarily the CHR format's first morning host) middays, Tarzan Dan afternoons, Cory Kimm and Taylor Kaye evenings, and Slim hosting "Slim Jams", a slow jam/R&B program in overnights.

[13] By 2002, somewhat ironically, the station moved to take CFXJ's turf with a complete shift to a rhythmic contemporary format billed as "Toronto's Hip Hop and R&B".

The station hired local urban flavoured talent DJX and Haddy, Axel, Kwame, DJ Baby Yu and RG.

In November 2005, Cardinal defended his decision in an interview with Michael Hainsworth of Report on Business Television and stated why he doesn't see commercial-free iPods and satellite radio as a threat to a non-DJ format.

The move to rock would further hamper CJAQ's overall share in the Toronto radio market (down 17%), even in the male target demographic (down 14%).

Brown and Klassen would be holding down both the morning and afternoon drive slots by May 2009, one month after "Jack FM" registered a dismal 2.0 share in the BBM ratings results for the Toronto market.

At 3 p.m. on June 5, 2009 (one day after the 6th anniversary of Jack's launch), after playing "Boy Inside the Man" by Tom Cochrane & Red Rider, the station reverted to contemporary hit radio as KiSS 92.5.

In 2013, the station's DJ Clymaxxx and Mocha won their 2nd consecutive Stylus Award for "Radio Mixshow DJs of the Year" for Set It Off.