He was known as a humanistic employer interested in the welfare of his employees, stating that his proudest moment was the introduction of a pension plan for Herald staff.

In January 2004, The Chronicle Herald became the first newspaper in Canada, and one of only several in the world, to operate a WIFAG offset press.

In 2002 the historic Herald headquarters on Argyle Street was listed for sale for $15 million and sold by the Dennis family to the cable TV mogul Charles Keating.

Dennis holds a "far less romantic view of the newspaper" than her father did, a characteristic that journalist Stephen Kimber said has made cost-cutting easy.

"[3] Shortly after taking over as CEO, Dennis championed the newspaper's independence, stating: "The fact that we're not controlled by someone in Ontario makes a big difference in what we can do.

[12] In February 2015, the Herald locked out its 13 unionized printing press workers, causing the first work stoppage in the company's history.

The Chronicle Herald refused any concessions offered by the union, and later on the striking staff launched a competing online newspaper called Local Xpress.

[9][18] The union agreed to wage cuts and increased working hours equating to an hourly pay decrease of 17 per cent, layoffs of a third of unionized staff, a cap on severance pay, reductions in vacation time and mileage allowance, a 25 per cent lower starting wage, and elimination of the defined benefit pension plan founded by Graham Dennis.

The newspaper was accused of making unreasonable demands with the aim of breaking the union, and hired lawyers advertising services in union-busting.

[19] During a round of bargaining in October 2016, Herald made numerous additional demands, including further cuts to the union's bargaining power, reduced sick leave pay, a further four per cent wage cut, eight more layoffs (amounting to a total of 26 layoffs), and the closure of Local Xpress and the signing-over of all Local Xpress content to the Herald.

[20] As a result of this strike, CEO Mark Lever won the labour news website rankandfile.ca's annual Scumbag of the Year award for 2016.

Several faculty members at the University of King's College, which is well-regarded for its journalism program, advised graduating students against crossing the picket line.

[22] Investigative journalist Tim Bousquet, of the Halifax Examiner, questioned the newspaper's practice of printing advertorial content nearly indistinguishable from regular news.

Boutilier stated that he could not find the piece on The Canadian Press news wire while Bousquet commented that aside from the Star, the Herald appears to have been the only other newspaper to print the story.

The story alleged that Syrian refugee children attending Chebucto Heights Elementary School were "choking, pushing, slapping and verbally abusing their fellow classmates".

[26] The paper was widely condemned as the story was unverified, having been based on a sole anonymous source, and was written with a highly sensational tone that alleged acts of "brutality" by children as young as five.

[27] In the face of public outcry the newspaper tweaked the article online, removing some details before deleting it from the Herald website altogether on Monday morning.

"[29][30] On 13 April 2017, Transcontinental announced that it had sold all of its newspapers in Atlantic Canada to SaltWire Network, a newly formed parent company of the Herald.

[31][32][33] The Halifax Typographical Union called the purchase evidence that the Herald's claim of impending financial collapse was a "total fabrication".

The agreement included an increase in the work week from 35 to 37.5 hours, the dismissal of 26 union staff (with 25 returning to the newspaper and one moving to Cape Breton), and wage cuts.