In October 1992, Derek Wilton became the new deputy caretaker at Weatherfield Comprehensive, under Harry. Headmistress Sue Jeffers gave Derek the job instead of Harry's nephew, who had been Harry's choice. Harry deliberately gave Derek a hard time by demeaning him and making him do most of the work while he skived, using council meetings as an excuse. He also caused Derek to get into trouble with teacher Ken Barlow by instructing him to throw out wallcharts when clearing a classroom and then denying doing so, letting Derek take the blame for the loss of a month's work. Derek reported Harry's bullying behaviour to Sue Jeffers (as Harry was the union rep as well as his boss), and was ordered to keep a log of Harry's misconduct as Mrs Jeffers shared his dislike of Harry and wanted an excuse to sack him. Derek endured Harry's slave driver routine until the following April, when he delivered the damning dossier to Mrs Jeffers, only to discover that Harry had just got a job as caretaker at Granston Technical College - with a glowing reference from Mrs Jeffers.
At the Town Hall, Harry was never far from a scandal. In January 1993, the residents of Coronation Street protested against a new one-way system in Oakhill which resulted in diverted traffic running through Coronation Street and causing congestion. Sally Webster and Percy Sugden were interviewed by the Gazette but Harry (getting involved purely for self-promotion purposes) interrupted the interview and was the one pictured in the newspaper article, much to Sally and Percy's ire. The council eventually dropped the one-way system, but only after Lisa Duckworth was hit by a car and lost her life.
Harry was not altogether popular on the council. When Harry decided to get on the Social Services Committee, he sought fellow councillor Alf Roberts's backing. Alf didn't like Harry but agreed to back him so that he would leave him alone. This backfired as Harry then counted Alf as an ally and they occasionally drank together in the Rovers afterwards. There, he became acquainted with landlady Bet Gilroy. He received first class treatment by Bet by giving her "inside information" about a council plan to widen Rosamund Street and demolish the Rovers. As he drip-fed information Bet's way and promised to fight her corner, Bet gave him drinks on the house. Later, Bet found out that he had also told Stella Rigby of the White Swan that the council were going to demolish her pub. Investigating, the pair discovered that he was conning all the local landladies. They got revenge by inviting him to Reg Holdsworth's engagement party and forcing him to buy drinks all round in exchange for their silence.
Harry came out of the woodwork again in June 1995 when Alf, who had just completed a term as Mayor of Weatherfield, came under suspicion of embezzling money from the Mayor's charity fund. Alf maintained his innocence, although his superior at the Town Hall, Jeremy Pilkington, couldn't see how anyone else could have done it as Alf signed the cheques for the charity fund and thus would have known where the money was going (although Alf had admitted that he often signed the cheques without reading them). Harry met up with Alf to tell him he had his support, although Alf looked far from happy when Harry remarked that "only in a moment of madness" would he do such a thing. Alf's innocence was established when Brian Bowes, the formal Mayoral limousine driver, told Audrey Roberts that Harry was having an affair with Connie Holroyd, who managed finances at the Town Hall and prepared the cheques for the Mayor, and that Harry used Arnold Hall as a non de plume when placing bets. When told about this, Alf recognised the name Arnold Hall as one of the fund's payees and realised that Harry was getting Connie to make up cheques for him. He then brought Brian before Jeremy Pilkington to repeat the story, but Pilkington didn't believe the incredible tale until Connie and Harry were brought in. On seeing Connie being questioned, Harry called her a daft cow and refused to say anything until he'd seen his solicitor. Alf was vindicated, and four months later Harry was found guilty of embezzlement and sentenced to nine months in prison.