A local contractor who worked as foreman on a Haines High School roof replacement in 1999 this week questioned a proposed $1.4 million bond for replacing the roof, saying decades-old leaks have persisted through multiple roofs and a major patch job.

Dan Humphrey said the history of the issue suggests water is infiltrating the school somewhere other than the roof, possibly through seams in a utility “penthouse” that sits atop the school, or through a…