Bob Raines, a former superintendent of the Shoreline Unified School District, began serving a 210-day sentence in July for molesting a child at district offices. Mr. Raines, 72, was convicted of engaging in lewd conduct in 2023. He was arrested at his Petaluma home in 2021 and charged with a felony, but the Marin District Attorney’s Office later dropped the charge to a misdemeanor. The lower charge did not require proving that he had touched the boy, only that he had engaged in disturbing behavior motivated by unnatural sexual interest. In addition to the jail sentence, he was ordered to register as a sex offender. The incident that led to his conviction occurred weeks before he was due to retire after a 43-year career in education, the last five years at Shoreline. But according to witnesses who testified during Mr. Raines’s 2024 trial, his behavior appeared to be part of a pattern. A former student of a school where Mr. Raines served as principal said he had been subjected to similar inappropriate behavior, and a former teacher recounted witnessing several students sitting on his lap. She said she had notified the school board and the Sonoma County Sheriff’s Office, but no charges were filed. Mr. Raines, who had appealed his sentence, surrendered at Marin County Jail on July 13.