A headteacher jailed for harassing a trainee has been accused of sending disturbing messages targeting an Ofsted inspector and senior education leaders. 

Gregory Hill, 49, faces three charges related to persistently sending or posting online messages while facing allegations that he had become obsessed with a young teacher after she spurned his romantic advances. 

The former head of Howard Junior School in King's Lynn was jailed earlier this month after being found guilty of harassment and resisting arrest. 

Former headteacher Greg Hill during his arrest in March 2023Former headteacher Greg Hill during his arrest in March 2023 (Image: Norfolk Constabulary)

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The new charges, which carry a maximum of six months imprisonment, allege that he persistently made use of public communication networks to cause annoyance, inconvenience and anxiety between December 2023 and February 2024.

They relate to online messages about Daniel Lambert, a lead inspector for Ofsted who carried out an emergency inspection of Howard Junior following the former headteacher’s arrest in March 2023.

Others include allegations over communications about Paul Shanks, chief executive of Eastern Multi-Academy Trust, and Phil Bugg, vice principal of King’s Lynn Academy. 

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Hill, of Valley Way in Fakenham, had been due before Norwich Magistrates’ Court via video link from prison but technical difficulties saw Deputy District Judge Sundeep Pankhania adjourned his case until August 27.

Bail conditions prevent him from contacting the three individuals or posting their names on social media.

Greg Hill is accused of messages against the Ofsted inspector who carried out emergency inspection of Howard Junior School in King's LynnGreg Hill is accused of messages against the Ofsted inspector who carried out emergency inspection of Howard Junior School in King's Lynn (Image: Newsquest/Chris Bishop)

Following the emergency Ofsted inspection Howard Junior was rated inadequate with Mr Lambert identifying “serious failings” which had gone “unchallenged for too long”.

The school was previously run by the Apollo Academies Trust, which Hill was chief executive of as well as being headteacher. 

READ MORE: King's Lynn Howard Junior rated inadequate after head arrest

During his trial he was found to have hounded 21-year-old probationary teacher Chloe Regester for more than a year and bombarded her with dozens of social media messages declaring his love for her. 

The judge described the outcome as a “significant and spectacular fall from grace”, adding "even now you fail to realise how wrong your behaviour was... you are an obsessive individual and you abused the power you held."