Prison officer faces jail for affairs with two inmates and smuggling in drugs

For Dan Sanderson
Isabelle Dale kept in touch with one of her lovers after he was transferred and smuggled drugs for him using love letters

A prison officer sobbed in court today as she was told she faces a ‘substantial’ jail sentence for brazenly carrying on with two inmates and sneaking drugs in for one of them.

Isabelle Dale, 23, posted two other inmates as lookouts while she had sex with convicted robber Shahid Sharif, 33, in the multi-faith prayer room at HMP Coldingley in Surrey.

Dale, who was 19 or 20 at the time, got Sharif’s nickname ‘Sneaks’ tattooed on the back of her neck, called herself ‘Miss Sneaky’ and hung a framed picture of them above her bed.

Meanwhile she was also in a sexual relationship with Connor Money, 28, who was serving nine years for killing his best friend by crashing his car while fleeing from police at 147mph.

Prosecutors said Dale and Sharif used the prayer room because it ‘is not covered by CCTV’.

Sign up for all of the latest stories

Start your day informed with Metro’s News Updates newsletter or get Breaking News alerts the moment it happens.

They were seeen entering the room together and leaving after four minutes, with Dale ‘appearing to readjust her belt’.

Shahid Sharif A prison officer has appeared in court charged with having sexual relationships with two inmates. Isabelle Dale, 23, allegedly had a fling with Shahid Sharif, 33, in high security HMP Swaleside on the Isle of Sheppey, Kent, between 1 September 2021 and 31 December 2022. Dale is also accused of having a sexual relationship with her second prisoner boyfriend, Connor Money, 28, at the same time. He was serving nine years for killing his best friend in a car crash while escaping police at 147mph. Central News
Caption: Shahid SharifA prison officer has appeared in court charged with having sexual relationships with two inmates.Isabelle Dale, 23, allegedly had a fling with Shahid Sharif, 33, in high security HMP Swaleside on the Isle of Sheppey, Kent, between 1 September 2021 and 31 December 2022.Dale is also accused of having a sexual relationship with her second prisoner boyfriend, Connor Money, 28, at the same time.He was serving nine years for killing his best friend in a car crash while escaping police at 147mph.Central News
Photographer: Central News/Web collect
Copyright: Central News/Web Collect(Credits: Central News/Web collect)

Sharif later texted her: ‘It was good sharing dat love today ur p**** [is] ammaazzzeeeingggggg.’

He was transferred to another prison but she kept in touch with him by phone and the ’email a prisoner’ system, also sending him money and paying him ‘social visits’ during which they were caught on CCTV kissing and hugging.

Dale also bought herself a £3,000 engagement ring for him to give her when he was free.

She then smuggled synthetic cannabis, or ‘Spice’, using love letters in which she told him of her dreams of their life together on the outside.

The 23-year-old soaked the letters in a liquid form of the drug, using a special type of paper that would conceal it from prison x-ray machines.

Connor Money A prison officer has appeared in court charged with having sexual relationships with two inmates. Isabelle Dale, 23, allegedly had a fling with Shahid Sharif, 33, in high security HMP Swaleside on the Isle of Sheppey, Kent, between 1 September 2021 and 31 December 2022. Dale is also accused of having a sexual relationship with her second prisoner boyfriend, Connor Money, 28, at the same time. He was serving nine years for killing his best friend in a car crash while escaping police at 147mph. Central News
Dale also had a sexual relationship with Conor Money, telling him he is ‘perfect’ in a message (Picture: Central News)

She was taught how to do so by Sharif, who had told her there was ‘big bread’ to be made selling Spice in prison and boasted he could make around £1,600 per envelope.

‘I literally worship the ground you walk on, you are my best friend, my motivation, the reason I keep fighting,’ she wrote.

‘I will do anything I can to help you and that’s because the love runs deep.’

Dale used Sharif’s drug-dealing Snapchat account to source the drug from an associate, Lilea Sallis, 27, from whom she made collections in Brighton.

Her relationship with Money was uncovered when police arrested her and searched through her phone.

For Dan Sanderson
Dale claimed she had a botched bum lift because her inmate lover ‘degraded’ her body

In one text Money asked ‘when will I get to feel them sexy lips around my hard d*ck’, to which Dale replied: ‘When you know you want me and only me lol xx’.

Messages with at least two other prisoners were also found on Dale’s phone.

The 23-year-old, who was just months into the job when she started her relationship with Sharif, said she gravitated towards the affection of inmates because her colleagues would mock her extensive tattoos.

She denied having sex with Sharif but admitted having ‘phone sex’ with him.

She told jurors she had bum-enhancing surgery on his instructions after he regularly ‘degraded’ her about her body, developing septic abcesses after it was botched.

Isabelle Dale arriving at Southwark Crown Court, London, where she is charged with with two counts of being a holder of a public office who wilfully misconducting herself, while a prison officer, had sexual relationships with two serving prisoners, between September 1 2021 and December 31 2022. Ms Dale is also charged with conspiring to bring controlled drugs into HMP Swaleside on the Isle of Sheppey, Kent. Picture date: Friday May 23, 2025. PA Photo. See PA story COURTS Dale. Photo credit should read: PA Wire
Dale was convicted of multiple offences and told she faces a hefty sentence behind bars (Picture: PA)

Dale also denied having sex with Money, claiming she only sent him flirty messages to appease him after he ‘threatened to stab me’ and ‘told me he hated me and wanted me to die’.

Dale was convicted of two counts of misconduct in a public office and conspiracy to convey a ‘List A’ prohibited article into prison.

Sallis was also convicted on the same smuggling charge.

They were granted unconditional bail ahead of sentencing, with the judge telling them: ”You have been convicted of very grave offences indeed. I can see no alternative to a substantial custodial sentence.’

Get in touch with our news team by emailing us at webnews@metro.co.uk.

For more stories like this, check our news page.

(Visited 1 times, 1 visits today)

Leave a Reply

Your email address will not be published. Required fields are marked *