A prison officer has been sentenced to three and a half years in jail for engaging in romantic entanglements with two inmates and conspiring to smuggle spice-laced envelopes.

Isabelle Dale, aged 23, was involved in intimate relationships with inmates Shahid Sharif and Connor Money, professing her “undying love” for both and expressing desires to be with them upon their release, as heard in Southwark Crown Court.

The officer, described as ‘devious,’ was engaged to 33-year-old Sharif, a convicted thief. Their affair included encounters in the worship area at HMP Coldingley, Surrey, with other prisoners acting as lookouts.

Dale further demonstrated her infatuation by tattooing Sharif’s nickname, “Sneaks,” on her neck and calling herself “Miss Sneaky.” A “garish” picture of the couple was prominently displayed above her bed.

She later conspired with Sharif and his associate, Lilea Sallis, to introduce the synthetic drug spice into HMP Swaleside, located on the Isle of Sheppey, Kent.

Testimony during the trial revealed a phone conversation where Sharif advised Dale of the lucrative potential of drug sales within the prison, cautioning that the packages must not “look obvious” and needed to be “carefully crafted.”

The ‘manipulative’ prison officer was arrested on her last visit with Sharif at HMP Swaleside on November 1.  

After her arrest, police also discovered she had a sexual encounter on at least one occasion with a second inmate, Money, 28. 

Isabelle Dale, 23, became romantically involved with both Shahid Sharif and Connor Money, swearing her ‘undying love’ to both

Dale arriving at Southwark Crown Court, London, on May 23, 2025. She has been sentenced to three and a half years behind bars

Dale first arrived at HMP Coldingley in September 2021 for what would be her first and only posting. 

By January, she and Sharif had had ‘at least some contact’ because she mentioned him to a senior colleague, and by May, they were engaged, the court heard.

And while it was heard the duo had sex in a chapel area of the prison, Judge Hehir said he could not know if they were intimate at the time. 

However, he added that text messages indicate they ‘clearly had a sexual relationship’ while other guards had ‘obviously clocked on to what was going on’.

Sharif was at the time serving a 12-year and 10-month sentence for an ‘extremely violent robbery of a jewellers on the south coast’, the judge added. 

Dale, who has since resigned from her post, planned alongside Sharif and Sallis, 28, to bring envelopes dipped in spice into Swaleside Prison.

Sharif had been transferred to jail following their encounter in the chapel, and Dale visited him three times between September and October 2022. 

But, a postal strike foiled their arrangements, so it was arranged that the guard would travel to Brighton to meet Sallis and collect the envelopes, the court heard.

However, due to a conflict about prices with Sharif and the content he was posting about her on social media, Sallis backed out, the judge said.

‘I don’t think she had a fit of conscience, to put it that way, but I think that’s why her enthusiasm cooled,’ he added.

A ‘rather garish’ picture of Dale and Sharif was found in the prison officer’s home above her bed, the court was told.  

She plotted with her inmate lover and his associate, Lilea Sallies, to smuggle the synthetic cannabinoid, commonly known as spice, into HMP Swaleside on the Isle of Sheppey, Kent 

The images were ‘spliced together’ with a white heart between them as well as the date May 17, 2022, believed to be when the pair got engaged.

The judge said evidence put to the jury showed Dale ‘well understood what corruption was and the risks and dangers relating to it’.

‘She wanted to do it. I think she’s attention seeking, and I think she seeks validation, and I think she did that through relationships with prisoners,’ he added.

Meanwhile, Dale had also shared sensitive information with Money, with whom she also had an intimate relationship.

He was locked up for nine years for killing his best friend in a car crash in a 147mph police chase on a motorway in Kent. 

And when he was concerned about losing his mobile phone during a cell search, Dale told him ‘Don’t worry, security aren’t too hot on you,’ the court was told.  

Syam Soni, defending Dale, said her offending was influenced by her mental health difficulties, including depression, anxiety, emotionally unstable personality disorder and post-traumatic stress disorder.

He alleged she was ‘ill-equipped’ for the prison environment and more vulnerable than others.

Dale, of Portsmouth, was sentenced to three and a half years’ imprisonment for two counts of misconduct in a public office between September 2021 and December 2022, and one count of conspiring to convey a List A article into prison.

Sharif, who is already in custody at HMP Wandsworth, and Sallis, were also jailed for the latter charge.

Sharif attended proceedings via video link from prison. He previously admitted conspiring to bring the drug into Swaleside.

Pictured left to right: Shahid Sharif and Connor Money – two inmates who Dale had illicit relationship with 

The two women, who had denied the charge, were convicted by a jury. Sallis was sentenced to two and a half years in jail, and Sharif received 27 months.

At Tuesday’s sentencing at Southwark Crown Court, the judge told Dale: ‘I have concluded that unfortunately, you are a thoroughly devious, untruthful and manipulative young woman.

‘I accept you have some vulnerabilities, but, as was apparent in your evidence, you seek to use them as a shield and an excuse for your actions. But they did not provide that.’

‘I suspect you actually joined the prison service with a view to becoming involved in criminal activities with prisoners.’