"Thoroughly devious and manipulative" - Portsmouth prison officer jailed after having sex with inmate and plotting to smuggle drugs into prison

A former prison officer from Portsmouth has been jailed after becoming romantically involved with two inmates and plotting to smuggle drug-soaked envelopes into jail.

Isabelle Dale, 23, of Cosham got engaged to “violent” robber Shahid Sharif and had a relationship with Connor Money, another inmate, when she was positioned at HMP Coldingley, in Surrey.

Dale 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. The second charges relates to Dale and Sharif’s plot to smuggle spice into a Kent prison after he had been moved there.

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

Upon sentencing the three at Southwark Crown Court on Tuesday, the judge told Dale: "I have concluded that unfortunately you are a thoroughly devious and 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."

The court heard how Dale started working at HMP Coldingley in September 2021 and by May her and Sharif were engaged.

Isabelle Dale, 23, of Cosham got engaged to “violent” robber Shahid Sharif and another inmate called Connor Money when she was positioned at HMP Coldingley, in Surrey.placeholder image
Isabelle Dale, 23, of Cosham got engaged to “violent” robber Shahid Sharif and another inmate called Connor Money when she was positioned at HMP Coldingley, in Surrey. | Google

The trial was told the prison officer, who has since resigned, had sex with Sharif in the chapel area of HMP Coldingley. Despite this Judge Hehir said he could not know if they were intimate in the chapel area but that text messages show they "clearly had a sexual relationship" and other prison officers had "obviously had clocked on to what was going on".

At the time Sharif was serving a 12-year and 10-month sentence for an "extremely violent robbery of a jewellers on the south coast", the judge added. In a search of Dale's home a "rather garish" picture of the couple was found hanging above her bed, the judge said.

The canvas was a picture of the two "spliced together" with a white heart between and the date May 17 2022, which was believed to be the day of their engagement. After the alleged sexual incident in the chapel, Sharif moved to Swaleside prison and Dale signed off work sick on reduced pay.

However, their relationship continued and Dale was involved in the drug smuggling conspiracy while still employed as prison officer, the court heard. Dale visited him five times in Swaleside between September and October 2022 , sometimes with his family members with whom she was by then in fairly regular contact, it was told.

She had joined his list of approved visitors by concealing her job role, the judge said.

In a demonstration of "quite how thoroughly corrupt you had become", Dale attempted to persuade Sharif's sister to sneak in a USB for him, he told the court, which the sibling declined to do.

The prison officer also passed messages to Sharif's criminal associates outside the jail "about the movement or sale of what I'm quite sure was illicit property", the judge said. She also posted stories and used the messaging service on his social media account on his behalf.

Dale resigned as a prison officer before she was arrested on her sixth visit. She was found to have Sharif's street name tattooed on her neck as well as an engagement ring and carbon paper in her car, the court heard. Carbon paper can be used to disguise contraband from x-rays.

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

He added: "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."

Syam Soni , defending Dale, had said her offending was influenced by her mental health difficulties, including depression, anxiety, emotionally unstable personality disorder and post-traumatic stress disorder. He had claimed she was "ill-equipped" for the prison environment and more vulnerable than others.

The court heard Dale also conveyed sensitive information to Money, with whom she also had an intimate relationship.

The judge said: "When he said he was worried about losing his mobile phone if his cell was searched, any right-thinking security officer would go in and seize the cell, but she said 'don't worry, security aren't too hot on you'."

Dale, Sharif and Lilea Sallis , 28, also planned to bring envelopes dipped in spice into Swaleside prison. Messages from Sharif showed him claiming he could make £3,000 a week from selling the spice inside jail, which Judge Hehir said may have been an exaggeration.

A postal strike foiled their arrangements and it was organised for Dale to travel to Brighton to meet Sallis and collect the envelopes, the court heard. However, Sallis backed out because of a conflict with Sharif about prices, and content he was posting about her on social media, the judge said.

The judge added: "I don't think she had a fit of conscience, to put it that way, but I think that's why her enthusiasm cooled,.”

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

Related topics:
News you can trust since 1877
Follow us
© 2026 Iconic Media Group Ltd. All rights reserved.Cookie SettingsTerms and ConditionsPrivacy notice