Isabelle Dale certainly went for a type – tattooed 'bad boys'.

And given her look – nose piercings, false eyelashes, acrylic nails and platinum-blonde hair – the then-19-year-old had no shortage of admirers.

All well and good in the real world, maybe.

But for a prison officer working amidst 420 hardened criminals in an all-male jail it was a recipe for disaster.

And, with depressing inevitability, so it proved to be.

Within months of starting at HMP Coldingley in Surrey, the teenager, whose previous work experience was as a sales assistant at Marks and Spencer, had embarked on sexual relationships with not one but two inmates at the prison. Indeed, there may have been more.

One of them was Connor Money, a 28-year-old jailed in 2020 after speeding away from police at 140mph and then crashing his car and running away, leaving his passenger to die at the scene.

The other was Shahid Sharif. He was locked up for 12 years for the armed robbery of a jewellers during which he threatened to maim passers-by with a bottle of ammonia.

Despite knowing that relationships with prisoners were not allowed, within months of starting at the jail Dale was involved in sexual activity with both men.

In one instance, she was caught on CCTV emerging from the multi-faith prayer room and adjusting her clothing – having spent four minutes alone inside with Sharif.

The 34-year-old convict messaged her later: 'It was good sharing dat love today ur p*****s ammaazzzeeeingggggg'.

Mills and Boon it most certainly was not. But Dale was hooked, penning love letters praising his rapping skills and gushing that she would 'take a bullet for him'.

When Sharif was moved to another prison, she transferred money and went to see him, kissing him in the visitor's room.

She thought he was going to propose to her, had a Brazilian butt lift at his request and mounted a framed canvas photo of the two of them above her bed.

But the authorities, alerted by messages found on a phone in Sharif's cell, were on to them.

As well as the illicit relationship, they also found evidence of the pair arranging to smuggle the drug 'spice' into prison. The plan was to impregnate envelopes with the liquid narcotic, which mimics the effects of cannabis, and then, once dried, for Dale to post them to the jail.

Yesterday, following an eight-day trial at Southwark Crown Court, the now 23-year-old was convicted of two counts of misconduct in public office as well as conspiring to smuggle a prohibited article into prison. She burst into tears as the verdicts were delivered.

Lilea Sallis, an associate of Sharif's based in Brighton, was also found guilty of the drugs plot. As for Sharif, he had earlier pleaded guilty to conspiring with the two women to bring spice into prison.

Judge Chris Hehir granted Dale and Sallis unconditional bail ahead of sentence on a date to be fixed in January.

He warned them both: 'You have been convicted of very grave offences indeed. I can see no alternative to a substantial custodial sentence.'

Dale's downfall means she joins a rapidly growing rollcall of inexperienced, female prison staff whose illicit relationships with inmates have raised serious questions about how they came to be in positions of authority in the first place.

Foremost amongst their number is Linda de Sousa Abreu, the OnlyFans model and self-confessed swinger who, within months of starting work at London's HMP Wandsworth, was videoed having sex with an inmate in his cell. The footage was subsequently leaked and went viral.

Jailed in January, months before becoming a prison officer Abreu had appeared on a Channel 4 show in which participants took part in threesomes and orgies. On Facebook she bragged that her 'type' were 'bandits, outlaws and criminals'.

While there is no suggestion that Dale had a similar background, her appointment clearly raised eyebrows amongst staff who, she complained, viewed her as a 'dolly' bird and were critical of her appearance.

'I felt that from the beginning the prisoners had more respect for me than the staff did,' she would tell the court.

But former colleagues last night told the Daily Mail that it was as much her attitude, as her age or the way she looked, that was the problem.

'She just wasn't mature or serious enough,' said one former colleague. 'I did wonder how she managed to get through training. The feeling was that she was very insecure - which is not surprising for a new prison officer but her way of coping was over-familiarity with the cons.

'It all starts with a con asking for a favour. It can be anything, something really basic and they draw you in. They become very manipulative and then once you've crossed the line you're trapped.'

Seasoned lags know that intimacy with prison staff opens the door for long-term manipulation, giving leverage to persuade or blackmail them to smuggle in drugs, weapons and phones - all items that compromise prison security.

Indeed, in her defence Dale unsuccessfully tried to make out that she had been coerced and threatened by Sharif.

She claimed she had fillers injected into her bottom after he was rude about her 'bum size'. She also said he had forced her to buy a sex toy to 'prove' she wasn't having sex with other people.

Another female prison officer who trained alongside Dale observed: 'Izzy was nice but I was never convinced she was going to make a career out of the prison service. She was always very flirty with the instructors and she stood out from the rest of the female officers because of her appearance.

'Honestly, looking back there were so many warning signs but just because someone behaves differently to you, you don't think they are going to get involved with a prisoner and end up smuggling drugs. That's just mad.

'But no one has any sympathy for her because of how much harder she will have made things for other female prison officers.'

Because the reality is that such relationships put the safety of other honest, hard-working women staff at risk, with such incidents emboldening inmates to also target them and to question their professionalism.

Dale was just 19 when she joined the prison service in 2021, fresh out of college in Portsmouth where she grew up. As well as studying for an A-level in Law and a BTEC in psychology, she had worked part-time at M&S and in the laundry of a care home.

She had ambitions to become a police officer and joined the prison service to get experience.

That September she was posted to Coldingley, where she underwent 'counter corruption' training. It included filling out a questionnaire about grooming that spelt out that relationships were banned as was bringing items into the prison.

Weeks after Dale began at the prison, Sharif was transferred there. Suffering from learning disabilities, the lag's lengthy criminal record culminated in a £600,000 robbery on a jewellers in Bournemouth, Dorset, in 2019.

When their relationship began is unclear but in July 2022 Dale was caught on camera heading into the prayer room with Sharif. Two inmates were placed outside as lookouts. Four minutes later Dale emerged and appeared to 'readjust her belt area'.

After the alleged encounter, Sharif was transferred to HMP Swaleside on the Isle of Sheppey in Kent. Dale visited him there, sent flirty images via email and transferred £100 to his prison account.

At the same time Sharif roped Dale into helping him smuggle envelopes 'laced with spice' into the jail.

The court heard that the prison officer operated Sharif's drug-dealing Snapchat account and was tasked with sourcing the synthetic cannabinoid drug from an associate of Sharif's based in Brighton called Lilea Sallis.

On November 1, 2022, Dale was arrested at Swaleside. Police searched her car and found a packet of carbon paper used to hide contraband from prison X-ray machines. Also present was an engagement ring said by Dale to have been bought for her by Sharif.

'The prison conducted a search of Mr Sharif's cell, where a quantity of love letters, as well as a number of provocative photographs from Miss Dale were recovered,' Kieran Brand, prosecuting, told the court.

Addressing the letters to 'Sneaky', Sharif's nickname, she wrote: 'I literally worship the ground you walk on, you are my best friend, my motivation, the reason I keep fighting. 

'I will remain right next to you in all that you do, whether it's through good or bad, I am right next to you.

'I will do anything I can to help you and that's because the love runs deep... Wearing your promise ring, having you tattooed on me for life are all things I take ownership in - there is nothing I feel more proud of than being known as your girl.'

Dale also imagined what their life would be like together following Sharif's eventual release from prison.

'If there is one thing I can promise you, with hand held on my heart, is that I will be stood at those gates when you walk out and - as you told me - stepping into a Lamborghini,' Dale wrote.

Concluding her letter, she told Sharif: 'I'm so excited for our future together, never change, you are beyond perfect: our energy matches and I like that. We are like two peas in the pod and I love it.'

But phone downloads obtained from Dale's seized handset revealed that from May 2022 she had been involved in another 'physical relationship' with an inmate known as 'Con' while at Coldingley. Connor Money was an inmate at the jail at the time and refused to engage with the subsequent investigation into Dale.

Mr Brand said: 'Miss Dale refers to watching a documentary on Belmarsh about prisoners grooming staff and includes a laughing face emoji.

'She says "you maybe just wanting to use me because I'm an officer but I don't think your like that xx". 

'They engage in sexual talk - Con asks "when will I get to feel them sexy lips around my hard d***" to which Miss Dale responds with "When you know you want me and only me lol xx".'

On another occasion, Money told Dale: 'Come to the laundry room tomorrow so I can give you a cuddle.' Dale agreed.

Mr Brand told the jury: 'There is also evidence on Miss Dale's phone showing that she communicated with two further prisoners via illegally held mobile phones and received numerous photos of serving prisoners, as well as communicating with Mr Sharif's relatives, all whilst employed as a serving prison officer.'

The prosecutor ran jurors through a number of recorded calls shared between Dale and Sharif while a prison officer.

In one call Sharif told Dale there was 'big bread' to be had selling Spice in prison, boasting that he could make 'like 16 bills off an envelope'.

But he warned her later that the envelopes had to look normal, telling Dale: 'They can't be stained or nothing, they gotta look diligent.'

Instructions included: 'You got the envelope yeah. See where you put the letter inside? You don't touch that… You don't need to do it inside there... you dip the front and then dip the bak'.

Giving evidence, Dale denied having a sexual relationship with either man. She claimed that Money had once kissed her on the lips but that she had backed away from him. She said that she had only later described him in a message as 'perfect' because she didn't want him to feel rejected.

She claimed that she didn't know it was illegal for inmates to have a phone in jail and said that even if she had she would not have done anything.

'I wouldn't ever challenge a prisoner like that, because I am a weak person,' she said.

And one entirely unsuited to the job she applied for – and was paid to do.