Laurel falls pregnant, delighting her and Ashley. While telling Shadrach Dingle (Andy Devine) off for drinking communion wine, Laurel realizes that she is in labour. Shadrach finds the church door is locked and rings the bells to get help. Laurel gets to hospital and has a baby boy that they name Daniel (Rachel Moonie). In February 2008, Laurel finds Daniel dead in his cot. Ashley and Laurel are devastated and Laurel moves out briefly, due to her grief. Hilary Potts (Paula Wilcox), Laurel's mother, suspects that Arthur Doland (Alfie Clarke) is actually Ashley and Laurel's biological son. Arthur's parents Greg (Shaun Prendergast) and Melanie Doland (Caroline Strong) worry that they might lose their son and try to emigrate but Ashley and Shadrach stop them. A DNA test confirms Ashley and Laurel are Arthur's biological parents and Ashley successfully fights for custody. Laurel initially struggles to accept Arthur is her son but later bonds with him.
Ashley begins a relationship with Bernice Blackstock (Samantha Giles). Ashley falls in love with Bernice but does not have the courage to tell her. He finds himself in a "right state" when he shares a tent with Bernice during a camping trip. As Middleton told Claire Brand from Inside Soap, Ashley could not handle scenarios involving females and now "he has to spend time with this woman who he clearly adores". While Ashley worries about the arrangement, Bernice remains "ignorant" to his feelings. The actor thought that Bernice had never contemplated a relationship with Ashley. He added that even "Ashley doesn't think Bernice would give him a second look even if he did tell her how he feels." The storyline had gained momentum off-screen as viewers had written to Middleton demanding a relationship between the two characters. While Inside Soap ran a poll which determined that readers wanted Bernice to leave Gavin Ferris (Robert Beck) in favour of Ashley. When the bishop learns of their romance he offers Ashley a job in Leeds, but Bernice does not like the idea. Giles told a Writer from Inside Soap that her character is reluctant to leave the village because "for once in her life, she has got some stability and she doesn't want to change that." Ashley tries to persuade Bernice to move by taking her to visit his potential work place; but Bernice is not impressed. Giles explained that Bernice dislikes it and she feels depressed. While she accepts Ashley's beliefs, his relationship with God creates problems during decision making. The Actress added that Bernice "naively thought that if they got engaged – their problems would be solved."
Emmerdale aired a special flashback episode on 22 October 2015 which revealed Ashley's whereabouts four weeks earlier. It was revealed he was at a doctor's appointment where he was told he is showing early signs of dementia. After the airing of the episode, it was announced Middleton had left his role after twenty years of playing Ashley. Middleton has reportedly chose to leave on "a high" after being handed the "best storyline of his career", comparing it to a footballer's career in the sense they leave after a good season. Middleton revealed that he had spoken with show boss, Kate Oates, earlier this year about his exit. He also mentioned that his contract does not end until the end of 2016, meaning his exit would air in early 2017. Speaking of his decision to leave, Middleton said it was and wasn't hard to leave the soap, "It's another roll of the dice. I'm very, very excited about that and I couldn't ask for a better storyline to leave the show on, I really couldn't." Middleton continued to mention how he has thought about leaving every year as well as recalling the meeting he had with Oates prior to choosing to leave: "She basically pitched the idea to me. She asked me, 'Are you happy to do this story? You probably want to think about it. I said immediately 'No I don't need time, I recognise this for what it is.'" Oates spoke of Middleton's exit, "I think this is going to be a really challenging story for us to tell. John and I have been talking about it for many, many months. We have heaped more agony on Ashley, but it's because John is an awesome actor and will do the storyline amazing justice." On 14 March 2017, it was confirmed that Middleton had recently filmed Ashley's departure scenes.
Among the next few months Ashley's dementia worsens and in October 2016 he is one of many residents injured in a large car pile up after he drives away from the village when he forgets Dotty's christening. Laurel later takes the hard decision to put Ashley into a home and is heartbroken when she finds out he has forgotten who she is and found another woman also a dementia sufferer. In March 2017, Ashley is visited by Laurel regularly however he begins suffering from a cold and after dancing with his friend Bob Hope he begins coughing blood and is taken to hospital. Laurel is distraught to hear that Ashley may only have a few days left to live and takes him back home to live with her. At home, Laurel is overjoyed when Ashley recognises her. When she leaves Ashley for a minute to get him more comfortable with pillows, he dies peacefully. Laurel returns and upon discovering Ashley has died, she hugs his body. Sandy, Arthur, Bernice and Gabby discover Laurel hugging his body and are devastated when they realise that he has died.
A Writer from Holy Soap named Ashley's most memorable moment as being the "dramatic race to the airport" to prevent Laurel from leaving. In August 2017, Middleton was longlisted for Best Actor and Best Exit at the Inside Soap Awards, while he and Bellamy were longlisted for Best Partnership and the episode from Ashley's viewpoint was longlisted for Best Show-Stopper. While the episode from Ashley's viewpoint did not make its shortlist, Middleton's other nominations did. On 6 November 2017, Middleton won the "Best Exit" accolade.
