O'Sullivan has had a quiet start to the 2026-27 season, with a run to the semi-finals of the Wuhan Open the only significant result in his five tournaments to date.
Two last-16 finishes preceded his final-four finish at that event, but he has been defeated in the first round in his two subsequent appearances, in Shenzhen and Belfast.
Having earned £513,750 at ranking events over two years, O'Sullivan is £99,350 ahead of Ali Carter, who holds 16th spot in the world rankings, and £154,650 clear of Zhou Yuelong, who sits in 17th, with winnings of £359,100.
On first glance, that appears to be a comfortable cushion, with only a set of significant runs from his rivals putting him at risk of having to qualify for the World Championships in May next year.
However, there are issues over the horizon, because over a third of O'Sullivan's winnings come from reaching the final of the Saudi Arabia Masters in August 2025.
The £200,000 he won in Jeddah will continue to count towards his ranking past the 2027 World Championship, but that money will slip out of the eligibility period soon after the start of the 2027-28 season.
O'Sullivan will also not be able to replace his earnings with another run at the event, after the tournament, which offered the highest prize money outside of UK-based competitions, was abolished in April.
That means he is likely to need strong performances over the next 18 months to remain in contention for an automatic spot at the 2028 World Championship.
O'Sullivan might improve his chances of earning ranking prize money by competing in more tournaments, having operated on a reduced schedule in recent years.
It should be noted he has cited medical reasons or the need to prioritise his mental health for his withdrawals from several tournaments in recent years.
He played predominantly in Asia in 2025-26, only competing in two tournaments in Britain - the UK Championship and World Championship.
His appearance in Belfast this week was his first in a ranking event in the United Kingdom outside the Triple Crown events (Masters, World Championship, UK Championship) since the British Open in September 2024.
His last ranking title came at the World Grand Prix in January of the same year.
After his defeat in the semi-finals of the Wuhan Open in August, O'Sullivan said he did not "want to throw in the towel just yet".
But he has also acknowledged he has limited time left in the sport, giving himself until 2028, external to beat Hendry's world title total by landing an eighth.
Should he slip out of the top 16, O'Sullivan has said he has no interest in competing in World Championship qualifying - held this year at the English Institute of Sport in Sheffield - stating he would retire from snooker instead.
There are 16 places available for the World Championship through the qualifying rounds, with Hendry, Mark Williams, Ding Junhui and Steve Davis among players past and present who have taken that route after slipping out of the elite 16 amid declining results.
It seemingly holds no appeal to O'Sullivan, though.
"I'd love to win another World Championship. I've got two attempts at it," O'Sullivan told World Snooker Tour in July.
"If I don't do it this season or the next season, then it'll definitely never happen.
"I'm not going to play qualifiers. You won't be seeing me go down to Barnsley trying to win qualifying matches and all that sort of stuff.
"I have to be realistic. If that happens, then obviously that's the end of my career. But hopefully, I can keep going for at least another two seasons."
Playing in more tournaments may be the most obvious way to avoid a difficult retirement decision, but O'Sullivan has spoken candidly about his battles with depression and anxiety and may feel he cannot compete more regularly.
O'Sullivan has threatened to retire on multiple occasions during his career before deciding to stick with the sport, going back as far as his teenage years.
Those have usually quickly been forgotten and the reality is that he has displayed remarkable longevity, with his first World Championship win coming in 2001 and his latest in 2022.
However, faced with fading powers and a resulting lack of prize money, we may be entering the end stage of the all-time great's career.