Depending on whether Sean Darcy recovers from a calf issue in time for Friday's match at Optus Stadium, Jackson will either go it alone or split Grundy-handling duties with his ruck partner.
There is a unique connection between Jackson and Grundy.
The former Collingwood big man was recruited to Melbourne at the end of 2022 to replace Jackson as Max Gawn's ruck partner after the young gun was traded to Fremantle.
But it didn't work out, and Grundy headed to Sydney in last year's trade period.
It's paid off, with the ruckman crucial to the ladder leaders' hot start.
Brodie Grundy (left) has been in match-winning form since moving to the Sydney Swans. (Joel Carrett/AAP PHOTOS)
Jackson is wary of Grundy, who is as dangerous around the ground as any small player.
"He's a really good player and it'll be a big challenge going up against him," Jackson told AAP.
"He's just a good overall player and a good ground-level player as well, so it'll definitely be a good contest."
Jackson, who has averaged a career-high 18 hitouts plus a goal a game, rucked solo early in the season when Darcy was sidelined, and did so again in the latter stages of Sunday's win over Richmond.
"I've played it enough to be used to it," he said.
The Dockers are raring to prove their mettle against consistent high achievers Sydney.
"It's a good challenge coming up," Jackson said.
"Friday night, so it'll be the big stage.
"It'll be a heavy game in the contest - a lot of stoppages I think. I'm looking forward to it."
Jackson is "loving" contributing up forward when Darcy is fit and firing, and is enjoying their budding partnership.
"It'll keep building the more we play," he said.
"We hardly played together last year, so we'll keep building."
Making Jackson's life in attack easier has been Josh Treacy's breakout campaign, with the forward booting a career-high 18 goals.
"So good. He's really developing at the moment," Jackson said.
"He's such a big guy down there and a really good target for us."
The Dockers were reeling after their shock derby loss to West Coast, but have won their past two games to steady their season at 5-3.
"We didn't play our way at all that night (against the Eagles), so it was good to rethink some things and get back on the horse," Jackson said.
"We're playing some good footy and it's starting to come together really well. All our positions are connecting, so it's good."
And what about life back in Western Australia?
"I love it," Jackson said.
"I can't complain about anything."
8°C