"I just worry that taking it off, quite frankly, means that he will get on the turps and we'll be back to square one," Judge Tony Greig said of removing Roebuck's tracking ankle bracelet.
"I really want this [rehab] to succeed. Because if this succeeds, Mr Roebuck will stop going to prison, he will stop hurting other people, everyone is a winner."
The judge said he had been trying to "nurse [Roebuck] through" to the point of rehab.
In September last year, he sentenced Roebuck to 20 months' jail for a number of drunken assaults.
At the time, Roebuck's defence counsel argued for intensive supervision coupled with judicial monitoring but Judge Greig opted for jail, saying in order to give Roebuck "the best shot" at staying sober and to keep the community safe, it was best to keep him locked up until he began rehab.
His sentence was later converted to 10 months' home detention.
At Friday's hearing, Roebuck told the judge he wanted to go to rehab and address his issues.
And he just wanted the weekend to get organised for the programme, he said.
"If my intention was to go out and go drinking, I would have done it already."
Probation advised the court that Roebuck had recently breached home detention by removing his anklet on one occasion and leaving his address for an hour without permission on another occasion.
Everything Roebuck wanted to do to prepare for rehab could be managed under home detention, and could be sufficiently achieved within a few hours, probation said.
Judge Greig said he would not give Roebuck complete freedom but was willing to give him some time.
Roebuck was granted leave to be absent from his address for six hours on Friday.
His home detention sentence was cancelled as of January 31 and instead of intensive supervision, nine months of post detention conditions were imposed with an added condition that Roebuck must travel directly to the rehab programme that same day.
"Good luck with the programme, I hope it all works out," Judge Greig told him.
