Dundee Football Club have been deducted 25 points by the Scottish Football League for going into administration.
The First Division outfit have also been banned from signing any new players until they exit administration.
The SFL board said in a statement: "We are of the opinion that lessons are not being learned."
The club's administrator Bryan Jackson said: "I shall be appealing this decision by the SFL as this is an outrageous punishment."
The deduction will leave the Dark Blues bottom of the First Division on minus 11 points, 20 behind the nearest team Morton, with 25 league games left to play.
As well as posing a major task for the team to save their Division One status, the position - and possible relegation - could put off any potential investors.
Jackson was appointed in September to take control of the club's business affairs after they failed to negotiate a deal over an outstanding tax bill of £420,000.
The SFL board added in their statement: "Clubs have to realise that they can't treat their Her Majesty's Revenue and Customs tax obligations as something akin to a credit card."
They also said they will "reconsider the matter and deal with the club as it sees fit", if the Tayside club are still in administration by 31 March 2011.
In an effort to streamline operational costs at Dundee, the management team and nine players were made redundant.
After a meeting with the SFL on Thursday where he explained the club's circumstance, Jackson told BBC Scotland he felt they could cope with a deduction of 10 points.
But, on hearing of the punishment, he said: "With almost guaranteed demotion from the First Division it will be much more difficult to attract investment or retain players.
"This could also ultimately affect the income of other First Division teams as we will be unable to attract a good away support if there is nothing to play for.
"Given that the club is fulfilling its fixtures with a credible team this seems a punitive and punishing blow which threatens the future existence of the club.
"Everyone involved at DFC is working hard to ensure that the club survives this administration but this penalty makes that situation much more difficult."
Dundee's benefactor Calum Melville had put in around £1.3m in to the club since he became involved March 2009.
He resigned from the Dens Park board in September, but lodged £200,000 as part-payment for the outstanding tax arrears.
Dundee also went into administration in 2003 when they were in the Scottish Premier League.
On arriving at Dens Park, Jackson had estimated the club's survival hopes at "50-50" and warned there was only enough money to continue until Christmas.
"Whilst I appreciate that the SFL had to be seen to act when the club fell into administration for the second time, it is questionable whether this punishment is not ultimately self-defeating by threatening the continued existence of the club," he added.
"Given the support which the club has had from the team, from the supporters, and from the city of Dundee, the response of the SFL has effectively been dismissive of this support.
"We can go on in the short-term but this action has made the future much less certain than it has been at any time since the administration began."
The SFL also plan an early-warning system with HMRC to alert them to any more clubs facing financial difficulties.
"We are fully aware of the impact this situation has had on all concerned, especially players, staff and fans of the club," added SFL chief executive David Longmuir.
"The SFL has a duty to protect the integrity and the ongoing smooth running of the league.
"Following a thorough process, as endorsed by the administrator, the board has decided that Dundee Football Club Limited is guilty of conduct contrary to the league rules, the interests of the league and its member clubs.
"It should be noted that Dundee Football Club has the right of appeal against these sanctions."
Source: BBC Sports