A claim for 100 days of back leave by the chief executive of the Council of the Isles of Scilly has been refused, the BBC understands.
Philip Hygate claimed he had accrued the time off in his post over 15 years.
At a meeting on Thursday night, councillors of the unitary authority voted not to allow him all of the days he was claiming, which went back to 1997 and was worth about £40,000.
He may be allowed some of the leave. If so, the amount has yet to be decided.
Before the meeting, Mr Hygate, who has held the post for about 20 years, defended his claim, saying there was "nothing sinister or strange" about it.
He said: "You can actually view it as a great sense of loyalty to an organisation which, when I came, was in considerable difficulty.
"I was loyal enough to stay at my post and get the council through those issues."
Council policy says only five days can be carried over from the year before.
Mr Hygate may appeal against the decision.