An early record of an escape – rather a liberation, concerned Kirkaldy of Grange who  in 1570 descended on the tolbooth from the castle with armed guards and forcibly removed a servant from custody, and on 1 May 1571  he again seized the tolbooth and Council House. His intervention with the judicial processes did him little good in the long run as on 3 August 1573 he and three others were hanged at the Mercat Cross for keeping the castle against the King and his Regent.

But it wasnt only the big city tolbooths where escapes happened. On 25 September 1612 a Thomas Johnstoune escaped from the tolbooth of Brechin. Subsequently the wrath of the Privy Council fell on no less than two baillies, seven councillors and five `keepers` of the tolbooth. They were brought before the Privy Council in Edinburgh for alleged inattention to their duty. The two baillies and four of the keepers  were found guilty of carelessness and warded in Edinburgh Tolbooth; the councillors were warded in
the town of Edinburgh for a time.

An unusual method of escape from the Edinburgh Tolbooth is recorded on 11 June 1667 – the execution day of a William Douglas, convicted of the murder of Sir James Home of Eccles.  The records of the Justiciary Court  states ” Mr William Douglas a little before  his Trial had almost escaped  out of the Tolbooth having cut the stenches [bars] of the windows with aqua fortis. Being ready to go away he was taken.” It does not say where he got the sulphuric acid from, but it was an ingenious attempt in its day, and he almost made it.

The period 1661-1688 is
covered in The Historical Notices of Sir John Lauder of Fountainhall, and includes references to escapes from the Edinburgh and Canongate Tolbooths. As in the case of Brechin (above) not even the gaol keepers were safe from being locked up in their own prison. They were held personally responsible for the custody of persons delivered to them and had to give caution ( including undertakings by others, or bond) for sums of money they often did not have. An example of such a default was an incident in October 1680 when the Secret Council  gave a severe reproof to John Wause, keeper of Edinburgh Tolbooth, for the escape of a woman prisoner  who, it was alleged, had assisted Donald Cargill in his escape at Queensferry in June.

On 4 May 1681 James Park and his assistant named Gordon, of the Canongate Tolbooth, were committed to prison. This was on occasion of the escape of a Covenanter named Weir who was at Bothwell Brig and held as an alleged ringleader ( and not eligible for the Kings Pardon  and Indemnity).

On the night of  15 September 1683  some 23 prisoners made their escape from the Edinburgh Tolbooth via a rope let down from a window. They had first filed through the stanchells or bars of the window. Some (2 or 3) were imprisoned for debt, but others included John Dick,  Aitkin and Lapsley and two dragoons held on charges of killing the son of Seton of Carriston. Some of the prisoners were due to be hung shortly. The story of the gaol keepers and their fate is told by Fountainhall as follows; John Dick was captured and hanged on 5 March 1684.

An interesting insight into judicial thinking is illustrated on the same Privy Council agenda, by the charges against Baillie Nicolson for whipping a suspected thief. The principal espoused was such treatment was necessary to obtain a confession “modica castigatio is certainly allowed against such inferior people.”  So much for equality under the law.

On 24 August 1684 some 8 or 10 prisoners, all alleged rebels, escaped from the Canongate Tolbooth. An attempt was made to make the Magistrates of Edinburgh responsible for dilatory control and the sentinell on duty was sentenced to be shot [ there is no record that he was ], although it was possible that the guard did not know what was happening as the escape was made by “passing throw the riggings of many houses” – breaking through the loft space in adjoining houses.

On 4 September 1684 Sir Alexander Gordon of Earlstoun (1650-1726), a noted Covenanter, attempted to escape over the roof tops from the Edinburgh Tolbooth but was apprehended at about 7.pm. It was suggested that his date of execution be brought forward, but it was decided that prison breaking was not a capital offence but only one of banishment. To maintain his future security Earlstoun was transferred to Blackness Castle on 30 September where his family joined him in his prison, and indeed at least one child was born there.

A short note dated 21 November 1685 states that the Canongate Tolbooth had been `broke` and five Privy Council prisoners escaped – they were being held for alleged conventicling. Subsequently  (28 January 1686) Walter Young the keeper, was libelled to appear before the Privy Council who deprived him of his office and had him locked up.

18 November 1686 – the keepers of the Edinburgh Tolbooth, John Wause and Arthur Udney were charged by Sir G Lockhart , Advocate, with dereliction of duty over the escape of the Covenanter minister, Alexander Shiells. The arguement was that the warrant committing him did not specify close confinement; Udney claimed that it was not during his month of duty but was declared liable anyway for any fines in the case of an escape. After much debate they were relieved of their offices; the Magistrates of Edinburgh threatened  with personal  fines, and the keys of the King`s prison were taken from them, although subsequently returned.

The matter did not end there as  on the night of 13 February 1687 sixteen prisoners escaped from the Tolbooth, but George Drummond, the keeper ( with family connections) was not pursued
– unlike Wause and Udney earlier for just one prisoner escaping. The circumstances were that  the prisoners escaped by the door dressed in women`s clothes, making their way through a hole dug  in a wall and descending on ropes. Two of the prisoners were later found at Kirkliston and condemned, one being hanged. The unfairness to the former keepers did not go unnoticed by the public.