Reliance has faced severe criticism in the past
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Staff from the prisoner escort firm Reliance are to begin shadowing police and prison officers in the Lothian and Borders area.
Edinburgh Prison and the high and appeal courts in the city will all take part in the exercise, along with nine district and nine sheriff courts.
All of the custody units of Lothian and Borders Police will also be involved.
Reliance has already shadowed staff in central Scotland before taking on extra custody responsibilities there.
The firm came under the spotlight after a number of prisoners were released in error when it began its £126m contract to provide prisoner escort services in the west of Scotland in April.
A number of prisoners and offenders were mistakenly set free and the extension of the contract was suspended until the problems were ironed out.
As well as central Scotland, Reliance is already responsible for prisoner escorting and court custody duties throughout the Strathclyde and Dumfries and Galloway areas.
A spokesman for the Scottish Prison Service said that responsibility for the security and welfare of prisoners would remain with the police and the prison service in Lothian and Borders during the shadowing phase.