[1][3] When the newspaper industry relocated their charter departure point for Scottish islands to Inverness in 1998, Highland won the contract to provide two BAe Jetstream 31 aircraft per day for this task.

Highland have largely moved away from oil industry work, and after recent concerns about the financial stability of the company the BAE contract has been terminated and is now operated by Eastern Airways.

General aviation and ground handling facilities were provided by Highland at Stornoway and Benbecula, servicing both the airline itself and other operators.

Highland also won a 5-year contract to operate, crew and maintain two Cessna F406 reconnaissance aircraft on behalf of the Scottish Fisheries Protection Agency.

In March 2007 Highland Airways underwent a management buyout from Atlantic Holdings led by A Mossman and had 100 employees (at January 2008).

[4] Highland operated a BN2 Islander aircraft from Oban to Coll, Colonsay and Tiree under a contract with Argyll and Bute Council On 24 March 2010, the airline was placed into voluntary administration, and all flights were cancelled, with no further bookings being taken.