Crown policy in the Middle March had always been affected by external considerations, in particular relations with England. Whilst successive Scottish governments had used disturbances in the Borders as a form of leverage in diplomatic negotiations with England, so had some governments, such as that of Morton, attempted to use the imposition of order to encourage amicable relations. In 1597 James's border policy was affected by a number of concerns, in particular his succession to the English throne, which had led to his involvement in secret negotiations with the earl of Essex. James was keen that these should not be prejudiced by any cross-border incident.

His relations with England were also influenced by his need for the English pension. This meant that he was vulnerable to any delay in its payment, as could be occasioned by a cross-border dispute such as the Kinmont Willie affair. In June 1596 Eure had written to Cecil that James ‘is displeased as yt is thought, that the Quene threatneth to withhold her pentione from him in regarde of Baclugh his layte acte to my Lord Scrope’. Payment was finally made in September 1596 but no payment was forthcoming throughout 1597. James's need for the money battled with his indignation at Elizabeth's attitude towards him. He expressed his fury at the queen's ‘threatening to stop the payment of his annuity, and treating him as her pensioner’. He thought ‘it a greater break of the League than his not giving up Buccleuch’. But the combination of James's concerns over the pension and the succession were to create a watershed, in 1597, in his attitude to the Borders: external concerns were to begin to outweigh his inclination to support his officials there.

Against this more conciliatory background, the English were also in need of amicable relations with Scotland. Throughout the 1590s English worries about a second Spanish Armada finding a landing in Scotland had been exacerbated by James's continuing indulgence of the Catholic earl of Huntly. At the same time, English attempts in Ulster to suppress the earl of Tyrone's rebellion needed James's co-operation in stopping any support for it from Scotland.