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 in the end effected through the influence of the Earl of March and Haliburton of Dirleton, on payment of a large ransom, and on condition of the restoration of the lands of March to the earl, which had been held by Douglas since 1400, but he retained Annandale and the castle of Lochmaben. After his return he entered into a bond of alliance on 30 June 1409 with Albany, which was confirmed by the marriage of his daughter Elizabeth with John Stewart, earl of Buchan, the second son of the regent.

In the spring of 1412 Douglas, with a considerable retinue, made his first journey to Paris. His family had always favoured the French alliance, and the efforts of the French knights to effect his release when a prisoner in England strengthened the tie. Bower relates that the earl was thrice driven back by hostile winds, and having, on the advice of Henry Sinclair, earl of Orkney, landed at Inchcolm in the Forth, and made an offering to St. Columba, the saint sent him with a prosperous wind to Flanders, and brought him safely home again. From Flanders he passed to Paris, and concluded a treaty with Jean Sans Peur, duke of Burgundy. Returning home, Douglas appears to have intended to revisit the continent in the following year, but the safe-conduct he received for that purpose from Henry V was not used. For the next ten years he pursued an ambiguous policy—at one time carrying on the border war against England, while at another he was negotiating the ransom of his young sovereign James I from Henry V. In this endeavour he appears to have been more sincere than Albany, whose desire to prolong his own regency made him indifferent, if not hostile, to the release of James I. In 1415 Douglas invaded England and burnt Penrith. In 1417 he was in command at the siege of Roxburgh, while Albany invested Berwick. The failure of both sieges, which were raised by the strong army of the Dukes of Bedford and Exeter, got for this expedition the name of the Foul Raid. In the interval between the two invasions Douglas had visited England along with several other nobles about the release of James I, but they were unable to come to terms with the English king.

In 1420 he made a third attack upon the English borders, and burnt Alnwick, but next year Henry V met him at York, and succeeded in gaining him over by a yearly pension of 200l., in return for which he engaged to provide two hundred horsemen. The change of front was probably due to the death of Albany, and the transmission of the regency to his feebler son Murdoch. But this defection was only temporary. The natural allies at this period of the Scots were the French, not the English. In 1419, shortly before the death of Albany, the Count of Vendôme had then sent, in the name of Charles VI, but really by his son the dauphin, afterwards Charles VII, for the king was prostrated by an attack of madness, to implore the support of Scotland on behalf of its ancient ally, which had never recovered from the defeat of Agincourt, and was now in great straits. The English were in possession of most of the north of the kingdom, and scoffingly called the dauphin king of Bourges. As a response to this request, the Scotch parliament voted a force of seven thousand men, who were sent under the command of John, earl of Buchan, the second son of Albany, Archibald, earl or lord of Wigton, the son of Douglas, and Sir John Stuart of Darnley. The victory of Beaugé, in which the Duke of Clarence was killed and the English routed, on 21 March 1421, was chiefly due to the Scotch troops. Buchan, their leader, was created constable of France. Wigton received the fief of Longueville, and Darnley that of D'Aubigny.

As a counter-stroke to the support the Scotch gave to the French, Henry V brought their captive king with him to France, hoping to detach them by the loyalty for which the Scotch were distinguished. According to one account James refused to lend himself to this stratagem, saying he was no king who had no kingdom. Another credits Buchan with refusing to serve a king who was a prisoner. The battle of Crévant in Burgundy, two years after Beaugé, in July 1423, in which the French and their allies were defeated by the Earl of Salisbury, Sir John Stuart of Darnley taken prisoner, and many Scots slain, led to a fresh appeal for reinforcements from Scotland, and the Earl of Buchan, who came for the purpose to Scotland in May 1423, persuaded his father-in-law, Douglas, to lead the new contingent. He landed at La Rochelle with ten thousand men, joined the court of Charles VII, who had now succeeded his father at Chatillon, and accompanied the king to Bourges. There he was appointed lieutenant-general of the French army, and granted the title of duke, along with the duchy of Touraine to him and his heirs male. On 19 April 1423 he took the oath of fealty at Bourges. The chamber of accounts of France declined to ratify the gift, as it was illegal without the consent of a parliament, and because it was their duty to oppose alienation of royal domains. But the king guaranteed them against the consequences, and obtained their reluctant consent. The people of Touraine showed their