[5] Urban III vigorously took up his predecessor's quarrels with Holy Roman Emperor Frederick I Barbarossa, including the standing dispute about the disposal of the territories of the countess Matilda of Tuscany.

Even after his elevation to the papacy, Urban III continued to hold the archbishopric of Milan, and in this capacity refused to crown as King of Italy Frederick I's son Henry, who had married Constance, the heiress of the kingdom of Sicily.

[5] Urban exerted himself to bring about peace between England and France, and on 23 June 1187, his legates by threats of excommunication prevented a pitched battle between the armies of the rival kings near Châteauroux, and brought about a two years' truce.

[5] While Henry in the south cooperated with the rebel Senate of Rome, his father Frederick blocked the passes of the Alps and cut off all communication between the Pope, then living in Verona, and his German adherents.

According to the chroniclers Ernoul and Benedict of Peterborough, Urban III died of shock and grief after Joscius, Archbishop of Tyre brought him news of the Christian defeat at the Battle of Hattin.