Monson was afterwards removed to the castle of Lisbon, from which an attempt on his part to escape was frustrated by the treachery of an English interpreter there, whom he had been forced to employ. Fortunately, the letter which he had entrusted to a page, who was to have conveyed it _in his boots_ to Lord Burleigh, became so saturated and obliterated by rain, that nothing could be made of it, and the whole matter was allowed to pass. Not so, however, after he had helped a Portuguese to escape, who had been condemned to death. The latter, aided by Monson’s skill, managed to pass the sentinels disguised as a soldier, and then lowering himself by a rope, effected his plans. The flight having been discovered, Monson was accused of having assisted him, and was taken before the judge. “But neither threats nor promises of liberty could induce him to confess. He pleaded that he was a prisoner of war, that he was subject to the law of honour and arms, and that it was lawful for him to seek his freedom: he urged the improbability of holding such intercourse as was imputed to him with one whose language he did not understand; and he concluded by cautioning them to be wary what violence they offered him, as he had friends in England, and was of a nation that could and would revenge his wrongs.” The latter argument probably it was that carried the day; but until released—no doubt by exchange—he was closely guarded. In 1593, Monson again joined Cumberland, and considering the fidelity which he had always shown to that admiral, the latter seems to have treated him very badly. In the course of their voyage, a dozen Spanish hulks laden with powder were taken, half of which were left to Monson to haul over, while his admiral put to sea with the rest. Monson had with him only about fifty men. What was his surprise towards night to find that Cumberland had released the hulks which he had taken, and that they were crowding on all sail to join their consorts in his charge, with hostile intent, which it would be madness on his part to attempt to frustrate. He barely escaped; when the enemy boarded him on one side of his vessel, he leaped into the long boat on the other side, receiving a wound which remained all his days. Southey certainly puts it mildly when he says, “The conduct of the Earl of Cumberland in this affair admits of no reasonable or satisfactory explanations,” for it looks far more like downright treachery. A couple of years afterwards, the Earl very plainly declared his colours by first inducing him to join him in his voyage, and then superseding him. Monson could not brook this, and returned, after some adventures, to England, where we soon find him with the Earl of Essex, in the expedition to Cadiz. At that most remarkable siege, he was in the thick of the fight ashore with Essex, where he received a shot through his scarf and breeches; another shot took away the handle and pommel of his sword, while he remained uninjured.