Sieges of Boulogne, 1544-46- As allies with Charles V, the Holy Roman Emperor, Henry invaded France again. There, he laid siege to, and captured, the town of Boulogne. Charles V made peace with France separately, and Boulogne was laid siege to by the French again, unsuccessfully. Henry ended up keeping Boulogne for the rest of his reign, but was unsuccessful in increasing his land in France past that.