How successful was Henry VII in fulfilling his foreign policy objectives?

Generally speaking, overall, Henry VII was successful in fulfilling his foreign policy objectives. Although he did not achieve a number of things in the way he endeavoured to, Henry VII achieved the majority of his foreign policy objectives one way or another.

Firstly, Brittany, a part of Europe where Henry spent a large part of his life, was under attack by the French and faced losing their independence, following an invasion in 1487. Henry felt as though he had a duty and sense of obligation to the Britons, and therefore summoned Parliament to grant him extraordinary revenue in order to raise an army sufficient enough to battle against the French. Crushing the potential French control of Brittany was very important to Henry, as by doing so would decrease the possibility of France invading England. This soon became one of Henry's main foreign policy objective, to defend Brittany and potentially, England. Additionally, England and Brittany signed the Treaty of Redon in 1489, in which, Duchess Anne would pay for a small English army to defend Brittany. Henry strived to strengthen is position by forming an alliance with Maximilian. Maximilian had contracted a marriage-by-proxy with Anne, and had no desire fro the Duchy of Brittany to fall into the French hands. The army went to Brittany to support their freedom, but Anne had lost her motive, and reluctantly married Charles VIII. To make things worse for Henry, Perkin Warbeck was simultaneously trying to gain support from the French. Henry launched a late invasion on France in 1492, in which, the French reacted immediately by trying to sought a peace settlement. The Treaty of Etaples were signed in November 1492, in which Charles VIII agreed to withdraw his support for Perkin Warbeck, and pay a pension to Henry VII as a form of compensation. Despite there being a number of difficulties and knock-backs for Henry in his goal of protecting Brittany, he ultimately managed to defend the national and dynastic interests. He had also improved his financial position and ensured a period of peace with Anglo-French relations.

Secondly, another one of Henry Tudor's foreign policy objectives was with Burgundy, the Netherlands and the Holy Roman Empire, which was arguably fulfilled successfully. The majority of England's exports went through the Netherlands, which came under Burgundy's jurisdiction. However, Margaret of Burgundy, the leading upholder of the Yorkists, enlisted the support of her stepson-in-law Maximilian I. Relations between England and Burgundy declined, predominantly due to the support that Maximilian and Philip was offering Perkin Warbeck. Henry believed that placing an embargo on English trade with Burgundy would ease the matter. Unfortunately, this was perhaps not a wise decision, given that many people believed that Henry was more focused on the dynastic stability, as opposed to the country;s economical and financial stability, which meant that he lost support. However, relations did improve once Perkin Warbeck left Burgundy, and Henry and Philip were able to sign the Intercursus Magnus in 1496, which brought the trade embargo to an end. Furthermore, one of the outcomes of the resulting Treaty of Windsor was the new trade agreement, the Intercursus Malus. He demanded a trade deal which would have given a much stronger trading position to English merchants in the Netherlands, had it been enforced. Also, Philip and Maximilian agreed to hand over their Yorkist fugitive, the Earl of Suffolk. As a result, Henry improved both England's trading position and also secured his dynasty.

However, despite Henry's foreing policy objectives being relatively successful up until this point, his next foreign policy objective, Spain, wasn't as successful as anticipated. For example, although Henry tried to develop good relations with Spain, a substantially popular country; the Treaty of Medina (which agreed not to harbour rebels, protect eachother in the event of an attack, and arranged a marriage alliance between Arthur and Catherine, Princess of Aragon) did not go as planned. There were a number of problems. For example, the arrangements for the marriage didn't go smoothly, Ferdinand was reluctant to let the marriage go ahead, so long as Warbeck still posed a threat on Henry's dynasty, and the two monarchs argued over the size of Catherine's dowry.

Lastly, Henry made it an essential objective to secure his dynasty by forming marriage alliances. That is seen over a number of decades within his reign. For example, Henry arranged his daughter Margaret to marry James IV of Scotland. This simultaneously enables Henry to form a close relation with Scotland- a place of previous hostility and tension. However, following the death of his wife Elizabeth in 1503, marriage alliances and foreign policy became more difficult for Henry, given that his dynastic security was significantly weakened.

Overall, despite Henry not achieving all of his foreign policy objectives, i.e. following the death of Isabella of Castile, Henry was isolated; Henry Tudor was successful in fulfilling his foreign policy objectives. One of his most significant and paramount objectives was to secure his dynasty. He had achieved this relatively smoothly, without any serious rebellions or challenges. In addition, Henry was able to form a number of alliances within Europe, which therefore boosted England's economy, while simultaneously securing his dynasty by forming marriages within the alliances. Furthermore, Henry fulfilled the vast majority of his foreign objectives without war or significant financial penalties- another aim Henry strived to achieve.