It's important to understand that the early modern period was not one in which any state was ever far from bankruptcy - or at the very least excessive debt. There are several ways in which we can investigate this question.

In the most literal state, England under Henry was never made bankrupt - it was never forced out of wars because of a lack of finance, and it did not default on its debts. This is not, however, to say that it was a prudently managed system; for much of Henry's reign, he skirted on the fringes of bankruptcy.

The first major charge we can level against Henry is that he effectively wasted the entirety of surplus finances left from his father's strict fiscal management on a futile war with the French in the first years of his reign; and although he took a small amount of land (notably the city of Tournai) the war was largely unsuccessful and hugely expensive. At the same time, Henry (without a financial manager of the likes of Empson or Dudley) let his ordinary revenues fall through extensive patronage and gifts to his friends to a level in 1517 of less than £20,000 per year. This was one of the reasons for Wolsey's rise; a prudent and dedicated financial manager, he restored Henry's ordinary (non-parliamentary) revenues significantly, and just as importantly pursued a peaceable policy which largely avoided significant war.

Under Thomas Cromwell's financial regime in the 1530s, Henry arguably inflated the wealth of the English monarchs by an unprecedented amount through the dissolution of the monasteries, which secured for him both a significant wealth of monastic treasure and an even more significant amount of land.

It is Henry's decision to sell much of this land to fund a program of both fortification and war in the 1540s that is, in my opinion, his most disastrous financial misstep. Across the early modern period, monarchs were seeking new ways to finance increasingly ruinous wars; the repossessed monastic lands offered the opportunity to give the English monarchy a sustainable and significant financial income which would at the very least allow them a greater independence from resort to "extraordinary" funding. But Henry's massive expenditure in his campaigns of the 1540s - he spent £2 million on the fortification of Boulogne, which was quickly recaptured by the French despite his investment, for example - was largely futile, and disposed of a vital resource for the English monarchs; while he did not precisely bankrupt England, he undoubtedly mismanaged his finances significantly.