Anne Boleyn’s pregnancies were not just personal struggles; they were pivotal moments that shaped the course of English history. From the initial hope that she would provide Henry VIII with the longed-for male heir to the heartbreak of multiple miscarriages, Anne’s pregnancies had profound consequences for her reign as queen. In this episode, we explore the intense pressure Anne faced to secure a male successor, the impact her pregnancies had on her relationship with Henry, and how these events ultimately contributed to her tragic downfall.
Join us as we uncover the human side of Anne Boleyn’s story, a tale of ambition, loss, and the fierce struggle for survival in the Tudor court.
Transcript of Anne Boleyn’s Pregnancies: Hopes, Losses, and the Final Miscarriage
This is the start of May and for many people in the Tudor world, May is a month when we remember Anne Boleyn and Anne Boleyn’s story. This episode is about Anne—specifically about her pregnancies and her miscarriages.
So I want to include a bit of a content warning: if you are sensitive to discussions about miscarriage and pregnancy loss, you might want to give this one a skip. We’re going to talk about her different pregnancies, how Henry reacted, and how the final miscarriage was really the breaking point that did her in—what made Henry decide he needed to put her aside.
I’ve shared before on this podcast—gosh, back in 2010—I lost a son. And funny—I mean, not funny, obviously it’s tragic—but I was already doing this podcast by then, and I talked about it on the show. Even now, people go back and start listening from the beginning and assume it just happened. I still get emails every once in a while saying, “I’m so sorry for your loss.” And I appreciate it, of course, but I think sometimes people miss the date on that—it was fifteen years ago. That said, the experience stays with you forever.
So I also just want to say: if you are dealing with pregnancy loss, miscarriage, or fertility struggles—I went through that myself. It’s kind of one of those sororities you don’t really want to join. But once you’re in it, you find it’s a very close-knit group of people. If you’re part of that group and you ever want to talk about it, consider me a resource. I’m always here—to talk about the babies, the ones who are here, and the ones who aren’t.
That’s what we’re going to talk about today. It’s a bit of a somber one, but I think it’s important. It’s a very human story—something many people still go through today. Katherine of Aragon dealt with it too. And I think talking about these things humanizes them. It connects us to their stories. It’s one of those deeply human experiences that has crossed centuries. Women have always gone through this, and still do. And of course, it affects fathers as well—I don’t mean to place it entirely on women—but physically, it’s something women endure. Alright. I’m rambling now. Let’s get into it.
Anne Boleyn’s First Pregnancy and Elizabeth’s Birth
When Anne Boleyn was crowned Queen of England in the summer of 1533, the entire country held its breath. Her coronation, carried out with more pomp and splendor than anything London had seen in a long, long time, was not just a celebration of Anne herself—it was a public bet, a grand wager that Anne would succeed where Katherine of Aragon had failed. Anne would give Henry VIII his longed-for son—the son who would secure the Tudor dynasty and end years of dynastic uncertainty.
She was already visibly pregnant when she processed through the streets, seated in a white litter, gliding above the crowds who jostled and craned their necks to glimpse the woman for whom kings had upended kingdoms.
There was no small amount of superstition tied to this pregnancy. Astrologers had consulted the stars and confidently predicted that a prince was on the way. Tapestries with human figures were removed from Anne’s birthing chamber, lest the images somehow influence the shape of the unborn child. Henry had tournaments and celebrations planned in advance, certain that Anne would deliver exactly what he had fought so hard to obtain.
In early September, Anne withdrew to her confinement at Greenwich Palace—a solemn ritual marking the final weeks of pregnancy. The court grew quiet, more reverent as the day approached.
Then, on September 7th, 1533, Anne gave birth not to the expected prince, but to a healthy, robust daughter. The baby, with her father’s distinctive Tudor coloring, would become Elizabeth I.
But in 1533, Elizabeth’s birth was not received as triumphantly as modern hindsight might suggest. Henry’s disappointment was palpable, even if cloaked in official good cheer. The court had prepared printed announcements celebrating the birth of a prince. Clerks scrambled after the fact, forced to manually add an S to transform prince into princess.
It was a patchwork fix for a patchwork triumph. The tournaments Henry had planned were quietly canceled. There were no triumphant processions, no week-long celebrations. Still, Henry tried to console Anne—and perhaps himself. He reassured her: they were both still young; sons would surely follow.
Anne was reportedly devoted to Elizabeth, pouring her hopes into the little girl’s cradle. But privately, she must have understood the stakes. In Henry’s world, a queen who failed to produce a male heir was a queen whose position was, at best, quite tenuous.
The Second Pregnancy and Its Mysterious End
The pressure didn’t ease. Only months after Elizabeth’s birth, Anne conceived again. News reached Eustace Chapuys, the ever-watchful Imperial Ambassador by January 1534. He reported that Anne was in good health and carrying another child. George Taylor, a servant at court, wrote enthusiastically to his master that the queen had a “goodly belly.”
Henry, buoyed by the news, commissioned a magnificent silver cradle studded with jewels—ready to welcome the son he was certain would soon arrive. For a brief moment that spring, the court’s optimism returned. This time, surely, fate would reward the king and his new queen. But that second pregnancy, so full of promise, would never actually reach its hoped-for conclusion.
By the summer of 1534, Anne was visibly pregnant—enough so that her brother, George Boleyn, was dispatched to France with apologies. Anne was so far gone with child that she could not accompany the king on a planned visit. Everything suggested a healthy pregnancy was advancing. Notably, Henry postponed diplomatic travel—a decision he would not have made lightly, given how much he prized foreign alliances.
Yet by September, whispers began to circulate. Chapuys, always eager to report anything that might discredit Anne, wrote to Emperor Charles V that Henry had begun to doubt whether his lady was “enceinte or not,” and had as a result renewed and increased his affection for another lady at court.
If Anne’s pregnancy had been progressing well, Henry’s attention would not have wavered so conspicuously. Still, the exact nature of this failure remains one of the quieter mysteries of Anne Boleyn’s life. No direct record survives of a miscarriage, a stillbirth, or even an official announcement that the pregnancy had ended.
It simply vanished from court conversation. One day Anne was pregnant; the next, she was not—and no one spoke openly about it. It was rather like what would later happen to her stepdaughter, Mary I, several decades later.
Historians have long debated what happened. Some, like Eric Ives, suggest that Anne likely suffered a miscarriage—perhaps in the summer months, perhaps later—but that the event was kept discreet to avoid further embarrassment. After all, to have miscarried again so soon after Elizabeth’s birth would have been a bitter blow to the queen’s public standing.
Others, however, have proposed that Anne experienced a false pregnancy—a rare condition in which the body mimics pregnancy symptoms without an actual fetus developing. Both Katherine of Aragon and, later, Mary Tudor would suffer these phantom pregnancies
In a period that lacked modern medical understanding, a queen could easily believe herself pregnant for months before realizing the truth. Chapuys’ phrasing in his September dispatch—that the king doubted whether Anne was pregnant—leaves open the possibility that even Henry had been deceived.
If Anne’s symptoms had mimicked pregnancy but the expected baby failed to materialize, it would have been a humiliation Henry was eager to forget. It might explain why the matter was dropped so quietly. Regardless of whether Anne miscarried or whether the pregnancy had been false, the impact was the same: no child was born, no son arrived to solidify Anne’s position.
Instead, Henry’s eye began to wander, and the cracks in the marriage started to show. Anne, for her part, would have understood the danger immediately. Her power, her influence, her very safety depended on producing a living male heir. And after the anticlimax of 1534, she knew the next pregnancy had to succeed. The stakes—already high—were about to become lethal.
The Third Pregnancy and Growing Tensions
The year 1535 brought no recorded pregnancy for Anne. If she conceived, it was either lost so early that no one remarked on it, or it never happened at all. A letter from Sir William Kingston mentioning the queen’s “fair belly” was once thought to hint at a pregnancy that year, but historians later realized that it referred to the previous year—adding yet another layer of confusion to the already murky record.
In reality, 1535 was a year of growing tension. Henry’s affection cooled noticeably. While Anne remained queen, she no longer held the singular grip on Henry’s heart that she once had.
Late that year, Jane Seymour—a quiet, seemingly docile lady-in-waiting—began to catch the king’s eye. At first, Jane’s presence was barely more than a flicker at the edge of court gossip, but it would soon burn far brighter.
Anne, sharp-tongued and proud, was ill-suited to share her husband’s attention. She had fought too hard to secure her place as queen to now sit quietly by while another woman rose in favor. Her temper—once part of her charm—now irritated Henry.
Chapuys, of course ever ready to report these missteps, recorded that Henry grew increasingly cold toward her over the course of 1535. There were arguments, frayed silences, visible signs of strain. Yet Anne had one way to win back Henry’s full devotion: another child.
The Final Pregnancy and Anne’s Downfall
By the autumn of 1535, she was again pregnant. This time, more than ever, success was essential. At first, all seemed to go well. By December, the court buzzed with optimism. Henry and Anne, perhaps cautiously hopeful, must have dared to imagine that the tide was turning in their favor. With Katherine of Aragon—Henry’s first wife and Anne’s rival in legitimacy—in declining health, the political landscape seemed poised to favor Anne at last.
On January 7th, 1536, Katherine died. In theory, Anne should have triumphed. Katherine’s death meant that Anne’s marriage could no longer be contested by a living rival claimant. She was, by any earthly measure, Henry’s sole wife.
Yet the court’s reaction was strange. Some said Henry and Anne wore yellow in celebration. Others noted that yellow was a mourning color in Spain. Either way, the moment was loaded with symbolism.
Anne was carrying the future—literally and politically—but underneath the surface, danger rippled. Henry’s growing attentions to Jane Seymour continued. Katherine’s death removed a political obstacle but did nothing to repair the cracks in Henry and Anne’s relationship. If anything, it gave Henry more freedom to act as he pleased, because with Katherine gone, the threat from the emperor was no longer there.
Then disaster struck. On January 24th, Henry participated in a joust at Greenwich. Always proud of his athleticism, Henry charged into the lists and suffered a terrifying fall. Thrown from his horse, the king lay motionless on the ground. Courtiers rushing to his side feared the worst—some thought him dead. For two long hours, Henry was unconscious, and the court held its breath.
Somewhere in her apartments, carrying what she prayed was her savior, Anne waited for news that would shatter her world. When the Duke of Norfolk arrived to deliver the news, he tread carefully. Anne was pregnant, already under strain, and very vulnerable. The Duke of Norfolk broke the news as gently as he could: the king had been injured, but he was alive, and there was no reason for alarm.
Anne’s reaction was immediate. She was horrified. Henry’s brush with death was not just a personal terror—it was a political catastrophe in the making. If Henry had died without a male heir, the Tudor dynasty itself would have been plunged into chaos. Elizabeth, a small girl barely two years old, would hardly have been accepted by the powerful, divided factions at court. And Anne herself, without Henry’s protection, would have been dangerously exposed.
The shock was too much. And days later, on January 29th, 1536—the same day that Katherine of Aragon was laid to rest at Peterborough—Anne miscarried. The child she lost was a boy, estimated to be around 15 weeks gestation.
Even Chapuys, who normally took a grim delight in Anne’s misfortunes, reported the event without triumph. On the day of the interment, he wrote to Emperor Charles V: “The concubine had an abortion, which seemed to be a male child of about three and a half months, at which the king has shown great distress.”
Charles Wriothesley, herald and chronicler, added further confirmation: Anne had miscarried “a male child, as it was said, before her time, before she had reckoned herself but 15 weeks gone with child.”
The reports are sober, grim—and crucially, at the time, they make no mention of deformity or anything abnormal about the fetus despite the later lurid rumors that would circulate. For Anne, the loss was an unmistakably public failure. A boy—finally, a boy—and he was gone. The emotional weight must have been crushing.
Anne, according to reports, blamed the miscarriage on the shock she suffered hearing about Henry’s accident. Contemporary medicine often linked strong emotions to the loss of a child, and Anne’s explanation would have seemed perfectly plausible to her contemporaries. After all, she had been carrying the hope of a dynasty in her womb, and the terror that it might all come crashing down with Henry’s fall could very well have been enough to precipitate a miscarriage.
Yet not everyone at court was willing to accept this explanation. Chapuys, who viewed Anne with unrelenting suspicion, noted skeptically that Norfolk had taken care to deliver the news cautiously, “in a way that she would not be alarmed.”
Others at court began to whisper that Anne’s miscarriage was no accident. Perhaps it was a sign that God disapproved of the union. Some even murmured that Anne’s body was somehow incapable of producing healthy male heirs.
As Anne grieved, she must have known that this loss would not simply be mourned—it would be weaponized. At first, Henry seemed genuinely devastated. For a few brief days after the miscarriage, he reportedly showed Anne real sorrow. This had been his son too—his longed-for prince—and the loss struck hard.
But Henry was not a man who dwelt long in grief. Almost immediately, his sadness curdled into something far more dangerous: disappointment, resentment, and the cold, calculating search for an alternative.
According to Chapuys, when Anne, desperate to explain herself, approached Henry in the aftermath of her miscarriage—pleading that the shock of his accident had caused her loss—Henry listened grimly and then, with chilling finality, told her that he now saw God did not wish to give him male children by her.
It was a devastating sentence, and Anne must have heard the full implication. Henry, who had moved heaven and earth to make her queen, was now suggesting that their union was cursed—that God Himself had withheld the male heir because of her.
This was a cosmic judgment on their marriage, and the parallels to Katherine of Aragon’s downfall were impossible to ignore. Years earlier, Henry had claimed that his first marriage was invalid because it had failed to produce a son—a failure he took as evidence that God had not blessed the match.
Now, with Anne, he was drawing the same ominous conclusion. Anne—newly miscarried, fragile in both body and spirit—found herself suddenly and terrifyingly alone. Reports from the weeks following the miscarriage suggest that Henry’s affection, already faltering, withdrew almost completely.
He spent less time with Anne. He grew increasingly open in his attentions to Jane Seymour, whose quiet, modest demeanor stood in sharp contrast to Anne’s proud and volatile personality. Jane, coached by her ambitious family, knew exactly how to play the part of the soothing, unthreatening alternative.
Meanwhile, Anne—still technically queen—moved through the court like a ghost. Her enemies, emboldened, began to circle. Even her supporters must have recognized how precarious her position had become.
Chapuys wrote gleefully that some at court speculated Henry would now take another wife. Others noted that Anne’s miscarriage had given Henry the very excuse he needed to set her aside if he wished.
Anne herself seems to have realized how badly she had miscalculated her own security. In private conversations with her ladies, she reportedly blamed jealousy—the stress of competing with Jane Seymour—for contributing to the loss of her child. A bitter irony, if true: the very fear of losing Henry may have helped bring about the catastrophe that made it inevitable.
In a few short weeks, Anne had fallen from a seemingly secure queen consort to a political liability. Her final chance had slipped through her fingers, and Henry—once bewitched by her wit and her charm—now looked at her with the cold eyes of a king seeking an exit. The clock was ticking.
In the weeks that followed, Anne’s position grew weaker by the day. Though outwardly still queen, she found herself isolated within her court. The elaborate rituals and courtesies due to a queen were maintained, but the warmth behind them had cooled. Fewer ladies flocked to her side. Fewer courtiers sought her favor. Those who had once fawned over her as the king’s darling now turned their eyes toward Jane Seymour, sensing a shift in the political winds.
Anne would have seen it too. She was no fool. Those same courtly instincts that had once propelled her rise would have made the change in atmosphere painfully obvious. She could hardly have missed the fact that Jane now received secret gifts from the king—including a locket containing Henry’s portrait—an insult that must have cut to the bone.
Henry, meanwhile, was moving from private disillusionment to quiet action. In March 1536, he began speaking more openly about his regrets over his marriage. To trusted courtiers, he allegedly hinted that his second marriage, like his first, might have been founded on false grounds. With Katherine dead, he no longer needed to justify himself to the Pope or foreign powers.
Anne’s precarious fertility record now gave him all the pretext he needed to seek a new solution. Thomas Cromwell, who now had his own grievances against Anne, recognized the opportunity. Whether acting on Henry’s unspoken wishes or out of his own initiative, Cromwell began to quietly construct the case against the queen.
At first, it was vague—certain matters regarding her conduct needed to be examined—but soon it would take a more sinister shape. Anne’s enemies were many, and they had long memories. Old grudges, jealousies, political slights, and personal humiliations now surfaced and attached themselves to Cromwell’s investigations like barnacles to a ship.
And yet, in early spring 1536, Anne still held the title of queen. She attended mass; she still moved through the court with regal dignity. She could not have known precisely how little time she had left, but the warning signs must have been impossible to ignore.
The miscarriage of January had done irreparable damage. Without a living son in her arms, Anne had no shield against the ambitions of others. Henry—ever impatient, ever hungry for certainty—had already started imagining a life beyond her. And the machinery of her downfall—the lies, the interrogations, the betrayals—had begun to grind into motion. Anne had lost more than a child in January 1536. She had lost her future.
The Aftermath and Historical Rumors
In the aftermath of Anne’s fall, the story of her final miscarriage began to take on a life of its own. At the time, the official accounts made no mention of anything unusual about the lost child. Chapuys described it simply as a male fetus about 15 weeks old. Charles Wriothesley, too, recorded that it was a male child born prematurely. Neither hinted at anything grotesque or unnatural.
To those present in 1536, the tragedy was grim but straightforward: a devastating loss of a much-hoped-for son. But as the decades passed, darker rumors began to creep into the narrative.
The most notorious came from Nicholas Sander, a Catholic exile writing fifty years later during the reign of Elizabeth, Anne’s daughter. Sander, bitterly opposed to Elizabeth’s Protestant rule, painted Anne as a monster in every sense. He is the one who claimed she had six fingers on one hand, a projecting tooth, a large goiter under her chin, and—most infamously—that she had miscarried a shapeless mass of flesh.
Sander’s grotesque description was pure invention. He had never met Anne; he was not even alive when she was queen. His goal was clearly political: to discredit Elizabeth by portraying her mother as unnatural and cursed.
But his accusations proved sticky. Over time, they filtered into popular imagination, blurring the line between fact and propaganda. Even today, Sander’s lies crop up in novels and films. Modern historians have pushed back firmly.
Eric Ives, Anne’s most meticulous biographer, found no contemporary evidence for any deformity in the lost fetus, nor did any contemporary chronicler. In Ives’s words, the suggestion that Anne miscarried a monstrous child is “a smear without foundation.”
Still, the idea had taken root deeply enough that even some serious historians grappled with it centuries later. In the 20th century, historian Retha Warnicke proposed a controversial theory that Anne’s miscarriage involved a malformed fetus, and that this shocking event spurred Henry and Cromwell to move against her so swiftly.
Warnicke’s argument built on the notion that a monstrous birth would have been seen as a divine sign of sexual sin—incest, adultery, witchcraft—and thus gave urgency to Anne’s destruction. It’s an intriguing idea, but it rests on a fragile foundation: Sander’s later account, which serious scholars generally dismiss as unreliable.
Not one single document from 1536—not a letter, not a court record, not a dispatch—mentions anything malformed. On the contrary, the descriptions suggest a tragically ordinary miscarriage.
Most historians today agree that the rumor of a monstrous miscarriage belongs firmly in the realm of later anti-Anne propaganda, not fact. Anne’s downfall can be explained without recourse to supernatural horror stories. Political betrayal, Henry’s dynastic desperation, and Anne’s own precarious position were more than enough.
Legacy of Anne Boleyn and Conclusion
The miscarriage of January 1536 was not, by itself, the cause of Anne’s destruction, but it was the moment when her vulnerability became undeniable. Historians have debated just how pivotal the event was.
There’s that famous phrase saying that Anne had “miscarried of her savior,” which captures her situation vividly. Had the child lived—had Anne delivered a healthy boy in the spring or summer of 1536—the course of English history might well have been very different.
A male heir would have strengthened Anne’s position beyond easy assault. Henry, so desperate for a son, might have been willing to overlook other irritations: her sharp tongue, her political meddling, her declining favor.
She would have placed a prince in his arms. The dynasty would have been secure. The Seymour family’s ambitions would have been checked before they could gain momentum. Cromwell’s schemes might never have ripened. But the child was lost. And with that loss, Anne’s enemies found their opening.
Historians like Eric Ives have cautioned that it would be a mistake to view the miscarriage as the sole trigger for Anne’s downfall. Anne’s situation was already deteriorating in late 1535, even before she became pregnant again. Henry’s attentions were already shifting toward Jane Seymour. Cromwell and Anne were clashing over political matters, especially the redistribution of monastic wealth.
The miscarriage, in Ives’s view, did not create Anne’s vulnerability, but it did expose it—fully and irrevocably. There’s no question that the loss hardened Henry’s resolve. After January 1536, Henry stopped pretending that he saw his marriage to Anne as a divinely sanctioned union. When he said, “God does not wish to give me sons by her,” he was showing himself to be a man searching for a way to justify what he already wanted—to move on.
It’s easy, 500 years later, to look at Anne’s pregnancies purely as political events—to see the births and the miscarriages, even the phantom pregnancy, perhaps, as chess moves in a brutal game of dynasty-building, successes or failures measured only in crowns and bloodlines.
But behind the royal titles, behind the expectations—remember, there was a woman. Anne would have known the risks every time she conceived. Childbirth in the 16th century was perilous, even in the best conditions. Miscarriages were common, infant mortality was high, and medical knowledge was limited. Every new pregnancy carried with it not only hope, but fear—fear of loss, fear of death, fear of disappointing a husband whose love was not unconditional.
She must have felt real joy when she first realized she was carrying Elizabeth, real pride when she felt her daughter’s kicks, real hope when she conceived again in 1534 and in 1535—and real, devastating grief when each of those pregnancies ended in silence.
But of course, that daughter she left behind would change the course of English history. Elizabeth would reign for 45 years, ushering in a golden age of exploration, culture, and stability. That “disappointment,” born in September 1533, would become one of the most celebrated monarchs in English history.
Anne’s enemies could tear down her reputation, they could blacken her name—but they couldn’t erase her daughter. And in the end, that’s the story that would outlast them all.
So there we are, my friends—a little bit about Anne’s pregnancies. Sometimes you hear these stories and they’re just sentences. But then you think about the people behind them, and the effect those events had on their lives, and it becomes a bit more real.
Related links:
Episode 130: Anne’s Pregnancy and Elizabeth’s Birth
Episode 024: Pregnancy and Childbirth in Renaissance England
Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast,  the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.
She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).
