diff --git a/Include/internal/pycore_obmalloc.h b/Include/internal/pycore_obmalloc.h
index 0b23bb48dd5c1b..d4dbe541e6da51 100644
--- a/Include/internal/pycore_obmalloc.h
+++ b/Include/internal/pycore_obmalloc.h
@@ -691,7 +691,11 @@ struct _obmalloc_state {
 
 
 /* Allocate memory directly from the O/S virtual memory system,
- * where supported. Otherwise fallback on malloc */
+ * where supported. Otherwise fallback on malloc.
+ *
+ * Large-page and huge-page backends may round the mapped size up
+ * internally, so pass the original requested size back to
+ * _PyObject_VirtualFree(). */
 void *_PyObject_VirtualAlloc(size_t size);
 void _PyObject_VirtualFree(void *, size_t size);
 
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-04-01-12-52-31.gh-issue-144319.iZk4hs.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-04-01-12-52-31.gh-issue-144319.iZk4hs.rst
new file mode 100644
index 00000000000000..f3f07ab35dbb01
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2026-04-01-12-52-31.gh-issue-144319.iZk4hs.rst
@@ -0,0 +1,3 @@
+Fix a bug that could cause applications with specific allocation patterns to
+leak memory via Huge Pages if compiled with Huge Page support. Patch by
+Pablo Galindo
diff --git a/Objects/obmalloc.c b/Objects/obmalloc.c
index 983bdddbf026a8..e2d5b012955c3e 100644
--- a/Objects/obmalloc.c
+++ b/Objects/obmalloc.c
@@ -14,6 +14,7 @@
 #include <stdlib.h>               // malloc()
 #include <stdbool.h>
 #include <stdio.h>                // fopen(), fgets(), sscanf()
+#include <errno.h>                // errno
 #ifdef WITH_MIMALLOC
 // Forward declarations of functions used in our mimalloc modifications
 static void _PyMem_mi_page_clear_qsbr(mi_page_t *page);
@@ -572,6 +573,49 @@ _pymalloc_system_hugepage_size(void)
 }
 #endif
 
+#if (defined(MS_WINDOWS) && defined(PYMALLOC_USE_HUGEPAGES)) || \
+    (defined(PYMALLOC_USE_HUGEPAGES) && defined(ARENAS_USE_MMAP) && defined(MAP_HUGETLB))
+static size_t
+_pymalloc_round_up_to_multiple(size_t size, size_t multiple)
+{
+    if (multiple == 0 || size == 0) {
+        return size;
+    }
+
+    size_t remainder = size % multiple;
+    if (remainder == 0) {
+        return size;
+    }
+
+    size_t padding = multiple - remainder;
+    if (size > SIZE_MAX - padding) {
+        return 0;
+    }
+    return size + padding;
+}
+#endif
+
+static size_t
+_pymalloc_virtual_alloc_size(size_t size)
+{
+#if defined(MS_WINDOWS) && defined(PYMALLOC_USE_HUGEPAGES)
+    if (_PyRuntime.allocators.use_hugepages) {
+        SIZE_T large_page_size = GetLargePageMinimum();
+        if (large_page_size > 0) {
+            return _pymalloc_round_up_to_multiple(size, (size_t)large_page_size);
+        }
+    }
+#elif defined(PYMALLOC_USE_HUGEPAGES) && defined(ARENAS_USE_MMAP) && defined(MAP_HUGETLB)
+    if (_PyRuntime.allocators.use_hugepages) {
+        size_t hp_size = _pymalloc_system_hugepage_size();
+        if (hp_size > 0) {
+            return _pymalloc_round_up_to_multiple(size, hp_size);
+        }
+    }
+#endif
+    return size;
+}
+
 void *
 _PyMem_ArenaAlloc(void *Py_UNUSED(ctx), size_t size)
 {
@@ -648,7 +692,11 @@ _PyMem_ArenaFree(void *Py_UNUSED(ctx), void *ptr,
     if (ptr == NULL) {
         return;
     }
-    munmap(ptr, size);
+    if (munmap(ptr, size) < 0) {
+        _Py_FatalErrorFormat(__func__,
+                             "munmap(%p, %zu) failed with errno %d",
+                             ptr, size, errno);
+    }
 #else
     free(ptr);
 #endif
@@ -1128,13 +1176,19 @@ PyObject_SetArenaAllocator(PyObjectArenaAllocator *allocator)
 void *
 _PyObject_VirtualAlloc(size_t size)
 {
-    return _PyObject_Arena.alloc(_PyObject_Arena.ctx, size);
+    size_t alloc_size = _pymalloc_virtual_alloc_size(size);
+    if (alloc_size == 0 && size != 0) {
+        return NULL;
+    }
+    return _PyObject_Arena.alloc(_PyObject_Arena.ctx, alloc_size);
 }
 
 void
 _PyObject_VirtualFree(void *obj, size_t size)
 {
-    _PyObject_Arena.free(_PyObject_Arena.ctx, obj, size);
+    size_t alloc_size = _pymalloc_virtual_alloc_size(size);
+    assert(alloc_size != 0 || size == 0);
+    _PyObject_Arena.free(_PyObject_Arena.ctx, obj, alloc_size);
 }