diff --git a/src/base/platform/memory.h b/src/base/platform/memory.h
index 0a68ee840f..cfd1379790 100644
--- a/src/base/platform/memory.h
+++ b/src/base/platform/memory.h
@@ -111,6 +111,8 @@ inline void AlignedFree(void* ptr) {
 // `AllocateAtLeast()` for a safe version.
 inline size_t MallocUsableSize(void* ptr) {
 #if V8_OS_WIN
+  // |_msize| cannot handle a null pointer.
+  if (!ptr) return 0;
   return _msize(ptr);
 #elif V8_OS_DARWIN
   return malloc_size(ptr);
@@ -130,7 +132,7 @@ struct AllocationResult {
 
 // Allocates at least `n * sizeof(T)` uninitialized storage but may allocate
 // more which is indicated by the return value. Mimics C++23
-// `allocate_ate_least()`.
+// `allocate_at_least()`.
 template <typename T>
 V8_NODISCARD AllocationResult<T*> AllocateAtLeast(size_t n) {
   const size_t min_wanted_size = n * sizeof(T);
@@ -140,6 +142,8 @@ V8_NODISCARD AllocationResult<T*> AllocateAtLeast(size_t n) {
 #else  // V8_HAS_MALLOC_USABLE_SIZE
   const size_t usable_size = MallocUsableSize(memory);
 #if V8_USE_UNDEFINED_BEHAVIOR_SANITIZER
+  if (memory == nullptr)
+    return {nullptr, 0};
   // UBSan (specifically, -fsanitize=bounds) assumes that any access outside
   // of the requested size for malloc is UB and will trap in ud2 instructions.
   // This can be worked around by using `Realloc()` on the specific memory
diff --git a/src/utils/allocation.cc b/src/utils/allocation.cc
index 5876de3cb4..2cbe91f384 100644
--- a/src/utils/allocation.cc
+++ b/src/utils/allocation.cc
@@ -129,6 +129,16 @@ void* AllocWithRetry(size_t size, MallocFn malloc_fn) {
   return result;
 }
 
+base::AllocationResult<void*> AllocAtLeastWithRetry(size_t size) {
+  base::AllocationResult<char*> result = {nullptr, 0u};
+  for (int i = 0; i < kAllocationTries; ++i) {
+    result = base::AllocateAtLeast<char>(size);
+    if (V8_LIKELY(result.ptr != nullptr)) break;
+    OnCriticalMemoryPressure();
+  }
+  return {result.ptr, result.count};
+}
+
 void* AlignedAllocWithRetry(size_t size, size_t alignment) {
   void* result = nullptr;
   for (int i = 0; i < kAllocationTries; ++i) {
diff --git a/src/utils/allocation.h b/src/utils/allocation.h
index b3aaf21d5e..87e30b43bd 100644
--- a/src/utils/allocation.h
+++ b/src/utils/allocation.h
@@ -94,6 +94,10 @@ using MallocFn = void* (*)(size_t);
 // Call free to release memory allocated with this function.
 void* AllocWithRetry(size_t size, MallocFn = base::Malloc);
 
+// Performs a malloc, with retry logic on failure. Returns nullptr on failure.
+// Call free to release memory allocated with this function.
+base::AllocationResult<void*> AllocAtLeastWithRetry(size_t size);
+
 V8_EXPORT_PRIVATE void* AlignedAllocWithRetry(size_t size, size_t alignment);
 V8_EXPORT_PRIVATE void AlignedFree(void* ptr);
 
diff --git a/src/zone/accounting-allocator.cc b/src/zone/accounting-allocator.cc
index d87981d632..f83bb86045 100644
--- a/src/zone/accounting-allocator.cc
+++ b/src/zone/accounting-allocator.cc
@@ -91,7 +91,9 @@ Segment* AccountingAllocator::AllocateSegment(size_t bytes,
                            kZonePageSize, PageAllocator::kReadWrite);
 
   } else {
-    memory = AllocWithRetry(bytes, zone_backing_malloc_);
+    auto result = AllocAtLeastWithRetry(bytes);
+    memory = result.ptr;
+    bytes = result.count;
   }
   if (memory == nullptr) return nullptr;
 
diff --git a/test/cctest/test-allocation.cc b/test/cctest/test-allocation.cc
index fa43733fd0..2a8d032c55 100644
--- a/test/cctest/test-allocation.cc
+++ b/test/cctest/test-allocation.cc
@@ -96,6 +96,8 @@ TEST_WITH_PLATFORM(AccountingAllocatorOOM, AllocationPlatform) {
   CHECK_EQ(result == nullptr, platform.oom_callback_called);
 }
 
+// We use |AllocateAtLeast| in the accounting allocator, so we check only that
+// we have _at least_ the expected amount of memory allocated.
 TEST_WITH_PLATFORM(AccountingAllocatorCurrentAndMax, AllocationPlatform) {
   v8::internal::AccountingAllocator allocator;
   static constexpr size_t kAllocationSizes[] = {51, 231, 27};
@@ -108,8 +110,8 @@ TEST_WITH_PLATFORM(AccountingAllocatorCurrentAndMax, AllocationPlatform) {
   for (size_t size : kAllocationSizes) {
     segments.push_back(allocator.AllocateSegment(size, support_compression));
     CHECK_NOT_NULL(segments.back());
-    CHECK_EQ(size, segments.back()->total_size());
-    expected_current += size;
+    CHECK_LE(size, segments.back()->total_size());
+    expected_current += segments.back()->total_size();
     if (expected_current > expected_max) expected_max = expected_current;
     CHECK_EQ(expected_current, allocator.GetCurrentMemoryUsage());
     CHECK_EQ(expected_max, allocator.GetMaxMemoryUsage());