diff --git a/port/win/env_win.cc b/port/win/env_win.cc
index 1da35c2698c..4dcfad54033 100644
--- a/port/win/env_win.cc
+++ b/port/win/env_win.cc
@@ -1227,13 +1227,13 @@ IOStatus WinFileSystem::Poll(std::vector<void*>& io_handles,
       }
     }
 
+    win_handle->is_finished = true;
+    win_handle->cb(req, win_handle->cb_arg);
+
     if (win_handle->overlapped.hEvent != NULL) {
       CloseHandle(win_handle->overlapped.hEvent);
       win_handle->overlapped.hEvent = NULL;
     }
-
-    win_handle->is_finished = true;
-    win_handle->cb(req, win_handle->cb_arg);
   }
   return IOStatus::OK();
 }
@@ -1245,6 +1245,12 @@ IOStatus WinFileSystem::AbortIO(std::vector<void*>& io_handles) {
       continue;
     }
 
+    if (win_handle->overlapped.hEvent == NULL) {
+      return IOStatus::InvalidArgument(
+          "AbortIO: Overlapped event is NULL for: " +
+          win_handle->file_data->GetName());
+    }
+
     if (FALSE == CancelIoEx(win_handle->file_data->GetFileHandle(),
                             &win_handle->overlapped)) {
       auto err = GetLastError();
@@ -1254,17 +1260,27 @@ IOStatus WinFileSystem::AbortIO(std::vector<void*>& io_handles) {
         return IOErrorFromWindowsError(
             "CancelIoEx failed: " + win_handle->file_data->GetName(), err);
       }
-    }
-
-    if (win_handle->overlapped.hEvent != NULL) {
-      CloseHandle(win_handle->overlapped.hEvent);
-      win_handle->overlapped.hEvent = NULL;
+    } else {
+      // CancelIoEx succeeded
+      // Wait for the operation to complete
+      DWORD bytes_read = 0;
+      if (!GetOverlappedResult(win_handle->file_data->GetFileHandle(),
+                               &win_handle->overlapped, &bytes_read, TRUE)) {
+        if (GetLastError() != ERROR_OPERATION_ABORTED) {
+          return IOErrorFromWindowsError(
+              "AbortIO failed: " + win_handle->file_data->GetName(),
+              GetLastError());
+        }
+      }
     }
 
     win_handle->is_finished = true;
     FSReadRequest req;
     req.status = IOStatus::Aborted();
     win_handle->cb(req, win_handle->cb_arg);
+
+    CloseHandle(win_handle->overlapped.hEvent);
+    win_handle->overlapped.hEvent = NULL;
   }
   return IOStatus::OK();
 }
diff --git a/port/win/io_win.cc b/port/win/io_win.cc
index 039b43b3f76..79a03e0a60c 100644
--- a/port/win/io_win.cc
+++ b/port/win/io_win.cc
@@ -1015,6 +1015,11 @@ IOStatus WinRandomAccessFileAsyncIo::ReadAsync(
         file_base_->GetName());
   }
 
+  HANDLE h_event = RX_CreateEvent(NULL, TRUE, FALSE, NULL);
+  if (h_event == NULL) {
+    return IOErrorFromWindowsError("CreateEvent failed", GetLastError());
+  }
+
   IOHandleDeleter deletefn = [](void* args) -> void {
     delete (static_cast<Win_IOHandle*>(args));
     args = nullptr;
@@ -1022,28 +1027,18 @@ IOStatus WinRandomAccessFileAsyncIo::ReadAsync(
 
   Win_IOHandle* win_handle = new Win_IOHandle(cb, cb_arg, req.offset, req.len,
                                               req.scratch, file_base_);
-
-  win_handle->overlapped.hEvent = RX_CreateEvent(NULL, TRUE, FALSE, NULL);
-  if (win_handle->overlapped.hEvent == NULL) {
-    return IOErrorFromWindowsError("CreateEvent failed", GetLastError());
-  }
+  win_handle->overlapped.hEvent = h_event;
 
   *io_handle = static_cast<void*>(win_handle);
   *del_fn = deletefn;
 
   IOStatus ios = IOStatus::OK();
   DWORD bytes_read = 0;
-  bool close_handle = true;
   if (FALSE == ReadFile(file_base_->GetFileHandle(), req.scratch,
                         static_cast<DWORD>(req.len), &bytes_read,
                         &win_handle->overlapped)) {
     DWORD last_error = GetLastError();
-    // Too many outstanding asynchronous I/O requests
-    if (last_error == ERROR_NOT_ENOUGH_MEMORY) {
-      CancelIoEx(file_base_->GetFileHandle(), &win_handle->overlapped);
-      ios = IOErrorFromWindowsError("ReadFile failed: " + file_base_->GetName(),
-                                    last_error);
-    } else if (last_error == ERROR_HANDLE_EOF) {
+    if (last_error == ERROR_HANDLE_EOF) {
       win_handle->is_finished = true;
       req.result = Slice(req.scratch, 0);
       req.status = IOStatus::OK();
@@ -1051,10 +1046,8 @@ IOStatus WinRandomAccessFileAsyncIo::ReadAsync(
     } else if (last_error != ERROR_IO_PENDING) {
       ios = IOErrorFromWindowsError("ReadFile failed: " + file_base_->GetName(),
                                     last_error);
-    } else {
-      close_handle = false;
     }
-
+    // else last_error is ERROR_IO_PENDING
   } else {
     win_handle->is_finished = true;
     req.result = Slice(req.scratch, bytes_read);
@@ -1062,7 +1055,7 @@ IOStatus WinRandomAccessFileAsyncIo::ReadAsync(
     cb(req, cb_arg);
   }
 
-  if (close_handle && win_handle->overlapped.hEvent != NULL) {
+  if (win_handle->is_finished && win_handle->overlapped.hEvent != NULL) {
     CloseHandle(win_handle->overlapped.hEvent);
     win_handle->overlapped.hEvent = NULL;
   }