diff --git a/test/ruby/test_io.rb b/test/ruby/test_io.rb
index 41cad1dec41..a11e1327d4f 100644
--- a/test/ruby/test_io.rb
+++ b/test/ruby/test_io.rb
@@ -1739,6 +1739,16 @@ class TestIO < Test::Unit::TestCase
     end
   end if /cygwin/ !~ RUBY_PLATFORM
 
+  def test_read_interrupted_by_wakeup
+    with_pipe do |r, w|
+      t = Thread.new { r.read }
+      Thread.pass until t.stop?
+      100_000.times { t.wakeup; w.write("x") }
+      w.close
+      assert_equal(100_000, t.value.size)
+    end
+  end
+
   def test_read
     pipe(proc do |w|
       w.write "foobarbaz"
diff --git a/win32/win32.c b/win32/win32.c
index 442b3824169..6851e94612c 100644
--- a/win32/win32.c
+++ b/win32/win32.c
@@ -7464,13 +7464,17 @@ rb_w32_read_internal(int fd, void *buf, size_t size, rb_off_t *offset)
                 errno = EINTR;
             else
                 errno = map_errno(GetLastError());
-            CloseHandle(ol.hEvent);
             CancelIo((HANDLE)_osfhnd(fd));
-            rb_acrt_lowio_unlock_fh(fd);
-            return -1;
+            /* the read may have completed before the cancel, and the kernel
+             * writes ol and buf until it ends either way */
+            GetOverlappedResult((HANDLE)_osfhnd(fd), &ol, &read, TRUE);
+            if (!read) {
+                CloseHandle(ol.hEvent);
+                rb_acrt_lowio_unlock_fh(fd);
+                return -1;
+            }
         }
-
-        if (!GetOverlappedResult((HANDLE)_osfhnd(fd), &ol, &read, TRUE) &&
+        else if (!GetOverlappedResult((HANDLE)_osfhnd(fd), &ol, &read, TRUE) &&
             (err = GetLastError()) != ERROR_HANDLE_EOF) {
             int ret = 0;
             if (err != ERROR_BROKEN_PIPE) {
@@ -7577,13 +7581,15 @@ rb_w32_write_internal(int fd, const void *buf, size_t size, rb_off_t *offset)
                 errno = EINTR;
             else
                 errno = map_errno(GetLastError());
-            CloseHandle(ol.hEvent);
             CancelIo((HANDLE)_osfhnd(fd));
-            rb_acrt_lowio_unlock_fh(fd);
-            return -1;
+            GetOverlappedResult((HANDLE)_osfhnd(fd), &ol, &written, TRUE);
+            if (!written) {
+                CloseHandle(ol.hEvent);
+                rb_acrt_lowio_unlock_fh(fd);
+                return -1;
+            }
         }
-
-        if (!GetOverlappedResult((HANDLE)_osfhnd(fd), &ol, &written, TRUE)) {
+        else if (!GetOverlappedResult((HANDLE)_osfhnd(fd), &ol, &written, TRUE)) {
             errno = map_errno(GetLastError());
             CloseHandle(ol.hEvent);
             CancelIo((HANDLE)_osfhnd(fd));