diff --git a/src/testing/testing.go b/src/testing/testing.go
index df4dfe4490..05d8f22aff 100644
--- a/src/testing/testing.go
+++ b/src/testing/testing.go
@@ -1122,7 +1122,7 @@ func removeAll(path string) error {
 	)
 	for {
 		err := os.RemoveAll(path)
-		if !isWindowsAccessDenied(err) {
+		if !isWindowsRetryable(err) {
 			return err
 		}
 		if start.IsZero() {
diff --git a/src/testing/testing_other.go b/src/testing/testing_other.go
index 29496d81bc..99a6276a4a 100644
--- a/src/testing/testing_other.go
+++ b/src/testing/testing_other.go
@@ -6,8 +6,8 @@
 
 package testing
 
-// isWindowsAccessDenied reports whether err is ERROR_ACCESS_DENIED,
-// which is defined only on Windows.
-func isWindowsAccessDenied(err error) bool {
+// isWindowsRetryable reports whether err is a Windows error code
+// that may be fixed by retrying a failed filesystem operation.
+func isWindowsRetryable(err error) bool {
 	return false
 }
diff --git a/src/testing/testing_windows.go b/src/testing/testing_windows.go
index bc76cb80cc..fd48ae9579 100644
--- a/src/testing/testing_windows.go
+++ b/src/testing/testing_windows.go
@@ -8,11 +8,25 @@ package testing
 
 import (
 	"errors"
+	"internal/syscall/windows"
 	"syscall"
 )
 
-// isWindowsAccessDenied reports whether err is ERROR_ACCESS_DENIED,
-// which is defined only on Windows.
-func isWindowsAccessDenied(err error) bool {
-	return errors.Is(err, syscall.ERROR_ACCESS_DENIED)
+// isWindowsRetryable reports whether err is a Windows error code
+// that may be fixed by retrying a failed filesystem operation.
+func isWindowsRetryable(err error) bool {
+	for {
+		unwrapped := errors.Unwrap(err)
+		if unwrapped == nil {
+			break
+		}
+		err = unwrapped
+	}
+	if err == syscall.ERROR_ACCESS_DENIED {
+		return true // Observed in https://go.dev/issue/50051.
+	}
+	if err == windows.ERROR_SHARING_VIOLATION {
+		return true // Observed in https://go.dev/issue/51442.
+	}
+	return false
 }