diff --git a/internal/lsp/fake/sandbox.go b/internal/lsp/fake/sandbox.go
index b4395646bc..72b01217ae 100644
--- a/internal/lsp/fake/sandbox.go
+++ b/internal/lsp/fake/sandbox.go
@@ -9,9 +9,11 @@ import (
 	"errors"
 	"fmt"
 	"io/ioutil"
+	"math/rand"
 	"os"
 	"path/filepath"
 	"strings"
+	"time"
 
 	"golang.org/x/tools/internal/gocommand"
 	"golang.org/x/tools/internal/testenv"
@@ -266,9 +268,36 @@ func (sb *Sandbox) Close() error {
 	if sb.gopath != "" {
 		goCleanErr = sb.RunGoCommand(context.Background(), "", "clean", []string{"-modcache"}, false)
 	}
-	err := os.RemoveAll(sb.rootdir)
+	err := removeAll(sb.rootdir)
 	if err != nil || goCleanErr != nil {
 		return fmt.Errorf("error(s) cleaning sandbox: cleaning modcache: %v; removing files: %v", goCleanErr, err)
 	}
 	return nil
 }
+
+// removeAll is copied from GOROOT/src/testing/testing.go
+//
+// removeAll is like os.RemoveAll, but retries Windows "Access is denied."
+// errors up to an arbitrary timeout.
+//
+// See https://go.dev/issue/50051 for additional context.
+func removeAll(path string) error {
+	const arbitraryTimeout = 2 * time.Second
+	var (
+		start     time.Time
+		nextSleep = 1 * time.Millisecond
+	)
+	for {
+		err := os.RemoveAll(path)
+		if !isWindowsRetryable(err) {
+			return err
+		}
+		if start.IsZero() {
+			start = time.Now()
+		} else if d := time.Since(start) + nextSleep; d >= arbitraryTimeout {
+			return err
+		}
+		time.Sleep(nextSleep)
+		nextSleep += time.Duration(rand.Int63n(int64(nextSleep)))
+	}
+}
diff --git a/internal/lsp/fake/workdir.go b/internal/lsp/fake/workdir.go
index 734f5fd819..0a72083bf2 100644
--- a/internal/lsp/fake/workdir.go
+++ b/internal/lsp/fake/workdir.go
@@ -77,6 +77,10 @@ func WriteFileData(path string, content []byte, rel RelativeTo) error {
 // on Windows.
 var isWindowsErrLockViolation = func(err error) bool { return false }
 
+// isWindowsRetryable reports whether err is a Windows error code
+// that may be fixed by retrying a failed filesystem operation.
+var isWindowsRetryable = func(err error) bool { return false }
+
 // Workdir is a temporary working directory for tests. It exposes file
 // operations in terms of relative paths, and fakes file watching by triggering
 // events on file operations.
diff --git a/internal/lsp/fake/workdir_windows.go b/internal/lsp/fake/workdir_windows.go
index bcd18b7a22..fc5ad1a89a 100644
--- a/internal/lsp/fake/workdir_windows.go
+++ b/internal/lsp/fake/workdir_windows.go
@@ -10,10 +10,31 @@ import (
 )
 
 func init() {
-	// from https://docs.microsoft.com/en-us/windows/win32/debug/system-error-codes--0-499-
-	const ERROR_LOCK_VIOLATION syscall.Errno = 33
+	// constants copied from GOROOT/src/internal/syscall/windows/syscall_windows.go
+	const (
+		ERROR_SHARING_VIOLATION syscall.Errno = 32
+		ERROR_LOCK_VIOLATION    syscall.Errno = 33
+	)
 
 	isWindowsErrLockViolation = func(err error) bool {
 		return errors.Is(err, ERROR_LOCK_VIOLATION)
 	}
+
+	// Copied from GOROOT/src/testing/testing_windows.go
+	isWindowsRetryable = func(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 == ERROR_SHARING_VIOLATION {
+			return true // Observed in https://go.dev/issue/51442.
+		}
+		return false
+	}
 }