diff --git a/bake/bake.go b/bake/bake.go
index 8dd3b979aeb..9a507cd6e83 100644
--- a/bake/bake.go
+++ b/bake/bake.go
@@ -1012,7 +1012,8 @@ func checkPath(p string) error {
 	if err != nil {
 		return err
 	}
-	if strings.HasPrefix(rel, ".."+string(os.PathSeparator)) {
+	parts := strings.Split(rel, string(os.PathSeparator))
+	if parts[0] == ".." {
 		return errors.Errorf("path %s is outside of the working directory, please set BAKE_ALLOW_REMOTE_FS_ACCESS=1", p)
 	}
 	return nil
diff --git a/tests/bake.go b/tests/bake.go
index a462be70962..130fb0bdf15 100644
--- a/tests/bake.go
+++ b/tests/bake.go
@@ -22,6 +22,8 @@ var bakeTests = []func(t *testing.T, sb integration.Sandbox){
 	testBakeRemoteCmdContext,
 	testBakeRemoteCmdContextOverride,
 	testBakeRemoteContextSubdir,
+	testBakeRemoteCmdContextEscapeRoot,
+	testBakeRemoteCmdContextEscapeRelative,
 }
 
 func testBakeRemote(t *testing.T, sb integration.Sandbox) {
@@ -161,3 +163,103 @@ COPY super-cool.txt /
 
 	require.FileExists(t, filepath.Join(dirDest, "super-cool.txt"))
 }
+
+func testBakeRemoteCmdContextEscapeRoot(t *testing.T, sb integration.Sandbox) {
+	dirSrc := tmpdir(
+		t,
+		fstest.CreateFile("foo", []byte("foo"), 0600),
+	)
+	dirSrc, err := filepath.Abs(dirSrc)
+	require.NoError(t, err)
+
+	dirCurrent := tmpdir(t)
+	dirCurrent, err = filepath.Abs(dirCurrent)
+	require.NoError(t, err)
+
+	bakefile := []byte(`
+target "default" {
+	context = "cwd://` + dirSrc + `"
+	dockerfile-inline = <<EOT
+FROM scratch
+COPY foo /foo
+EOT
+}
+`)
+	dirSpec := tmpdir(
+		t,
+		fstest.CreateFile("docker-bake.hcl", bakefile, 0600),
+	)
+	dirDest := t.TempDir()
+
+	git, err := gitutil.New(gitutil.WithWorkingDir(dirSpec))
+	require.NoError(t, err)
+
+	gitutil.GitInit(git, t)
+	gitutil.GitAdd(git, t, "docker-bake.hcl")
+	gitutil.GitCommit(git, t, "initial commit")
+	addr := gitutil.GitServeHTTP(git, t)
+
+	out, err := bakeCmd(
+		sb,
+		withDir(dirCurrent),
+		withArgs(addr, "--set", "*.output=type=local,dest="+dirDest),
+	)
+	require.Error(t, err, out)
+	require.Contains(t, out, "outside of the working directory, please set BAKE_ALLOW_REMOTE_FS_ACCESS")
+
+	out, err = bakeCmd(
+		sb,
+		withDir(dirCurrent),
+		withArgs(addr, "--set", "*.output=type=local,dest="+dirDest),
+		withEnv("BAKE_ALLOW_REMOTE_FS_ACCESS=1"),
+	)
+	require.NoError(t, err, out)
+	require.FileExists(t, filepath.Join(dirDest, "foo"))
+}
+
+func testBakeRemoteCmdContextEscapeRelative(t *testing.T, sb integration.Sandbox) {
+	bakefile := []byte(`
+target "default" {
+	context = "cwd://../"
+	dockerfile-inline = <<EOT
+FROM scratch
+COPY foo /foo
+EOT
+}
+`)
+	dirSpec := tmpdir(
+		t,
+		fstest.CreateFile("docker-bake.hcl", bakefile, 0600),
+	)
+	dirSrc := tmpdir(
+		t,
+		fstest.CreateFile("foo", []byte("foo"), 0600),
+		fstest.CreateDir("subdir", 0700),
+	)
+	dirDest := t.TempDir()
+
+	git, err := gitutil.New(gitutil.WithWorkingDir(dirSpec))
+	require.NoError(t, err)
+
+	gitutil.GitInit(git, t)
+	gitutil.GitAdd(git, t, "docker-bake.hcl")
+	gitutil.GitCommit(git, t, "initial commit")
+	addr := gitutil.GitServeHTTP(git, t)
+
+	out, err := bakeCmd(
+		sb,
+		withDir(filepath.Join(dirSrc, "subdir")),
+		withArgs(addr, "--set", "*.output=type=local,dest="+dirDest),
+	)
+	require.Error(t, err, out)
+	require.Contains(t, out, "outside of the working directory, please set BAKE_ALLOW_REMOTE_FS_ACCESS")
+
+	out, err = bakeCmd(
+		sb,
+		withDir(filepath.Join(dirSrc, "subdir")),
+		withArgs(addr, "--set", "*.output=type=local,dest="+dirDest),
+		withEnv("BAKE_ALLOW_REMOTE_FS_ACCESS=1"),
+	)
+	require.NoError(t, err, out)
+	require.FileExists(t, filepath.Join(dirDest, "foo"))
+}
diff --git a/tests/integration.go b/tests/integration.go
index 9582bc5068f..538cf6bd51d 100644
--- a/tests/integration.go
+++ b/tests/integration.go
@@ -20,6 +20,12 @@ func tmpdir(t *testing.T, appliers ...fstest.Applier) string {
 
 type cmdOpt func(*exec.Cmd)
 
+func withEnv(env ...string) cmdOpt {
+	return func(cmd *exec.Cmd) {
+		cmd.Env = append(cmd.Env, env...)
+	}
+}
+
 func withArgs(args ...string) cmdOpt {
 	return func(cmd *exec.Cmd) {
 		cmd.Args = append(cmd.Args, args...)