diff --git a/internal/import_dir_test.go b/internal/import_dir_test.go
new file mode 100644
index 000000000..27a53d5f3
--- /dev/null
+++ b/internal/import_dir_test.go
@@ -0,0 +1,81 @@
+package internal
+
+import (
+	"bytes"
+	"context"
+	"io"
+	"path"
+	"regexp"
+	"testing"
+
+	"github.com/databricks/cli/libs/filer"
+	"github.com/databricks/databricks-sdk-go"
+	"github.com/databricks/databricks-sdk-go/service/workspace"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestWorkspaceImportDir(t *testing.T) {
+	t.Log(GetEnvOrSkipTest(t, "CLOUD_ENV"))
+
+	ctx := context.Background()
+	w := databricks.Must(databricks.NewWorkspaceClient())
+	tmpdir := TemporaryWorkspaceDir(t, w)
+
+	// run import_dir command
+	RequireSuccessfulRun(t, "workspace", "import_dir", "./testdata/import_dir/default", tmpdir)
+
+	// assert files are uploaded
+	f, err := filer.NewWorkspaceFilesClient(w, tmpdir)
+	require.NoError(t, err)
+	assertFileContains(t, ctx, f, "foo.txt", "hello, world")
+	assertFileContains(t, ctx, f, ".gitignore", ".databricks")
+	assertFileContains(t, ctx, f, "bar/apple.py", "print(1)")
+	assertNotebookExists(t, ctx, w, path.Join(tmpdir, "bar/mango"))
+}
+
+func TestWorkspaceImportDirOverwriteFlag(t *testing.T) {
+	// t.Log(GetEnvOrSkipTest(t, "CLOUD_ENV"))
+
+	// ctx := context.Background()
+	w := databricks.Must(databricks.NewWorkspaceClient())
+	tmpdir := TemporaryWorkspaceDir(t, w)
+
+	// run import_dir command
+	RequireSuccessfulRun(t, "workspace", "import_dir", "./testdata/import_dir/override/a", tmpdir)
+
+	// // assert files are uploaded
+	// f, err := filer.NewWorkspaceFilesClient(w, tmpdir)
+	// require.NoError(t, err)
+	// assertFileContains(t, ctx, f, "bar.txt", "from directory A")
+
+
+	// Assert another run fails with path already exists error from the server
+	_, _, err := RequireErrorRun(t, "workspace", "import_dir", "./testdata/import_dir/override/b", tmpdir)
+	assert.Regexp(t, regexp.MustCompile("Path (.*) already exists."), err.Error())
+
+	// // Succeeds with the overwrite flag
+	// RequireSuccessfulRun(t, "workspace", "import_dir", "./testdata/import_dir/override/b", tmpdir, "--overwrite")
+	// require.NoError(t, err)
+	// assertFileContains(t, ctx, f, "bar.txt", "from directory B")
+}
+
+func assertFileContains(t *testing.T, ctx context.Context, f filer.Filer, name, contents string) {
+	r, err := f.Read(ctx, name)
+	require.NoError(t, err)
+
+	var b bytes.Buffer
+	_, err = io.Copy(&b, r)
+	require.NoError(t, err)
+
+	assert.Contains(t, b.String(), contents)
+}
+
+func assertNotebookExists(t *testing.T, ctx context.Context, w *databricks.WorkspaceClient, path string) {
+	info, err := w.Workspace.ListAll(ctx, workspace.ListWorkspaceRequest{
+		Path: path,
+	})
+	require.NoError(t, err)
+	assert.Len(t, info, 1)
+	assert.Equal(t, info[0].ObjectType, workspace.ObjectTypeNotebook)
+}