diff --git a/internal/repofiles_test.go b/internal/repofiles_test.go
new file mode 100644
index 000000000..055fe0c24
--- /dev/null
+++ b/internal/repofiles_test.go
@@ -0,0 +1,155 @@
+package internal
+
+import (
+	"context"
+	"os"
+	"path"
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/databricks/cli/libs/filer"
+	"github.com/databricks/cli/libs/sync/repofiles"
+	"github.com/databricks/databricks-sdk-go"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// TODO: skip if not cloud env, these are integration tests
+// TODO: split into a separate PR
+
+func TestRepoFilesPutFile(t *testing.T) {
+	w, err := databricks.NewWorkspaceClient()
+	require.NoError(t, err)
+	ctx := context.Background()
+
+	// initialize client
+	wsfsTmpDir := TemporaryWorkspaceDir(t, w)
+	localTmpDir := t.TempDir()
+	r, err := repofiles.Create(wsfsTmpDir, localTmpDir, w, &repofiles.RepoFileOptions{
+		OverwriteIfExists: true,
+	})
+	require.NoError(t, err)
+	f, err := filer.NewWorkspaceFilesClient(w, wsfsTmpDir)
+	require.NoError(t, err)
+
+	// create local file
+	err = os.WriteFile(filepath.Join(localTmpDir, "foo.txt"), []byte(`hello, world`), os.ModePerm)
+	require.NoError(t, err)
+	err = r.PutFile(ctx, "foo.txt")
+	require.NoError(t, err)
+
+	require.NoError(t, f.Mkdir(ctx, "bar"))
+
+	entries, err := f.ReadDir(ctx, "bar")
+	require.NoError(t, err)
+	require.Len(t, entries, 1)
+
+	assertFileContains(t, ctx, f, "foo.txt", "hello, world")
+}
+
+func TestRepoFilesFileOverwritesNotebook(t *testing.T) {
+	w, err := databricks.NewWorkspaceClient()
+	require.NoError(t, err)
+	ctx := context.Background()
+
+	// initialize client
+	wsfsTmpDir := TemporaryWorkspaceDir(t, w)
+	localTmpDir := t.TempDir()
+	r, err := repofiles.Create(wsfsTmpDir, localTmpDir, w, &repofiles.RepoFileOptions{
+		OverwriteIfExists: true,
+	})
+	require.NoError(t, err)
+	f, err := filer.NewWorkspaceFilesClient(w, wsfsTmpDir)
+	require.NoError(t, err)
+
+	// create local notebook
+	err = os.WriteFile(filepath.Join(localTmpDir, "foo.py"), []byte("#Databricks notebook source\nprint(1)"), os.ModePerm)
+	require.NoError(t, err)
+
+	// upload notebook
+	err = r.PutFile(ctx, "foo.py")
+	require.NoError(t, err)
+	assertNotebookExists(t, ctx, w, path.Join(wsfsTmpDir, "foo"))
+
+	// upload file, and assert that it overwrites the notebook
+	err = os.WriteFile(filepath.Join(localTmpDir, "foo"), []byte("I am going to overwrite the notebook"), os.ModePerm)
+	require.NoError(t, err)
+	err = r.PutFile(ctx, "foo")
+	require.NoError(t, err)
+	assertFileContains(t, ctx, f, "foo", "I am going to overwrite the notebook")
+}
+
+func TestRepoFilesFileOverwritesEmptyDirectoryTree(t *testing.T) {
+	w, err := databricks.NewWorkspaceClient()
+	require.NoError(t, err)
+	ctx := context.Background()
+
+	// initialize client
+	wsfsTmpDir := TemporaryWorkspaceDir(t, w)
+	localTmpDir := t.TempDir()
+	r, err := repofiles.Create(wsfsTmpDir, localTmpDir, w, &repofiles.RepoFileOptions{
+		OverwriteIfExists: true,
+	})
+	require.NoError(t, err)
+	f, err := filer.NewWorkspaceFilesClient(w, wsfsTmpDir)
+	require.NoError(t, err)
+
+	// create local file
+	err = os.WriteFile(filepath.Join(localTmpDir, "foo"), []byte(`hello, world`), os.ModePerm)
+	require.NoError(t, err)
+
+	// construct a directory tree without files in the workspace
+	err = f.Mkdir(ctx, "foo/a/b/c")
+	require.NoError(t, err)
+	err = f.Mkdir(ctx, "foo/a/b/d/e")
+	require.NoError(t, err)
+	err = f.Mkdir(ctx, "foo/f/g/i")
+	require.NoError(t, err)
+
+	// assert the directories exist
+	entries, err := f.ReadDir(ctx, "foo")
+	require.NoError(t, err)
+	assert.Len(t, entries, 2)
+	assert.True(t, entries[0].IsDir())
+	assert.True(t, entries[1].IsDir())
+
+	// upload file, and assert that it overwrites the empty directories
+	err = r.PutFile(ctx, "foo")
+	require.NoError(t, err)
+	assertFileContains(t, ctx, f, "foo", "hello, world")
+
+	// assert the directories do not exist anymore
+	_, err = f.ReadDir(ctx, "foo")
+	assert.ErrorIs(t, err, filer.ErrNotADirectory)
+}
+
+func TestRepoFilesFileInDirOverwritesExistingNotebook(t *testing.T) {
+	w, err := databricks.NewWorkspaceClient()
+	require.NoError(t, err)
+	ctx := context.Background()
+
+	// initialize client
+	wsfsTmpDir := TemporaryWorkspaceDir(t, w)
+	localTmpDir := t.TempDir()
+	r, err := repofiles.Create(wsfsTmpDir, localTmpDir, w, &repofiles.RepoFileOptions{
+		OverwriteIfExists: true,
+	})
+	require.NoError(t, err)
+	f, err := filer.NewWorkspaceFilesClient(w, wsfsTmpDir)
+	require.NoError(t, err)
+
+	// create local notebook
+	err = f.Write(ctx, "foo.py", strings.NewReader("#Databricks notebook source\nprint(1)"))
+	require.NoError(t, err)
+	assertNotebookExists(t, ctx, w, path.Join(wsfsTmpDir, "foo"))
+
+	// upload file
+	err = os.Mkdir(filepath.Join(localTmpDir, "foo"), os.ModePerm)
+	require.NoError(t, err)
+	err = os.WriteFile(filepath.Join(localTmpDir, "foo/bar.txt"), []byte("I am going to overwrite the notebook"), os.ModePerm)
+	require.NoError(t, err)
+	err = r.PutFile(ctx, "foo/bar.txt")
+	require.NoError(t, err)
+	assertFileContains(t, ctx, f, "foo/bar.txt", "I am going to overwrite the notebook")
+}