diff --git a/acceptance/acceptance_test.go b/acceptance/acceptance_test.go
index 5f1181313c..850d3bf9d6 100644
--- a/acceptance/acceptance_test.go
+++ b/acceptance/acceptance_test.go
@@ -137,6 +137,13 @@ func runTest(t *testing.T, dir, coverDir string, repls testdiff.ReplacementsCont
 		tmpDir = t.TempDir()
 	}
 
+	repls.Set("/private"+tmpDir, "$TMPDIR")
+	repls.Set("/private"+filepath.Dir(tmpDir), "$TMPPARENT")
+	repls.Set("/private"+filepath.Dir(filepath.Dir(tmpDir)), "$TMPGPARENT")
+	repls.Set(tmpDir, "$TMPDIR")
+	repls.Set(filepath.Dir(tmpDir), "$TMPPARENT")
+	repls.Set(filepath.Dir(filepath.Dir(tmpDir)), "$TMPGPARENT")
+
 	scriptContents := readMergedScriptContents(t, dir)
 	testutil.WriteFile(t, filepath.Join(tmpDir, EntryPointScript), scriptContents)
 
diff --git a/acceptance/bundle/sync-paths-dotdot/databricks.yml b/acceptance/bundle/sync-paths-dotdot/databricks.yml
new file mode 100644
index 0000000000..7215ffea29
--- /dev/null
+++ b/acceptance/bundle/sync-paths-dotdot/databricks.yml
@@ -0,0 +1,5 @@
+bundle:
+  name: test-bundle
+sync:
+  paths:
+    - ..
diff --git a/acceptance/bundle/sync-paths-dotdot/output.txt b/acceptance/bundle/sync-paths-dotdot/output.txt
new file mode 100644
index 0000000000..11db3e9ee0
--- /dev/null
+++ b/acceptance/bundle/sync-paths-dotdot/output.txt
@@ -0,0 +1,11 @@
+Error: path "$TMPPARENT" is not within repository root "$TMPDIR"
+
+Name: test-bundle
+Target: default
+Workspace:
+  User: $USERNAME
+  Path: /Workspace/Users/$USERNAME/.bundle/test-bundle/default
+
+Found 1 error
+
+Exit code: 1
diff --git a/acceptance/bundle/sync-paths-dotdot/script b/acceptance/bundle/sync-paths-dotdot/script
new file mode 100644
index 0000000000..72555b332a
--- /dev/null
+++ b/acceptance/bundle/sync-paths-dotdot/script
@@ -0,0 +1 @@
+$CLI bundle validate