diff --git a/app/src/androidTest/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivityTest.java b/app/src/androidTest/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivityTest.java
new file mode 100644
index 0000000..3970862
--- /dev/null
+++ b/app/src/androidTest/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivityTest.java
@@ -0,0 +1,79 @@
+package com.wbrawner.simplemarkdown.view.activity;
+
+import android.Manifest;
+import android.content.Intent;
+import android.support.test.rule.ActivityTestRule;
+import android.support.test.rule.GrantPermissionRule;
+import android.widget.TextView;
+
+import com.wbrawner.simplemarkdown.R;
+import com.wbrawner.simplemarkdown.utility.Constants;
+
+import org.junit.Rule;
+import org.junit.Test;
+
+import java.util.HashMap;
+
+import static android.support.test.espresso.Espresso.onData;
+import static android.support.test.espresso.Espresso.onView;
+import static android.support.test.espresso.action.ViewActions.click;
+import static android.support.test.espresso.assertion.ViewAssertions.matches;
+import static android.support.test.espresso.matcher.ViewMatchers.withId;
+import static android.support.test.espresso.matcher.ViewMatchers.withParent;
+import static android.support.test.espresso.matcher.ViewMatchers.withText;
+import static org.hamcrest.Matchers.allOf;
+import static org.hamcrest.Matchers.instanceOf;
+import static org.hamcrest.Matchers.is;
+
+public class ExplorerActivityTest {
+    @Rule
+    public ActivityTestRule<ExplorerActivity> explorerActivityActivityTestRule
+            = new ActivityTestRule<>(ExplorerActivity.class, false, false);
+    @Rule
+    public GrantPermissionRule readFilesPermissionRule =
+            GrantPermissionRule.grant(Manifest.permission.READ_EXTERNAL_STORAGE);
+    @Rule
+    public GrantPermissionRule writeFilesPermissionRule =
+            GrantPermissionRule.grant(Manifest.permission.WRITE_EXTERNAL_STORAGE);
+
+    @Test
+    public void firstItemInDirectoryIsGoUpTest() {
+        Intent startIntent = new Intent();
+        startIntent.putExtra(Constants.EXTRA_REQUEST_CODE, Constants.REQUEST_OPEN_FILE);
+        explorerActivityActivityTestRule.launchActivity(startIntent);
+        // We should start in the Documents directory
+        onView(allOf(instanceOf(TextView.class), withParent(withId(R.id.toolbar))))
+                .check(matches(withText("Documents")));
+
+        // Check that the first item in the list is our navigate up a directory item and click it
+        onData(is(instanceOf(HashMap.class)))
+                .atPosition(0)
+                .check(matches(withText(
+                        explorerActivityActivityTestRule.getActivity().getString(R.string.directory_up)
+                )))
+                .perform(click());
+
+        // Check that we're in the parent of the Documents directory
+        onView(allOf(instanceOf(TextView.class), withParent(withId(R.id.toolbar))))
+                .check(matches(withText("0")));
+
+        // Enter the Android/data/data directory, which should almost certainly have other
+        // directories, and check that each directory shows the "Go up" option as the first option
+        // in the list
+        onView(withText("Android"))
+                .perform(click());
+        onData(is(instanceOf(HashMap.class)))
+                .atPosition(0)
+                .check(matches(withText(
+                        explorerActivityActivityTestRule.getActivity().getString(R.string.directory_up)
+                )));
+
+        onView(withText("data"))
+                .perform(click());
+        onData(is(instanceOf(HashMap.class)))
+                .atPosition(0)
+                .check(matches(withText(
+                        explorerActivityActivityTestRule.getActivity().getString(R.string.directory_up)
+                )));
+    }
+}
\ No newline at end of file
diff --git a/app/src/main/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivity.java b/app/src/main/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivity.java
index 504b230..59b2906 100644
--- a/app/src/main/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivity.java
+++ b/app/src/main/java/com/wbrawner/simplemarkdown/view/activity/ExplorerActivity.java
@@ -172,13 +172,6 @@ public class ExplorerActivity extends AppCompatActivity {
         TreeSet<HashMap<String, Object>> dirs = new TreeSet<HashMap<String, Object>>((o1, o2) ->
                 ((String) o1.get("name")).compareToIgnoreCase((String) o2.get("name"))) {
         };
-        if (docsDir.getParentFile() != null && docsDir.getParentFile().canRead()) {
-            HashMap<String, Object> fileHashMap = new HashMap<>();
-            fileHashMap.put("name", getString(R.string.directory_up));
-            fileHashMap.put("file", docsDir.getParentFile());
-
-            dirs.add(fileHashMap);
-        }
 
         if (docsDir.listFiles() != null) {
             for (File file : docsDir.listFiles()) {
@@ -202,7 +195,16 @@ public class ExplorerActivity extends AppCompatActivity {
             }
         }
 
-        List<HashMap<String, Object>> sortedFiles = new ArrayList<>(dirs);
+        List<HashMap<String, Object>> sortedFiles = new ArrayList<>();
+        if (docsDir.getParentFile() != null && docsDir.getParentFile().canRead()) {
+            HashMap<String, Object> fileHashMap = new HashMap<>();
+            fileHashMap.put("name", getString(R.string.directory_up));
+            fileHashMap.put("file", docsDir.getParentFile());
+
+            sortedFiles.add(fileHashMap);
+        }
+
+        sortedFiles.addAll(dirs);
         sortedFiles.addAll(files);
 
         return sortedFiles;