diff --git a/src/tests/antunit/taskdefs/uptodate-test.xml b/src/tests/antunit/taskdefs/uptodate-test.xml
new file mode 100644
index 000000000..83d1b3291
--- /dev/null
+++ b/src/tests/antunit/taskdefs/uptodate-test.xml
@@ -0,0 +1,86 @@
+<?xml version="1.0"?>
+<!--
+  Licensed to the Apache Software Foundation (ASF) under one or more
+  contributor license agreements.  See the NOTICE file distributed with
+  this work for additional information regarding copyright ownership.
+  The ASF licenses this file to You under the Apache License, Version 2.0
+  (the "License"); you may not use this file except in compliance with
+  the License.  You may obtain a copy of the License at
+
+      http://www.apache.org/licenses/LICENSE-2.0
+
+  Unless required by applicable law or agreed to in writing, software
+  distributed under the License is distributed on an "AS IS" BASIS,
+  WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+  See the License for the specific language governing permissions and
+  limitations under the License.
+-->
+<project default="antunit" xmlns:au="antlib:org.apache.ant.antunit">
+  <import file="../antunit-base.xml" />
+
+  <target name="testModifiedDirectories"
+          description="https://issues.apache.org/bugzilla/show_bug.cgi?id=39122
+                       and
+                       https://issues.apache.org/bugzilla/show_bug.cgi?id=44300">
+    <mkdir dir="${input}/source"/>
+    <mkdir dir="${output}"/>
+    <sleep seconds="2"/>
+    <touch file="${input}/source/file"/>
+    <au:assertFalse>
+      <uptodate>
+        <srcresources>
+          <fileset dir="${input}"/>
+          <dirset dir="${input}"/>
+        </srcresources>
+        <globmapper from="*" to="${output}/*"/>
+      </uptodate>
+    </au:assertFalse>
+    <mkdir dir="${output}/source"/>
+    <touch file="${output}/source/file"/>
+    <au:assertTrue>
+      <uptodate targetfile="${output}">
+        <srcresources>
+          <fileset dir="${input}"/>
+          <dirset dir="${input}"/>
+        </srcresources>
+        <globmapper from="*" to="${output}/*"/>
+      </uptodate>
+    </au:assertTrue>
+    <sleep seconds="2"/>
+    <touch>
+      <file file="${input}/source"/>
+    </touch>
+    <au:assertFalse>
+      <uptodate targetfile="${output}">
+        <srcresources>
+          <fileset dir="${input}"/>
+          <dirset dir="${input}"/>
+        </srcresources>
+        <globmapper from="*" to="${output}/*"/>
+      </uptodate>
+    </au:assertFalse>
+    <touch>
+      <file file="${output}/source"/>
+    </touch>
+    <au:assertTrue>
+      <uptodate targetfile="${output}">
+        <srcresources>
+          <fileset dir="${input}"/>
+          <dirset dir="${input}"/>
+        </srcresources>
+        <globmapper from="*" to="${output}/*"/>
+      </uptodate>
+    </au:assertTrue>
+    <sleep seconds="2"/>
+    <delete file="${input}/source/file"/>
+    <au:assertFalse>
+      <uptodate targetfile="${output}">
+        <srcresources>
+          <fileset dir="${input}"/>
+          <dirset dir="${input}"/>
+        </srcresources>
+        <globmapper from="*" to="${output}/*"/>
+      </uptodate>
+    </au:assertFalse>
+  </target>
+</project>