diff --git a/WHATSNEW b/WHATSNEW
index bd7f59ec3..862447ea7 100644
--- a/WHATSNEW
+++ b/WHATSNEW
@@ -42,8 +42,11 @@ Fixed bugs:
 * XmlProperty overrides previously set property value when handling duplicate 
   elements. Bugzilla 41080.
 
-* Having many tasks causes OOM.
-  Bugzilla 41049.
+* Having many tasks causes OOM.  Bugzilla 41049.
+
+* Regression: <path> was evaluating nested content only once, so that it could
+  not e.g. pick up files that didn't exist the first time through.
+  Bugzilla 41151.
 
 Other changes:
 --------------
diff --git a/src/main/org/apache/tools/ant/types/Path.java b/src/main/org/apache/tools/ant/types/Path.java
index cb9a64be8..6a5201ca2 100644
--- a/src/main/org/apache/tools/ant/types/Path.java
+++ b/src/main/org/apache/tools/ant/types/Path.java
@@ -277,6 +277,7 @@ public class Path extends DataType implements Cloneable, ResourceCollection {
         if (union == null) {
             union = new Union();
             union.setProject(getProject());
+            union.setCache(false);
         }
         union.add(c);
         setChecked(false);
diff --git a/src/tests/antunit/types/resources/latepath-test.xml b/src/tests/antunit/types/resources/latepath-test.xml
new file mode 100644
index 000000000..1468237b0
--- /dev/null
+++ b/src/tests/antunit/types/resources/latepath-test.xml
@@ -0,0 +1,17 @@
+<project xmlns:au="antlib:org.apache.ant.antunit">
+
+  <target name="testLatePath" depends="tearDown">
+    <path id="p">
+      <fileset file="testLatePath" />
+    </path>
+    <pathconvert refid="p" />
+    <touch file="testLatePath" />
+    <au:assertTrue>
+      <resourcecount when="eq" count="1" refid="p" />
+    </au:assertTrue>
+  </target>
+
+  <target name="tearDown">
+    <delete file="testLatePath" />
+  </target>
+</project>