diff --git a/libs/entitlement/src/main/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTree.java b/libs/entitlement/src/main/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTree.java
index 98076af51ae60..660459f06d58b 100644
--- a/libs/entitlement/src/main/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTree.java
+++ b/libs/entitlement/src/main/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTree.java
@@ -49,8 +49,24 @@ private FileAccessTree(FilesEntitlement filesEntitlement, PathLookup pathLookup)
         readPaths.sort(String::compareTo);
         writePaths.sort(String::compareTo);
 
-        this.readPaths = readPaths.toArray(new String[0]);
-        this.writePaths = writePaths.toArray(new String[0]);
+        this.readPaths = pruneSortedPaths(readPaths).toArray(new String[0]);
+        this.writePaths = pruneSortedPaths(writePaths).toArray(new String[0]);
+    }
+
+    private static List<String> pruneSortedPaths(List<String> paths) {
+        List<String> prunedReadPaths = new ArrayList<>();
+        if (paths.isEmpty() == false) {
+            String currentPath = paths.get(0);
+            prunedReadPaths.add(currentPath);
+            for (int i = 1; i < paths.size(); ++i) {
+                String nextPath = paths.get(i);
+                if (nextPath.startsWith(currentPath) == false) {
+                    prunedReadPaths.add(nextPath);
+                    currentPath = nextPath;
+                }
+            }
+        }
+        return prunedReadPaths;
     }
 
     public static FileAccessTree of(FilesEntitlement filesEntitlement, PathLookup pathLookup) {
diff --git a/libs/entitlement/src/test/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTreeTests.java b/libs/entitlement/src/test/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTreeTests.java
index 218fc0c956723..4eb3620c276ff 100644
--- a/libs/entitlement/src/test/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTreeTests.java
+++ b/libs/entitlement/src/test/java/org/elasticsearch/entitlement/runtime/policy/FileAccessTreeTests.java
@@ -96,6 +96,27 @@ public void testReadWriteUnderRead() {
         assertThat(tree.canWrite(path("foo/bar")), is(true));
     }
 
+    public void testPrunedPaths() {
+        var tree = accessTree(entitlement("foo", "read", "foo/baz", "read", "foo/bar", "read"));
+        assertThat(tree.canRead(path("foo")), is(true));
+        assertThat(tree.canWrite(path("foo")), is(false));
+        assertThat(tree.canRead(path("foo/bar")), is(true));
+        assertThat(tree.canWrite(path("foo/bar")), is(false));
+        assertThat(tree.canRead(path("foo/baz")), is(true));
+        assertThat(tree.canWrite(path("foo/baz")), is(false));
+        // also test a non-existent subpath
+        assertThat(tree.canRead(path("foo/barf")), is(true));
+        assertThat(tree.canWrite(path("foo/barf")), is(false));
+
+        tree = accessTree(entitlement("foo", "read", "foo/bar", "read_write"));
+        assertThat(tree.canRead(path("foo")), is(true));
+        assertThat(tree.canWrite(path("foo")), is(false));
+        assertThat(tree.canRead(path("foo/bar")), is(true));
+        assertThat(tree.canWrite(path("foo/bar")), is(true));
+        assertThat(tree.canRead(path("foo/baz")), is(true));
+        assertThat(tree.canWrite(path("foo/baz")), is(false));
+    }
+
     public void testReadWithRelativePath() {
         for (var dir : List.of("config", "home")) {
             var tree = accessTree(entitlement(Map.of("relative_path", "foo", "mode", "read", "relative_to", dir)));