diff --git a/geowebcache/core/src/test/java/org/geowebcache/config/XMLConfigurationTest.java b/geowebcache/core/src/test/java/org/geowebcache/config/XMLConfigurationTest.java
index 9511050db..3b3151116 100644
--- a/geowebcache/core/src/test/java/org/geowebcache/config/XMLConfigurationTest.java
+++ b/geowebcache/core/src/test/java/org/geowebcache/config/XMLConfigurationTest.java
@@ -581,8 +581,25 @@ public void loadFromReadOnlyDirectory() throws GeoWebCacheException {
     @Test
     public void loadFromEmptyReadOnlyDirectoryFails() throws GeoWebCacheException, IOException {
         File roEmptyDir = this.temp.newFolder();
-        Assume.assumeTrue(
-                "Ignore if setWritable(false) does not succeed, may happen on Windows", roEmptyDir.setWritable(false));
+
+        // Try to make it read-only
+        roEmptyDir.setWritable(false);
+
+        // Actively probe whether the directory is still writable (for gwc-release Docker on Windows)
+        File probe = new File(roEmptyDir, "probe");
+        boolean canWrite;
+        try {
+            canWrite = probe.createNewFile();
+            if (canWrite) {
+                probe.delete();
+            }
+        } catch (IOException e) {
+            canWrite = false;
+        }
+
+        // Skip if we can still write, this may happen on Windows
+        Assume.assumeTrue("Skipping: directory is still writable", !canWrite);
+
         try {
             config = new XMLConfiguration(null, roEmptyDir.getAbsolutePath());
             config.setGridSetBroker(gridSetBroker);