diff --git a/jetty-util/src/main/java/org/eclipse/jetty/util/RolloverFileOutputStream.java b/jetty-util/src/main/java/org/eclipse/jetty/util/RolloverFileOutputStream.java
index e30b443acf1..94bfae53f89 100644
--- a/jetty-util/src/main/java/org/eclipse/jetty/util/RolloverFileOutputStream.java
+++ b/jetty-util/src/main/java/org/eclipse/jetty/util/RolloverFileOutputStream.java
@@ -233,9 +233,19 @@ public class RolloverFileOutputStream extends OutputStream
             File file = new File(_filename);
             _filename = file.getCanonicalPath();
             file = new File(_filename);
-            File dir = new File(file.getParent());
-            if (!dir.isDirectory() || !dir.canWrite())
+            File dir = file.getParentFile();
+            if (!dir.exists())
+            {
+                throw new IOException("Log directory does not exist. Path=" + dir);
+            }
+            else if (!dir.isDirectory())
+            {
+                throw new IOException("Path for Log directory is not a directory. Path=" + dir);
+            }
+            else if (!dir.canWrite())
+            {
                 throw new IOException("Cannot write log directory " + dir);
+            }
 
             // Is this a rollover file?
             String filename = file.getName();
diff --git a/jetty-util/src/test/java/org/eclipse/jetty/util/RolloverFileOutputStreamTest.java b/jetty-util/src/test/java/org/eclipse/jetty/util/RolloverFileOutputStreamTest.java
index ee3872f98ea..c19bc4184fe 100644
--- a/jetty-util/src/test/java/org/eclipse/jetty/util/RolloverFileOutputStreamTest.java
+++ b/jetty-util/src/test/java/org/eclipse/jetty/util/RolloverFileOutputStreamTest.java
@@ -36,7 +36,10 @@ import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.extension.ExtendWith;
 
 import static org.hamcrest.MatcherAssert.assertThat;
+import static org.hamcrest.Matchers.containsString;
+import static org.hamcrest.Matchers.instanceOf;
 import static org.hamcrest.Matchers.is;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
 
 @ExtendWith(WorkDirExtension.class)
 public class RolloverFileOutputStreamTest
@@ -181,6 +184,26 @@ public class RolloverFileOutputStreamTest
         assertSequence(midnight, expected);
     }
 
+    @Test
+    public void testMissingDirectory()
+    {
+
+        String templateString = "missingDir/test-rofos-yyyy_mm_dd.log";
+        Throwable error;
+        try (RolloverFileOutputStream rofos = new RolloverFileOutputStream(templateString))
+        {
+            throw new IllegalStateException();
+        }
+        catch (Throwable  t)
+        {
+            error = t;
+        }
+        assertNotNull(error);
+        assertThat(error, instanceOf(IOException.class));
+        error.getMessage();
+        assertThat(error.getMessage(), containsString("Log directory does not exist."));
+    }        
+
     @Test
     public void testFileHandling() throws Exception
     {