diff --git a/src/main/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImpl.java b/src/main/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImpl.java
index 7eecd1a6653..8aa8ed9d308 100644
--- a/src/main/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImpl.java
+++ b/src/main/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImpl.java
@@ -40,6 +40,7 @@ public class OutboundFileZipGeneratorImpl implements OutboundFileZipGenerator {
     private static final String DAUDIO = "daudio";
     private static final String LOCALAUDIO = "localaudio";
     private static final String VIQ_METADATA_TYPE = "Zip";
+    private static final int CASE_NUMBER_SPLIT_INDEX = 5;
     private final AudioConfigurationProperties audioConfigurationProperties;
     private final OutboundFileZipGeneratorHelper outboundFileZipGeneratorHelper;
 
@@ -156,11 +157,14 @@ private Map<Path, Path> generateZipStructure(List<List<AudioFileInfo>> audioSess
     private Path generateZipPath(String caseNumber, int directoryIndex, AudioFileInfo audioFileInfo) {
         var nameElement1 = DAUDIO;
         var nameElement2 = LOCALAUDIO;
-        var nameElement3 = caseNumber.substring(0, 5);
-        var nameElement4 = caseNumber.substring(5);
         var nameElement5 = String.format("%04d", directoryIndex + 1);
         var filename = String.format("%s.a%02d", nameElement5, audioFileInfo.getChannel() - 1);
+        if (caseNumber.length() <= CASE_NUMBER_SPLIT_INDEX) {
+            return Path.of(nameElement1, nameElement2, caseNumber, nameElement5, filename);
+        }
 
+        var nameElement3 = caseNumber.substring(0, CASE_NUMBER_SPLIT_INDEX);
+        var nameElement4 = caseNumber.substring(CASE_NUMBER_SPLIT_INDEX);
         return Path.of(nameElement1, nameElement2, nameElement3, nameElement4, nameElement5, filename);
     }
 
@@ -187,4 +191,4 @@ private void writeZip(Map<Path, Path> sourceToDestinationPaths, Path outputPath)
         log.debug("Produced zip file: {}", outputPath);
     }
 
-}
\ No newline at end of file
+}
diff --git a/src/test/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImplTest.java b/src/test/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImplTest.java
index 9b57783907f..ec80ea3b9c0 100644
--- a/src/test/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImplTest.java
+++ b/src/test/java/uk/gov/hmcts/darts/audio/component/impl/OutboundFileZipGeneratorImplTest.java
@@ -80,7 +80,7 @@ void setUp() throws IOException, ParserConfigurationException {
     }
 
     @Test
-    void generateAndWriteZipShouldProduceZipWithTheExpectedFileStructure() {
+    void generateAndWriteZip_ShouldProduceZipWithTheExpectedFileStructure_WhenNineDigitCaseNumber() {
         var audioWithSession1AndChannel1 = createDummyFileAndAudioFileInfo(1);
         var audioWithSession1AndChannel2 = createDummyFileAndAudioFileInfo(2);
         List<AudioFileInfo> session1 = List.of(
@@ -113,6 +113,46 @@ void generateAndWriteZipShouldProduceZipWithTheExpectedFileStructure() {
         assertThat(paths, hasItem("daudio/localaudio/T2019/0024/0002/annotations.xml"));
     }
 
+    @Test
+    void generateAndWriteZip_ShouldProduceZip_WhenSingleCharacterCaseNumber() {
+        var audioWithSession1AndChannel1 = createDummyFileAndAudioFileInfo(1);
+
+        Path path = outboundFileZipGenerator.generateAndWriteZip(
+            List.of(List.of(audioWithSession1AndChannel1)),
+            createDummyMediaRequestEntity("b")
+        );
+
+        assertTrue(Files.exists(path));
+
+        List<String> paths = readZipStructure(path);
+
+        assertEquals(4, paths.size());
+        assertThat(paths, hasItem("readMe.txt"));
+        assertThat(paths, hasItem("playlist.xml"));
+        assertThat(paths, hasItem("daudio/localaudio/b/0001/0001.a00"));
+        assertThat(paths, hasItem("daudio/localaudio/b/0001/annotations.xml"));
+    }
+
+    @Test
+    void generateAndWriteZip_ShouldProduceZip_WhenFiveCharacterCaseNumber() {
+        var audioWithSession1AndChannel1 = createDummyFileAndAudioFileInfo(1);
+
+        Path path = outboundFileZipGenerator.generateAndWriteZip(
+            List.of(List.of(audioWithSession1AndChannel1)),
+            createDummyMediaRequestEntity("T2019")
+        );
+
+        assertTrue(Files.exists(path));
+
+        List<String> paths = readZipStructure(path);
+
+        assertEquals(4, paths.size());
+        assertThat(paths, hasItem("readMe.txt"));
+        assertThat(paths, hasItem("playlist.xml"));
+        assertThat(paths, hasItem("daudio/localaudio/T2019/0001/0001.a00"));
+        assertThat(paths, hasItem("daudio/localaudio/T2019/0001/annotations.xml"));
+    }
+
     private MediaRequestEntity createDummyMediaRequestEntity(String caseNumber) {
 
         HearingEntity mockHearingEntity = mock(HearingEntity.class);