diff --git a/server/src/main/java/org/eclipse/openvsx/LocalRegistryService.java b/server/src/main/java/org/eclipse/openvsx/LocalRegistryService.java
index 142ed69cb..3721fa15c 100644
--- a/server/src/main/java/org/eclipse/openvsx/LocalRegistryService.java
+++ b/server/src/main/java/org/eclipse/openvsx/LocalRegistryService.java
@@ -173,7 +173,7 @@ private ExtensionVersion findExtensionVersion(String namespace, String extension
     @Transactional
     public ResponseEntity<byte[]> getFile(String namespace, String extensionName, String targetPlatform, String version, String fileName) {
         var extVersion = findExtensionVersion(namespace, extensionName, targetPlatform, version);
-        var resource = repositories.findFileByName(extVersion, fileName);
+        var resource = isType(fileName) ? repositories.findFileByType(extVersion, fileName.toLowerCase()) : repositories.findFileByName(extVersion, fileName);
         if (resource == null)
             throw new NotFoundException();
         if (resource.getType().equals(DOWNLOAD))
@@ -182,6 +182,11 @@ public ResponseEntity<byte[]> getFile(String namespace, String extensionName, St
         return storageUtil.getFileResponse(resource);
     }
 
+    public boolean isType (String fileName){
+        var expectedTypes = Arrays.asList(FileResource.MANIFEST, FileResource.README, FileResource.LICENSE, FileResource.ICON, FileResource.DOWNLOAD, FileResource.CHANGELOG);
+        return expectedTypes.stream().anyMatch(fileName::equalsIgnoreCase);
+    }
+
     @Override
     public ReviewListJson getReviews(String namespace, String extensionName) {
         var extension = repositories.findExtension(extensionName, namespace);
diff --git a/server/src/test/java/org/eclipse/openvsx/RegistryAPITest.java b/server/src/test/java/org/eclipse/openvsx/RegistryAPITest.java
index a007ff656..619dd3301 100644
--- a/server/src/test/java/org/eclipse/openvsx/RegistryAPITest.java
+++ b/server/src/test/java/org/eclipse/openvsx/RegistryAPITest.java
@@ -464,6 +464,14 @@ public void testUnknownFile() throws Exception {
                 .andExpect(status().isNotFound());
     }
 
+    @Test
+    public void testLatestFile() throws Exception {
+        mockLatest();
+        mockMvc.perform(get("/api/{namespace}/{extension}/{version}/file/{fileName}", "foo", "bar", "latest", "DOWNLOAD"))
+                .andExpect(status().isOk())
+                .andExpect(content().string("latest download"));
+    }
+
     @Test
     public void testReviews() throws Exception {
         mockReviews();
@@ -1886,6 +1894,8 @@ private FileResource mockReadme(String targetPlatform) {
         Mockito.when(entityManager.merge(resource)).thenReturn(resource);
         Mockito.when(repositories.findFileByName(extVersion, "README"))
                 .thenReturn(resource);
+        Mockito.when(repositories.findFileByType(extVersion, FileResource.README))
+                .thenReturn(resource);
         return resource;
     }
 
@@ -1900,6 +1910,8 @@ private FileResource mockChangelog() {
         Mockito.when(entityManager.merge(resource)).thenReturn(resource);
         Mockito.when(repositories.findFileByName(extVersion, "CHANGELOG"))
                 .thenReturn(resource);
+        Mockito.when(repositories.findFileByType(extVersion, FileResource.CHANGELOG))
+                .thenReturn(resource);
         return resource;
     }
 
@@ -1914,6 +1926,22 @@ private FileResource mockLicense() {
         Mockito.when(entityManager.merge(resource)).thenReturn(resource);
         Mockito.when(repositories.findFileByName(extVersion, "LICENSE"))
                 .thenReturn(resource);
+        Mockito.when(repositories.findFileByType(extVersion, FileResource.LICENSE))
+                .thenReturn(resource);
+        return resource;
+    }
+
+    private FileResource mockLatest() {
+        var extVersion = mockExtension();
+        var resource = new FileResource();
+        resource.setExtension(extVersion);
+        resource.setName("DOWNLOAD");
+        resource.setType(FileResource.DOWNLOAD);
+        resource.setContent("latest download".getBytes());
+        resource.setStorageType(FileResource.STORAGE_DB);
+        Mockito.when(entityManager.merge(resource)).thenReturn(resource);
+        Mockito.when(repositories.findFileByType(extVersion, FileResource.DOWNLOAD))
+                .thenReturn(resource);
         return resource;
     }