diff --git a/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/FileConversionServiceImpl.java b/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/FileConversionServiceImpl.java
index ad2a05bcb195..054f2fb7118f 100644
--- a/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/FileConversionServiceImpl.java
+++ b/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/FileConversionServiceImpl.java
@@ -154,6 +154,10 @@ public void startIfEnabled() {
                                 log.debug("Converted file id: {}, site id: {} ", convertedFileName, siteId);
 
                                 byte[] convertedFileBytes = LoolFileConverter.convert(converterBaseUrl, source.streamContent());
+                                
+                                if (convertedFileBytes == null) {
+                                    throw new RuntimeException("File conversion failed - no bytes returned from converter");
+                                }
 
                                 ResourcePropertiesEdit properties = contentHostingService.newResourceProperties();
                                 properties.addProperty(ResourceProperties.PROP_DISPLAY_NAME, convertedFileName);
diff --git a/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/converters/LoolFileConverter.java b/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/converters/LoolFileConverter.java
index 0be85b881f2b..8c55540ca690 100644
--- a/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/converters/LoolFileConverter.java
+++ b/kernel/kernel-impl/src/main/java/org/sakaiproject/content/impl/converters/LoolFileConverter.java
@@ -25,38 +25,46 @@
 import java.io.IOException;
 
 import org.apache.http.HttpEntity;
-import org.apache.http.client.config.RequestConfig;
-import org.apache.http.client.methods.CloseableHttpResponse;
+import org.apache.http.HttpResponse;
+import org.apache.http.HttpStatus;
 import org.apache.http.client.methods.HttpPost;
 import org.apache.http.entity.ContentType;
-import org.apache.http.entity.mime.HttpMultipartMode;
 import org.apache.http.entity.mime.MultipartEntityBuilder;
 import org.apache.http.impl.client.CloseableHttpClient;
-import org.apache.http.impl.client.HttpClientBuilder;
+import org.apache.http.impl.client.HttpClients;
 import org.apache.http.util.EntityUtils;
 
-public class LoolFileConverter {
-
-    public static byte[] convert(String baseUrl, InputStream sourceInputStream) throws IOException {
-
-        int timeoutMillis = 5000;
-        RequestConfig config = RequestConfig.custom()
-            .setConnectTimeout(timeoutMillis)
-            .setConnectionRequestTimeout(timeoutMillis)
-            .setSocketTimeout(timeoutMillis * 1000).build();
-        CloseableHttpClient client = HttpClientBuilder.create().setDefaultRequestConfig(config).build();
+import lombok.extern.slf4j.Slf4j;
 
-        HttpPost httpPost = new HttpPost(baseUrl + "/lool/convert-to/pdf");
+@Slf4j
+public class LoolFileConverter {
 
-        HttpEntity multipart = MultipartEntityBuilder.create()
-            .setMode(HttpMultipartMode.BROWSER_COMPATIBLE)
-            .addBinaryBody("data", sourceInputStream, ContentType.MULTIPART_FORM_DATA, "anything")
-            .build();
+    public static byte[] convert(String baseUrl, InputStream sourceInputStream) {
+        final HttpPost httpPost = new HttpPost(baseUrl + "/lool/convert-to/pdf");
 
+        final MultipartEntityBuilder builder = MultipartEntityBuilder.create();
+        builder.addBinaryBody("data", sourceInputStream, ContentType.MULTIPART_FORM_DATA, "anything");
+        
+        final HttpEntity multipart = builder.build();
         httpPost.setEntity(multipart);
-        CloseableHttpResponse response = client.execute(httpPost);
-        byte[] convertedFileBytes = EntityUtils.toByteArray(response.getEntity());
-        client.close();
-        return convertedFileBytes;
+
+        try (CloseableHttpClient client = HttpClients.createDefault()) {
+            HttpResponse response = client.execute(httpPost);
+            final int statusCode = response.getStatusLine().getStatusCode();
+            
+            if (statusCode == HttpStatus.SC_OK) {
+                return EntityUtils.toByteArray(response.getEntity());
+            } else {
+                log.error("File conversion failed with HTTP status code: {}. URL: {}", 
+                    statusCode, baseUrl + "/lool/convert-to/pdf");
+                return null;
+            }
+        } catch (IOException e) {
+            log.warn("Error during file conversion: {}", e.getMessage(), e);
+            return null;
+        } catch (Exception e) {
+            log.warn("Unexpected error during file conversion: {}", e.getMessage(), e);
+            return null;
+        }
     }
 }