diff --git a/scm-webapp/src/main/java/sonia/scm/net/ahc/DefaultAdvancedHttpClient.java b/scm-webapp/src/main/java/sonia/scm/net/ahc/DefaultAdvancedHttpClient.java
index be3c8bee64..9ea181dd46 100644
--- a/scm-webapp/src/main/java/sonia/scm/net/ahc/DefaultAdvancedHttpClient.java
+++ b/scm-webapp/src/main/java/sonia/scm/net/ahc/DefaultAdvancedHttpClient.java
@@ -193,12 +193,18 @@ public class DefaultAdvancedHttpClient extends AdvancedHttpClient
     try (Span span = tracer.span(request.getSpanKind())) {
       span.label("url", request.getUrl());
       span.label("method", request.getMethod());
-      DefaultAdvancedHttpResponse response = doRequest(request);
-      span.label("status", response.getStatus());
-      if (!response.isSuccessful()) {
+      try {
+        DefaultAdvancedHttpResponse response = doRequest(request);
+        span.label("status", response.getStatus());
+        if (!response.isSuccessful()) {
+          span.failed();
+        }
+        return response;
+      } catch (IOException ex) {
+        span.label("exception", ex.getMessage());
         span.failed();
+        throw ex;
       }
-      return response;
     }
   }
 
diff --git a/scm-webapp/src/test/java/sonia/scm/net/ahc/DefaultAdvancedHttpClientTest.java b/scm-webapp/src/test/java/sonia/scm/net/ahc/DefaultAdvancedHttpClientTest.java
index 4ca513b4e5..24b857ea9e 100644
--- a/scm-webapp/src/test/java/sonia/scm/net/ahc/DefaultAdvancedHttpClientTest.java
+++ b/scm-webapp/src/test/java/sonia/scm/net/ahc/DefaultAdvancedHttpClientTest.java
@@ -29,36 +29,29 @@ package sonia.scm.net.ahc;
 import org.junit.Before;
 import org.junit.Test;
 import org.junit.runner.RunWith;
-
-import org.mockito.Answers;
 import org.mockito.Mock;
 import org.mockito.junit.MockitoJUnitRunner;
-
 import sonia.scm.config.ScmConfiguration;
+import sonia.scm.net.SSLContextProvider;
 import sonia.scm.net.TrustAllHostnameVerifier;
 import sonia.scm.trace.Span;
 import sonia.scm.trace.Tracer;
 import sonia.scm.util.HttpUtil;
 
-import static org.junit.Assert.*;
-
-import static org.mockito.Mockito.*;
-
-//~--- JDK imports ------------------------------------------------------------
-
+import javax.net.ssl.HttpsURLConnection;
+import javax.net.ssl.SSLSocketFactory;
 import java.io.ByteArrayOutputStream;
 import java.io.IOException;
-
 import java.net.HttpURLConnection;
 import java.net.SocketAddress;
 import java.net.URL;
-
 import java.util.HashSet;
 import java.util.Set;
 
-import javax.net.ssl.HttpsURLConnection;
-import javax.net.ssl.SSLSocketFactory;
-import sonia.scm.net.SSLContextProvider;
+import static org.junit.Assert.*;
+import static org.mockito.Mockito.*;
+
+//~--- JDK imports ------------------------------------------------------------
 
 /**
  *
@@ -294,6 +287,26 @@ public class DefaultAdvancedHttpClientTest
     verify(span).close();
   }
 
+  @Test
+  public void shouldCreateFailedTracingSpanOnIOException() throws IOException {
+    when(connection.getResponseCode()).thenThrow(new IOException("failed"));
+
+    boolean thrown = false;
+    try {
+      new AdvancedHttpRequest(client, HttpMethod.DELETE, "http://failing.host").spanKind("failures").request();
+    } catch (IOException ex) {
+      thrown = true;
+    }
+    assertTrue(thrown);
+
+    verify(tracer).span("failures");
+    verify(span).label("url", "http://failing.host");
+    verify(span).label("method", "DELETE");
+    verify(span).label("exception", "failed");
+    verify(span).failed();
+    verify(span).close();
+  }
+
   //~--- set methods ----------------------------------------------------------
 
   /**