diff --git a/api/src/main/java/org/commonjava/maven/galley/config/TransportManagerConfig.java b/api/src/main/java/org/commonjava/maven/galley/config/TransportManagerConfig.java
index 322ad51e0..37d6b7e35 100644
--- a/api/src/main/java/org/commonjava/maven/galley/config/TransportManagerConfig.java
+++ b/api/src/main/java/org/commonjava/maven/galley/config/TransportManagerConfig.java
@@ -30,7 +30,8 @@ public class TransportManagerConfig
     final long DEFAULT_WAIT_RETRY_SCALING_INCREMENT = DEFAULT_THRESHOLD_WAIT_RETRY_SIZE;
             // how many times we retry depends on this.
 
-    final float DEFAULT_TIMEOUT_OVEREXTENSION_FACTOR = 1.25f;
+    final float DEFAULT_TIMEOUT_OVEREXTENSION_FACTOR = 2.25f;
+            // Use proxy retry will probably exceed one default request timeout, at least twice as much time to the first request timeout.
 
     private final long thresholdWaitRetrySize;
 
diff --git a/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/Http.java b/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/Http.java
index aba67bad6..2e6a2e74e 100644
--- a/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/Http.java
+++ b/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/Http.java
@@ -28,7 +28,7 @@ public interface Http
     extends Closeable
 {
 
-    CloseableHttpClient createClient( HttpLocation location, boolean isProxy )
+    CloseableHttpClient createClient( HttpLocation location, boolean doProxy )
             throws GalleyException;
 
     CloseableHttpClient createClient( HttpLocation location )
diff --git a/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/HttpImpl.java b/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/HttpImpl.java
index 6f6e2a53f..2afc2bedc 100644
--- a/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/HttpImpl.java
+++ b/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/HttpImpl.java
@@ -93,7 +93,7 @@ public CloseableHttpClient createClient( final HttpLocation location )
     }
 
     @Override
-    public CloseableHttpClient createClient( final HttpLocation location, final boolean isProxy )
+    public CloseableHttpClient createClient( final HttpLocation location, final boolean doProxy )
             throws GalleyException
     {
         try
@@ -111,7 +111,7 @@ public CloseableHttpClient createClient( final HttpLocation location, final bool
                              .withUser( location.getUser() )
                              .withIgnoreHostnameVerification( location.isIgnoreHostnameVerification() )
                              .withMaxConnections( maxConnections );
-                if ( isProxy )
+                if ( doProxy )
                 {
                     logger.trace( "The location class: {}", location.getClass().getSimpleName() );
                     configBuilder.withProxyHost( location.getProxyHost() )
diff --git a/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/internal/AbstractHttpJob.java b/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/internal/AbstractHttpJob.java
index 8e81f3f33..c39279ade 100644
--- a/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/internal/AbstractHttpJob.java
+++ b/transports/httpclient/src/main/java/org/commonjava/maven/galley/transport/htcli/internal/AbstractHttpJob.java
@@ -101,35 +101,80 @@ public long getTransferSize()
     protected boolean executeHttp()
         throws TransferException
     {
-        boolean result = true;
+        int tries = 1;
+        boolean doProxy = false;
         try
         {
-            result = doExecuteHttp();
-        }
-        catch ( final NoHttpResponseException | ConnectTimeoutException | SocketTimeoutException e )
-        {
-            // For those are not in the iad2 tenant egress rules, will throw timeout so use the configured proxy to retry
-            result = executeProxyHttp();
-        }
-        catch ( final IOException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "I/O" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw new TransferLocationException( location, "Repository remote request failed for: {}. Reason: {}", e, url,
-                                         e.getMessage() );
-        }
-        catch ( TransferLocationException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "no transport" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw e;
-        }
-        catch ( final GalleyException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "unknown" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw new TransferException( "Repository remote request failed for: {}. Reason: {}", e, url,
-                                         e.getMessage() );
+            while ( tries > 0 )
+            {
+                tries--;
+                try
+                {
+                    client = http.createClient( location, doProxy );
+                    response = client.execute( request, http.createContext( location ) );
+
+                    final StatusLine line = response.getStatusLine();
+                    final int sc = line.getStatusCode();
+
+                    logger.trace( "{} {} : {}", request.getMethod(), line, url );
+
+                    if ( sc > 399 && sc != 404 && sc != 408 && sc != 502 && sc != 503 && sc != 504 )
+                    {
+                        throw new TransferLocationException( location,
+                                                             "Server misconfigured or not responding normally for url %s: '%s'",
+                                                             url, line );
+                    }
+                    else if ( !successStatuses.contains( sc ) )
+                    {
+                        logger.trace( "Detected failure respon se: " + sc );
+                        success = TransferResponseUtils.handleUnsuccessfulResponse( request, response, location, url );
+                        logger.trace( "Returning non-error failure response for code: " + sc );
+                        return false;
+                    }
+                }
+                catch ( final NoHttpResponseException | ConnectTimeoutException | SocketTimeoutException e )
+                {
+                    // For those are not in the iad2 tenant egress rules, will throw timeout so use the configured proxy to retry
+                    if ( tries > 0 )
+                    {
+                    }
+                    else if ( !doProxy ) // never do with proxy, retry with proxy
+                    {
+                        tries = 1;
+                        doProxy = true;
+                        logger.debug( "Retry to execute with global proxy for {}", url );
+                    }
+                    else // already did proxy, still timeout
+                    {
+                        addFieldToActiveSpan( "target-error-reason", "timeout" );
+                        addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
+                        throw new TransferTimeoutException( location, url,
+                                                            "Repository remote request failed for: {}. Reason: {}", e,
+                                                            url, e.getMessage() );
+                    }
+                }
+                catch ( final IOException e )
+                {
+                    addFieldToActiveSpan( "target-error-reason", "I/O" );
+                    addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
+                    throw new TransferLocationException( location,
+                                                         "Repository remote request failed for: {}. Reason: {}", e, url,
+                                                         e.getMessage() );
+                }
+                catch ( TransferLocationException e )
+                {
+                    addFieldToActiveSpan( "target-error-reason", "no transport" );
+                    addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
+                    throw e;
+                }
+                catch ( final GalleyException e )
+                {
+                    addFieldToActiveSpan( "target-error-reason", "unknown" );
+                    addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
+                    throw new TransferException( "Repository remote request failed for: {}. Reason: {}", e, url,
+                                                 e.getMessage() );
+                }
+            }
         }
         finally
         {
@@ -149,76 +194,6 @@ protected boolean executeHttp()
                 }
             }
         }
-
-        return result;
-    }
-
-    protected boolean executeProxyHttp()
-            throws TransferException
-    {
-        try
-        {
-            return doExecuteHttp( true );
-        }
-        catch ( final NoHttpResponseException | ConnectTimeoutException | SocketTimeoutException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "timeout" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw new TransferTimeoutException( location, url, "Repository remote request failed for: {}. Reason: {}",
-                                                e, url, e.getMessage() );
-        }
-        catch ( final IOException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "I/O" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw new TransferLocationException( location, "Repository remote request failed for: {}. Reason: {}", e,
-                                                 url, e.getMessage() );
-        }
-        catch ( TransferLocationException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "no transport" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw e;
-        }
-        catch ( final GalleyException e )
-        {
-            addFieldToActiveSpan( "target-error-reason", "unknown" );
-            addFieldToActiveSpan( "target-error", e.getClass().getSimpleName() );
-            throw new TransferException( "Repository remote request failed for: {}. Reason: {}", e, url,
-                                         e.getMessage() );
-        }
-    }
-
-    private boolean doExecuteHttp()
-            throws GalleyException, IOException
-    {
-        return doExecuteHttp( false );
-    }
-
-    private boolean doExecuteHttp( boolean isProxy )
-            throws GalleyException, IOException
-    {
-        client = http.createClient( location, isProxy );
-        response = client.execute( request, http.createContext( location ) );
-
-        final StatusLine line = response.getStatusLine();
-        final int sc = line.getStatusCode();
-
-        logger.trace( "{} {} : {}", request.getMethod(), line, url );
-
-        if ( sc > 399 && sc != 404 && sc != 408 && sc != 502 && sc != 503 && sc != 504 )
-        {
-            throw new TransferLocationException( location,
-                                                 "Server misconfigured or not responding normally for url %s: '%s'",
-                                                 url, line );
-        }
-        else if ( !successStatuses.contains( sc ) )
-        {
-            logger.trace( "Detected failure respon se: " + sc );
-            success = TransferResponseUtils.handleUnsuccessfulResponse( request, response, location, url );
-            logger.trace( "Returning non-error failure response for code: " + sc );
-            return false;
-        }
         return true;
     }