diff --git a/core/Microsoft.Mcp.Core/src/Commands/BaseCommand.cs b/core/Microsoft.Mcp.Core/src/Commands/BaseCommand.cs
index 80a33df534..dca50c35b9 100644
--- a/core/Microsoft.Mcp.Core/src/Commands/BaseCommand.cs
+++ b/core/Microsoft.Mcp.Core/src/Commands/BaseCommand.cs
@@ -110,6 +110,7 @@ protected virtual void HandleException(CommandContext context, Exception ex)
     {
         ArgumentException => HttpStatusCode.BadRequest,  // Bad Request for invalid arguments
         InvalidOperationException => HttpStatusCode.UnprocessableEntity,  // Unprocessable Entity for configuration errors
+        HttpRequestException httpEx => httpEx.StatusCode ?? HttpStatusCode.ServiceUnavailable,
         _ => HttpStatusCode.InternalServerError  // Internal Server Error for unexpected errors
     };
 
diff --git a/core/Microsoft.Mcp.Core/src/Commands/GlobalCommand.cs b/core/Microsoft.Mcp.Core/src/Commands/GlobalCommand.cs
index c5a20680b5..881ac19108 100644
--- a/core/Microsoft.Mcp.Core/src/Commands/GlobalCommand.cs
+++ b/core/Microsoft.Mcp.Core/src/Commands/GlobalCommand.cs
@@ -121,7 +121,7 @@ protected override TOptions BindOptions(ParseResult parseResult)
         KeyNotFoundException => HttpStatusCode.NotFound,
         AuthenticationFailedException => HttpStatusCode.Unauthorized,
         RequestFailedException rfEx => (HttpStatusCode)rfEx.Status,
-        HttpRequestException => HttpStatusCode.ServiceUnavailable,
+        HttpRequestException httpEx => httpEx.StatusCode ?? HttpStatusCode.ServiceUnavailable,
         _ => HttpStatusCode.InternalServerError
     };
 
diff --git a/servers/Azure.Mcp.Server/changelog-entries/1774379055021.yaml b/servers/Azure.Mcp.Server/changelog-entries/1774379055021.yaml
new file mode 100644
index 0000000000..959e060310
--- /dev/null
+++ b/servers/Azure.Mcp.Server/changelog-entries/1774379055021.yaml
@@ -0,0 +1,3 @@
+changes:
+  - section: "Other Changes"
+    description: "Update HttpRequestException to attempt to return a more specific status code for better troubleshooting"
\ No newline at end of file
diff --git a/servers/Fabric.Mcp.Server/changelog-entries/1774379067978.yaml b/servers/Fabric.Mcp.Server/changelog-entries/1774379067978.yaml
new file mode 100644
index 0000000000..959e060310
--- /dev/null
+++ b/servers/Fabric.Mcp.Server/changelog-entries/1774379067978.yaml
@@ -0,0 +1,3 @@
+changes:
+  - section: "Other Changes"
+    description: "Update HttpRequestException to attempt to return a more specific status code for better troubleshooting"
\ No newline at end of file