diff --git a/modules/auxiliary/scanner/smtp/smtp_relay.rb b/modules/auxiliary/scanner/smtp/smtp_relay.rb
index 287316508f13..141eca030c72 100644
--- a/modules/auxiliary/scanner/smtp/smtp_relay.rb
+++ b/modules/auxiliary/scanner/smtp/smtp_relay.rb
@@ -84,6 +84,11 @@ def do_test_relay(testnumber, mailfrom, mailto)
 
       res = raw_send_recv("EHLO X\r\n")
       vprint_status("#{res.inspect}")
+      # check if the EHLO is actually supported. In case it's not, try the HELO command instead
+      if res.to_s =~ /^5\d\d/
+        res = raw_send_recv("HELO X\r\n")
+        vprint_status("#{res.inspect}")
+      end
 
       res = raw_send_recv("#{mailfrom}\r\n")
       vprint_status("#{res.inspect}")