diff --git a/CHANGELOG.md b/CHANGELOG.md
index 85aa1d1..e7c264b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,12 @@
 
 Notable changes to Mailpit will be documented in this file.
 
+## [v1.27.7]
+
+### Fix
+- Move HELO/EHLO hostname setting to the correct position in SMTP client creation ([#558](https://github.com/axllent/mailpit/issues/558))
+
+
 ## [v1.27.6]
 
 ### Feature
diff --git a/internal/smtpd/forward.go b/internal/smtpd/forward.go
index 98fe9cf..e439e3c 100644
--- a/internal/smtpd/forward.go
+++ b/internal/smtpd/forward.go
@@ -51,6 +51,13 @@ func createForwardingSMTPClient(config config.SMTPForwardConfigStruct, addr stri
 		return nil, fmt.Errorf("error connecting to %s: %v", addr, err)
 	}
 
+	// Set the hostname for HELO/EHLO
+	if hostname, err := os.Hostname(); err == nil {
+		if err := client.Hello(hostname); err != nil {
+			return nil, fmt.Errorf("error saying HELO/EHLO to %s: %v", addr, err)
+		}
+	}
+
 	if config.STARTTLS {
 		tlsConf := &tls.Config{ServerName: config.Host} // #nosec
 		tlsConf.InsecureSkipVerify = config.AllowInsecure
@@ -61,13 +68,6 @@ func createForwardingSMTPClient(config config.SMTPForwardConfigStruct, addr stri
 		}
 	}
 
-	// Set the hostname for HELO/EHLO
-	if hostname, err := os.Hostname(); err == nil {
-		if err := client.Hello(hostname); err != nil {
-			return nil, fmt.Errorf("error saying HELO/EHLO to %s: %v", addr, err)
-		}
-	}
-
 	// Note: The caller is responsible for closing the client
 	return client, nil
 }
diff --git a/internal/smtpd/relay.go b/internal/smtpd/relay.go
index 5e94b0a..c76e6a7 100644
--- a/internal/smtpd/relay.go
+++ b/internal/smtpd/relay.go
@@ -85,6 +85,13 @@ func createRelaySMTPClient(config config.SMTPRelayConfigStruct, addr string) (*s
 		return nil, fmt.Errorf("error connecting to %s: %v", addr, err)
 	}
 
+	// Set the hostname for HELO/EHLO
+	if hostname, err := os.Hostname(); err == nil {
+		if err := client.Hello(hostname); err != nil {
+			return nil, fmt.Errorf("error saying HELO/EHLO to %s: %v", addr, err)
+		}
+	}
+
 	if config.STARTTLS {
 		tlsConf := &tls.Config{ServerName: config.Host} // #nosec
 		tlsConf.InsecureSkipVerify = config.AllowInsecure
@@ -95,13 +102,6 @@ func createRelaySMTPClient(config config.SMTPRelayConfigStruct, addr string) (*s
 		}
 	}
 
-	// Set the hostname for HELO/EHLO
-	if hostname, err := os.Hostname(); err == nil {
-		if err := client.Hello(hostname); err != nil {
-			return nil, fmt.Errorf("error saying HELO/EHLO to %s: %v", addr, err)
-		}
-	}
-
 	// Note: The caller is responsible for closing the client
 	return client, nil
 }