diff --git a/coderd/notifications/dispatch/smtp.go b/coderd/notifications/dispatch/smtp.go
index e0c1b89f6154e..7bbff3fcb8879 100644
--- a/coderd/notifications/dispatch/smtp.go
+++ b/coderd/notifications/dispatch/smtp.go
@@ -183,7 +183,6 @@ func (s *SMTPHandler) dispatch(subject, htmlBody, plainBody, to string) Delivery
 		if err != nil {
 			return true, xerrors.Errorf("message transmission: %w", err)
 		}
-		defer message.Close()
 
 		// Create message headers.
 		msg := &bytes.Buffer{}
@@ -251,6 +250,10 @@ func (s *SMTPHandler) dispatch(subject, htmlBody, plainBody, to string) Delivery
 			return false, xerrors.Errorf("write body buffer: %w", err)
 		}
 
+		if err = message.Close(); err != nil {
+			return true, xerrors.Errorf("delivery failure: %w", err)
+		}
+
 		// Returning false, nil indicates successful send (i.e. non-retryable non-error)
 		return false, nil
 	}
diff --git a/coderd/notifications/dispatch/smtp_test.go b/coderd/notifications/dispatch/smtp_test.go
index dbafabc969bc4..7576c4c936fa4 100644
--- a/coderd/notifications/dispatch/smtp_test.go
+++ b/coderd/notifications/dispatch/smtp_test.go
@@ -62,6 +62,7 @@ func TestSMTP(t *testing.T) {
 		expectedErr      string
 		retryable        bool
 		useTLS           bool
+		failOnDataFn     func() error
 	}{
 		/**
 		 * LOGIN auth mechanism
@@ -381,6 +382,21 @@ func TestSMTP(t *testing.T) {
 			toAddrs:          []string{to},
 			expectedAuthMeth: sasl.Plain,
 		},
+		/**
+		 * Other errors
+		 */
+		{
+			name: "Rejected on DATA",
+			cfg: codersdk.NotificationsEmailConfig{
+				Hello: hello,
+				From:  from,
+			},
+			failOnDataFn: func() error {
+				return &smtp.SMTPError{Code: 501, EnhancedCode: smtp.EnhancedCode{5, 5, 4}, Message: "Rejected!"}
+			},
+			expectedErr: "SMTP error 501: Rejected!",
+			retryable:   true,
+		},
 	}
 
 	// nolint:paralleltest // Reinitialization is not required as of Go v1.22.
@@ -398,6 +414,8 @@ func TestSMTP(t *testing.T) {
 				AcceptedIdentity: tc.cfg.Auth.Identity.String(),
 				AcceptedUsername: username,
 				AcceptedPassword: password,
+
+				FailOnDataFn: tc.failOnDataFn,
 			})
 
 			// Create a mock SMTP server which conditionally listens for plain or TLS connections.
diff --git a/coderd/notifications/dispatch/smtp_util_test.go b/coderd/notifications/dispatch/smtp_util_test.go
index 659a17bec4a08..44cb8725c5d8c 100644
--- a/coderd/notifications/dispatch/smtp_util_test.go
+++ b/coderd/notifications/dispatch/smtp_util_test.go
@@ -24,6 +24,7 @@ var (
 type Config struct {
 	AuthMechanisms                                       []string
 	AcceptedIdentity, AcceptedUsername, AcceptedPassword string
+	FailOnDataFn                                         func() error
 }
 
 type Message struct {
@@ -147,6 +148,10 @@ func (s *Session) Data(r io.Reader) error {
 		return err
 	}
 
+	if s.backend.cfg.FailOnDataFn != nil {
+		return s.backend.cfg.FailOnDataFn()
+	}
+
 	s.backend.lastMsg.Contents = string(b)
 
 	return nil