diff --git a/internal/web/service/email/email.go b/internal/web/service/email/email.go
index 7031183fa..f6f2a0c95 100644
--- a/internal/web/service/email/email.go
+++ b/internal/web/service/email/email.go
@@ -5,6 +5,7 @@ import (
 	"crypto/rand"
 	"crypto/tls"
 	"encoding/hex"
+	"errors"
 	"fmt"
 	"mime"
 	"net"
@@ -42,6 +43,54 @@ const smtpConnectTimeout = 10 * time.Second
 
 var smtpDeadline = 30 * time.Second
 
+// smtpMaxServerBytes caps what one session reads from the server, TLS handshake
+// included: net/smtp buffers a reply of any length, so the deadline alone is no bound.
+const smtpMaxServerBytes = 1 << 20
+
+var errSMTPReplyTooLarge = errors.New("smtp server sent more data than a session may read")
+
+// limitedConn fails every Read once the peer has sent remaining bytes.
+type limitedConn struct {
+	net.Conn
+	remaining int64
+}
+
+func (c *limitedConn) Read(p []byte) (int, error) {
+	if c.remaining <= 0 {
+		return 0, errSMTPReplyTooLarge
+	}
+	if int64(len(p)) > c.remaining {
+		p = p[:c.remaining]
+	}
+	n, err := c.Conn.Read(p)
+	c.remaining -= int64(n)
+	return n, err
+}
+
+// dialSMTP opens a connection capped at smtpMaxServerBytes; timeout covers the
+// dial and, with implicitTLS, the handshake.
+func dialSMTP(addr, host string, timeout time.Duration, implicitTLS bool) (net.Conn, error) {
+	ctx, cancel := context.WithTimeout(context.Background(), timeout)
+	defer cancel()
+
+	raw, err := (&net.Dialer{}).DialContext(ctx, "tcp", addr)
+	if err != nil {
+		return nil, err
+	}
+	// The cap sits below TLS: net/smtp allows PLAIN auth only on a *tls.Conn,
+	// and this keeps it in force across a later STARTTLS upgrade.
+	limited := &limitedConn{Conn: raw, remaining: smtpMaxServerBytes}
+	if !implicitTLS {
+		return limited, nil
+	}
+	conn := tls.Client(limited, &tls.Config{ServerName: host})
+	if err = conn.HandshakeContext(ctx); err != nil {
+		raw.Close()
+		return nil, err
+	}
+	return conn, nil
+}
+
 // Send sends an HTML email to all configured recipients.
 func (s *EmailService) Send(subject, body string) error {
 	host, err := s.settingService.GetSmtpHost()
@@ -139,19 +188,7 @@ func (s *EmailService) TestConnection() SMTPTestResult {
 	addr := net.JoinHostPort(host, fmt.Sprintf("%d", port))
 
 	// Stage 1: Connect
-	var conn net.Conn
-	dialer := &net.Dialer{Timeout: 5 * time.Second}
-
-	switch encryptionType {
-	case "tls":
-		conn, err = (&tls.Dialer{NetDialer: dialer, Config: &tls.Config{
-			ServerName:         host,
-			InsecureSkipVerify: false,
-		}}).DialContext(context.Background(), "tcp", addr)
-	default:
-		conn, err = dialer.Dial("tcp", addr)
-	}
-
+	conn, err := dialSMTP(addr, host, 5*time.Second, encryptionType == "tls")
 	if err != nil {
 		return SMTPTestResult{false, "connect", classifySMTPError(err)}
 	}
@@ -216,12 +253,7 @@ func (s *EmailService) TestConnection() SMTPTestResult {
 }
 
 func (s *EmailService) sendWithTLS(addr string, auth smtp.Auth, from string, to []string, msg []byte, host string) error {
-	// Dial with explicit timeout
-	dialer := &net.Dialer{Timeout: smtpConnectTimeout}
-	conn, err := (&tls.Dialer{NetDialer: dialer, Config: &tls.Config{
-		ServerName:         host,
-		InsecureSkipVerify: false,
-	}}).DialContext(context.Background(), "tcp", addr)
+	conn, err := dialSMTP(addr, host, smtpConnectTimeout, true)
 	if err != nil {
 		return err
 	}
@@ -266,7 +298,7 @@ func (s *EmailService) sendWithTLS(addr string, auth smtp.Auth, from string, to
 // timeout and arms a connection deadline, so a server that never speaks or
 // stalls mid-protocol cannot block the sender goroutine past smtpDeadline.
 func (s *EmailService) sendPlain(addr string, auth smtp.Auth, from string, to []string, msg []byte, host string) error {
-	conn, err := (&net.Dialer{Timeout: smtpConnectTimeout}).Dial("tcp", addr)
+	conn, err := dialSMTP(addr, host, smtpConnectTimeout, false)
 	if err != nil {
 		return err
 	}
diff --git a/internal/web/service/email/email_deadline_test.go b/internal/web/service/email/email_deadline_test.go
index 17d36c423..dc926f2aa 100644
--- a/internal/web/service/email/email_deadline_test.go
+++ b/internal/web/service/email/email_deadline_test.go
@@ -1,6 +1,9 @@
 package email
 
 import (
+	"bufio"
+	"bytes"
+	"errors"
 	"net"
 	"testing"
 	"time"
@@ -44,3 +47,49 @@ func TestSendPlainReturnsOnStalledServer(t *testing.T) {
 		t.Fatal("sendPlain did not return on a stalled server within the deadline")
 	}
 }
+
+// The flood is capped well above smtpMaxServerBytes: without the cap the client
+// buffers it all and then fails on the closed socket, not errSMTPReplyTooLarge.
+func TestSendPlainStopsReadingOversizedReply(t *testing.T) {
+	tests := []struct {
+		name     string
+		greeting string
+		flood    []byte
+	}{
+		{"greeting line that never ends", "220 ", bytes.Repeat([]byte("a"), 64<<10)},
+		{"EHLO reply that never ends", "220 ready\r\n", bytes.Repeat([]byte("250-X\r\n"), 8<<10)},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			ln, err := net.Listen("tcp", "127.0.0.1:0")
+			if err != nil {
+				t.Fatalf("listen: %v", err)
+			}
+			defer ln.Close()
+
+			go func() {
+				conn, err := ln.Accept()
+				if err != nil {
+					return
+				}
+				defer conn.Close()
+				_, _ = conn.Write([]byte(tt.greeting))
+				if tt.greeting[len(tt.greeting)-1] == '\n' {
+					_, _ = bufio.NewReader(conn).ReadString('\n')
+				}
+				for sent := 0; sent < 16<<20; sent += len(tt.flood) {
+					if _, err := conn.Write(tt.flood); err != nil {
+						return
+					}
+				}
+			}()
+
+			s := &EmailService{}
+			err = s.sendPlain(ln.Addr().String(), nil, "from@example.com",
+				[]string{"to@example.com"}, []byte("body"), "example.com")
+			if !errors.Is(err, errSMTPReplyTooLarge) {
+				t.Fatalf("sendPlain error = %v, want %v", err, errSMTPReplyTooLarge)
+			}
+		})
+	}
+}