signer: MIME headers and Message-ID signed; a long header line logged (audit M6, M8)

Security audit 2026-10-17, M6 and M8 (nits), stage 6.

M6: Content-Type, MIME-Version and Message-ID were not in h= (as in
OpenDKIM's default list): a relay could change a MIME boundary or the type
and the signature still verified. They are signed when present; Message-ID
is not over-signed, since cleanup adds one a message lacks after the
milters and an absent name in h= would refuse it.

M8: a header line over smtp_line_length_limit (998) is broken by Postfix's
smtp client after signing and the signature fails silently; only body
lines were logged. longHeaderLine names the header, once per message, in
the same words.

Tests: TestSignLinesCoverTheMIMEHeadersAndLongHeaderLinesAreNamed; the h=
expectations gain Message-ID; e2e dkim_shapes expects content-type: in h=
(and the receiver's verification over it). Docs: security.md,
architecture.md, guide; CHANGELOG.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

CHANGELOG.md

@@ -46,6 +46,9 @@ Format follows [Keep a Changelog](https://keepachangelog.com/en/1.1.0/); version
   on the image's binaries before a release is pushed; a weekly check says
   when a Debian package the mail path runs on has moved, so that a patch
   release follows.
+- **The signature covers `Content-Type`, `MIME-Version` and `Message-ID`**
+  when the message has them (audit M6), and a header line too long to be
+  delivered unbroken is named in the log as a body line is (M8).
 - **The TLS private key no longer has to be readable by Postfix** (audit
   I1): the guide gave it to group 10998 for the panel's backup, and
   `postfix` is in that group, so every Postfix daemon - an smtpd talking to

docs/architecture.md

@@ -294,8 +294,10 @@ then OpenDKIM did, in a program of its own
 - **What is signed** — `relaxed/simple`, `rsa-sha256`, with
   `github.com/emersion/go-msgauth` v0.7.0 (`dkim`). `h=`: every header of
   the message whose name is in RFC 6376 § 5.4.1's list as OpenDKIM's
-  `dkim_should_signhdrs[]` held it, and `Sender` and `List-Unsubscribe-Post`
+  `dkim_should_signhdrs[]` held it, and `Sender`, `List-Unsubscribe-Post`,
-  besides (`signHeaders`), each occurrence, in message order; then, once
+  `Content-Type`, `MIME-Version` and `Message-ID` besides (`signHeaders`;
+  `Message-ID` is not over-signed: cleanup adds one a message lacks after the
+  milters), each occurrence, in message order; then, once
   more, each of `Subject`, `Date`, `To`, `Cc`, `Reply-To` and `Sender` the
   message has (`overSign` - only those present: Postfix's cleanup adds a
   missing `Date:` after the milters, out of their sight, and a name in `h=`

docs/guide.md

@@ -1529,12 +1529,13 @@ DMARC counts that signature only when its domain aligns with the domain of
 signature as another of its domains, or as the server itself.
 
 **Lines of more than 998 bytes.** The signer signs the message as the
-application handed it over. Postfix's SMTP client breaks a body line longer
+application handed it over. Postfix's SMTP client breaks a line longer
-than 998 bytes when it delivers the message (`smtp_line_length_limit`),
+than 998 bytes, in the body or in a header, when it delivers the message (`smtp_line_length_limit`),
 after the signature was made, and the receiver's check of the signature
 then fails. Such a message is still sent; the container log names its
 domain and login (`dkim-signer: example.com (login "shop"): a body line
-longer than 998 bytes - ...`). Mail libraries keep lines short with
+longer than 998 bytes - ...`, or `a line of the Subject header is longer
+than 998 bytes - ...`). Mail libraries keep lines short with
 quoted-printable or base64; an application that writes its own body has to
 as well. A message whose header section is over 1 MiB is refused,
 `552 5.3.4`.

docs/security.md

@@ -324,8 +324,10 @@ operator can act on it.
   server's key may sign it. What cannot be signed (a login with no domain, a
   name with no key, a read error) is deferred, never sent unsigned. Port 25
   has no signer. `relaxed/simple`, rsa-sha256; `h=` names every header of
-  RFC 6376 § 5.4.1's list the message has, and `Sender` and
+  RFC 6376 § 5.4.1's list the message has, and `Sender`,
-  `List-Unsubscribe-Post`, then once more each of the shown ones present
+  `List-Unsubscribe-Post`, `Content-Type`, `MIME-Version` and `Message-ID`
+  (the last three since `2.14.4`, audit M6: unsigned, a relay could change a
+  MIME boundary and the signature still verified), then once more each of the shown ones present
   (Subject, Date, To, Cc, Reply-To, Sender) and `From` last, so one of those
   added after signing breaks the signature. Until `2.8.0` OpenDKIM signed - a
   2018 beta with three 2026 CVEs open and nobody upstream to fix them

internal/milter/sign.go

@@ -30,9 +30,14 @@ import (
 // signHeaders is the set of header names signed when present: RFC 6376
 // § 5.4.1's list, as OpenDKIM's dkim_should_signhdrs[] held it (OpenDKIM
 // 2.11.0~beta2, libopendkim/dkim.c:223-246), which SelfPost signed with until
-// 2.8.0; and two that list leaves out: Sender, which a mail program shows
+// 2.8.0; and those that list leaves out: Sender, which a mail program shows
-// beside From ("on behalf of"), and List-Unsubscribe-Post, which RFC 8058
+// beside From ("on behalf of"), List-Unsubscribe-Post, which RFC 8058 § 4
-// § 4 wants signed for a one-click unsubscribe to be honoured. Every
+// wants signed for a one-click unsubscribe to be honoured, and since 2.14.4
+// Content-Type, MIME-Version and Message-ID (security audit 2026-10-17, M6):
+// unsigned, a relay could change a MIME boundary or the type and the
+// signature still verified. Message-ID is not over-signed: cleanup adds one a
+// message lacks after the milters, and a name in h= that is absent would
+// refuse it. Every
 // occurrence is signed, in message order, and the shown ones once more
 // (signLines).
 var signHeaders = map[string]bool{
@@ -41,6 +46,7 @@ var signHeaders = map[string]bool{
 	"in-reply-to": true, "references": true,
 	"list-id": true, "list-help": true, "list-unsubscribe": true, "list-unsubscribe-post": true,
 	"list-subscribe": true, "list-post": true, "list-owner": true, "list-archive": true,
+	"content-type": true, "mime-version": true, "message-id": true,
 }
 
 // overSign are the signed headers a mail program shows: each that the message
@@ -292,6 +298,9 @@ func (s *signSession) Headers(h textproto.MIMEHeader, m *milter.Modifier) (milte
 		log.Printf("dkim-signer: %v - deferring", err)
 		return milter.RespTempFail, nil
 	}
+	if name := longHeaderLine(s.headers); name != "" {
+		log.Printf("dkim-signer: %s (login %q): a line of the %s header is longer than %d bytes - Postfix breaks it on delivery and the signature will not verify", s.domain, s.login, name, smtpLineLimit)
+	}
 	keys, block := signLines(s.headers)
 	s.headers = nil // the block is what is kept now
 	signer, err := dkim.NewSigner(&dkim.SignOptions{
@@ -362,6 +371,27 @@ func signLines(headers []field) ([]string, []byte) {
 	return append(keys, "From"), []byte(b.String())
 }
 
+// longHeaderLine names the first header with a line longer than
+// smtpLineLimit, "" when none has: Postfix's SMTP client breaks such a line
+// on the way out, after it was signed whole, as it breaks a body line
+// (security audit 2026-10-17, M8: only body lines were logged). A header's
+// first line is "Name:" and the value with its leading space; its folded
+// lines come as "\n"-separated parts of the value (Header).
+func longHeaderLine(headers []field) string {
+	for _, h := range headers {
+		lines := strings.Split(h.value, "\n")
+		if len(h.name)+1+len(lines[0]) > smtpLineLimit {
+			return h.name
+		}
+		for _, l := range lines[1:] {
+			if len(strings.TrimRight(l, "\r")) > smtpLineLimit {
+				return h.name
+			}
+		}
+	}
+	return ""
+}
+
 // BodyChunk hashes the body as it comes. Postfix 3.10.13,
 // src/milter/milter8.c:2470-2500, milter8_body(): every line ends "\r\n".
 // A line longer than smtpLineLimit is logged, once a message: its signature

internal/milter/sign_test.go

@@ -193,7 +193,7 @@ func TestSignerSignsWithTheLoginsDomain(t *testing.T) {
 	if !strings.HasPrefix(sig.HeaderValue, " ") {
 		t.Errorf("the signature's value does not bring its space: %q", sig.HeaderValue)
 	}
-	for _, want := range []string{"c=relaxed/simple;", "s=sel;", "h=From:To:Subject:Date:To:Subject:Date:From;"} {
+	for _, want := range []string{"c=relaxed/simple;", "s=sel;", "h=From:To:Subject:Date:Message-ID:To:Subject:Date:From;"} {
 		if !strings.Contains(strings.Join(strings.Fields(sig.HeaderValue), ""), want) {
 			t.Errorf("signature lacks %q: %s", want, sig.HeaderValue)
 		}
@@ -354,7 +354,7 @@ func TestSignerRefusesAHugeHeaderSection(t *testing.T) {
 // signLines writes the block Postfix will deliver and names what is signed.
 func TestSignLines(t *testing.T) {
 	keys, block := signLines(testHeaders)
-	if got := strings.Join(keys, ":"); got != "From:To:Subject:Date:To:Subject:Date:From" {
+	if got := strings.Join(keys, ":"); got != "From:To:Subject:Date:Message-ID:To:Subject:Date:From" {
 		t.Errorf("keys %s", got)
 	}
 	// Every occurrence is signed; a shown one is named once more, once.
@@ -374,3 +374,24 @@ func TestSignLines(t *testing.T) {
 		t.Errorf("block\n%q\nwant\n%q", block, want)
 	}
 }
+
+// Content-Type, MIME-Version and Message-ID are signed when present and not
+// over-signed (security audit 2026-10-17, M6); a header line past the SMTP
+// client's limit is named in the log (M8).
+func TestSignLinesCoverTheMIMEHeadersAndLongHeaderLinesAreNamed(t *testing.T) {
+	keys, _ := signLines([]field{
+		{"From", " a@example.org"}, {"MIME-Version", " 1.0"}, {"Content-Type", " text/plain"}, {"Message-ID", " <x@example.org>"},
+	})
+	if got := strings.Join(keys, ":"); got != "From:MIME-Version:Content-Type:Message-ID:From" {
+		t.Errorf("h= %s", got)
+	}
+	if got := longHeaderLine([]field{{"Subject", " " + strings.Repeat("x", 998)}}); got != "Subject" {
+		t.Errorf("a 1007-byte Subject line: %q", got)
+	}
+	if got := longHeaderLine([]field{{"To", " a@example.org,\n " + strings.Repeat("b", 999)}}); got != "To" {
+		t.Errorf("a long folded line: %q", got)
+	}
+	if got := longHeaderLine([]field{{"Subject", " short"}, {"To", " a,\n b"}}); got != "" {
+		t.Errorf("short lines named %q", got)
+	}
+}

test/e2e/dkim_shapes_test.go

@@ -59,7 +59,7 @@ func testSignatureOverAwkwardHeaders(t *testing.T, sc *scenario) {
 	// Both To: lines, the one Cc:, the Subject and List-Unsubscribe-Post are
 	// signed, the shown ones once more.
 	signedNames := strings.ToLower(dkimTagsOf(t, delivered)["h"])
-	for _, want := range []string{"to:to:", "cc:", "subject:", "list-unsubscribe-post:"} {
+	for _, want := range []string{"to:to:", "cc:", "subject:", "list-unsubscribe-post:", "content-type:"} {
 		if !strings.Contains(signedNames, want) {
 			t.Errorf("h=%s lacks %q", signedNames, want)
 		}