Merge tag 'debian/0.16-1' into buster-bpo

mailscripts release 0.16-1 for unstable (sid) [dgit]

[dgit distro=debian no-split --quilt=linear]

# gpg: Signature made Thu 28 Nov 2019 11:30:44 AM MST
# gpg:                using RSA key 9B917007AE030E36E4FC248B695B7AE4BF066240
# gpg: Good signature from "Sean Whitton <spwhitton@spwhitton.name>" [ultimate]
# Primary key fingerprint: 8DC2 487E 51AB DD90 B5C4  753F 0F56 D055 3B6D 411B
#      Subkey fingerprint: 9B91 7007 AE03 0E36 E4FC  248B 695B 7AE4 BF06 6240

24 files changed, 504 insertions, 27 deletions

diff --git a/Makefile b/Makefile
index cd8f592..af30616 100644
--- a/Makefile
+++ b/Makefile
@@ -7,9 +7,13 @@ COMPLETIONS=completions/bash/email-print-mime-structure
 
 all: $(MANPAGES) $(COMPLETIONS)
 
+check:
+	./tests/email-print-mime-structure.sh
+	mypy --strict ./email-print-mime-structure
+
 clean:
 	rm -f $(MANPAGES)
-	rm -rf completions
+	rm -rf completions .mypy_cache
 
 %.1: %.1.pod
 	pod2man --section=1 --date="Debian Project" --center="User Commands" \
diff --git a/debian/changelog b/debian/changelog
index 25929cc..3d6c274 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,27 @@
+mailscripts (0.16-1) unstable; urgency=medium
+
+  email-print-mime-structure:
+  * Add a test suite (Closes: #945451).
+    - Add <!nocheck> builddeps on
+      + python3
+      + python3-pgpy
+      + gpg
+      + gpg-agent
+      + mypy.
+  * Add capability to decrypt S/MIME-encrypted messages (Closes: #945195).
+    - Add gpgsm, openssl to Build-Depends and Suggests.
+    - Add <!nocheck> build-dep on dirmngr.
+  * Add capability to handle one-part PKCS#7 signature objects.
+    - Add gnutls-bin to Build-Depends and Suggests.
+  * Fully decode encrypted parts before passing to any decryption
+    mechanism.
+    See <https://bugs.debian.org/945195#100>.
+
+    Thanks to Daniel Kahn Gillmor for two patch series implementing these
+    improvements.
+
+ -- Sean Whitton <spwhitton@spwhitton.name>  Thu, 28 Nov 2019 11:27:38 -0700
+
 mailscripts (0.15-1~bpo10+1) buster-backports; urgency=medium
 
   * Rebuild for buster-backports.
diff --git a/debian/control b/debian/control
index 72b57c3..3de5b11 100644
--- a/debian/control
+++ b/debian/control
@@ -7,8 +7,17 @@ Build-Depends:
  bash-completion,
  debhelper (>= 10),
  dh-elpa,
+ dirmngr <!nocheck>,
+ gnutls-bin <!nocheck>,
+ gpg <!nocheck>,
+ gpg-agent <!nocheck>,
+ gpgsm <!nocheck>,
+ mypy <!nocheck>,
+ openssl <!nocheck>,
  perl,
+ python3 <!nocheck>,
  python3-argcomplete,
+ python3-pgpy <!nocheck>,
 Vcs-Git: https://git.spwhitton.name/mailscripts
 Vcs-Browser: https://git.spwhitton.name/mailscripts
 
@@ -44,8 +53,11 @@ Recommends:
  python3-argcomplete,
  python3-pgpy,
 Suggests:
+ gnutls-bin,
  gpg,
  gpg-agent,
+ gpgsm,
+ openssl,
 Architecture: all
 Description: collection of scripts for manipulating e-mail on Debian
  This package provides a collection of scripts for manipulating e-mail
diff --git a/debian/elpa-test b/debian/elpa-test
new file mode 100644
index 0000000..4d6556c
--- /dev/null
+++ b/debian/elpa-test
@@ -0,0 +1 @@
+disable = true
diff --git a/email-print-mime-structure b/email-print-mime-structure
index 27fb532..b7646e0 100755
--- a/email-print-mime-structure
+++ b/email-print-mime-structure
@@ -32,6 +32,7 @@ something like "cat -n"
 '''
 import os
 import sys
+import enum
 import email
 import logging
 import subprocess
@@ -51,6 +52,8 @@ try:
 except ImportError:
     argcomplete = None
 
+EncType = enum.Enum('EncType', ['PGPMIME', 'SMIME'])
+
 class MimePrinter(object):
     def __init__(self, args:Namespace):
         self.args = args
@@ -79,32 +82,66 @@ class MimePrinter(object):
 
         print(f'{prefix}{z.get_content_type()}{cset}{disposition}{fname} {nbytes:d} bytes')
         cryptopayload:Optional[Message] = None
-        ciphertext:Union[List[Message],str,bytes,None] = None
         try_pgp_decrypt:bool = self.args.pgpkey or self.args.use_gpg_agent
+        try_cms_decrypt:bool = self.args.cmskey or self.args.use_gpg_agent
 
         if try_pgp_decrypt and \
            (parent is not None) and \
            (parent.get_content_type().lower() == 'multipart/encrypted') and \
            (str(parent.get_param('protocol')).lower() == 'application/pgp-encrypted') and \
            (num == 2):
-            ciphertext = z.get_payload()
-            if not isinstance(ciphertext, str):
-                logging.warning('encrypted part was not a leaf mime part somehow')
-                return
-            if self.args.pgpkey:
-                cryptopayload = self.pgpy_decrypt(self.args.pgpkey, ciphertext)
-            if cryptopayload is None and self.args.use_gpg_agent:
-                cryptopayload = self.gpg_decrypt(ciphertext)
-            if cryptopayload is None:
-                logging.warning(f'Unable to decrypt')
-                return
+            cryptopayload = self.decrypt_part(z, EncType.PGPMIME)
+
+        if try_cms_decrypt and \
+           cryptopayload is None and \
+           z.get_content_type().lower() == 'application/pkcs7-mime' and \
+           str(z.get_param('smime-type')).lower() in ['authenveloped-data',
+                                                      'enveloped-data']:
+            cryptopayload = self.decrypt_part(z, EncType.SMIME)
 
         if cryptopayload is not None:
             newprefix = prefix[:-3] + ' '
             print(f'{newprefix}↧ (decrypts to)')
             self.print_tree(cryptopayload, newprefix + '└', z, 0)
-
-    def pgpy_decrypt(self, keys:List[str], ciphertext:str) -> Optional[Message]:
+        else:
+            if z.get_content_type().lower() == 'application/pkcs7-mime' and \
+               str(z.get_param('smime-type')).lower() == 'signed-data':
+                bodypart:Union[List[Message],str,bytes,None] = z.get_payload(decode=True)
+                if isinstance(bodypart, bytes):
+                    unwrapped = self.pipe_transform(bodypart, ['certtool', '--p7-show-data', '--p7-info', '--inder'])
+                    if unwrapped:
+                        newprefix = prefix[:-3] + ' '
+                        print(f'{newprefix}⇩ (unwraps to)')
+                        self.print_tree(unwrapped, newprefix + '└', z, 0)
+                    else:
+                        logging.warning(f'Unable to unwrap one-part PKCS#7 signed message (maybe try "apt install gnutls-bin")')
+
+
+    def decrypt_part(self, msg:Message, flavor:EncType) -> Optional[Message]:
+        ciphertext:Union[List[Message],str,bytes,None] = msg.get_payload(decode=True)
+        cryptopayload:Optional[Message] = None
+        if not isinstance(ciphertext, bytes):
+            logging.warning('encrypted part was not a leaf mime part somehow')
+            return None
+        if flavor == EncType.PGPMIME:
+            if self.args.pgpkey:
+                cryptopayload = self.pgpy_decrypt(self.args.pgpkey, ciphertext)
+            if cryptopayload is None and self.args.use_gpg_agent:
+                cryptopayload = self.pipe_transform(ciphertext, ['gpg', '--batch', '--decrypt'])
+        elif flavor == EncType.SMIME:
+            if self.args.cmskey:
+                for keyname in self.args.cmskey:
+                    cmd = ['openssl', 'smime', '-decrypt', '-inform', 'DER', '-inkey', keyname]
+                    cryptopayload = self.pipe_transform(ciphertext, cmd)
+                    if cryptopayload:
+                        return cryptopayload
+            if self.args.use_gpg_agent:
+                cryptopayload = self.pipe_transform(ciphertext, ['gpgsm', '--batch', '--decrypt'])
+        if cryptopayload is None:
+            logging.warning(f'Unable to decrypt')
+        return cryptopayload
+
+    def pgpy_decrypt(self, keys:List[str], ciphertext:bytes) -> Optional[Message]:
         if pgpy is None:
             logging.warning(f'Python module pgpy is not available, not decrypting (try "apt install python3-pgpy")')
             return None
@@ -121,13 +158,13 @@ class MimePrinter(object):
                 pass
         return None
 
-    def gpg_decrypt(self, ciphertext:str) -> Optional[Message]:
+    def pipe_transform(self, ciphertext:bytes, cmd:List[str]) -> Optional[Message]:
         inp:int
         outp:int
         inp, outp = os.pipe()
-        with open(outp, 'w') as outf:
+        with open(outp, 'wb') as outf:
             outf.write(ciphertext)
-        out:subprocess.CompletedProcess[bytes] = subprocess.run(['gpg', '--batch', '--decrypt'],
+        out:subprocess.CompletedProcess[bytes] = subprocess.run(cmd,
                                                                 stdin=inp,
                                                                 capture_output=True)
         if out.returncode == 0:
@@ -157,7 +194,9 @@ def main() -> None:
     parser:ArgumentParser = ArgumentParser(description='Read RFC2822 MIME message from stdin and emit a tree diagram to stdout.',
                                            epilog="Example: email-print-mime-structure <message.eml")
     parser.add_argument('--pgpkey', metavar='KEYFILE', action='append',
-                        help='OpenPGP Transferable Secret Key for decrypting')
+                        help='OpenPGP Transferable Secret Key for decrypting PGP/MIME')
+    parser.add_argument('--cmskey', metavar='KEYFILE', action='append',
+                        help='X.509 Private Key for decrypting S/MIME')
     parser.add_argument('--use-gpg-agent', action='store_true',
                         help='Ask local GnuPG installation for decryption')
     parser.add_argument('--no-use-gpg-agent', action='store_false',
diff --git a/email-print-mime-structure.1.pod b/email-print-mime-structure.1.pod
index d8545ad..037c1a9 100644
--- a/email-print-mime-structure.1.pod
+++ b/email-print-mime-structure.1.pod
@@ -32,15 +32,26 @@ key.
 OpenPGP secret keys listed in B<--pgpkey=> are used ephemerally, and
 do not interact with any local GnuPG keyring.
 
+=item B<--cmskey=>I<KEYFILE>
+
+I<KEYFILE> should name a PEM- or DER-encoded X.509 private key that is
+not password-protected.  If an S/MIME-encrypted message that uses CMS
+is found on standard input, this key will be tried for decryption.
+May be used multiple times if you want to try decrypting with more
+than one such key.
+
+X.509 private keys listed in B<--cmskey=> are used ephemerally, and do
+not interact with any local GnuPG keyring.
+
 =item B<--use-gpg-agent>
 
 If this flag is present, and B<email-print-mime-structure> encounters
-a PGP/MIME-encrypted part, it will try to decrypt the part using the
-secret keys found in the local installation of GnuPG.
+a PGP/MIME- or S/MIME-encrypted part, it will try to decrypt the part
+using the secret keys found in the local installation of GnuPG.
 
-If both B<--pgpkey=>I<KEYFILE> and B<--use-gpg-agent> are
-supplied, I<KEYFILE> arguments will be tried before falling back to
-GnuPG.
+If B<--use-gpg-agent> is supplied along with either
+B<--pgpkey=>I<KEYFILE> or B<--cmskey=>I<KEYFILE> arguments, the
+I<KEYFILE> arguments will be tried before falling back to GnuPG.
 
 If B<email-print-mime-structure> has been asked to decrypt parts with
 either B<--pgpkey=>I<KEYFILE> or with B<--use-gpg-agent>, and it
@@ -49,8 +60,8 @@ stderr.
 
 =item B<--no-use-gpg-agent>
 
-Don't try to decrypt PGP/MIME-encrypted parts using secret keys found
-in the local installation of GnuPG.  This is the default.
+Don't try to decrypt PGP/MIME- or S/MIME-encrypted parts using secret
+keys found in the local installation of GnuPG.  This is the default.
 
 =item B<--help>, B<-h>
 
diff --git a/mailscripts.el b/mailscripts.el
index 9c51f73..6872dd6 100644
--- a/mailscripts.el
+++ b/mailscripts.el
@@ -1,7 +1,7 @@
 ;;; mailscripts.el --- functions to access tools in the mailscripts package
 
 ;; Author: Sean Whitton <spwhitton@spwhitton.name>
-;; Version: 0.15
+;; Version: 0.16
 ;; Package-Requires: (notmuch projectile)
 
 ;; Copyright (C) 2018, 2019 Sean Whitton
diff --git a/tests/email-print-mime-structure.sh b/tests/email-print-mime-structure.sh
new file mode 100755
index 0000000..b45294e
--- /dev/null
+++ b/tests/email-print-mime-structure.sh
@@ -0,0 +1,40 @@
+#!/bin/bash
+
+set -e
+
+test_eml() {
+    message="$1"
+    shift
+    diff -u "$message.out" <(./email-print-mime-structure "$@" <"$message.eml")
+}
+
+for eml in tests/email-print-mime-structure/*.eml; do
+    base="${eml%%.eml}"
+    pgpkey="$base.pgpkey"
+    p12key="$base.p12"
+    if [ -e "$pgpkey" ]; then
+        printf "Testing %s (PGPy)\n" "${eml##*/}"
+        test_eml "$base" --pgpkey "$pgpkey"
+
+        testgpghome=$(mktemp -d)
+        printf "Testing %s (GnuPG PGP/MIME)\n" "${eml##*/}"
+        gpg --homedir="$testgpghome" --batch --quiet --import <"$pgpkey"
+        GNUPGHOME="$testgpghome" test_eml "$base" --use-gpg-agent
+        rm -rf "$testgpghome"
+    elif [ -e "$p12key" ]; then
+        printf "Testing %s (OpenSSL)\n" "${eml##*/}"
+        grep -v ^- < "$p12key" | base64 -d | \
+            openssl pkcs12 -nocerts -nodes -passin pass: -passout pass: -out "$base.pemkey"
+        test_eml "$base" --cmskey "$base.pemkey"
+        rm -f "$base.pemkey"
+
+        testgpghome=$(mktemp -d)
+        printf "Testing %s (GnuPG S/MIME)\n" "${eml##*/}"
+        gpgsm --pinentry-mode=loopback --passphrase-fd 4 4<<<'' --homedir="$testgpghome" --batch --quiet --import <"$p12key"
+        GNUPGHOME="$testgpghome" test_eml "$base" --use-gpg-agent
+        rm -rf "$testgpghome"
+    else
+        printf "Testing %s\n" "${eml##*/}"
+        test_eml "$base"
+    fi
+done
diff --git a/tests/email-print-mime-structure/alternative.eml b/tests/email-print-mime-structure/alternative.eml
new file mode 100644
index 0000000..9b7723d
--- /dev/null
+++ b/tests/email-print-mime-structure/alternative.eml
@@ -0,0 +1,18 @@
+Date: Sun, 24 Nov 2019 21:13:45 -0500

+Subject: test message

+Message-ID: <alternative@mailscripts.example>

+From: Alice <alice@mailscripts.example>

+To: Bob <bob@mailscripts.example>

+Content-Type: multipart/alternative; boundary="abc123"

+

+--abc123

+Content-Type: text/plain

+

+This is a simple message

+

+--abc123

+Content-Type: text/html

+

+<html><head></head><body><p>This is a simple message</p></body></html>

+

+--abc123--

diff --git a/tests/email-print-mime-structure/alternative.out b/tests/email-print-mime-structure/alternative.out
new file mode 100644
index 0000000..1c0165a
--- /dev/null
+++ b/tests/email-print-mime-structure/alternative.out
@@ -0,0 +1,3 @@
+└┬╴multipart/alternative 414 bytes
+ ├─╴text/plain 26 bytes
+ └─╴text/html 72 bytes
diff --git a/tests/email-print-mime-structure/attachment.eml b/tests/email-print-mime-structure/attachment.eml
new file mode 100644
index 0000000..31baa7c
--- /dev/null
+++ b/tests/email-print-mime-structure/attachment.eml
@@ -0,0 +1,26 @@
+Date: Sun, 24 Nov 2019 21:13:45 -0500

+Subject: test message

+Message-ID: <attachment@mailscripts.example>

+From: Alice <alice@mailscripts.example>

+To: Bob <bob@mailscripts.example>

+Content-Type: multipart/mixed; boundary="xyz"

+

+--xyz

+Content-Type: multipart/alternative; boundary="abc123"

+

+--abc123

+Content-Type: text/plain

+

+This is a simple message

+

+--abc123

+Content-Type: text/html

+

+<html><head></head><body><p>This is a simple message</p></body></html>

+

+--abc123--

+--xyz

+Content-Type: text/plain

+Content-Disposition: attachment; filename="test.txt"

+

+This is a simple attachment file.

diff --git a/tests/email-print-mime-structure/attachment.out b/tests/email-print-mime-structure/attachment.out
new file mode 100644
index 0000000..f2ca543
--- /dev/null
+++ b/tests/email-print-mime-structure/attachment.out
@@ -0,0 +1,5 @@
+└┬╴multipart/mixed 594 bytes
+ ├┬╴multipart/alternative 234 bytes
+ │├─╴text/plain 26 bytes
+ │└─╴text/html 72 bytes
+ └─╴text/plain attachment [test.txt] 33 bytes
diff --git a/tests/email-print-mime-structure/bob.key b/tests/email-print-mime-structure/bob.key
new file mode 100644
index 0000000..59e981b
--- /dev/null
+++ b/tests/email-print-mime-structure/bob.key
@@ -0,0 +1,82 @@
+-----BEGIN PGP PRIVATE KEY BLOCK-----
+Comment: Bob's OpenPGP Transferable Secret Key
+
+lQVYBF2lnPIBDAC5cL9PQoQLTMuhjbYvb4Ncuuo0bfmgPRFywX53jPhoFf4Zg6mv
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diff --git a/tests/email-print-mime-structure/bob.p12 b/tests/email-print-mime-structure/bob.p12
new file mode 100644
index 0000000..9fab0f7
--- /dev/null
+++ b/tests/email-print-mime-structure/bob.p12
@@ -0,0 +1,75 @@
+-----BEGIN PKCS12-----
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diff --git a/tests/email-print-mime-structure/encrypted.eml b/tests/email-print-mime-structure/encrypted.eml
new file mode 100644
index 0000000..5a28719
--- /dev/null
+++ b/tests/email-print-mime-structure/encrypted.eml
@@ -0,0 +1,37 @@
+Date: Sun, 24 Nov 2019 21:13:45 -0500
+Subject: test message
+Message-ID: <pgpmime-encrypted@mailscripts.example>
+From: Alice <alice@mailscripts.example>
+To: Bob <bob@mailscripts.example>
+Content-Type: multipart/encrypted; boundary="eeee";
+ protocol="application/pgp-encrypted"
+
+--eeee
+content-type: application/pgp-encrypted
+
+Version: 1
+
+--eeee
+content-type: application/octet-stream
+
+-----BEGIN PGP MESSAGE-----
+
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+-----END PGP MESSAGE-----
+
+--eeee--
+
diff --git a/tests/email-print-mime-structure/encrypted.out b/tests/email-print-mime-structure/encrypted.out
new file mode 100644
index 0000000..a2db072
--- /dev/null
+++ b/tests/email-print-mime-structure/encrypted.out
@@ -0,0 +1,9 @@
+└┬╴multipart/encrypted 1366 bytes
+ ├─╴application/pgp-encrypted 11 bytes
+ └─╴application/octet-stream 971 bytes
+  ↧ (decrypts to)
+  └┬╴multipart/mixed 415 bytes
+   ├┬╴multipart/alternative 234 bytes
+   │├─╴text/plain 26 bytes
+   │└─╴text/html 72 bytes
+   └─╴text/plain attachment [test.txt] 33 bytes
diff --git a/tests/email-print-mime-structure/encrypted.pgpkey b/tests/email-print-mime-structure/encrypted.pgpkey
new file mode 120000
index 0000000..9ba5070
--- /dev/null
+++ b/tests/email-print-mime-structure/encrypted.pgpkey
@@ -0,0 +1 @@
+bob.key
\ No newline at end of file
diff --git a/tests/email-print-mime-structure/simple.eml b/tests/email-print-mime-structure/simple.eml
new file mode 100644
index 0000000..36facec
--- /dev/null
+++ b/tests/email-print-mime-structure/simple.eml
@@ -0,0 +1,9 @@
+Date: Sun, 24 Nov 2019 21:13:45 -0500

+Subject: test message

+Message-ID: <simple@mailscripts.example>

+From: Alice <alice@mailscripts.example>

+To: Bob <bob@mailscripts.example>

+

+This is a simple message

+

+

diff --git a/tests/email-print-mime-structure/simple.out b/tests/email-print-mime-structure/simple.out
new file mode 100644
index 0000000..7ac3514
--- /dev/null
+++ b/tests/email-print-mime-structure/simple.out
@@ -0,0 +1 @@
+└─╴text/plain 30 bytes
diff --git a/tests/email-print-mime-structure/smime-encrypted.eml b/tests/email-print-mime-structure/smime-encrypted.eml
new file mode 100644
index 0000000..d24bcb3
--- /dev/null
+++ b/tests/email-print-mime-structure/smime-encrypted.eml
@@ -0,0 +1,24 @@
+Date: Sun, 24 Nov 2019 21:13:45 -0500

+Subject: test message

+Message-ID: <smime-encrypted@mailscripts.example>

+From: Alice <alice@mailscripts.example>

+To: Bob <bob@mailscripts.example>

+Content-Type: application/pkcs7-mime; smime-type="enveloped-data"

+Content-Transfer-Encoding: base64

+

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diff --git a/tests/email-print-mime-structure/smime-encrypted.out b/tests/email-print-mime-structure/smime-encrypted.out
new file mode 100644
index 0000000..071be70
--- /dev/null
+++ b/tests/email-print-mime-structure/smime-encrypted.out
@@ -0,0 +1,7 @@
+└─╴application/pkcs7-mime 1196 bytes
+ ↧ (decrypts to)
+ └┬╴multipart/mixed 415 bytes
+  ├┬╴multipart/alternative 234 bytes
+  │├─╴text/plain 26 bytes
+  │└─╴text/html 72 bytes
+  └─╴text/plain attachment [test.txt] 33 bytes
diff --git a/tests/email-print-mime-structure/smime-encrypted.p12 b/tests/email-print-mime-structure/smime-encrypted.p12
new file mode 120000
index 0000000..ecb0ede
--- /dev/null
+++ b/tests/email-print-mime-structure/smime-encrypted.p12
@@ -0,0 +1 @@
+bob.p12
\ No newline at end of file
diff --git a/tests/email-print-mime-structure/smime-signed.eml b/tests/email-print-mime-structure/smime-signed.eml
new file mode 100644
index 0000000..3929d6b
--- /dev/null
+++ b/tests/email-print-mime-structure/smime-signed.eml
@@ -0,0 +1,41 @@
+Date: Sun, 24 Nov 2019 21:13:45 -0500

+Subject: test message

+Message-ID: <smime-signed@mailscripts.example>

+From: Alice <alice@mailscripts.example>

+To: Bob <bob@mailscripts.example>

+Content-Type: application/pkcs7-mime; smime-type="signed-data"

+Content-Transfer-Encoding: base64

+

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diff --git a/tests/email-print-mime-structure/smime-signed.out b/tests/email-print-mime-structure/smime-signed.out
new file mode 100644
index 0000000..293a271
--- /dev/null
+++ b/tests/email-print-mime-structure/smime-signed.out
@@ -0,0 +1,7 @@
+└─╴application/pkcs7-mime 2538 bytes
+ ⇩ (unwraps to)
+ └┬╴multipart/mixed 415 bytes
+  ├┬╴multipart/alternative 234 bytes
+  │├─╴text/plain 26 bytes
+  │└─╴text/html 72 bytes
+  └─╴text/plain attachment [test.txt] 33 bytes