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notmuch/test/T350-crypto.sh
Daniel Kahn Gillmor 4cb789aa09 cli/show: emit new whole-message crypto status output 
This allows MUAs that don't want to think about per-mime-part
cryptographic status to have a simple high-level overview of the
message's cryptographic state.

Sensibly structured encrypted and/or signed messages will work fine
with this.  The only requirement for the simplest encryption + signing
is that the message have all of its encryption and signing protection
(the "cryptographic envelope") in a contiguous set of MIME layers at
the very outside of the message itself.

This is because messages with some subparts signed or encrypted, but
with other subparts with no cryptographic protection is very difficult
to reason about, and even harder for the user to make sense of or work
with.

For further characterization of the Cryptographic Envelope and some of
the usability tradeoffs, see here:

   https://dkg.fifthhorseman.net/blog/e-mail-cryptography.html#cryptographic-envelope
2019-05-26 08:20:23 -03:00

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#!/usr/bin/env bash
# TODO:
# - decryption/verification with signer key not available
# - verification of signatures from expired/revoked keys
test_description='PGP/MIME signature verification and decryption'
. $(dirname "$0")/test-lib.sh || exit 1
##################################################
add_gnupg_home
test_begin_subtest "emacs delivery of signed message"
test_expect_success \
'emacs_fcc_message \
"test signed message 001" \
"This is a test signed message." \
"(mml-secure-message-sign)"'
test_begin_subtest "signed part content-type indexing"
output=$(notmuch search mimetype:multipart/signed and mimetype:application/pgp-signature | notmuch_search_sanitize)
test_expect_equal "$output" "thread:XXX 2000-01-01 [1/1] Notmuch Test Suite; test signed message 001 (inbox signed)"
test_begin_subtest "signature verification"
output=$(notmuch show --format=json --verify subject:"test signed message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|g')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"crypto": {"signed": {"status": [{ "status": "good", "created": 946728000, "fingerprint": "'$FINGERPRINT'", "userid": "'"$SELF_USERID"'"}]}},
"headers": {"Subject": "test signed message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [{"status": "good",
"fingerprint": "'$FINGERPRINT'",
"created": 946728000,
"userid": "'"$SELF_USERID"'"}],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "This is a test signed message.\n"},
{"id": 3,
"content-type": "application/pgp-signature",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "detection of modified signed contents"
emacs_fcc_message \
"bad signed message 001" \
"Incriminating stuff. This is a test signed message." \
"(mml-secure-message-sign)"
file=$(notmuch search --output=files subject:"bad signed message 001")
sed -i 's/Incriminating stuff. //' ${file}
output=$(notmuch show --format=json --verify subject:"bad signed message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"crypto": {"signed": {"status": [{ "status": "bad", "keyid": "'$(echo $FINGERPRINT | cut -c 25-)'"}]}},
"headers": {"Subject": "bad signed message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [{"status": "bad",
"keyid": "'$(echo $FINGERPRINT | cut -c 25-)'"}],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "This is a test signed message.\n"},
{"id": 3,
"content-type": "application/pgp-signature",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "corrupted pgp/mime signature"
emacs_fcc_message \
"bad signed message 002" \
"Incriminating stuff. This is a test signed message." \
"(mml-secure-message-sign)"
file=$(notmuch search --output=files subject:"bad signed message 002")
awk '/-----BEGIN PGP SIGNATURE-----/{flag=1;print;next} \
/-----END PGP SIGNATURE-----/{flag=0;print;next} \
flag{gsub(/[A-Za-z]/,"0");print}!flag{print}' $file > $file.new
rm $file
mv $file.new $file
output=$(notmuch show --format=json --verify subject:"bad signed message 002" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected='[[[{"id": "XXXXX",
"crypto": {},
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"headers": {"Subject": "bad signed message 002",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "Incriminating stuff. This is a test signed message.\n"},
{"id": 3,
"content-type": "application/pgp-signature",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "signature verification without full user ID validity"
# give the key no owner trust, removes validity on all user IDs of the
# certificate in the absence of other trusted certifiers:
gpg --quiet --batch --no-tty --export-ownertrust > "$GNUPGHOME/ownertrust.bak"
echo "${FINGERPRINT}:3:" | gpg --quiet --batch --no-tty --import-ownertrust
output=$(notmuch show --format=json --verify subject:"test signed message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|g')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"crypto": {"signed": {"status": [{ "status": "good", "created": 946728000, "fingerprint": "'$FINGERPRINT'"}]}},
"headers": {"Subject": "test signed message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [{"status": "good",
"fingerprint": "'$FINGERPRINT'",
"created": 946728000}],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "This is a test signed message.\n"},
{"id": 3,
"content-type": "application/pgp-signature",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
gpg --quiet --batch --no-tty --import-ownertrust < "$GNUPGHOME/ownertrust.bak"
test_begin_subtest "signature verification with signer key unavailable"
# move the gnupghome temporarily out of the way
mv "${GNUPGHOME}"{,.bak}
output=$(notmuch show --format=json --verify subject:"test signed message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|g')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"crypto": {"signed": {"status": [{"errors": {"key-missing": true}, "keyid": "'$(echo $FINGERPRINT | cut -c 25-)'", "status": "error"}]}},
"headers": {"Subject": "test signed message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [{"status": "error",
"keyid": "'$(echo $FINGERPRINT | cut -c 25-)'",
"errors": {"key-missing": true}}],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "This is a test signed message.\n"},
{"id": 3,
"content-type": "application/pgp-signature",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
mv "${GNUPGHOME}"{.bak,}
test_begin_subtest "emacs delivery of encrypted message with attachment"
# create a test encrypted message with attachment
cat <<EOF >TESTATTACHMENT
This is a test file.
EOF
test_expect_success \
'emacs_fcc_message \
"test encrypted message 001" \
"This is a test encrypted message.\n" \
"(mml-attach-file \"TESTATTACHMENT\") (mml-secure-message-encrypt)"'
test_begin_subtest "encrypted part content-type indexing"
output=$(notmuch search mimetype:multipart/encrypted and mimetype:application/pgp-encrypted and mimetype:application/octet-stream | notmuch_search_sanitize)
test_expect_equal "$output" "thread:XXX 2000-01-01 [1/1] Notmuch Test Suite; test encrypted message 001 (encrypted inbox)"
test_begin_subtest "decryption, --format=text"
output=$(notmuch show --format=text --decrypt=true subject:"test encrypted message 001" \
| notmuch_show_sanitize_all \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected=' message{ id:XXXXX depth:0 match:1 excluded:0 filename:XXXXX
header{
Notmuch Test Suite <test_suite@notmuchmail.org> (2000-01-01) (encrypted inbox)
Subject: test encrypted message 001
From: Notmuch Test Suite <test_suite@notmuchmail.org>
To: test_suite@notmuchmail.org
Date: Sat, 01 Jan 2000 12:00:00 +0000
header}
body{
part{ ID: 1, Content-type: multipart/encrypted
part{ ID: 2, Content-type: application/pgp-encrypted
Non-text part: application/pgp-encrypted
part}
part{ ID: 3, Content-type: multipart/mixed
part{ ID: 4, Content-type: text/plain
This is a test encrypted message.
part}
attachment{ ID: 5, Filename: TESTATTACHMENT, Content-type: application/octet-stream
Non-text part: application/octet-stream
attachment}
part}
part}
body}
message}'
test_expect_equal \
"$output" \
"$expected"
test_begin_subtest "decryption, --format=json"
output=$(notmuch show --format=json --decrypt=true subject:"test encrypted message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["encrypted","inbox"],
"crypto": {"decrypted": {"status": "full"}},
"headers": {"Subject": "test encrypted message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"encstatus": [{"status": "good"}],
"content-type": "multipart/encrypted",
"content": [{"id": 2,
"content-type": "application/pgp-encrypted",
"content-length": "NONZERO"},
{"id": 3,
"content-type": "multipart/mixed",
"content": [{"id": 4,
"content-type": "text/plain",
"content": "This is a test encrypted message.\n"},
{"id": 5,
"content-type": "application/octet-stream",
"content-disposition": "attachment",
"content-length": "NONZERO",
"content-transfer-encoding": "base64",
"filename": "TESTATTACHMENT"}]}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "decryption, --format=json, --part=4"
output=$(notmuch show --format=json --part=4 --decrypt=true subject:"test encrypted message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected='{"id": 4,
"content-type": "text/plain",
"content": "This is a test encrypted message.\n"}'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "decrypt attachment (--part=5 --format=raw)"
notmuch show \
--format=raw \
--part=5 \
--decrypt=true \
subject:"test encrypted message 001" >OUTPUT
test_expect_equal_file TESTATTACHMENT OUTPUT
test_begin_subtest "decryption failure with missing key"
mv "${GNUPGHOME}"{,.bak}
output=$(notmuch show --format=json --decrypt=true subject:"test encrypted message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected='[[[{"id": "XXXXX",
"crypto": {},
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["encrypted","inbox"],
"headers": {"Subject": "test encrypted message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"encstatus": [{"status": "bad"}],
"content-type": "multipart/encrypted",
"content": [{"id": 2,
"content-type": "application/pgp-encrypted",
"content-length": "NONZERO"},
{"id": 3,
"content-type": "application/octet-stream",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
mv "${GNUPGHOME}"{.bak,}
test_begin_subtest "emacs delivery of encrypted + signed message"
test_expect_success \
'emacs_fcc_message \
"test encrypted message 002" \
"This is another test encrypted message.\n" \
"(mml-secure-message-sign-encrypt)"'
test_begin_subtest "decryption + signature verification"
output=$(notmuch show --format=json --decrypt=true subject:"test encrypted message 002" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|g')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["encrypted","inbox"],
"crypto": {"signed": {"status": [{ "status": "good", "created": 946728000, "fingerprint": "'$FINGERPRINT'", "userid": "'"$SELF_USERID"'"}],
"encrypted": true },
"decrypted": {"status": "full"}},
"headers": {"Subject": "test encrypted message 002",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"encstatus": [{"status": "good"}],
"sigstatus": [{"status": "good",
"fingerprint": "'$FINGERPRINT'",
"created": 946728000,
"userid": "'"$SELF_USERID"'"}],
"content-type": "multipart/encrypted",
"content": [{"id": 2,
"content-type": "application/pgp-encrypted",
"content-length": "NONZERO"},
{"id": 3,
"content-type": "text/plain",
"content": "This is another test encrypted message.\n"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "reply to encrypted message"
output=$(notmuch reply --decrypt=true subject:"test encrypted message 002" \
| notmuch_drop_mail_headers In-Reply-To References)
expected='From: Notmuch Test Suite <test_suite@notmuchmail.org>
Subject: Re: test encrypted message 002
To: test_suite@notmuchmail.org
On 01 Jan 2000 12:00:00 -0000, Notmuch Test Suite <test_suite@notmuchmail.org> wrote:
> This is another test encrypted message.'
test_expect_equal \
"$output" \
"$expected"
test_begin_subtest "Reply within emacs to an encrypted message"
test_emacs "(let ((message-hidden-headers '())
(notmuch-crypto-process-mime 't))
(notmuch-show \"subject:test.encrypted.message.002\")
(notmuch-show-reply)
(test-output))"
grep -v -e '^In-Reply-To:' -e '^References:' -e '^Fcc:' < OUTPUT > OUTPUT.clean
cat <<EOF >EXPECTED
From: Notmuch Test Suite <test_suite@notmuchmail.org>
To: test_suite@notmuchmail.org
Subject: Re: test encrypted message 002
--text follows this line--
<#secure method=pgpmime mode=signencrypt>
Notmuch Test Suite <test_suite@notmuchmail.org> writes:
> This is another test encrypted message.
EOF
test_expect_equal_file EXPECTED OUTPUT.clean
test_begin_subtest "signature verification with revoked key"
# generate revocation certificate and load it to revoke key
echo "y
1
Notmuch Test Suite key revocation (automated) $(date '+%F_%T%z')
y
" \
| gpg --no-tty --quiet --command-fd 0 --armor --gen-revoke "0x${FINGERPRINT}!" 2>/dev/null \
| gpg --no-tty --quiet --import
output=$(notmuch show --format=json --verify subject:"test signed message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [1234567890]*|"created": 946728000|')
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"crypto": {"signed": {"status": [{"errors": {"key-revoked": true}, "keyid": "'$(echo $FINGERPRINT | cut -c 25-)'", "status": "error"}]}},
"headers": {"Subject": "test signed message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [{"status": "error",
"keyid": "6D92612D94E46381",
"errors": {"key-revoked": true}}],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "This is a test signed message.\n"},
{"id": 3,
"content-type": "application/pgp-signature",
"content-length": "NONZERO"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_done
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