notmuch/test/T355-smime.sh
Daniel Kahn Gillmor 2e351d10c2 tests/smime: Use gpgsm instead of openssl for mml creation of S/MIME msgs
The documentation for message mode clearly states that EasyPG (which
uses GnuPG) is the default and recommended way to use S/MIME with
mml-secure:

[0] https://www.gnu.org/software/emacs/manual/html_node/message/Using-S_002fMIME.html

To ensure that this mode works, we just need to import the secret key
in question into gpgsm in addition to the public key.  gpgsm should be
able pick the right keys+certificates to use based on To/From headers,
so we don't have to specify anything manually in the #secure mml tag.

The import process from the OpenSSL-preferred form (cert+secretkey) is
rather ugly, because gpgsm wants to see a PKCS#12 object when
importing secret keys.

Note that EasyPG generates the more modern Content-Type:
application/pkcs7-signature instead of application/x-pkcs7-signature
for the detached signature.

We are also obliged to manually set gpgsm's include-certs setting to 1
because gpgsm defaults to send "everything but the root cert".  In our
weird test case, the certificate we're using is self-signed, so it
*is* the root cert, which means that gpgsm doesn't include it by
default.  Setting it to 1 forces inclusion of the signer's cert, which
satisfies openssl's smime subcommand. See https://dev.gnupg.org/T4878
for more details.

Signed-off-by: Daniel Kahn Gillmor <dkg@fifthhorseman.net>
2020-04-30 17:54:37 -03:00

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#!/usr/bin/env bash
test_description='S/MIME signature verification and decryption'
. $(dirname "$0")/test-lib.sh || exit 1
test_require_external_prereq openssl
test_require_external_prereq gpgsm
cp $NOTMUCH_SRCDIR/test/smime/key+cert.pem test_suite.pem
FINGERPRINT=$(openssl x509 -fingerprint -in test_suite.pem -noout | sed -e 's/^.*=//' -e s/://g)
add_gpgsm_home
test_begin_subtest "emacs delivery of S/MIME signed message"
test_expect_success \
'emacs_fcc_message \
"test signed message 001" \
"This is a test signed message." \
"(mml-secure-message-sign \"smime\")"'
test_begin_subtest "emacs delivery of S/MIME encrypted + signed message"
# Hard code the MML to avoid several interactive questions
test_expect_success \
'emacs_fcc_message \
"test encrypted message 001" \
"<#secure method=smime mode=signencrypt>\nThis is a test encrypted message.\n"'
test_begin_subtest "Signature verification (openssl)"
notmuch show --format=raw subject:"test signed message 001" |\
openssl smime -verify -CAfile $NOTMUCH_SRCDIR/test/smime/test.crt 2>OUTPUT
cat <<EOF > EXPECTED
Verification successful
EOF
test_expect_equal_file EXPECTED OUTPUT
test_begin_subtest "signature verification (notmuch CLI)"
output=$(notmuch show --format=json --verify subject:"test signed message 001" \
| notmuch_json_show_sanitize \
| sed -e 's|"created": [-1234567890]*|"created": 946728000|g' \
-e 's|"expires": [-1234567890]*|"expires": 424242424|g' )
expected='[[[{"id": "XXXXX",
"match": true,
"excluded": false,
"filename": ["YYYYY"],
"timestamp": 946728000,
"date_relative": "2000-01-01",
"tags": ["inbox","signed"],
"crypto": {"signed": {"status": [{"fingerprint": "'$FINGERPRINT'", "status": "good","userid": "CN=Notmuch Test Suite","expires": 424242424, "created": 946728000}]}},
"headers": {"Subject": "test signed message 001",
"From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
"To": "test_suite@notmuchmail.org",
"Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
"body": [{"id": 1,
"sigstatus": [{"fingerprint": "'$FINGERPRINT'",
"status": "good",
"userid": "CN=Notmuch Test Suite",
"expires": 424242424,
"created": 946728000}],
"content-type": "multipart/signed",
"content": [{"id": 2,
"content-type": "text/plain",
"content": "This is a test signed message.\n"},
{"id": 3,
"content-disposition": "attachment",
"content-length": "NONZERO",
"content-transfer-encoding": "base64",
"content-type": "application/pkcs7-signature",
"filename": "smime.p7s"}]}]},
[]]]]'
test_expect_equal_json \
"$output" \
"$expected"
test_begin_subtest "Decryption and signature verification (openssl)"
notmuch show --format=raw subject:"test encrypted message 001" |\
openssl smime -decrypt -recip test_suite.pem |\
openssl smime -verify -CAfile $NOTMUCH_SRCDIR/test/smime/test.crt 2>OUTPUT
cat <<EOF > EXPECTED
Verification successful
EOF
test_expect_equal_file EXPECTED OUTPUT
test_begin_subtest "Decryption (notmuch CLI)"
test_subtest_known_broken
notmuch show --decrypt=true subject:"test encrypted message 001" |\
grep "^This is a" > OUTPUT
cat <<EOF > EXPECTED
This is a test encrypted message.
EOF
test_expect_equal_file EXPECTED OUTPUT
test_done