git.notmuchmail.org Git - notmuch/blob - test/T355-smime.sh

   1 #!/usr/bin/env bash
   2
   3 test_description='S/MIME signature verification and decryption'
   4 . $(dirname "$0")/test-lib.sh || exit 1
   5 . $NOTMUCH_SRCDIR/test/test-lib-emacs.sh || exit 1
   6
   7 test_require_emacs
   8 test_require_external_prereq openssl
   9 test_require_external_prereq gpgsm
  10
  11 FINGERPRINT=$(openssl x509 -sha1 -fingerprint -in "$NOTMUCH_SRCDIR/test/smime/key+cert.pem" -noout | sed -e 's/^.*=//' -e s/://g)
  12
  13 add_gpgsm_home
  14
  15 test_begin_subtest "emacs delivery of S/MIME signed message"
  16 test_expect_success \
  17      'emacs_fcc_message \
  18      "test signed message 001" \
  19      "This is a test signed message." \
  20      "(mml-secure-message-sign \"smime\")"'
  21
  22 test_begin_subtest "emacs delivery of S/MIME encrypted + signed message"
  23 # Hard code the MML to avoid several interactive questions
  24 test_expect_success \
  25 'emacs_fcc_message \
  26     "test encrypted message 001" \
  27     "<#secure method=smime mode=signencrypt>\nThis is a test encrypted message.\n"'
  28
  29 test_begin_subtest "Signature verification (openssl)"
  30 notmuch show --format=raw subject:"test signed message 001" |\
  31     openssl smime -verify -CAfile $NOTMUCH_SRCDIR/test/smime/test.crt 2>OUTPUT
  32 cat <<EOF > EXPECTED
  33 Verification successful
  34 EOF
  35 test_expect_equal_file EXPECTED OUTPUT
  36
  37 test_begin_subtest "signature verification (notmuch CLI)"
  38 if [ $NOTMUCH_GMIME_EMITS_ANGLE_BRACKETS == 1 ]; then
  39    EXPECTED_EMAIL_ADDR='<test_suite@notmuchmail.org>'
  40 else
  41    EXPECTED_EMAIL_ADDR='test_suite@notmuchmail.org'
  42 fi
  43 output=$(notmuch show --format=json --verify subject:"test signed message 001" \
  44     | notmuch_json_show_sanitize \
  45     | sed -e 's|"created": [-1234567890]*|"created": 946728000|g' \
  46           -e 's|"expires": [-1234567890]*|"expires": 424242424|g' )
  47 expected='[[[{"id": "XXXXX",
  48  "match": true,
  49  "excluded": false,
  50  "filename": ["YYYYY"],
  51  "timestamp": 946728000,
  52  "date_relative": "2000-01-01",
  53  "tags": ["inbox","signed"],
  54  "crypto": {"signed": {"status": [{"fingerprint": "'$FINGERPRINT'", "status": "good","userid": "CN=Notmuch Test Suite", "email": "'$EXPECTED_EMAIL_ADDR'", "expires": 424242424, "created": 946728000}]}},
  55  "headers": {"Subject": "test signed message 001",
  56  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
  57  "To": "test_suite@notmuchmail.org",
  58  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
  59  "body": [{"id": 1,
  60  "sigstatus": [{"fingerprint": "'$FINGERPRINT'",
  61  "status": "good",
  62  "userid": "CN=Notmuch Test Suite",
  63  "email": "'$EXPECTED_EMAIL_ADDR'",
  64  "expires": 424242424,
  65  "created": 946728000}],
  66  "content-type": "multipart/signed",
  67  "content": [{"id": 2,
  68  "content-type": "text/plain",
  69  "content": "This is a test signed message.\n"},
  70  {"id": 3,
  71   "content-disposition": "attachment",
  72   "content-length": "NONZERO",
  73   "content-transfer-encoding": "base64",
  74   "content-type": "application/pkcs7-signature",
  75   "filename": "smime.p7s"}]}]},
  76  []]]]'
  77 test_expect_equal_json \
  78     "$output" \
  79     "$expected"
  80
  81 test_begin_subtest "Decryption and signature verification (openssl)"
  82 notmuch show --format=raw subject:"test encrypted message 001" |\
  83     openssl smime -decrypt -recip $NOTMUCH_SRCDIR/test/smime/key+cert.pem |\
  84     openssl smime -verify -CAfile $NOTMUCH_SRCDIR/test/smime/test.crt 2>OUTPUT
  85 cat <<EOF > EXPECTED
  86 Verification successful
  87 EOF
  88 test_expect_equal_file EXPECTED OUTPUT
  89
  90 test_begin_subtest "Decryption (notmuch CLI)"
  91 notmuch show --decrypt=true subject:"test encrypted message 001" |\
  92     grep "^This is a" > OUTPUT
  93 cat <<EOF > EXPECTED
  94 This is a test encrypted message.
  95 EOF
  96 test_expect_equal_file EXPECTED OUTPUT
  97
  98 test_begin_subtest "Cryptographic message status (encrypted+signed)"
  99 output=$(notmuch show --format=json --decrypt=true subject:"test encrypted message 001")
 100 test_json_nodes <<<"$output" \
 101                 'crypto_encrypted:[0][0][0]["crypto"]["decrypted"]["status"]="full"' \
 102                 'crypto_sigok:[0][0][0]["crypto"]["signed"]["status"][0]["status"]="good"' \
 103                 'crypto_fpr:[0][0][0]["crypto"]["signed"]["status"][0]["fingerprint"]="616F46CD73834C63847756AF0DFB64A6E0972A47"' \
 104                 'crypto_uid:[0][0][0]["crypto"]["signed"]["status"][0]["userid"]="CN=Notmuch Test Suite"'
 105
 106 test_begin_subtest "encrypted+signed message is known to be encrypted, but signature is unknown"
 107 output=$(notmuch search subject:"test encrypted message 001")
 108 test_expect_equal "$output" "thread:0000000000000002   2000-01-01 [1/1] Notmuch Test Suite; test encrypted message 001 (encrypted inbox)"
 109
 110 test_begin_subtest "Encrypted body is not indexed"
 111 output=$(notmuch search 'this is a test encrypted message')
 112 test_expect_equal "$output" ""
 113
 114 test_begin_subtest "Reindex cleartext"
 115 test_expect_success "notmuch reindex --decrypt=true subject:'test encrypted message 001'"
 116
 117 test_begin_subtest "signature is now known"
 118 output=$(notmuch search subject:"test encrypted message 001")
 119 test_expect_equal "$output" "thread:0000000000000002   2000-01-01 [1/1] Notmuch Test Suite; test encrypted message 001 (encrypted inbox signed)"
 120
 121 test_begin_subtest "Encrypted body is indexed"
 122 output=$(notmuch search 'this is a test encrypted message')
 123 test_expect_equal "$output" "thread:0000000000000002   2000-01-01 [1/1] Notmuch Test Suite; test encrypted message 001 (encrypted inbox signed)"
 124
 125 add_email_corpus pkcs7
 126
 127 test_begin_subtest "index PKCS#7 SignedData message"
 128 output=$(notmuch search --output=messages Thanks)
 129 expected=id:smime-onepart-signed@protected-headers.example
 130 test_expect_equal "$expected" "$output"
 131
 132 test_begin_subtest "do not index embedded certificates from PKCS#7 SignedData"
 133 output=$(notmuch search --output=messages 'LAMPS Certificate')
 134 expected=''
 135 test_expect_equal "$expected" "$output"
 136
 137 test_begin_subtest "know the MIME type of the embedded part in PKCS#7 SignedData"
 138 output=$(notmuch search --output=messages 'mimetype:text/plain')
 139 expected=id:smime-onepart-signed@protected-headers.example
 140 test_expect_equal "$expected" "$output"
 141
 142 test_begin_subtest "PKCS#7 SignedData message is tagged 'signed'"
 143 output=$(notmuch dump id:smime-onepart-signed@protected-headers.example)
 144 expected='#notmuch-dump batch-tag:3 config,properties,tags
 145 +inbox +signed +unread -- id:smime-onepart-signed@protected-headers.example'
 146 test_expect_equal "$expected" "$output"
 147
 148 test_begin_subtest "show contents of PKCS#7 SignedData message"
 149 output=$(notmuch show --format=raw --part=2 id:smime-onepart-signed@protected-headers.example)
 150 whitespace=' '
 151 expected="Bob, we need to cancel this contract.
 152
 153 Please start the necessary processes to make that happen today.
 154
 155 Thanks, Alice
 156 --${whitespace}
 157 Alice Lovelace
 158 President
 159 OpenPGP Example Corp"
 160 test_expect_equal "$expected" "$output"
 161
 162 test_begin_subtest "reply to PKCS#7 SignedData message with proper quoting and attribution"
 163 output=$(notmuch reply id:smime-onepart-signed@protected-headers.example)
 164 expected="From: Notmuch Test Suite <test_suite@notmuchmail.org>
 165 Subject: Re: The FooCorp contract
 166 To: Alice Lovelace <alice@smime.example>, Bob Babbage <bob@smime.example>
 167 In-Reply-To: <smime-onepart-signed@protected-headers.example>
 168 References: <smime-onepart-signed@protected-headers.example>
 169
 170 On Tue, 26 Nov 2019 20:11:29 -0400, Alice Lovelace <alice@smime.example> wrote:
 171 > Bob, we need to cancel this contract.
 172 >${whitespace}
 173 > Please start the necessary processes to make that happen today.
 174 >${whitespace}
 175 > Thanks, Alice
 176 > --${whitespace}
 177 > Alice Lovelace
 178 > President
 179 > OpenPGP Example Corp"
 180 test_expect_equal "$expected" "$output"
 181
 182 test_begin_subtest "show PKCS#7 SignedData outputs valid JSON"
 183 output=$(notmuch show --format=json id:smime-onepart-signed@protected-headers.example)
 184 test_valid_json "$output"
 185
 186 if [ -z "${NOTMUCH_TEST_INSTALLED-}" ]; then
 187 test_begin_subtest "Verify signature on PKCS#7 SignedData message"
 188 if [ "${NOTMUCH_HAVE_64BIT_TIME_T-0}" != "1" ]; then
 189     test_subtest_known_broken
 190 fi
 191 output=$(notmuch show --format=json id:smime-onepart-signed@protected-headers.example)
 192
 193 test_json_nodes <<<"$output" \
 194                 'created:[0][0][0]["crypto"]["signed"]["status"][0]["created"]=1574813489' \
 195                 'expires:[0][0][0]["crypto"]["signed"]["status"][0]["expires"]=2611032858' \
 196                 'fingerprint:[0][0][0]["crypto"]["signed"]["status"][0]["fingerprint"]="702BA4B157F1E2B7D16B0C6A5FFC8A7DE2057DEB"' \
 197                 'status:[0][0][0]["crypto"]["signed"]["status"][0]["status"]="good"'
 198 fi # NOTMUCH_TEST_INSTALLED undefined / empty
 199
 200 test_begin_subtest "Verify signature on PKCS#7 SignedData message signer User ID"
 201 if [ $NOTMUCH_GMIME_X509_CERT_VALIDITY -ne 1 ]; then
 202     test_subtest_known_broken
 203 fi
 204 test_json_nodes <<<"$output" \
 205                 'userid:[0][0][0]["crypto"]["signed"]["status"][0]["userid"]="CN=Alice Lovelace"'
 206
 207 test_done