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