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