git.notmuchmail.org Git - notmuch/blob - test/T350-crypto.sh

   1 #!/usr/bin/env bash
   2
   3 # TODO:
   4 # - decryption/verification with signer key not available
   5 # - verification of signatures from expired/revoked keys
   6
   7 test_description='PGP/MIME signature verification and decryption'
   8 . ./test-lib.sh || exit 1
   9
  10 add_gnupg_home ()
  11 {
  12     local output
  13     [ -d ${GNUPGHOME} ] && return
  14     _gnupg_exit () { gpgconf --kill all 2>/dev/null || true; }
  15     at_exit_function _gnupg_exit
  16     mkdir -m 0700 "$GNUPGHOME"
  17     gpg --no-tty --import <$TEST_DIRECTORY/gnupg-secret-key.asc >"$GNUPGHOME"/import.log 2>&1
  18     test_debug "cat $GNUPGHOME/import.log"
  19     if (gpg --quick-random --version >/dev/null 2>&1) ; then
  20         echo quick-random >> "$GNUPGHOME"/gpg.conf
  21     elif (gpg --debug-quick-random --version >/dev/null 2>&1) ; then
  22         echo debug-quick-random >> "$GNUPGHOME"/gpg.conf
  23     fi
  24     echo no-emit-version >> "$GNUPGHOME"/gpg.conf
  25 }
  26
  27 ##################################################
  28
  29 add_gnupg_home
  30 # Change this if we ship a new test key
  31 FINGERPRINT="5AEAB11F5E33DCE875DDB75B6D92612D94E46381"
  32
  33 test_begin_subtest "emacs delivery of signed message"
  34 test_expect_success \
  35 'emacs_fcc_message \
  36     "test signed message 001" \
  37     "This is a test signed message." \
  38     "(mml-secure-message-sign)"'
  39
  40 test_begin_subtest "signed part content-type indexing"
  41 test_subtest_known_broken
  42 output=$(notmuch search mimetype:multipart/signed and mimetype:application/pgp-signature | notmuch_search_sanitize)
  43 test_expect_equal "$output" "thread:XXX   2000-01-01 [1/1] Notmuch Test Suite; test signed message 001 (inbox signed)"
  44
  45 test_begin_subtest "signature verification"
  46 output=$(notmuch show --format=json --verify subject:"test signed message 001" \
  47     | notmuch_json_show_sanitize \
  48     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
  49 expected='[[[{"id": "XXXXX",
  50  "match": true,
  51  "excluded": false,
  52  "filename": ["YYYYY"],
  53  "timestamp": 946728000,
  54  "date_relative": "2000-01-01",
  55  "tags": ["inbox","signed"],
  56  "headers": {"Subject": "test signed message 001",
  57  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
  58  "To": "test_suite@notmuchmail.org",
  59  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
  60  "body": [{"id": 1,
  61  "sigstatus": [{"status": "good",
  62  "fingerprint": "'$FINGERPRINT'",
  63  "created": 946728000}],
  64  "content-type": "multipart/signed",
  65  "content": [{"id": 2,
  66  "content-type": "text/plain",
  67  "content": "This is a test signed message.\n"},
  68  {"id": 3,
  69  "content-type": "application/pgp-signature",
  70  "content-length": "NONZERO"}]}]},
  71  []]]]'
  72 test_expect_equal_json \
  73     "$output" \
  74     "$expected"
  75
  76 test_begin_subtest "detection of modified signed contents"
  77 emacs_fcc_message \
  78     "bad signed message 001" \
  79     "Incriminating stuff. This is a test signed message." \
  80     "(mml-secure-message-sign)"
  81
  82 file=$(notmuch search --output=files subject:"bad signed message 001")
  83
  84 sed -i 's/Incriminating stuff. //' ${file}
  85
  86 output=$(notmuch show --format=json --verify subject:"bad signed message 001" \
  87     | notmuch_json_show_sanitize \
  88     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
  89 expected='[[[{"id": "XXXXX",
  90  "match": true,
  91  "excluded": false,
  92  "filename": ["YYYYY"],
  93  "timestamp": 946728000,
  94  "date_relative": "2000-01-01",
  95  "tags": ["inbox","signed"],
  96  "headers": {"Subject": "bad signed message 001",
  97  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
  98  "To": "test_suite@notmuchmail.org",
  99  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 100  "body": [{"id": 1,
 101  "sigstatus": [{"status": "bad",
 102  "keyid": "'$(echo $FINGERPRINT | cut -c 25-)'"}],
 103  "content-type": "multipart/signed",
 104  "content": [{"id": 2,
 105  "content-type": "text/plain",
 106  "content": "This is a test signed message.\n"},
 107  {"id": 3,
 108  "content-type": "application/pgp-signature",
 109  "content-length": "NONZERO"}]}]},
 110  []]]]'
 111 test_expect_equal_json \
 112     "$output" \
 113     "$expected"
 114
 115 test_begin_subtest "corrupted pgp/mime signature"
 116 emacs_fcc_message \
 117     "bad signed message 002" \
 118     "Incriminating stuff. This is a test signed message." \
 119     "(mml-secure-message-sign)"
 120
 121 file=$(notmuch search --output=files subject:"bad signed message 002")
 122
 123 awk '/-----BEGIN PGP SIGNATURE-----/{flag=1;print;next} \
 124      /-----END PGP SIGNATURE-----/{flag=0;print;next} \
 125      flag{gsub(/[A-Za-z]/,"0");print}!flag{print}' $file > $file.new
 126
 127 rm $file
 128 mv $file.new $file
 129
 130 output=$(notmuch show --format=json --verify subject:"bad signed message 002" \
 131     | notmuch_json_show_sanitize \
 132     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 133 expected='[[[{"id": "XXXXX",
 134  "match": true,
 135  "excluded": false,
 136  "filename": ["YYYYY"],
 137  "timestamp": 946728000,
 138  "date_relative": "2000-01-01",
 139  "tags": ["inbox","signed"],
 140  "headers": {"Subject": "bad signed message 002",
 141  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 142  "To": "test_suite@notmuchmail.org",
 143  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 144  "body": [{"id": 1,
 145  "sigstatus": [],
 146  "content-type": "multipart/signed",
 147  "content": [{"id": 2,
 148  "content-type": "text/plain",
 149  "content": "Incriminating stuff. This is a test signed message.\n"},
 150  {"id": 3,
 151  "content-type": "application/pgp-signature",
 152  "content-length": "NONZERO"}]}]},
 153  []]]]'
 154 test_expect_equal_json \
 155     "$output" \
 156     "$expected"
 157
 158 test_begin_subtest "signature verification with full owner trust"
 159 test_subtest_broken_gmime_2
 160 # give the key full owner trust
 161 echo "${FINGERPRINT}:6:" | gpg --no-tty --import-ownertrust >>"$GNUPGHOME"/trust.log 2>&1
 162 gpg --no-tty --check-trustdb >>"$GNUPGHOME"/trust.log 2>&1
 163 output=$(notmuch show --format=json --verify subject:"test signed message 001" \
 164     | notmuch_json_show_sanitize \
 165     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 166 expected='[[[{"id": "XXXXX",
 167  "match": true,
 168  "excluded": false,
 169  "filename": ["YYYYY"],
 170  "timestamp": 946728000,
 171  "date_relative": "2000-01-01",
 172  "tags": ["inbox","signed"],
 173  "headers": {"Subject": "test signed message 001",
 174  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 175  "To": "test_suite@notmuchmail.org",
 176  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 177  "body": [{"id": 1,
 178  "sigstatus": [{"status": "good",
 179  "fingerprint": "'$FINGERPRINT'",
 180  "created": 946728000,
 181  "userid": "Notmuch Test Suite <test_suite@notmuchmail.org> (INSECURE!)"}],
 182  "content-type": "multipart/signed",
 183  "content": [{"id": 2,
 184  "content-type": "text/plain",
 185  "content": "This is a test signed message.\n"},
 186  {"id": 3,
 187  "content-type": "application/pgp-signature",
 188  "content-length": "NONZERO"}]}]},
 189  []]]]'
 190 test_expect_equal_json \
 191     "$output" \
 192     "$expected"
 193
 194 test_begin_subtest "signature verification with signer key unavailable"
 195 # move the gnupghome temporarily out of the way
 196 mv "${GNUPGHOME}"{,.bak}
 197 output=$(notmuch show --format=json --verify subject:"test signed message 001" \
 198     | notmuch_json_show_sanitize \
 199     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 200 expected='[[[{"id": "XXXXX",
 201  "match": true,
 202  "excluded": false,
 203  "filename": ["YYYYY"],
 204  "timestamp": 946728000,
 205  "date_relative": "2000-01-01",
 206  "tags": ["inbox","signed"],
 207  "headers": {"Subject": "test signed message 001",
 208  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 209  "To": "test_suite@notmuchmail.org",
 210  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 211  "body": [{"id": 1,
 212  "sigstatus": [{"status": "error",
 213  "keyid": "'$(echo $FINGERPRINT | cut -c 25-)'",
 214  "errors": {"key-missing": true}}],
 215  "content-type": "multipart/signed",
 216  "content": [{"id": 2,
 217  "content-type": "text/plain",
 218  "content": "This is a test signed message.\n"},
 219  {"id": 3,
 220  "content-type": "application/pgp-signature",
 221  "content-length": "NONZERO"}]}]},
 222  []]]]'
 223 test_expect_equal_json \
 224     "$output" \
 225     "$expected"
 226 mv "${GNUPGHOME}"{.bak,}
 227
 228 test_begin_subtest "emacs delivery of encrypted message with attachment"
 229 # create a test encrypted message with attachment
 230 cat <<EOF >TESTATTACHMENT
 231 This is a test file.
 232 EOF
 233 test_expect_success \
 234 'emacs_fcc_message \
 235     "test encrypted message 001" \
 236     "This is a test encrypted message.\n" \
 237     "(mml-attach-file \"TESTATTACHMENT\") (mml-secure-message-encrypt)"'
 238
 239 test_begin_subtest "encrypted part content-type indexing"
 240 test_subtest_known_broken
 241 output=$(notmuch search mimetype:multipart/encrypted and mimetype:application/pgp-encrypted and mimetype:application/octet-stream | notmuch_search_sanitize)
 242 test_expect_equal "$output" "thread:XXX   2000-01-01 [1/1] Notmuch Test Suite; test encrypted message 001 (encrypted inbox)"
 243
 244 test_begin_subtest "decryption, --format=text"
 245 output=$(notmuch show --format=text --decrypt subject:"test encrypted message 001" \
 246     | notmuch_show_sanitize_all \
 247     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 248 expected='\fmessage{ id:XXXXX depth:0 match:1 excluded:0 filename:XXXXX
 249 \fheader{
 250 Notmuch Test Suite <test_suite@notmuchmail.org> (2000-01-01) (encrypted inbox)
 251 Subject: test encrypted message 001
 252 From: Notmuch Test Suite <test_suite@notmuchmail.org>
 253 To: test_suite@notmuchmail.org
 254 Date: Sat, 01 Jan 2000 12:00:00 +0000
 255 \fheader}
 256 \fbody{
 257 \fpart{ ID: 1, Content-type: multipart/encrypted
 258 \fpart{ ID: 2, Content-type: application/pgp-encrypted
 259 Non-text part: application/pgp-encrypted
 260 \fpart}
 261 \fpart{ ID: 3, Content-type: multipart/mixed
 262 \fpart{ ID: 4, Content-type: text/plain
 263 This is a test encrypted message.
 264 \fpart}
 265 \fattachment{ ID: 5, Filename: TESTATTACHMENT, Content-type: application/octet-stream
 266 Non-text part: application/octet-stream
 267 \fattachment}
 268 \fpart}
 269 \fpart}
 270 \fbody}
 271 \fmessage}'
 272 test_expect_equal \
 273     "$output" \
 274     "$expected"
 275
 276 test_begin_subtest "decryption, --format=json"
 277 output=$(notmuch show --format=json --decrypt subject:"test encrypted message 001" \
 278     | notmuch_json_show_sanitize \
 279     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 280 expected='[[[{"id": "XXXXX",
 281  "match": true,
 282  "excluded": false,
 283  "filename": ["YYYYY"],
 284  "timestamp": 946728000,
 285  "date_relative": "2000-01-01",
 286  "tags": ["encrypted","inbox"],
 287  "headers": {"Subject": "test encrypted message 001",
 288  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 289  "To": "test_suite@notmuchmail.org",
 290  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 291  "body": [{"id": 1,
 292  "encstatus": [{"status": "good"}],
 293  "sigstatus": [],
 294  "content-type": "multipart/encrypted",
 295  "content": [{"id": 2,
 296  "content-type": "application/pgp-encrypted",
 297  "content-length": "NONZERO"},
 298  {"id": 3,
 299  "content-type": "multipart/mixed",
 300  "content": [{"id": 4,
 301  "content-type": "text/plain",
 302  "content": "This is a test encrypted message.\n"},
 303  {"id": 5,
 304  "content-type": "application/octet-stream",
 305  "content-disposition": "attachment",
 306  "content-length": "NONZERO",
 307  "content-transfer-encoding": "base64",
 308  "filename": "TESTATTACHMENT"}]}]}]},
 309  []]]]'
 310 test_expect_equal_json \
 311     "$output" \
 312     "$expected"
 313
 314 test_begin_subtest "decryption, --format=json, --part=4"
 315 output=$(notmuch show --format=json --part=4 --decrypt subject:"test encrypted message 001" \
 316     | notmuch_json_show_sanitize \
 317     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 318 expected='{"id": 4,
 319  "content-type": "text/plain",
 320  "content": "This is a test encrypted message.\n"}'
 321 test_expect_equal_json \
 322     "$output" \
 323     "$expected"
 324
 325 test_begin_subtest "decrypt attachment (--part=5 --format=raw)"
 326 notmuch show \
 327     --format=raw \
 328     --part=5 \
 329     --decrypt \
 330     subject:"test encrypted message 001" >OUTPUT
 331 test_expect_equal_file TESTATTACHMENT OUTPUT
 332
 333 test_begin_subtest "decryption failure with missing key"
 334 mv "${GNUPGHOME}"{,.bak}
 335 output=$(notmuch show --format=json --decrypt subject:"test encrypted message 001" \
 336     | notmuch_json_show_sanitize \
 337     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 338 expected='[[[{"id": "XXXXX",
 339  "match": true,
 340  "excluded": false,
 341  "filename": ["YYYYY"],
 342  "timestamp": 946728000,
 343  "date_relative": "2000-01-01",
 344  "tags": ["encrypted","inbox"],
 345  "headers": {"Subject": "test encrypted message 001",
 346  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 347  "To": "test_suite@notmuchmail.org",
 348  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 349  "body": [{"id": 1,
 350  "encstatus": [{"status": "bad"}],
 351  "content-type": "multipart/encrypted",
 352  "content": [{"id": 2,
 353  "content-type": "application/pgp-encrypted",
 354  "content-length": "NONZERO"},
 355  {"id": 3,
 356  "content-type": "application/octet-stream",
 357  "content-length": "NONZERO"}]}]},
 358  []]]]'
 359 test_expect_equal_json \
 360     "$output" \
 361     "$expected"
 362 mv "${GNUPGHOME}"{.bak,}
 363
 364 test_begin_subtest "emacs delivery of encrypted + signed message"
 365 test_expect_success \
 366 'emacs_fcc_message \
 367     "test encrypted message 002" \
 368     "This is another test encrypted message.\n" \
 369     "(mml-secure-message-sign-encrypt)"'
 370
 371 test_begin_subtest "decryption + signature verification"
 372 test_subtest_broken_gmime_2
 373 output=$(notmuch show --format=json --decrypt subject:"test encrypted message 002" \
 374     | notmuch_json_show_sanitize \
 375     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 376 expected='[[[{"id": "XXXXX",
 377  "match": true,
 378  "excluded": false,
 379  "filename": ["YYYYY"],
 380  "timestamp": 946728000,
 381  "date_relative": "2000-01-01",
 382  "tags": ["encrypted","inbox"],
 383  "headers": {"Subject": "test encrypted message 002",
 384  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 385  "To": "test_suite@notmuchmail.org",
 386  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 387  "body": [{"id": 1,
 388  "encstatus": [{"status": "good"}],
 389  "sigstatus": [{"status": "good",
 390  "fingerprint": "'$FINGERPRINT'",
 391  "created": 946728000,
 392  "userid": "Notmuch Test Suite <test_suite@notmuchmail.org> (INSECURE!)"}],
 393  "content-type": "multipart/encrypted",
 394  "content": [{"id": 2,
 395  "content-type": "application/pgp-encrypted",
 396  "content-length": "NONZERO"},
 397  {"id": 3,
 398  "content-type": "text/plain",
 399  "content": "This is another test encrypted message.\n"}]}]},
 400  []]]]'
 401 test_expect_equal_json \
 402     "$output" \
 403     "$expected"
 404
 405 test_begin_subtest "reply to encrypted message"
 406 output=$(notmuch reply --decrypt subject:"test encrypted message 002" \
 407     | notmuch_drop_mail_headers In-Reply-To References)
 408 expected='From: Notmuch Test Suite <test_suite@notmuchmail.org>
 409 Subject: Re: test encrypted message 002
 410
 411 On 01 Jan 2000 12:00:00 -0000, Notmuch Test Suite <test_suite@notmuchmail.org> wrote:
 412 > This is another test encrypted message.'
 413 test_expect_equal \
 414     "$output" \
 415     "$expected"
 416
 417 test_begin_subtest "Reply within emacs to an encrypted message"
 418 test_emacs "(let ((message-hidden-headers '())
 419       (notmuch-crypto-process-mime 't))
 420   (notmuch-show \"subject:test.encrypted.message.002\")
 421   (notmuch-show-reply)
 422   (test-output))"
 423 # the empty To: is probably a bug, but it's not to do with encryption
 424 grep -v -e '^In-Reply-To:' -e '^References:' -e '^Fcc:' -e 'To:' < OUTPUT > OUTPUT.clean
 425 cat <<EOF >EXPECTED
 426 From: Notmuch Test Suite <test_suite@notmuchmail.org>
 427 Subject: Re: test encrypted message 002
 428 --text follows this line--
 429 <#secure method=pgpmime mode=signencrypt>
 430 Notmuch Test Suite <test_suite@notmuchmail.org> writes:
 431
 432 > This is another test encrypted message.
 433 EOF
 434 test_expect_equal_file EXPECTED OUTPUT.clean
 435
 436 test_begin_subtest "signature verification with revoked key"
 437 # generate revocation certificate and load it to revoke key
 438 echo "y
 439 1
 440 Notmuch Test Suite key revocation (automated) $(date '+%F_%T%z')
 441
 442 y
 443
 444 " \
 445     | gpg --no-tty --quiet --command-fd 0 --armor --gen-revoke "0x${FINGERPRINT}!" 2>/dev/null \
 446     | gpg --no-tty --quiet --import
 447 output=$(notmuch show --format=json --verify subject:"test signed message 001" \
 448     | notmuch_json_show_sanitize \
 449     | sed -e 's|"created": [1234567890]*|"created": 946728000|')
 450 expected='[[[{"id": "XXXXX",
 451  "match": true,
 452  "excluded": false,
 453  "filename": ["YYYYY"],
 454  "timestamp": 946728000,
 455  "date_relative": "2000-01-01",
 456  "tags": ["inbox","signed"],
 457  "headers": {"Subject": "test signed message 001",
 458  "From": "Notmuch Test Suite <test_suite@notmuchmail.org>",
 459  "To": "test_suite@notmuchmail.org",
 460  "Date": "Sat, 01 Jan 2000 12:00:00 +0000"},
 461  "body": [{"id": 1,
 462  "sigstatus": [{"status": "error",
 463  "keyid": "6D92612D94E46381",
 464  "errors": {"key-revoked": true}}],
 465  "content-type": "multipart/signed",
 466  "content": [{"id": 2,
 467  "content-type": "text/plain",
 468  "content": "This is a test signed message.\n"},
 469  {"id": 3,
 470  "content-type": "application/pgp-signature",
 471  "content-length": "NONZERO"}]}]},
 472  []]]]'
 473 test_expect_equal_json \
 474     "$output" \
 475     "$expected"
 476
 477 test_done