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