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