[PATCH 05/15] tests/smime: Use gpgsm instead of openssl for mml creation of S/MIME msgs

Subject: [PATCH 05/15] tests/smime: Use gpgsm instead of openssl for mml creation of S/MIME msgs

Date: Tue, 28 Apr 2020 14:57:13 -0400

To: Notmuch Mail


From: Daniel Kahn Gillmor

The documentation for message mode clearly states that EasyPG (which
uses GnuPG) is the default and recommended way to use S/MIME with

[0] https://www.gnu.org/software/emacs/manual/html_node/message/Using-S_002fMIME.html

To ensure that this mode works, we just need to import the secret key
in question into gpgsm in addition to the public key.  gpgsm should be
able pick the right keys+certificates to use based on To/From headers,
so we don't have to specify anything manually in the #secure mml tag.

The import process from the OpenSSL-preferred form (cert+secretkey) is
rather ugly, because gpgsm wants to see a PKCS#12 object when
importing secret keys.

Note that EasyPG generates the more modern Content-Type:
application/pkcs7-signature instead of application/x-pkcs7-signature
for the detached signature.

We are also obliged to manually set gpgsm's include-certs setting to 1
because gpgsm defaults to send "everything but the root cert".  In our
weird test case, the certificate we're using is self-signed, so it
*is* the root cert, which means that gpgsm doesn't include it by
default.  Setting it to 1 forces inclusion of the signer's cert, which
satisfies openssl's smime subcommand. See https://dev.gnupg.org/T4878
for more details.

Signed-off-by: Daniel Kahn Gillmor <dkg@fifthhorseman.net>
 test/T355-smime.sh |  4 ++--
 test/test-lib.el   | 10 ----------
 test/test-lib.sh   |  6 +++++-
 3 files changed, 7 insertions(+), 13 deletions(-)

diff --git a/test/T355-smime.sh b/test/T355-smime.sh
index 84be515a..9debf2da 100755
--- a/test/T355-smime.sh
+++ b/test/T355-smime.sh
@@ -24,7 +24,7 @@ test_begin_subtest "emacs delivery of S/MIME encrypted + signed message"
 test_expect_success \
 'emacs_fcc_message \
     "test encrypted message 001" \
-    "<#secure method=smime mode=signencrypt keyfile=\\\"test_suite.pem\\\" certfile=\\\"test_suite.pem\\\">\nThis is a test encrypted message.\n"'
+    "<#secure method=smime mode=signencrypt>\nThis is a test encrypted message.\n"'
 test_begin_subtest "Signature verification (openssl)"
 notmuch show --format=raw subject:"test signed message 001" |\
@@ -65,7 +65,7 @@ expected='[[[{"id": "XXXXX",
   "content-disposition": "attachment",
   "content-length": "NONZERO",
   "content-transfer-encoding": "base64",
-  "content-type": "application/x-pkcs7-signature",
+  "content-type": "application/pkcs7-signature",
   "filename": "smime.p7s"}]}]},
 test_expect_equal_json \
diff --git a/test/test-lib.el b/test/test-lib.el
index 3ae7a090..b47b388e 100644
--- a/test/test-lib.el
+++ b/test/test-lib.el
@@ -193,13 +193,3 @@ nothing."
 ;; environments
 (setq mm-text-html-renderer 'html2text)
-;; Set some variables for S/MIME tests.
-(setq smime-keys '(("" "test_suite.pem" nil)))
-(setq mml-smime-use 'openssl)
-;; all test keys are without passphrase
-(eval-after-load 'smime
-  '(defun smime-ask-passphrase (cache)  nil))
diff --git a/test/test-lib.sh b/test/test-lib.sh
index 31f37ed7..ac1b9315 100644
--- a/test/test-lib.sh
+++ b/test/test-lib.sh
@@ -136,11 +136,15 @@ add_gpgsm_home ()
     _gnupg_exit () { gpgconf --kill all 2>/dev/null || true; }
     at_exit_function _gnupg_exit
     mkdir -m 0700 "$GNUPGHOME"
-    gpgsm --batch --no-tty --no-common-certs-import --disable-dirmngr --import < $NOTMUCH_SRCDIR/test/smime/test.crt >"$GNUPGHOME"/import.log 2>&1
+    openssl pkcs12 -export -passout pass: -inkey "$NOTMUCH_SRCDIR/test/smime/key+cert.pem" \
+        < "$NOTMUCH_SRCDIR/test/smime/test.crt" | \
+        gpgsm --batch --no-tty --no-common-certs-import --pinentry-mode=loopback --passphrase-fd 3 \
+              --disable-dirmngr --import  >"$GNUPGHOME"/import.log 2>&1 3<<<''
     fpr=$(gpgsm --batch --list-key test_suite@notmuchmail.org | sed -n 's/.*fingerprint: //p')
     echo "$fpr S relax" >> "$GNUPGHOME/trustlist.txt"
     gpgsm --quiet --batch --no-tty --no-common-certs-import --disable-dirmngr --import < $NOTMUCH_SRCDIR/test/smime/ca.crt
     echo "4D:E0:FF:63:C0:E9:EC:01:29:11:C8:7A:EE:DA:3A:9A:7F:6E:C1:0D S" >> "$GNUPGHOME/trustlist.txt"
+    echo include-certs::1 | gpgconf --output /dev/null --change-options gpgsm
     test_debug "cat $GNUPGHOME/import.log"

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