Test the ability of notmuch-mua-mail to send S/MIME signed (and
encrypted) messages; this really relies on existing functionality in
message-mode.

The dependency on openssl to generate keys seems acceptable since
that's the method I got to work for smime signing in emacs.

The generated keys and messages will later be useful for testing the
notmuch CLI.
---
 test/T355-smime.sh             | 53 ++++++++++++++++++++++++++++++++++++++++++
 test/smime/openssl-ca-req.conf | 13 +++++++++++
 test/smime/openssl-req.conf    | 13 +++++++++++
 test/test-lib.el               | 10 ++++++++
 test/test-lib.sh               |  1 +
 5 files changed, 90 insertions(+)
 create mode 100755 test/T355-smime.sh
 create mode 100644 test/smime/openssl-ca-req.conf
 create mode 100644 test/smime/openssl-req.conf

diff --git a/test/T355-smime.sh b/test/T355-smime.sh
new file mode 100755
index 0000000..5f3ff12
--- /dev/null
+++ b/test/T355-smime.sh
@@ -0,0 +1,53 @@
+#!/usr/bin/env bash
+
+test_description='S/MIME signature verification and decryption'
+. ./test-lib.sh
+
+test_require_external_prereq openssl
+
+test_begin_subtest "Generate CA Cert"
+openssl genpkey -algorithm RSA -out ca.key -pass pass:test -des3 1024
+openssl req -new -x509 -key ca.key -passin pass:test \
+	-config $TEST_DIRECTORY/smime/openssl-ca-req.conf -out ca.crt
+test_expect_equal "$(openssl verify ca.crt | tail -1)" "OK"
+
+test_begin_subtest "Generate User Cert"
+openssl genpkey -algorithm RSA  -out smime.key 1024
+openssl req -config $TEST_DIRECTORY/smime/openssl-req.conf \
+	-new -key smime.key -passin pass:test -nodes \
+	-out smime.csr
+openssl x509 -req -in smime.csr -passin pass:test -CA ca.crt -CAkey ca.key -set_serial 1 -out test_suite.crt -setalias "Self Signed SMIME" -addtrust emailProtection -addreject clientAuth -addreject serverAuth -trustout
+# we need one file with the cert and private key
+cat test_suite.crt smime.key > test_suite.pem
+test_expect_equal "$(openssl verify -purpose smimesign -CAfile ca.crt test_suite.pem)" "test_suite.pem: OK"
+
+test_expect_success 'emacs delivery of S/MIME signed message' \
+     'emacs_fcc_message \
+     "test signed message 001" \
+     "This is a test signed message." \
+     "(mml-secure-message-sign \"smime\")"'
+
+# Hard code the MML to avoid several interactive questions
+test_expect_success 'emacs delivery of S/MIME encrypted + signed message' \
+'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"'
+
+test_begin_subtest "Signature verification (openssl)"
+notmuch show --format=raw subject:"test signed message 001" |\
+    openssl smime -verify -CAfile ca.crt 2>OUTPUT
+cat <<EOF > EXPECTED
+Verification successful
+EOF
+test_expect_equal_file OUTPUT EXPECTED
+
+test_begin_subtest "Decryption and signature verification (openssl)"
+notmuch show --format=raw subject:"test encrypted message 001" |\
+    openssl smime -decrypt -recip test_suite.pem |\
+    openssl smime -verify -CAfile ca.crt 2>OUTPUT
+cat <<EOF > EXPECTED
+Verification successful
+EOF
+test_expect_equal_file OUTPUT EXPECTED
+
+test_done
diff --git a/test/smime/openssl-ca-req.conf b/test/smime/openssl-ca-req.conf
new file mode 100644
index 0000000..49572ee
--- /dev/null
+++ b/test/smime/openssl-ca-req.conf
@@ -0,0 +1,13 @@
+ [ req ]
+ distinguished_name     = req_distinguished_name
+ prompt                 = no
+
+
+ [ req_distinguished_name ]
+ C                      = OZ
+ ST                     = Munchkinlandia
+ L                      = Emerald City
+ O                      = Organization Name
+ OU                     = Dept. of Fake Certs
+ CN                     = Fast Eddies Certs and Chips
+ emailAddress           = fake-ca@example.com
diff --git a/test/smime/openssl-req.conf b/test/smime/openssl-req.conf
new file mode 100644
index 0000000..c6b9de7
--- /dev/null
+++ b/test/smime/openssl-req.conf
@@ -0,0 +1,13 @@
+ [ req ]
+ distinguished_name     = req_distinguished_name
+ prompt                 = no
+
+
+ [ req_distinguished_name ]
+ C                      = OZ
+ ST                     = Munchkinlandia
+ L                      = Emerald City
+ O                      = Not much organization
+ OU                     = Dept. of Testing
+ CN                     = Notmuch Test Suite
+ emailAddress           = test_suite@notmuchmail.org
diff --git a/test/test-lib.el b/test/test-lib.el
index 04c8d63..596a705 100644
--- a/test/test-lib.el
+++ b/test/test-lib.el
@@ -188,3 +188,13 @@ 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 6057238..00612d9 100644
--- a/test/test-lib.sh
+++ b/test/test-lib.sh
@@ -1304,3 +1304,4 @@ test_declare_external_prereq gdb
 test_declare_external_prereq gpg
 test_declare_external_prereq python
 test_declare_external_prereq python2
+test_declare_external_prereq openssl
-- 
2.1.4