From a7c364bf90a4593cfbc7911b1b7536dc66b1c879 Mon Sep 17 00:00:00 2001 From: Guilhem Moulin Date: Sun, 10 Nov 2019 05:39:41 +0100 Subject: Test suite: add new tests for SSL/TLS. MIME-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit SSL connections are accepted on TCP port 10993. Also, fix STARTTLS directive, broken since fba1c36… --- tests/list | 9 +++ tests/snippets/dovecot/dhparams.pem | 8 +++ tests/snippets/dovecot/dovecot.key | 5 ++ tests/snippets/dovecot/dovecot.pem | 11 ++++ tests/snippets/dovecot/imapd.conf | 4 ++ tests/snippets/dovecot/ssl.conf | 4 ++ tests/starttls-logindisabled/interimap.remote | 4 ++ tests/starttls-logindisabled/remote.conf | 5 ++ tests/starttls-logindisabled/t | 19 +++++++ tests/starttls/interimap.remote | 4 ++ tests/starttls/remote.conf | 2 + tests/starttls/t | 27 +++++++++ tests/sync-live-tls/interimap.remote | 1 + tests/sync-live-tls/local.conf | 1 + tests/sync-live-tls/remote.conf | 6 ++ tests/sync-live-tls/t | 1 + tests/tls-pin-fingerprint/interimap.remote | 1 + tests/tls-pin-fingerprint/remote.conf | 1 + tests/tls-pin-fingerprint/t | 33 +++++++++++ tests/tls-protocols/interimap.remote | 1 + tests/tls-protocols/remote.conf | 1 + tests/tls-protocols/t | 39 +++++++++++++ tests/tls-verify-peer/interimap.remote | 2 + tests/tls-verify-peer/remote.conf | 1 + tests/tls-verify-peer/t | 80 +++++++++++++++++++++++++++ tests/tls/interimap.remote | 3 + tests/tls/remote.conf | 2 + tests/tls/t | 14 +++++ 28 files changed, 289 insertions(+) create mode 100644 tests/snippets/dovecot/dhparams.pem create mode 100644 tests/snippets/dovecot/dovecot.key create mode 100644 tests/snippets/dovecot/dovecot.pem create mode 100644 tests/snippets/dovecot/ssl.conf create mode 100644 tests/starttls-logindisabled/interimap.remote create mode 100644 tests/starttls-logindisabled/remote.conf create mode 100644 tests/starttls-logindisabled/t create mode 100644 tests/starttls/interimap.remote create mode 100644 tests/starttls/remote.conf create mode 100644 tests/starttls/t create mode 120000 tests/sync-live-tls/interimap.remote create mode 120000 tests/sync-live-tls/local.conf create mode 100644 tests/sync-live-tls/remote.conf create mode 120000 tests/sync-live-tls/t create mode 120000 tests/tls-pin-fingerprint/interimap.remote create mode 120000 tests/tls-pin-fingerprint/remote.conf create mode 100644 tests/tls-pin-fingerprint/t create mode 120000 tests/tls-protocols/interimap.remote create mode 120000 tests/tls-protocols/remote.conf create mode 100644 tests/tls-protocols/t create mode 100644 tests/tls-verify-peer/interimap.remote create mode 120000 tests/tls-verify-peer/remote.conf create mode 100644 tests/tls-verify-peer/t create mode 100644 tests/tls/interimap.remote create mode 100644 tests/tls/remote.conf create mode 100644 tests/tls/t (limited to 'tests') diff --git a/tests/list b/tests/list index 86034ef..bc8d144 100644 --- a/tests/list +++ b/tests/list @@ -38,7 +38,16 @@ repair --repair auth-logindisabled LOGINDISABLED auth-noplaintext abort when STARTTLS is not offered +. SSL/TLS + starttls-logindisabled LOGINDISABLED STARTTLS + starttls STARTTLS + tls SSL/TLS handshake + ... tls-verify-peer + tls-pin-fingerprint pubkey fingerprint pinning + tls-protocols force TLS protocol versions + . Live synchronization (60s) sync-live local/remote simulation sync-live-crippled local/remote simulation (crippled remote) + sync-live-tls local/remote simulation (TLS remote) sync-live-multi local/remote1+remote2+remote3 simulation (3 local namespaces) diff --git a/tests/snippets/dovecot/dhparams.pem b/tests/snippets/dovecot/dhparams.pem new file mode 100644 index 0000000..7734d2a --- /dev/null +++ b/tests/snippets/dovecot/dhparams.pem @@ -0,0 +1,8 @@ +-----BEGIN DH PARAMETERS----- +MIIBCAKCAQEA0J1dU8erRgIk4bMCBMLezjx32pcQpXrdNgl04dxZVxnJ5Ik2gGhA +uQRbbZhAlHNHtFtp9s4TdQ3Ddrv9SuWXYul8U5BWbcxs4nOtwFU8912SfiuVr/kc +4ok2zQ1hdMODtaqWS2ZKBmwcuk4QM6e7fMEAkuZX+Dtf2u8bG5G9B7OL5LggYtrP +cFVNQDtfhs64D+sUKJLWkgeg5NH6nbf+0Gs5a8v3/urHKvoxdVScGmKzF+LsFsBm +ycQjYeVtA9gLr41mo80rrFysUQqZtNkbdkaXOIA2r9JGTYex1l/XaediR8J94ck9 +dwAe2ubRqWcPjmoLJYQIPKiCbvXuJAd0wwIBAg== +-----END DH PARAMETERS----- diff --git a/tests/snippets/dovecot/dovecot.key b/tests/snippets/dovecot/dovecot.key new file mode 100644 index 0000000..95c9846 --- /dev/null +++ b/tests/snippets/dovecot/dovecot.key @@ -0,0 +1,5 @@ +-----BEGIN EC PRIVATE KEY----- +MHcCAQEEIGkqkKq69zVeF17S3y2U2HkQWh8z9M/xeblCztkKIfzJoAoGCCqGSM49 +AwEHoUQDQgAE1LLppulKw8KjINrDhOjEd0NTax5iDCds+vpA2PwsvvtGoprNAjQM +zX+40u30N3CE0r591txqohSBQ/X+nvG2ug== +-----END EC PRIVATE KEY----- diff --git a/tests/snippets/dovecot/dovecot.pem b/tests/snippets/dovecot/dovecot.pem new file mode 100644 index 0000000..7e53d90 --- /dev/null +++ b/tests/snippets/dovecot/dovecot.pem @@ -0,0 +1,11 @@ +-----BEGIN CERTIFICATE----- +MIIBkzCCATmgAwIBAgIUQ+3hBMsPJcl59xDDujDDfexurOswCgYIKoZIzj0EAwIw +HzEdMBsGA1UEAwwUSW50ZXJJTUFQIHRlc3Qgc3VpdGUwHhcNMTkxMTEwMTM1NDAw +WhcNMjkxMTA3MTM1NDAwWjAfMR0wGwYDVQQDDBRJbnRlcklNQVAgdGVzdCBzdWl0 +ZTBZMBMGByqGSM49AgEGCCqGSM49AwEHA0IABNSy6abpSsPCoyDaw4ToxHdDU2se +YgwnbPr6QNj8LL77RqKazQI0DM1/uNLt9DdwhNK+fdbcaqIUgUP1/p7xtrqjUzBR +MB0GA1UdDgQWBBRlh8nSwyX+VlhwuhV7RKYwvKLyDzAfBgNVHSMEGDAWgBRlh8nS +wyX+VlhwuhV7RKYwvKLyDzAPBgNVHRMBAf8EBTADAQH/MAoGCCqGSM49BAMCA0gA +MEUCIQDK8xPPHTbYW5JnZ1Siy8ChZ6GOu2sRwQu7OgtGYGZRSQIgFKn1oAhnq2Oi +aIPqxjvBPMsK/sjrdI/rNsr2XgaulU4= +-----END CERTIFICATE----- diff --git a/tests/snippets/dovecot/imapd.conf b/tests/snippets/dovecot/imapd.conf index c9926ce..18c60f8 100644 --- a/tests/snippets/dovecot/imapd.conf +++ b/tests/snippets/dovecot/imapd.conf @@ -9,4 +9,8 @@ service imap-login { inet_listener imap { port = 10143 } + inet_listener imaps { + port = 10993 + ssl = yes + } } diff --git a/tests/snippets/dovecot/ssl.conf b/tests/snippets/dovecot/ssl.conf new file mode 100644 index 0000000..240f24b --- /dev/null +++ b/tests/snippets/dovecot/ssl.conf @@ -0,0 +1,4 @@ +ssl = required +ssl_cert = "$TMPDIR/capability" + +sed -ri 's/^remote: S: \* OK \[CAPABILITY (.*)\]$/\1/' "$TMPDIR/capability" +tr " " "\\n" <"$TMPDIR/capability" >"$TMPDIR/capabilities" +grep -Fx "IMAP4rev1" <"$TMPDIR/capabilities" || error +grep -Fx "LOGINDISABLED" <"$TMPDIR/capabilities" || error + +# make sure we upgraded the connection and check the capability again +grep -Fx "STARTTLS" <"$TMPDIR/capabilities" || error +grep -Fx "remote: C: 000000 STARTTLS" <"$STDERR" || error +grep -Fx "remote: C: 000001 CAPABILITY" <"$STDERR" || error + +# can't go further as the capability string still has the manually +# enforced 'LOGINDISABLED' + +# vim: set filetype=sh : diff --git a/tests/starttls/interimap.remote b/tests/starttls/interimap.remote new file mode 100644 index 0000000..5d7571d --- /dev/null +++ b/tests/starttls/interimap.remote @@ -0,0 +1,4 @@ +type = imap +host = 127.0.0.1 +port = 10143 +SSL_verify = no diff --git a/tests/starttls/remote.conf b/tests/starttls/remote.conf new file mode 100644 index 0000000..3d07ea9 --- /dev/null +++ b/tests/starttls/remote.conf @@ -0,0 +1,2 @@ +!include conf.d/imapd.conf +!include conf.d/ssl.conf diff --git a/tests/starttls/t b/tests/starttls/t new file mode 100644 index 0000000..99a39c2 --- /dev/null +++ b/tests/starttls/t @@ -0,0 +1,27 @@ +for ((i = 0; i < 32; i++)); do + u="$(shuf -n1 -e "local" "remote")" + sample_message | deliver -u "$u" +done + +interimap --debug || error + +# double check the presence of 'STARTTLS' in the preauth capability list +grep -oE -m1 '^remote: S: \* OK \[CAPABILITY IMAP4rev1( [^]]*)? AUTH=[^]]*\]' <"$STDERR" >"$TMPDIR/capability" + +sed -ri 's/^remote: S: \* OK \[CAPABILITY (.*)\]$/\1/' "$TMPDIR/capability" +tr " " "\\n" <"$TMPDIR/capability" >"$TMPDIR/capabilities" +grep -Fx "IMAP4rev1" <"$TMPDIR/capabilities" || error +grep -Fx "STARTTLS" <"$TMPDIR/capabilities" || error + +# make sure we upgraded the connection and check the capability again +grep -Fx "remote: C: 000000 STARTTLS" <"$STDERR" || error +grep -Fx "remote: C: 000001 CAPABILITY" <"$STDERR" || error + +grep -Fx "remote: Disabling SSL protocols: SSLv3, TLSv1, TLSv1.1" <"$STDERR" || error +grep -Fx "remote: Peer certificate fingerprint: sha256\$35944e3bd3300d3ac310bb497a32cc1eef6931482a587ddbc95343740cdf1323" <"$STDERR" || error +grep "^remote: SSL protocol: TLSv1\.[23] " <"$STDERR" || error +grep "^remote: SSL cipher: " <"$STDERR" || error + +check_mailbox_status "INBOX" + +# vim: set filetype=sh : diff --git a/tests/sync-live-tls/interimap.remote b/tests/sync-live-tls/interimap.remote new file mode 120000 index 0000000..daf3741 --- /dev/null +++ b/tests/sync-live-tls/interimap.remote @@ -0,0 +1 @@ +../tls/interimap.remote \ No newline at end of file diff --git a/tests/sync-live-tls/local.conf b/tests/sync-live-tls/local.conf new file mode 120000 index 0000000..ad27dd1 --- /dev/null +++ b/tests/sync-live-tls/local.conf @@ -0,0 +1 @@ +../sync-live/local.conf \ No newline at end of file diff --git a/tests/sync-live-tls/remote.conf b/tests/sync-live-tls/remote.conf new file mode 100644 index 0000000..b2af2d2 --- /dev/null +++ b/tests/sync-live-tls/remote.conf @@ -0,0 +1,6 @@ +namespace inbox { + separator = ^ +} + +!include conf.d/imapd.conf +!include conf.d/ssl.conf diff --git a/tests/sync-live-tls/t b/tests/sync-live-tls/t new file mode 120000 index 0000000..189360e --- /dev/null +++ b/tests/sync-live-tls/t @@ -0,0 +1 @@ +../sync-live/t \ No newline at end of file diff --git a/tests/tls-pin-fingerprint/interimap.remote b/tests/tls-pin-fingerprint/interimap.remote new file mode 120000 index 0000000..daf3741 --- /dev/null +++ b/tests/tls-pin-fingerprint/interimap.remote @@ -0,0 +1 @@ +../tls/interimap.remote \ No newline at end of file diff --git a/tests/tls-pin-fingerprint/remote.conf b/tests/tls-pin-fingerprint/remote.conf new file mode 120000 index 0000000..6029749 --- /dev/null +++ b/tests/tls-pin-fingerprint/remote.conf @@ -0,0 +1 @@ +../tls/remote.conf \ No newline at end of file diff --git a/tests/tls-pin-fingerprint/t b/tests/tls-pin-fingerprint/t new file mode 100644 index 0000000..1b84390 --- /dev/null +++ b/tests/tls-pin-fingerprint/t @@ -0,0 +1,33 @@ +# backup config +install -m0600 "$XDG_CONFIG_HOME/interimap/config" "$XDG_CONFIG_HOME/interimap/config~" +with_remote_config() { + install -m0600 "$XDG_CONFIG_HOME/interimap/config~" "$XDG_CONFIG_HOME/interimap/config" + cat >>"$XDG_CONFIG_HOME/interimap/config" +} + +# pinned valid fingerprint +with_remote_config <<-EOF + SSL_fingerprint = sha256\$e8fc8d03ffe75e03897136a2f1c5647bf8c36be7136a6883a732a8c4961c1614 +EOF + +for ((i = 0; i < 32; i++)); do + u="$(shuf -n1 -e "local" "remote")" + sample_message | deliver -u "$u" +done +interimap_init +check_mailbox_status "INBOX" + + +# and now an invalid one +with_remote_config <<-EOF + SSL_fingerprint = sha256\$deadbeefdeadbeefdeadbeefdeadbeefdeadbeefdeadbeefdeadbeefdeadbeef +EOF +! interimap --debug || error + +grep -Fx "remote: ERROR: Can't initiate TLS/SSL handshake" <"$STDERR" || error +grep -Fx "remote: WARNING: Fingerprint doesn't match! MiTM in action?" <"$STDERR" || error +grep -Fx "remote: ERROR: Can't initiate TLS/SSL handshake" <"$STDERR" || error +# make sure we didn't send any credentials +! grep -E "^remote: C: .* (AUTHENTICATE|LOGIN) " <"$STDERR" || error + +# vim: set filetype=sh : diff --git a/tests/tls-protocols/interimap.remote b/tests/tls-protocols/interimap.remote new file mode 120000 index 0000000..daf3741 --- /dev/null +++ b/tests/tls-protocols/interimap.remote @@ -0,0 +1 @@ +../tls/interimap.remote \ No newline at end of file diff --git a/tests/tls-protocols/remote.conf b/tests/tls-protocols/remote.conf new file mode 120000 index 0000000..6029749 --- /dev/null +++ b/tests/tls-protocols/remote.conf @@ -0,0 +1 @@ +../tls/remote.conf \ No newline at end of file diff --git a/tests/tls-protocols/t b/tests/tls-protocols/t new file mode 100644 index 0000000..f34a95b --- /dev/null +++ b/tests/tls-protocols/t @@ -0,0 +1,39 @@ +# backup config +install -m0600 "$XDG_CONFIG_HOME/interimap/config" "$XDG_CONFIG_HOME/interimap/config~" +with_remote_tls_protocols() { + install -m0600 "$XDG_CONFIG_HOME/interimap/config~" "$XDG_CONFIG_HOME/interimap/config" + printf "SSL_protocols = %s\\n" "$*" >>"$XDG_CONFIG_HOME/interimap/config" +} + +# default +interimap --debug || error +grep -Fx "remote: Disabling SSL protocols: SSLv3, TLSv1, TLSv1.1" <"$STDERR" || error +grep -E "^remote: SSL protocol: TLSv1\.[23] " <"$STDERR" || error + +# also disable TLSv1.2 +with_remote_tls_protocols "!SSLv2" "!SSLv3" "!TLSv1" "!TLSv1.1" "!TLSv1.2" +interimap --debug || error +grep -Fx "remote: Disabling SSL protocols: SSLv3, TLSv1, TLSv1.1, TLSv1.2" <"$STDERR" || error +grep -E "^remote: SSL protocol: TLSv1\.3 " <"$STDERR" || error + +# force TLSv1.2 +with_remote_tls_protocols "TLSv1.2" +interimap --debug || error +grep -Fx "remote: Disabling SSL protocols: SSLv3, TLSv1, TLSv1.1, TLSv1.3" <"$STDERR" || error +grep -E "^remote: SSL protocol: TLSv1\.2 " <"$STDERR" || error + +# force TLSv1 to TLSv1.2 +with_remote_tls_protocols "TLSv1" "TLSv1.1" "TLSv1.2" +interimap --debug || error +grep -Fx "remote: Disabling SSL protocols: SSLv3, TLSv1.3" <"$STDERR" || error +grep -E "^remote: SSL protocol: TLSv(1\.[12])? " <"$STDERR" || error + +# force SSLv2 and SSLv3, fails as it's disabled server side +with_remote_tls_protocols "SSLv2" "SSLv3" +! interimap --debug || error +grep -Fx "remote: Disabling SSL protocols: TLSv1, TLSv1.1, TLSv1.2, TLSv1.3" <"$STDERR" || error +grep -Fx "remote: ERROR: Can't initiate TLS/SSL handshake" <"$STDERR" || error +# make sure we didn't send any credentials +! grep -E "^remote: C: .* (AUTHENTICATE|LOGIN) " <"$STDERR" || error + +# vim: set filetype=sh : diff --git a/tests/tls-verify-peer/interimap.remote b/tests/tls-verify-peer/interimap.remote new file mode 100644 index 0000000..b02fcd0 --- /dev/null +++ b/tests/tls-verify-peer/interimap.remote @@ -0,0 +1,2 @@ +host = ::1 +port = 10993 diff --git a/tests/tls-verify-peer/remote.conf b/tests/tls-verify-peer/remote.conf new file mode 120000 index 0000000..6029749 --- /dev/null +++ b/tests/tls-verify-peer/remote.conf @@ -0,0 +1 @@ +../tls/remote.conf \ No newline at end of file diff --git a/tests/tls-verify-peer/t b/tests/tls-verify-peer/t new file mode 100644 index 0000000..d84328a --- /dev/null +++ b/tests/tls-verify-peer/t @@ -0,0 +1,80 @@ +CERT=~/.dovecot/conf.d/dovecot.pem + +unverified_peer() { + ! interimap --debug || error + + grep -Fx "remote: ERROR: Can't initiate TLS/SSL handshake" <"$STDERR" || error + sed -nr "s/remote: \[[0-9]+\] (preverify=[0-9]+)$/\1/p" <"$STDERR" >"$TMPDIR/preverify" + [ -s "$TMPDIR/preverify" ] || error + ! grep -Fvx "preverify=0" <"$TMPDIR/preverify" || error + + # make sure we didn't send any credentials + ! grep -E "^remote: C: .* (AUTHENTICATE|LOGIN) " <"$STDERR" || error +} +verified_peer() { + local i u + for ((i = 0; i < 32; i++)); do + u="$(shuf -n1 -e "local" "remote")" + sample_message | deliver -u "$u" + done + interimap --debug || error + + sed -nr "s/remote: \[[0-9]+\] (preverify=[0-9]+)$/\1/p" <"$STDERR" >"$TMPDIR/preverify" + [ -s "$TMPDIR/preverify" ] || error + ! grep -Fvx "preverify=1" <"$TMPDIR/preverify" || error + + grep "^remote: SSL protocol: TLSv1\.[23] " <"$STDERR" || error + grep "^remote: SSL cipher: " <"$STDERR" || error + + check_mailbox_status "INBOX" +} + +# backup config +install -m0600 "$XDG_CONFIG_HOME/interimap/config" "$XDG_CONFIG_HOME/interimap/config~" +with_remote_config() { + install -m0600 "$XDG_CONFIG_HOME/interimap/config~" "$XDG_CONFIG_HOME/interimap/config" + cat >>"$XDG_CONFIG_HOME/interimap/config" +} + +step_start "peer verification enabled by default" +unverified_peer +step_done + +step_start "peer verification result honored when pinned pubkey matches" +pkey_sha256="$(openssl x509 -pubkey <"$CERT" | openssl pkey -pubin -outform DER \ + | openssl dgst -sha256 | sed -rn "/^.*=\\s*/ {s///p;q}")" +with_remote_config <<-EOF + SSL_fingerprint = sha256\$$pkey_sha256 +EOF +unverified_peer +! grep -Fx "remote: WARNING: Fingerprint doesn't match! MiTM in action?" <"$STDERR" || error +step_done + + +step_start "SSL_CAfile" +if [ -f "/etc/ssl/certs/ca-certificates.crt" ]; then + # the self-signed cert should not be in there + with_remote_config <<<"SSL_CAfile = /etc/ssl/certs/ca-certificates.crt" + unverified_peer +fi +with_remote_config <<<"SSL_CAfile = $CERT" +verified_peer +step_done + + +step_start "SSL_CApath" +if [ -d "/etc/ssl/certs" ]; then + # the self-signed cert should not be in there + with_remote_config <<<"SSL_CApath = /etc/ssl/certs" + unverified_peer +fi + +capath=$(mktemp --tmpdir="$TMPDIR" --directory capath.XXXXXX) +cp -t"$capath" "$CERT" +c_rehash "$capath" + +with_remote_config <<<"SSL_CApath = $capath" +verified_peer +step_done + +# vim: set filetype=sh : diff --git a/tests/tls/interimap.remote b/tests/tls/interimap.remote new file mode 100644 index 0000000..2c0e37e --- /dev/null +++ b/tests/tls/interimap.remote @@ -0,0 +1,3 @@ +host = ::1 +port = 10993 +SSL_verify = no diff --git a/tests/tls/remote.conf b/tests/tls/remote.conf new file mode 100644 index 0000000..3d07ea9 --- /dev/null +++ b/tests/tls/remote.conf @@ -0,0 +1,2 @@ +!include conf.d/imapd.conf +!include conf.d/ssl.conf diff --git a/tests/tls/t b/tests/tls/t new file mode 100644 index 0000000..dd6d955 --- /dev/null +++ b/tests/tls/t @@ -0,0 +1,14 @@ +for ((i = 0; i < 32; i++)); do + u="$(shuf -n1 -e "local" "remote")" + sample_message | deliver -u "$u" +done + +interimap --debug || error +grep -Fx "remote: Disabling SSL protocols: SSLv3, TLSv1, TLSv1.1" <"$STDERR" || error +grep -Fx "remote: Peer certificate fingerprint: sha256\$35944e3bd3300d3ac310bb497a32cc1eef6931482a587ddbc95343740cdf1323" <"$STDERR" || error +grep "^remote: SSL protocol: TLSv1\.[23] " <"$STDERR" || error +grep "^remote: SSL cipher: " <"$STDERR" || error + +check_mailbox_status "INBOX" + +# vim: set filetype=sh : -- cgit v1.2.3