notmuch/test/T356-protected-headers.sh
Daniel Kahn Gillmor b14d9ae204 smime: tests of X.509 certificate validity are known-broken on GMime < 3.2.7
When checking cryptographic signatures, Notmuch relies on GMime to
tell it whether the certificate that signs a message has a valid User
ID or not.

If the User ID is not valid, then notmuch does not report the signer's
User ID to the user.  This means that the consumer of notmuch's
cryptographic summary of a message (or of its protected headers) can
be confident in relaying the reported identity to the user.

However, some versions of GMime before 3.2.7 cannot report Certificate
validity for X.509 certificates.  This is resolved upstream in GMime
at https://github.com/jstedfast/gmime/pull/90.

We adapt to this by marking tests of reported User IDs for
S/MIME-signed messages as known-broken if GMime is older than 3.2.7
and has not been patched.

If GMime >= 3.2.7 and certificate validity still doesn't work for
X.509 certs, then there has likely been a regression in GMime and we
should fail early, during ./configure.

To break out these specific User ID checks from other checks, i had to
split some tests into two parts, and reuse $output across the two
subtests.

Signed-off-by: Daniel Kahn Gillmor <dkg@fifthhorseman.net>
2020-05-22 22:04:57 -03:00

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#!/usr/bin/env bash
test_description='Message decryption with protected headers'
. $(dirname "$0")/test-lib.sh || exit 1
##################################################
test_require_external_prereq gpgsm
add_gnupg_home
add_gpgsm_home
add_email_corpus protected-headers
test_begin_subtest "verify protected header is not visible without decryption"
output=$(notmuch show --format=json id:protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'no_crypto_info:[0][0][0]["crypto"]={}' \
'subject:[0][0][0]["headers"]["Subject"]="Subject Unavailable"'
test_begin_subtest "verify protected header is visible with decryption"
output=$(notmuch show --decrypt=true --format=json id:protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full", "header-mask": {"Subject": "Subject Unavailable"}}}' \
'subject:[0][0][0]["headers"]["Subject"]="This is a protected header"'
test_begin_subtest "when no external header is present, show masked subject as null"
output=$(notmuch show --decrypt=true --format=json id:subjectless-protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full", "header-mask": {"Subject": null}}}' \
'subject:[0][0][0]["headers"]["Subject"]="This is a protected header"'
test_begin_subtest "misplaced protected headers should not be made visible during decryption"
output=$(notmuch show --decrypt=true --format=json id:misplaced-protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full"}}' \
'subject:[0][0][0]["headers"]["Subject"]="Subject Unavailable"'
test_begin_subtest "verify double-wrapped phony protected header is not visible when inner decryption fails"
output=$(notmuch show --decrypt=true --format=json id:double-wrapped-with-phony-protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full"}}' \
'subject:[0][0][0]["headers"]["Subject"]="Subject Unavailable"'
test_begin_subtest "cleartext phony protected headers should not be made visible when decryption fails"
output=$(notmuch show --decrypt=true --format=json id:phony-protected-header-bad-encryption@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'no_crypto_info:[0][0][0]["crypto"]={}' \
'subject:[0][0][0]["headers"]["Subject"]="Subject Unavailable"'
test_begin_subtest "wrapped protected headers should not be made visible during decryption"
output=$(notmuch show --decrypt=true --format=json id:wrapped-protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "partial"}}' \
'subject:[0][0][0]["headers"]["Subject"]="[mailing-list] Subject Unavailable"'
test_begin_subtest "internal headers without protected-header attribute should be skipped"
output=$(notmuch show --decrypt=true --format=json id:no-protected-header-attribute@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full"}}' \
'subject:[0][0][0]["headers"]["Subject"]="Subject Unavailable"'
test_begin_subtest "verify nested message/rfc822 protected header is visible"
output=$(notmuch show --decrypt=true --format=json id:nested-rfc822-message@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full", "header-mask": {"Subject": "Subject Unavailable"}}}' \
'subject:[0][0][0]["headers"]["Subject"]="This is a message using draft-melnikov-smime-header-signing"'
test_begin_subtest "show cryptographic envelope on signed mail"
output=$(notmuch show --verify --format=json id:simple-signed-mail@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"signed": {"status": [{"created": 1525609971, "fingerprint": "'$FINGERPRINT'", "userid": "'"$SELF_USERID"'", "status": "good"}]}}'
test_begin_subtest "verify signed protected header"
output=$(notmuch show --verify --format=json id:signed-protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"signed": {"status": [{"created": 1525350527, "fingerprint": "'$FINGERPRINT'", "userid": "'"$SELF_USERID"'", "status": "good"}], "headers": ["Subject"]}}'
test_begin_subtest "protected subject does not leak by default in replies"
output=$(notmuch reply --decrypt=true --format=json id:protected-header@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:["original"]["crypto"]={"decrypted": {"status": "full", "header-mask": {"Subject": "Subject Unavailable"}}}' \
'subject:["original"]["headers"]["Subject"]="This is a protected header"' \
'reply-subject:["reply-headers"]["Subject"]="Re: Subject Unavailable"'
test_begin_subtest "protected subject is not indexed by default"
output=$(notmuch search --output=messages 'subject:"This is a protected header"')
test_expect_equal "$output" ''
test_begin_subtest "reindex message with protected header"
test_expect_success 'notmuch reindex --decrypt=true id:protected-header@crypto.notmuchmail.org'
test_begin_subtest "protected subject is indexed when cleartext is indexed"
output=$(notmuch search --output=messages 'subject:"This is a protected header"')
test_expect_equal "$output" 'id:protected-header@crypto.notmuchmail.org'
test_begin_subtest "indexed protected subject is visible in search"
output=$(notmuch search --format=json 'id:protected-header@crypto.notmuchmail.org')
test_json_nodes <<<"$output" \
'subject:[0]["subject"]="This is a protected header"'
test_begin_subtest "indexed protected subject is not visible in reply header"
output=$(notmuch reply --format=json 'id:protected-header@crypto.notmuchmail.org')
test_json_nodes <<<"$output" \
'subject:["original"]["headers"]["Subject"]="This is a protected header"' \
'reply-subject:["reply-headers"]["Subject"]="Re: Subject Unavailable"'
test_begin_subtest "verify correct protected header when submessage exists"
output=$(notmuch show --decrypt=true --format=json id:encrypted-message-with-forwarded-attachment@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={"decrypted": {"status": "full", "header-mask": {"Subject": "Subject Unavailable"}}}' \
'subject:[0][0][0]["headers"]["Subject"]="This is the cryptographic envelope subject"'
test_begin_subtest "verify protected header is both signed and encrypted"
output=$(notmuch show --decrypt=true --format=json id:encrypted-signed@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={
"signed":{"status": [{"status": "good", "fingerprint": "'$FINGERPRINT'", "userid": "'"$SELF_USERID"'", "created": 1525812676}],
"encrypted": true, "headers": ["Subject"]},"decrypted": {"status": "full", "header-mask": {"Subject": "Subject Unavailable"}}}' \
'subject:[0][0][0]["headers"]["Subject"]="Rhinoceros dinner"'
test_begin_subtest "verify protected header is signed even when not masked"
output=$(notmuch show --decrypt=true --format=json id:encrypted-signed-not-masked@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'crypto:[0][0][0]["crypto"]={
"signed":{"status": [{"status": "good", "fingerprint": "'$FINGERPRINT'", "userid": "'"$SELF_USERID"'", "created": 1525812676}],
"encrypted": true, "headers": ["Subject"]},"decrypted": {"status": "full"}}' \
'subject:[0][0][0]["headers"]["Subject"]="Rhinoceros dinner"'
test_begin_subtest "reindex everything, ensure headers are as expected"
notmuch reindex --decrypt=true from:test_suite@notmuchmail.org
output=$(notmuch search --output=messages 'subject:"protected header" or subject:"Rhinoceros" or subject:"draft-melnikov-smime-header-signing" or subject:"valid"' | sort)
test_expect_equal "$output" 'id:encrypted-signed-not-masked@crypto.notmuchmail.org
id:encrypted-signed@crypto.notmuchmail.org
id:nested-rfc822-message@crypto.notmuchmail.org
id:protected-header@crypto.notmuchmail.org
id:subjectless-protected-header@crypto.notmuchmail.org'
test_begin_subtest "when rendering protected headers, avoid rendering legacy-display part"
output=$(notmuch show --format=json id:protected-with-legacy-display@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'subject:[0][0][0]["headers"]["Subject"]="Interrupting Cow"' \
'no_legacy_display:[0][0][0]["body"][0]["content"][1]["content-type"]="text/plain"'
test_begin_subtest "when replying, avoid rendering legacy-display part"
output=$(notmuch reply --format=json id:protected-with-legacy-display@crypto.notmuchmail.org)
test_json_nodes <<<"$output" \
'no_legacy_display:["original"]["body"][0]["content"][1]["content-type"]="text/plain"'
test_begin_subtest "do not treat legacy-display part as body when indexing"
output=$(notmuch search --output=messages body:interrupting)
test_expect_equal "$output" ''
test_begin_subtest "identify message that had a legacy display part skipped during indexing"
output=$(notmuch search --output=messages property:index.repaired=skip-protected-headers-legacy-display)
test_expect_equal "$output" id:protected-with-legacy-display@crypto.notmuchmail.org
for variant in multipart-signed onepart-signed; do
test_begin_subtest "verify signed PKCS#7 subject ($variant)"
[ "$variant" = multipart-signed ] || test_subtest_known_broken
output=$(notmuch show --verify --format=json "id:smime-${variant}@protected-headers.example")
test_json_nodes <<<"$output" \
'signed_subject:[0][0][0]["crypto"]["signed"]["headers"]=["Subject"]' \
'sig_good:[0][0][0]["crypto"]["signed"]["status"][0]["status"]="good"' \
'sig_fpr:[0][0][0]["crypto"]["signed"]["status"][0]["fingerprint"]="702BA4B157F1E2B7D16B0C6A5FFC8A7DE2057DEB"' \
'not_encrypted:[0][0][0]["crypto"]!"decrypted"'
test_begin_subtest "verify signed PKCS#7 subject ($variant) signer User ID"
if [ $NOTMUCH_GMIME_X509_CERT_VALIDITY -ne 1 ] || [ "$variant" != multipart-signed ]; then
test_subtest_known_broken
fi
test_json_nodes <<<"$output" \
'sig_uid:[0][0][0]["crypto"]["signed"]["status"][0]["userid"]="CN=Alice Lovelace"'
done
for variant in sign+enc sign+enc+legacy-disp; do
test_begin_subtest "confirm signed and encrypted PKCS#7 subject ($variant)"
test_subtest_known_broken
output=$(notmuch show --decrypt=true --format=json "id:smime-${variant}@protected-headers.example")
test_json_nodes <<<"$output" \
'signed_subject:[0][0][0]["crypto"]["signed"]["headers"]=["Subject"]' \
'sig_good:[0][0][0]["crypto"]["signed"]["status"][0]["status"]="good"' \
'sig_fpr:[0][0][0]["crypto"]["signed"]["status"][0]["fingerprint"]="702BA4B157F1E2B7D16B0C6A5FFC8A7DE2057DEB"' \
'encrypted:[0][0][0]["crypto"]["decrypted"]={"status":"full","header-mask":{"Subject":"..."}}'
test_begin_subtest "confirm signed and encrypted PKCS#7 subject ($variant) signer User ID"
test_subtest_known_broken
test_json_nodes <<<"$output" \
'sig_uid:[0][0][0]["crypto"]["signed"]["status"][0]["userid"]="CN=Alice Lovelace"'
done
test_begin_subtest "confirm encryption-protected PKCS#7 subject (enc+legacy-disp)"
test_subtest_known_broken
output=$(notmuch show --decrypt=true --format=json "id:smime-enc+legacy-disp@protected-headers.example")
test_json_nodes <<<"$output" \
'encrypted:[0][0][0]["crypto"]["decrypted"]={"status":"full","header-mask":{"Subject":"..."}}' \
'no_sig:[0][0][0]["crypto"]!"signed"'
# TODO: test that a part that looks like a legacy-display in
# multipart/signed, but not encrypted, is indexed and not stripped.
# TODO: test that a legacy-display in a decrypted subpart (not in the
# cryptographic payload) is indexed and not stripped.
# TODO: test that a legacy-display inside multiple MIME layers that
# include an encryption layer (e.g. multipart/encrypted around
# multipart/signed) is stripped and not indexed.
test_done