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merged 2 commits into from
Jul 31, 2025
Merged

pkcs7: clean up tests #921

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c11c663
pkcs7: only set error_string in the error path
rhenium Jul 31, 2025
58f0022
pkcs7: clean up tests
rhenium Jul 24, 2025
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1 change: 0 additions & 1 deletion Rakefile
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Original file line number Diff line number Diff line change
Expand Up @@ -34,7 +34,6 @@ Rake::TestTask.new(:test_fips_internal) do |t|
'test/openssl/test_ns_spki.rb',
'test/openssl/test_ocsp.rb',
'test/openssl/test_pkcs12.rb',
'test/openssl/test_pkcs7.rb',
'test/openssl/test_ssl.rb',
'test/openssl/test_ts.rb',
'test/openssl/test_x509cert.rb',
Expand Down
15 changes: 8 additions & 7 deletions ext/openssl/ossl_pkcs7.c
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Original file line number Diff line number Diff line change
Expand Up @@ -770,7 +770,6 @@ ossl_pkcs7_verify(int argc, VALUE *argv, VALUE self)
BIO *in, *out;
PKCS7 *p7;
VALUE data;
const char *msg;

GetPKCS7(self, p7);
rb_scan_args(argc, argv, "22", &certs, &store, &indata, &flags);
Expand All @@ -794,14 +793,16 @@ ossl_pkcs7_verify(int argc, VALUE *argv, VALUE self)
ok = PKCS7_verify(p7, x509s, x509st, in, out, flg);
BIO_free(in);
sk_X509_pop_free(x509s, X509_free);
if (ok < 0) ossl_raise(ePKCS7Error, "PKCS7_verify");
msg = ERR_reason_error_string(ERR_peek_error());
ossl_pkcs7_set_err_string(self, msg ? rb_str_new2(msg) : Qnil);
ossl_clear_error();
data = ossl_membio2str(out);
ossl_pkcs7_set_data(self, data);

return (ok == 1) ? Qtrue : Qfalse;
if (ok != 1) {
const char *msg = ERR_reason_error_string(ERR_peek_error());
ossl_pkcs7_set_err_string(self, msg ? rb_str_new_cstr(msg) : Qnil);
ossl_clear_error();
return Qfalse;
}
ossl_pkcs7_set_err_string(self, Qnil);
return Qtrue;
}

static VALUE
Expand Down
172 changes: 109 additions & 63 deletions test/openssl/test_pkcs7.rb
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Original file line number Diff line number Diff line change
Expand Up @@ -6,95 +6,125 @@
class OpenSSL::TestPKCS7 < OpenSSL::TestCase
def setup
super
@rsa1024 = Fixtures.pkey("rsa1024")
@rsa2048 = Fixtures.pkey("rsa2048")
ca = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/CN=CA")
ee1 = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/CN=EE1")
ee2 = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/CN=EE2")
@ca_key = Fixtures.pkey("rsa-1")
@ee1_key = Fixtures.pkey("rsa-2")
@ee2_key = Fixtures.pkey("rsa-3")
ca = OpenSSL::X509::Name.new([["CN", "CA"]])
ee1 = OpenSSL::X509::Name.new([["CN", "EE1"]])
ee2 = OpenSSL::X509::Name.new([["CN", "EE2"]])

ca_exts = [
["basicConstraints","CA:TRUE",true],
["keyUsage","keyCertSign, cRLSign",true],
["subjectKeyIdentifier","hash",false],
["authorityKeyIdentifier","keyid:always",false],
["basicConstraints", "CA:TRUE", true],
["keyUsage", "keyCertSign, cRLSign", true],
["subjectKeyIdentifier", "hash", false],
["authorityKeyIdentifier", "keyid:always", false],
]
@ca_cert = issue_cert(ca, @rsa2048, 1, ca_exts, nil, nil)
@ca_cert = issue_cert(ca, @ca_key, 1, ca_exts, nil, nil)
ee_exts = [
["keyUsage","Non Repudiation, Digital Signature, Key Encipherment",true],
["authorityKeyIdentifier","keyid:always",false],
["extendedKeyUsage","clientAuth, emailProtection, codeSigning",false],
["keyUsage", "nonRepudiation, digitalSignature, keyEncipherment", true],
["authorityKeyIdentifier", "keyid:always", false],
["extendedKeyUsage", "clientAuth, emailProtection, codeSigning", false],
]
@ee1_cert = issue_cert(ee1, @rsa1024, 2, ee_exts, @ca_cert, @rsa2048)
@ee2_cert = issue_cert(ee2, @rsa1024, 3, ee_exts, @ca_cert, @rsa2048)
@ee1_cert = issue_cert(ee1, @ee1_key, 2, ee_exts, @ca_cert, @ca_key)
@ee2_cert = issue_cert(ee2, @ee2_key, 3, ee_exts, @ca_cert, @ca_key)
end

def test_signed
store = OpenSSL::X509::Store.new
store.add_cert(@ca_cert)

data = "aaaaa\nbbbbb\nccccc\n"
ca_certs = [@ca_cert]
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @ee1_key, data, ca_certs)
# TODO: #data contains untranslated content
assert_equal("aaaaa\nbbbbb\nccccc\n", tmp.data)
assert_nil(tmp.error_string)

data = "aaaaa\r\nbbbbb\r\nccccc\r\n"
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, ca_certs)
p7 = OpenSSL::PKCS7.new(tmp.to_der)
assert_nil(p7.data)
assert_nil(p7.error_string)

assert_true(p7.verify([], store))
# AWS-LC does not appear to convert to CRLF automatically
assert_equal("aaaaa\r\nbbbbb\r\nccccc\r\n", p7.data) unless aws_lc?
assert_nil(p7.error_string)

certs = p7.certificates
signers = p7.signers
assert(p7.verify([], store))
assert_equal(data, p7.data)
assert_equal(2, certs.size)
assert_equal(@ee1_cert.subject.to_s, certs[0].subject.to_s)
assert_equal(@ca_cert.subject.to_s, certs[1].subject.to_s)
assert_equal(@ee1_cert.subject, certs[0].subject)
assert_equal(@ca_cert.subject, certs[1].subject)

signers = p7.signers
assert_equal(1, signers.size)
assert_equal(@ee1_cert.serial, signers[0].serial)
assert_equal(@ee1_cert.issuer.to_s, signers[0].issuer.to_s)
assert_equal(@ee1_cert.issuer, signers[0].issuer)
# AWS-LC does not generate authenticatedAttributes
assert_in_delta(Time.now, signers[0].signed_time, 10) unless aws_lc?

assert_false(p7.verify([@ca_cert], OpenSSL::X509::Store.new))
end

def test_signed_flags
store = OpenSSL::X509::Store.new
store.add_cert(@ca_cert)

# Normally OpenSSL tries to translate the supplied content into canonical
# MIME format (e.g. a newline character is converted into CR+LF).
# If the content is a binary, PKCS7::BINARY flag should be used.

#
# PKCS7::NOATTR flag suppresses authenticatedAttributes.
data = "aaaaa\nbbbbb\nccccc\n"
flag = OpenSSL::PKCS7::BINARY | OpenSSL::PKCS7::NOATTR
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, ca_certs, flag)
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @ee1_key, data, [@ca_cert], flag)
p7 = OpenSSL::PKCS7.new(tmp.to_der)
certs = p7.certificates
signers = p7.signers
assert(p7.verify([], store))

assert_true(p7.verify([], store))
assert_equal(data, p7.data)

certs = p7.certificates
assert_equal(2, certs.size)
assert_equal(@ee1_cert.subject.to_s, certs[0].subject.to_s)
assert_equal(@ca_cert.subject.to_s, certs[1].subject.to_s)
assert_equal(@ee1_cert.subject, certs[0].subject)
assert_equal(@ca_cert.subject, certs[1].subject)

signers = p7.signers
assert_equal(1, signers.size)
assert_equal(@ee1_cert.serial, signers[0].serial)
assert_equal(@ee1_cert.issuer.to_s, signers[0].issuer.to_s)
assert_equal(@ee1_cert.issuer, signers[0].issuer)
assert_raise(OpenSSL::PKCS7::PKCS7Error) { signers[0].signed_time }
end

def test_signed_multiple_signers
store = OpenSSL::X509::Store.new
store.add_cert(@ca_cert)

# A signed-data which have multiple signatures can be created
# through the following steps.
# 1. create two signed-data
# 2. copy signerInfo and certificate from one to another

tmp1 = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, [], flag)
tmp2 = OpenSSL::PKCS7.sign(@ee2_cert, @rsa1024, data, [], flag)
data = "aaaaa\r\nbbbbb\r\nccccc\r\n"
tmp1 = OpenSSL::PKCS7.sign(@ee1_cert, @ee1_key, data)
tmp2 = OpenSSL::PKCS7.sign(@ee2_cert, @ee2_key, data)
tmp1.add_signer(tmp2.signers[0])
tmp1.add_certificate(@ee2_cert)

p7 = OpenSSL::PKCS7.new(tmp1.to_der)
certs = p7.certificates
signers = p7.signers
assert(p7.verify([], store))
assert_true(p7.verify([], store))
assert_equal(data, p7.data)

certs = p7.certificates
assert_equal(2, certs.size)

signers = p7.signers
assert_equal(2, signers.size)
assert_equal(@ee1_cert.serial, signers[0].serial)
assert_equal(@ee1_cert.issuer.to_s, signers[0].issuer.to_s)
assert_equal(@ee1_cert.issuer, signers[0].issuer)
assert_equal(@ee2_cert.serial, signers[1].serial)
assert_equal(@ee2_cert.issuer.to_s, signers[1].issuer.to_s)
assert_equal(@ee2_cert.issuer, signers[1].issuer)
end

def test_signed_add_signer
data = "aaaaa\nbbbbb\nccccc\n"
psi = OpenSSL::PKCS7::SignerInfo.new(@ee1_cert, @rsa1024, "sha256")
psi = OpenSSL::PKCS7::SignerInfo.new(@ee1_cert, @ee1_key, "sha256")
p7 = OpenSSL::PKCS7.new
p7.type = :signed
p7.add_signer(psi)
Expand All @@ -113,27 +143,33 @@ def test_signed_add_signer
def test_detached_sign
store = OpenSSL::X509::Store.new
store.add_cert(@ca_cert)
ca_certs = [@ca_cert]

data = "aaaaa\nbbbbb\nccccc\n"
ca_certs = [@ca_cert]
flag = OpenSSL::PKCS7::BINARY|OpenSSL::PKCS7::DETACHED
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, ca_certs, flag)
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @ee1_key, data, ca_certs, flag)
p7 = OpenSSL::PKCS7.new(tmp.to_der)
assert_nothing_raised do
OpenSSL::ASN1.decode(p7)
end
assert_predicate(p7, :detached?)
assert_true(p7.detached)

certs = p7.certificates
signers = p7.signers
assert(!p7.verify([], store))
assert(p7.verify([], store, data))
assert_false(p7.verify([], store))
# FIXME: Should it be nil?
assert_equal("", p7.data)
assert_match(/no content|NO_CONTENT/, p7.error_string)

assert_true(p7.verify([], store, data))
assert_equal(data, p7.data)
assert_nil(p7.error_string)

certs = p7.certificates
assert_equal(2, certs.size)
assert_equal(@ee1_cert.subject.to_s, certs[0].subject.to_s)
assert_equal(@ca_cert.subject.to_s, certs[1].subject.to_s)
assert_equal(@ee1_cert.subject, certs[0].subject)
assert_equal(@ca_cert.subject, certs[1].subject)

signers = p7.signers
assert_equal(1, signers.size)
assert_equal(@ee1_cert.serial, signers[0].serial)
assert_equal(@ee1_cert.issuer.to_s, signers[0].issuer.to_s)
assert_equal(@ee1_cert.issuer, signers[0].issuer)
end

def test_signed_authenticated_attributes
Expand Down Expand Up @@ -181,6 +217,8 @@ def test_signed_authenticated_attributes
end

def test_enveloped
omit_on_fips # PKCS #1 v1.5 padding

certs = [@ee1_cert, @ee2_cert]
cipher = OpenSSL::Cipher::AES.new("128-CBC")
data = "aaaaa\nbbbbb\nccccc\n"
Expand All @@ -191,15 +229,20 @@ def test_enveloped
assert_equal(:enveloped, p7.type)
assert_equal(2, recip.size)

assert_equal(@ca_cert.subject.to_s, recip[0].issuer.to_s)
assert_equal(2, recip[0].serial)
assert_equal(data, p7.decrypt(@rsa1024, @ee1_cert))
assert_equal(@ca_cert.subject, recip[0].issuer)
assert_equal(@ee1_cert.serial, recip[0].serial)
assert_equal(16, @ee1_key.decrypt(recip[0].enc_key).size)
assert_equal(data, p7.decrypt(@ee1_key, @ee1_cert))

assert_equal(@ca_cert.subject.to_s, recip[1].issuer.to_s)
assert_equal(3, recip[1].serial)
assert_equal(data, p7.decrypt(@rsa1024, @ee2_cert))
assert_equal(@ca_cert.subject, recip[1].issuer)
assert_equal(@ee2_cert.serial, recip[1].serial)
assert_equal(data, p7.decrypt(@ee2_key, @ee2_cert))

assert_equal(data, p7.decrypt(@rsa1024))
assert_equal(data, p7.decrypt(@ee1_key))

assert_raise(OpenSSL::PKCS7::PKCS7Error) {
p7.decrypt(@ca_key, @ca_cert)
}

# Default cipher has been removed in v3.3
assert_raise_with_message(ArgumentError, /RC2-40-CBC/) {
Expand Down Expand Up @@ -232,7 +275,8 @@ def test_data
# PKCS7#verify can't distinguish verification failure and other errors
store = OpenSSL::X509::Store.new
assert_equal(false, p7.verify([@ee1_cert], store))
assert_raise(OpenSSL::PKCS7::PKCS7Error) { p7.decrypt(@rsa1024) }
assert_match(/wrong content type|WRONG_CONTENT_TYPE/, p7.error_string)
assert_raise(OpenSSL::PKCS7::PKCS7Error) { p7.decrypt(@ee1_key) }
end

def test_empty_signed_data_ruby_bug_19974
Expand Down Expand Up @@ -293,7 +337,7 @@ def test_smime
ca_certs = [@ca_cert]

data = "aaaaa\r\nbbbbb\r\nccccc\r\n"
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, ca_certs)
tmp = OpenSSL::PKCS7.sign(@ee1_cert, @ee1_key, data, ca_certs)
p7 = OpenSSL::PKCS7.new(tmp.to_der)
smime = OpenSSL::PKCS7.write_smime(p7)
assert_equal(true, smime.start_with?(<<END))
Expand Down Expand Up @@ -355,6 +399,8 @@ def test_degenerate_pkcs7
end

def test_decode_ber_constructed_string
omit_on_fips # PKCS #1 v1.5 padding

p7 = OpenSSL::PKCS7.encrypt([@ee1_cert], "content", "aes-128-cbc")

# Make an equivalent BER to p7.to_der. Here we convert the encryptedContent
Expand All @@ -378,8 +424,8 @@ def test_decode_ber_constructed_string
assert_not_equal(p7.to_der, asn1.to_der)
assert_equal(p7.to_der, OpenSSL::PKCS7.new(asn1.to_der).to_der)

assert_equal("content", OpenSSL::PKCS7.new(p7.to_der).decrypt(@rsa1024))
assert_equal("content", OpenSSL::PKCS7.new(asn1.to_der).decrypt(@rsa1024))
assert_equal("content", OpenSSL::PKCS7.new(p7.to_der).decrypt(@ee1_key))
assert_equal("content", OpenSSL::PKCS7.new(asn1.to_der).decrypt(@ee1_key))
end
end

Expand Down
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