[ruby/openssl] pkcs7: fix test failure on RHEL 9

The test case test_split_content fails on RHEL 9 and Fedora 41 because
their OpenSSL packages do not accept SHA-1 signatures. This was only
caught after commit https://github.com/ruby/openssl/commit/69fd7f886313 added the missing assertion.

While the example PKCS#7 structures could be simply regenerated with
SHA-256, this test case could be simplified because it is checking two
different things.

Replace test_split_content with separate test cases: one verifying
signed-data authenticatedAttributes and another for decoding BER input.

Fixes https://github.com/ruby/openssl/issues/875

https://github.com/ruby/openssl/commit/b32406b0c1

1 files changed, 76 insertions, 75 deletions

diff --git a/test/openssl/test_pkcs7.rb b/test/openssl/test_pkcs7.rb
index 0ade5bb164..e8973f73fe 100644
--- a/test/openssl/test_pkcs7.rb
+++ b/test/openssl/test_pkcs7.rb
@@ -46,13 +46,15 @@ class OpenSSL::TestPKCS7 < OpenSSL::TestCase
     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)
+    # AWS-LC does not generate authenticatedAttributes
+    assert_in_delta(Time.now, signers[0].signed_time, 10) unless aws_lc?
 
     # 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.
 
     data = "aaaaa\nbbbbb\nccccc\n"
-    flag = OpenSSL::PKCS7::BINARY
+    flag = OpenSSL::PKCS7::BINARY | OpenSSL::PKCS7::NOATTR
     tmp = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, ca_certs, flag)
     p7 = OpenSSL::PKCS7.new(tmp.to_der)
     certs = p7.certificates
@@ -65,6 +67,7 @@ class OpenSSL::TestPKCS7 < OpenSSL::TestCase
     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_raise(OpenSSL::PKCS7::PKCS7Error) { signers[0].signed_time }
 
     # A signed-data which have multiple signatures can be created
     # through the following steps.
@@ -133,6 +136,50 @@ class OpenSSL::TestPKCS7 < OpenSSL::TestCase
     assert_equal(@ee1_cert.issuer.to_s, signers[0].issuer.to_s)
   end
 
+  def test_signed_authenticated_attributes
+    # Using static PEM data because AWS-LC does not support generating one
+    # with authenticatedAttributes.
+    #
+    # p7 was generated with OpenSSL 3.4.1 with this program with commandline
+    # "faketime 2025-04-03Z ruby prog.rb":
+    #
+    #   require_relative "test/openssl/utils"
+    #   include OpenSSL::TestUtils
+    #   key = Fixtures.pkey("p256")
+    #   cert = issue_cert(OpenSSL::X509::Name.new([["CN", "cert"]]), key, 1, [], nil, nil)
+    #   p7 = OpenSSL::PKCS7.sign(cert, key, "content", [])
+    #   puts p7.to_pem
+    p7 = OpenSSL::PKCS7.new(<<~EOF)
+-----BEGIN PKCS7-----
+MIICvgYJKoZIhvcNAQcCoIICrzCCAqsCAQExDzANBglghkgBZQMEAgEFADAWBgkq
+hkiG9w0BBwGgCQQHY29udGVudKCCAQ4wggEKMIGxoAMCAQICAQEwCgYIKoZIzj0E
+AwIwDzENMAsGA1UEAwwEY2VydDAeFw0yNTA0MDIyMzAwMDFaFw0yNTA0MDMwMTAw
+MDFaMA8xDTALBgNVBAMMBGNlcnQwWTATBgcqhkjOPQIBBggqhkjOPQMBBwNCAAQW
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+87Ukp0XiomZLf11eekQ2MAoGCCqGSM49BAMCA0gAMEUCIEg1fDI8b3hZAArgniVk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+-----END PKCS7-----
+    EOF
+
+    cert = p7.certificates[0]
+    store = OpenSSL::X509::Store.new.tap { |store|
+      store.time = Time.utc(2025, 4, 3)
+      store.add_cert(cert)
+    }
+    assert_equal(true, p7.verify([], store))
+    assert_equal(1, p7.signers.size)
+    signer = p7.signers[0]
+    assert_in_delta(Time.utc(2025, 4, 3), signer.signed_time, 10)
+  end
+
   def test_enveloped
     certs = [@ee1_cert, @ee2_cert]
     cipher = OpenSSL::Cipher::AES.new("128-CBC")
@@ -307,80 +354,34 @@ END
     end
   end
 
-  def test_split_content
-     pend "AWS-LC ASN.1 parsers has no current support for parsing indefinite BER constructed strings" if aws_lc?
-
-     pki_message_pem = <<END
------BEGIN PKCS7-----
-MIIHSwYJKoZIhvcNAQcCoIIHPDCCBzgCAQExCzAJBgUrDgMCGgUAMIIDiAYJKoZI
-hvcNAQcBoIIDeQSCA3UwgAYJKoZIhvcNAQcDoIAwgAIBADGCARAwggEMAgEAMHUw
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-/LYOMY+/b6UDCUSR7RTN7XfrtAqDEzSdzdJkOWm1jvM8gkLmxpZdvxG3ZvDYnEQE
-5Nq+un5nAny1wf3rWierBAjE5ntiAmgs5AAAAAAAAAAAAACgggHqMIIB5jCCAU+g
-AwIBAgIBATANBgkqhkiG9w0BAQUFADAvMS0wKwYDVQQDEyQwQUM5RjAyNi1EQ0VB
-LTRDMTItOTEyNy1DMEZEN0QyQThCNUEwHhcNMTIxMDE5MDk0NTQ3WhcNMTMxMDE5
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-BzEqEygwRkU3QzJEQTVEMDc2NzFFOTcxNDlCNUE3MDRCMERDNkM4MDYwRDJBMA0G
-CSqGSIb3DQEBAQUABIGAWUNdzvU2iiQOtihBwF0h48Nnw/2qX8uRjg6CVTOMcGji
-BxjUMifEbT//KJwljshl4y3yBLqeVYLOd04k6aKSdjgdZnrnUPI6p5tL5PfJkTAE
-L6qflZ9YCU5erE4T5U98hCQBMh4nOYxgaTjnZzhpkKQuEiKq/755cjzTzlI/eok=
------END PKCS7-----
-END
-    pki_message_content_pem = <<END
------BEGIN PKCS7-----
-MIIDawYJKoZIhvcNAQcDoIIDXDCCA1gCAQAxggEQMIIBDAIBADB1MHAxEDAOBgNV
-BAoMB2V4YW1wbGUxFzAVBgNVBAMMDlRBUk1BQyBST09UIENBMSIwIAYJKoZIhvcN
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-tcH961onq8Tme2ICaCzk
------END PKCS7-----
-END
-    pki_msg = OpenSSL::PKCS7.new(pki_message_pem)
-    store = OpenSSL::X509::Store.new
-    assert_equal(true, pki_msg.verify(nil, store, nil, OpenSSL::PKCS7::NOVERIFY))
-    p7enc = OpenSSL::PKCS7.new(pki_msg.data)
-    assert_equal(pki_message_content_pem, p7enc.to_pem)
+  def test_decode_ber_constructed_string
+    pend "AWS-LC ASN.1 parsers has no current support for parsing indefinite BER constructed strings" if aws_lc?
+
+    p7 = OpenSSL::PKCS7.encrypt([@ee1_cert], "content", "aes-128-cbc")
+
+    # Make an equivalent BER to p7.to_der. Here we convert the encryptedContent
+    # field of EncryptedContentInfo into a constructed encoding using the
+    # indefinite length form.
+    # See https://www.rfc-editor.org/rfc/rfc2315#section-10.1
+    asn1 = OpenSSL::ASN1.decode(p7.to_der)
+    asn1.indefinite_length = true
+    enveloped_data_explicit_tag = asn1.value[1]
+    enveloped_data_explicit_tag.indefinite_length = true
+    enveloped_data = enveloped_data_explicit_tag.value[0]
+    enveloped_data.indefinite_length = true
+    encrypted_content_info = enveloped_data.value[2]
+    encrypted_content_info.indefinite_length = true
+    orig = encrypted_content_info.value[2]
+    encrypted_content_info.value[2] = OpenSSL::ASN1::ASN1Data.new([
+      OpenSSL::ASN1::OctetString(orig.value[...5]),
+      OpenSSL::ASN1::OctetString(orig.value[5...]),
+    ], 0, :CONTEXT_SPECIFIC).tap { |x| x.indefinite_length = true }
+
+    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))
   end
 end