Hello,

I am a system administrator trying to integrate two pieces of software using 
the SCEP protocol (more on that later in the More Context section) .
Integration was working but one side (SaaS product) changed the algorithms it 
uses for signing and encryption within the PKCS7 message.
After that I am unable to decrypt the PKCS7 messages on my end and get the 
error: "ERROR 139701710696896:error:06065064:digital envelope 
routines:EVP_DecryptFinal_ex:bad decrypt:../crypto/evp/evp_enc.c:597:
message_static_functions.c:221: decryption failed"

>From my current state of investigation it looks highly likely there is a 
>problem with PKCS7_decrypt method which might be unable decrypt the PKCS7/CMS 
>payload if the RSA is used together with OAEP padding.

1. What is a diffrences between pkcs7 
https://github.com/openssl/openssl/tree/681618cfc18b4f01f2c07e823308d30f6f47504b/crypto/pkcs7
 and CMS 
https://github.com/openssl/openssl/tree/681618cfc18b4f01f2c07e823308d30f6f47504b/crypto/cms
 implementations?

If I understand correctly CMS is just newer name for PKCS7 adopted by newer 
RFCs?
Do these two implementations overlap?
Or are there some kind of major diffrence like PKCS7 module being there for 
compatibility with older code and CMS is basically replacement to use for the 
future?

2. Is PKCS7_decrypt method in 
https://github.com/openssl/openssl/blob/681618cfc18b4f01f2c07e823308d30f6f47504b/crypto/pkcs7/pk7_smime.c
 capable of decrypting the PKCS7 payload whebf OAEP padding is used together 
with RSA to encrypt it? If it is indeed not capable of doing that would it be a 
bug or desired behavior?

If found a few pointers:

- 
https://stackoverflow.com/questions/56941480/how-to-set-padding-oaep-for-pkcs7-decrypt-function-using-openssl
 <- Developer is unable to use PKCS7_decrypt with RSA OAEP and forced to switch 
to CMS_decrypt method.
- 
https://stackoverflow.com/questions/34304570/how-to-resolve-the-evp-decryptfinal-ex-bad-decrypt-during-file-decryption
 <- Padding being a source problem of EVP_DecryptFinal_ex:bad decrypt error 
message.

3. How to replace PKCS7_decrypt method CMS_decrypt as easily as possible?

I have no hard proof of the PKCS7_decrypt being the culprit here so I started 
working on simple C program to reproduce the issue.
Problem is my C skills are very rusty and I have no experience working with 
OpenSSL C library.

int PKCS7_decrypt(PKCS7 *p7,                    EVP_PKEY *pkey, X509 *cert, BIO 
*data,                                  int flags);
int CMS_decrypt    (CMS_ContentInfo *cms, EVP_PKEY *pkey, X509 *cert, BIO 
*dcont, BIO *out, unsigned int flags);

Methods are very similiar but input data format it different. It there an 
easyway to convert PKCS7 struct into CMS_ContentInfo struct?

Original usage of PKCS7_decrypt here -> 
https://github.com/openxpki/libscep/blob/4067eae283ce0b3025d414e9d3b6af30def8c093/src/message_static_functions.c


# More Context

My goal is to obtain signed client certificate using the SCEP protocol.

SCEP server: OpenXPKI https://github.com/openxpki/openxpki (Perl) with libscep 
https://github.com/openxpki/libscep library (C). libscep used the OpenSSL.
SCEP client: VMware Workspace ONE UEM SaaS (WSO). Black box. From the error 
codes client produces I strongly suspect they use OpenSSL within .Net code.

Originally WSO SCEP client used these three algorithms for PKCS7 operation: 
SHA-1, RSA (PKCS 1.5 padding or no padding <- can't tell which) and 3DES-CBC.
They made some sort of change (unannouced) and since the last SaaS upgdate WSO 
client uses SHA-2 (256bit), RSA with OAEP padding and AES-256-CBC.
Compare the attached PKCS7 messages (libscep_wso*.p7b). I use 
https://lapo.it/asn1js to decode them easily.
After the change I am unable to decrypt the PKIOperation message on the server 
side.

I suspect the RSA with OAEP is the cause of the problem because using different 
client with SHA-256, AES-256-CBC and RSA decryption works without any problem 
(libscep_sscep_ok.p7b).

Best Regards,
Michal Moravec


Attachment: libscep_wso_after_broken.p7b
Description: libscep_wso_after_broken.p7b

Attachment: libscep_wso_before_ok.p7b
Description: libscep_wso_before_ok.p7b

Attachment: libscep_sscep_ok.p7b
Description: libscep_sscep_ok.p7b

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