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fix(mail): S/MIME improvements

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Fixes #4891
Fixes #5450
This commit is contained in:
Francis Lachapelle
2022-01-21 16:24:13 -05:00
parent b061046992
commit 54b163da2d
6 changed files with 262 additions and 100 deletions
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6
SoObjects/Mailer/NSData+SMIME.h
View File

@@ -28,13 +28,15 @@
@interface NSData (SOGoMailSMIME)
- (NSData *) signUsingCertificateAndKey: (NSData *) theData;
- (NSData *) encryptUsingCertificate: (NSData *) theData;
- (NSData *) encryptUsingCertificate: (NSData *) theData
andAlgos: (NSArray *) theAlgos;
- (NSData *) decryptUsingCertificate: (NSData *) theData;
- (NGMimeMessage *) messageFromEncryptedDataAndCertificate: (NSData *) theCertificate;
- (NSData *) embeddedContent;
- (NGMimeMessage *) messageFromOpaqueSignedData;
- (NSData *) convertPKCS12ToPEMUsingPassword: (NSString *) thePassword;
- (NSData *) signersFromPKCS7;
- (NSData *) signersFromCMS;
- (NSArray *) algosFromCMS;
- (NSDictionary *) certificateDescription;
@end

299
SoObjects/Mailer/NSData+SMIME.m
View File

@@ -18,6 +18,7 @@
* Boston, MA 02111-1307, USA.
*/
#import <Foundation/NSValue.h>
#import <Foundation/NSArray.h>
#import <Foundation/NSDictionary.h>
#import <Foundation/NSString.h>
@@ -27,12 +28,13 @@
#import <NGExtensions/NSString+Encoding.h>
#import <NGExtensions/NSObject+Logs.h>
#import <NGMime/NGMimeType.h>
#import <NGMail/NGMimeMessageParser.h>
#if defined(HAVE_OPENSSL) || defined(HAVE_GNUTLS)
#include <openssl/bio.h>
#include <openssl/err.h>
#include <openssl/pkcs7.h>
#include <openssl/cms.h>
#include <openssl/pkcs12.h>
#include <openssl/pem.h>
#endif
@@ -54,18 +56,18 @@
X509 *link = NULL;
STACK_OF(X509) *chain = NULL;
EVP_PKEY *skey = NULL;
PKCS7 *p7 = NULL;
CMS_ContentInfo *cms = NULL;
BUF_MEM *bptr;
unsigned int len, slen;
const char* bytes;
const char* sbytes;
int flags = PKCS7_STREAM | PKCS7_DETACHED | PKCS7_CRLFEOL;
int flags = CMS_STREAM | CMS_DETACHED | CMS_CRLFEOL;
OpenSSL_add_all_algorithms();
ERR_load_crypto_strings();
bytes = [theData bytes];
len = [theData length];
tbio = BIO_new_mem_buf((void *)bytes, len);
@@ -77,13 +79,13 @@
NSLog(@"FATAL: failed to read certificate for signing.");
goto cleanup;
}
chain = sk_X509_new_null();
while (link = PEM_read_bio_X509_AUX(tbio, NULL, 0, NULL))
sk_X509_unshift(chain, link);
BIO_reset(tbio);
skey = PEM_read_bio_PrivateKey(tbio, NULL, 0, NULL);
if (!skey)
@@ -91,34 +93,34 @@
NSLog(@"FATAL: failed to read private key for signing.");
goto cleanup;
}
// We sign
sbytes = [self bytes];
slen = [self length];
sbio = BIO_new_mem_buf((void *)sbytes, slen);
p7 = PKCS7_sign(scert, skey, (sk_X509_num(chain) > 0) ? chain : NULL, sbio, flags);
cms = CMS_sign(scert, skey, (sk_X509_num(chain) > 0) ? chain : NULL, sbio, flags);
if (!p7)
if (!cms)
{
NSLog(@"FATAL: failed to sign message.");
goto cleanup;
}
// We output
obio = BIO_new(BIO_s_mem());
SMIME_write_PKCS7(obio, p7, sbio, flags);
SMIME_write_CMS(obio, cms, sbio, flags);
BIO_get_mem_ptr(obio, &bptr);
output = [NSData dataWithBytes: bptr->data length: bptr->length];
cleanup:
PKCS7_free(p7);
CMS_ContentInfo_free(cms);
sk_X509_pop_free(chain, X509_free);
X509_free(scert);
X509_free(scert);
BIO_free(tbio);
BIO_free(sbio);
BIO_free(obio);
return output;
}
@@ -126,21 +128,25 @@
//
//
- (NSData *) encryptUsingCertificate: (NSData *) theData
andAlgos: (NSArray *) theAlgos
{
NSData *output = NULL;
BUF_MEM *bptr = NULL;
BIO *tbio = NULL, *sbio = NULL, *obio = NULL;
X509 *rcert = NULL;
PKCS7 *p7 = NULL;
CMS_ContentInfo *cms = NULL;
STACK_OF(X509) *recips = NULL;
int i;
const EVP_CIPHER *cipher = NULL;
unsigned int len, slen;
const char* bytes;
const char* sbytes;
int flags = PKCS7_STREAM;
int flags = CMS_STREAM;
OpenSSL_add_all_algorithms();
ERR_load_crypto_strings();
@@ -162,9 +168,9 @@
NSLog(@"FATAL: unable to read certificate for encryption");
goto cleanup;
}
recips = sk_X509_new_null();
if (!recips || !sk_X509_push(recips, rcert))
{
NSLog(@"FATAL: unable to push certificate into stack");
@@ -173,15 +179,70 @@
rcert = NULL;
if (theAlgos)
{
// pick first supported cipher suggested by peer
for (i = 0; cipher == NULL && i < [theAlgos count]; i++)
{
int nid = [[theAlgos objectAtIndex: i] intValue];
switch (nid)
{
// ciphers from RFC8551
//No support for AuthEnvelopedData in OpenSSL yet
//case NID_chacha20_poly1305:
//case NID_aes_256_gcm:
//case NID_aes_128_gcm:
#ifdef NID_aes_128_cbc
case NID_aes_128_cbc:
#endif
// plus ciphers from RFC5751
#ifdef NID_aes_192_cbc
case NID_aes_192_cbc:
#endif
#ifdef NID_aes_256_cbc
case NID_aes_256_cbc:
#endif
#ifdef NID_des_ede3_cbc
case NID_des_ede3_cbc:
#endif
cipher = EVP_get_cipherbynid(nid);
break;
default:
break;
}
}
// no matching cipher - use default cipher
if (cipher == NULL)
#ifndef OPENSSL_NO_AES
cipher = EVP_aes_128_cbc();
#elif !defined(OPENSSL_NO_DES)
cipher = EVP_des_ede3_cbc();
#else
#error "Neither AES nor 3DES available"
#endif
}
else
{
// ATM theAlgos == NULL means we're storing a draft with the writer's own key
#ifndef OPENSSL_NO_AES
cipher = EVP_aes_128_cbc();
#elif !defined(OPENSSL_NO_DES)
cipher = EVP_des_ede3_cbc();
#else
#error "Neither AES nor 3DES available"
#endif
}
// Get the bytes to encrypt
sbytes = [self bytes];
slen = [self length];
sbio = BIO_new_mem_buf((void *)sbytes, slen);
// Encrypt
p7 = PKCS7_encrypt(recips, sbio, EVP_des_ede3_cbc(), flags);
cms = CMS_encrypt(recips, sbio, cipher, flags);
if (!p7)
if (!cms)
{
NSLog(@"FATAL: unable to encrypt message");
goto cleanup;
@@ -189,19 +250,19 @@
// We output the S/MIME encrypted message
obio = BIO_new(BIO_s_mem());
if (!SMIME_write_PKCS7(obio, p7, sbio, flags))
if (!SMIME_write_CMS(obio, cms, sbio, flags))
{
NSLog(@"FATAL: unable to write PKCS7 output");
NSLog(@"FATAL: unable to write CMS output");
goto cleanup;
}
BIO_get_mem_ptr(obio, &bptr);
output = [NSData dataWithBytes: bptr->data length: bptr->length];
cleanup:
PKCS7_free(p7);
X509_free(rcert);
CMS_ContentInfo_free(cms);
X509_free(rcert);
BIO_free(tbio);
BIO_free(sbio);
BIO_free(obio);
@@ -216,16 +277,16 @@
{
NSData *output = NULL;
BIO *tbio, *sbio, *obio;
BIO *tbio, *sbio = NULL, *obio = NULL;
BUF_MEM *bptr;
X509 *scert = NULL;
EVP_PKEY *skey = NULL;
PKCS7 *p7 = NULL;
CMS_ContentInfo *cms = NULL;
unsigned int len, slen;
const char* bytes;
const char* sbytes;
OpenSSL_add_all_algorithms();
ERR_load_crypto_strings();
@@ -241,8 +302,8 @@
{
NSLog(@"FATAL: could not read certificate for decryption");
goto cleanup;
}
}
BIO_reset(tbio);
skey = PEM_read_bio_PrivateKey(tbio, NULL, 0, NULL);
@@ -251,15 +312,15 @@
{
NSLog(@"FATAL: could not read private key for decryption");
goto cleanup;
}
}
sbytes = [self bytes];
slen = [self length];
sbio = BIO_new_mem_buf((void *)sbytes, slen);
p7 = SMIME_read_PKCS7(sbio, NULL);
cms = SMIME_read_CMS(sbio, NULL);
if (!p7)
if (!cms)
{
NSLog(@"FATAL: could not read the content to be decrypted");
goto cleanup;
@@ -267,24 +328,24 @@
// We output the S/MIME encrypted message
obio = BIO_new(BIO_s_mem());
if (!PKCS7_decrypt(p7, skey, scert, obio, 0))
if (!CMS_decrypt(cms, skey, scert, NULL, obio, 0))
{
NSLog(@"FATAL: could not decrypt content");
goto cleanup;
}
BIO_get_mem_ptr(obio, &bptr);
output = [NSData dataWithBytes: bptr->data length: bptr->length];
cleanup:
PKCS7_free(p7);
X509_free(scert);
CMS_ContentInfo_free(cms);
X509_free(scert);
BIO_free(sbio);
BIO_free(tbio);
BIO_free(obio);
return output;
}
@@ -295,10 +356,10 @@
{
NGMimeMessageParser *parser;
NGMimeMessage *message;
NSData *decryptedData;
NSData *decryptedData;
NGMimeType *contentType;
NSString *type, *subtype, *smimetype;
decryptedData = [self decryptUsingCertificate: theCertificate];
parser = [[NGMimeMessageParser alloc] init];
message = [parser parsePartFromData: decryptedData];
@@ -329,15 +390,15 @@
{
NSData *output = NULL;
BIO *sbio, *obio;
BIO *sbio, *obio = NULL;
BUF_MEM *bptr;
PKCS7 *p7 = NULL;
CMS_ContentInfo *cms = NULL;
sbio = BIO_new_mem_buf((void *)[self bytes], [self length]);
p7 = SMIME_read_PKCS7(sbio, NULL);
cms = SMIME_read_CMS(sbio, NULL);
if (!p7)
if (!cms)
{
NSLog(@"FATAL: could not read the signature");
goto cleanup;
@@ -346,7 +407,7 @@
// We output the S/MIME encrypted message
obio = BIO_new(BIO_s_mem());
if (!PKCS7_verify(p7, NULL, NULL, NULL, obio, PKCS7_NOVERIFY|PKCS7_NOSIGS))
if (!CMS_verify(cms, NULL, NULL, NULL, obio, CMS_NOVERIFY|CMS_NOSIGS))
{
NSLog(@"FATAL: could not extract content");
goto cleanup;
@@ -357,7 +418,7 @@
output = [NSData dataWithBytes: bptr->data length: bptr->length];
cleanup:
PKCS7_free(p7);
CMS_ContentInfo_free(cms);
BIO_free(sbio);
BIO_free(obio);
@@ -388,7 +449,7 @@
{
NSData *output = NULL;
BIO *ibio, *obio;
BIO *ibio, *obio = NULL;
EVP_PKEY *pkey;
BUF_MEM *bptr;
PKCS12 *p12;
@@ -396,7 +457,7 @@
const char* bytes;
int i, len;
STACK_OF(X509) *ca = NULL;
OpenSSL_add_all_algorithms();
@@ -405,7 +466,7 @@
bytes = [self bytes];
len = [self length];
ibio = BIO_new_mem_buf((void *)bytes, len);
p12 = d2i_PKCS12_bio(ibio, NULL);
if (!p12)
@@ -419,7 +480,7 @@
NSLog(@"FATAL: could not parse PKCS12 certificate with provided password");
return nil;
}
// We output everything in PEM
obio = BIO_new(BIO_s_mem());
@@ -433,7 +494,7 @@
{
PEM_write_bio_X509(obio, cert);
}
if (ca && sk_X509_num(ca))
{
for (i = 0; i < sk_X509_num(ca); i++)
@@ -446,46 +507,50 @@
cleanup:
PKCS12_free(p12);
BIO_free(ibio);
BIO_free(obio);
BIO_free(ibio);
BIO_free(obio);
return output;
}
//
//
//
- (NSData *) signersFromPKCS7
- (NSData *) signersFromCMS
{
NSData *output = NULL;
STACK_OF(X509) *certs = NULL;
BIO *ibio, *obio;
BIO *ibio, *obio = NULL, *dummybio = NULL;
BUF_MEM *bptr;
PKCS7 *p7;
CMS_ContentInfo *cms;
const char* bytes;
int i, len;
OpenSSL_add_all_algorithms();
ERR_load_crypto_strings();
bytes = [self bytes];
len = [self length];
ibio = BIO_new_mem_buf((void *)bytes, len);
p7 = d2i_PKCS7_bio(ibio, NULL);
if (!p7)
cms = d2i_CMS_bio(ibio, NULL);
if (!cms)
{
NSLog(@"FATAL: could not read PKCS7 content");
NSLog(@"FATAL: could not read CMS content");
goto cleanup;
}
// before calling CMS_get0_signers(), CMS_verify() must be called
dummybio = BIO_new(BIO_s_mem());
CMS_verify(cms, NULL, NULL, dummybio, NULL, CMS_NO_SIGNER_CERT_VERIFY | CMS_NO_ATTR_VERIFY | CMS_NO_CONTENT_VERIFY);
ERR_clear_error();
// We output everything in PEM
obio = BIO_new(BIO_s_mem());
certs = PKCS7_get0_signers(p7, NULL, 0);
certs = CMS_get0_signers(cms);
if (certs != NULL)
{
X509 *x;
@@ -503,13 +568,93 @@
output = [NSData dataWithBytes: bptr->data length: bptr->length];
cleanup:
PKCS7_free(p7);
BIO_free(ibio);
BIO_free(obio);
CMS_ContentInfo_free(cms);
BIO_free(dummybio);
BIO_free(ibio);
BIO_free(obio);
return output;
}
// Implementation based on "STACK_OF(X509_ALGOR) *PKCS7_get_smimecap(PKCS7_SIGNER_INFO *si)"
STACK_OF(X509_ALGOR) *CMS_get_smimecap(CMS_SignerInfo *si)
{
X509_ATTRIBUTE *attr;
ASN1_TYPE *cap;
const unsigned char *p;
attr = CMS_signed_get_attr(si, CMS_signed_get_attr_by_NID(si, NID_SMIMECapabilities, -1));
if (!attr)
return NULL;
cap = X509_ATTRIBUTE_get0_type(attr, 0);
if (!cap || (cap->type != V_ASN1_SEQUENCE))
return NULL;
p = cap->value.sequence->data;
return (STACK_OF(X509_ALGOR) *)
ASN1_item_d2i(NULL, &p, cap->value.sequence->length,
ASN1_ITEM_rptr(X509_ALGORS));
}
- (NSArray *) algosFromCMS
{
NSMutableArray *algos = [[NSMutableArray alloc] initWithCapacity: 10];
STACK_OF(CMS_SignerInfo) *signerinfos;
BIO *ibio;
CMS_ContentInfo *cms;
const ASN1_OBJECT *paobj;
int pptype;
int nid;
const char* bytes;
int i, j, len;
OpenSSL_add_all_algorithms();
ERR_load_crypto_strings();
bytes = [self bytes];
len = [self length];
ibio = BIO_new_mem_buf((void *)bytes, len);
cms = d2i_CMS_bio(ibio, NULL);
if (!cms)
{
NSLog(@"FATAL: could not read CMS content");
goto cleanup;
}
signerinfos = CMS_get0_SignerInfos(cms);
if (signerinfos != NULL)
{
for (i = 0; i < sk_CMS_SignerInfo_num(signerinfos); i++)
{
CMS_SignerInfo *si = sk_CMS_SignerInfo_value(signerinfos, i);
STACK_OF(X509_ALGOR) *smimecap = CMS_get_smimecap(si);
if (smimecap != NULL)
{
for (j = 0; j < sk_X509_ALGOR_num(smimecap); j++)
{
X509_ALGOR_get0(&paobj, &pptype, NULL, sk_X509_ALGOR_value(smimecap, j));
nid = OBJ_obj2nid(paobj);
// Of all ciphers commonly used for S/MIME only RC2 has a keylength parameter
// As RC2 is outdated it's ok to ignore all ciphers with parameter
if (nid != NID_undef && pptype == V_ASN1_UNDEF)
[algos addObject: [NSNumber numberWithInt: nid]];
}
}
}
}
cleanup:
CMS_ContentInfo_free(cms);
BIO_free(ibio);
return algos;
}
/**
* Extract usefull information from PEM certificate
*/

14
SoObjects/Mailer/SOGoDraftObject.m
View File

@@ -1866,7 +1866,8 @@ static NSString *userAgent = nil;
{
NGMimeMessageGenerator *generator, *partGenerator;
NGMimeMessage *mimeMessage;
NSData *certificate, *content;
NSData *certificate, *content, *p7s;
NSArray *algos;
NGMutableHashMap *hashMap;
NGMimeMessage *message;
NSMutableData *d;
@@ -1910,17 +1911,22 @@ static NSString *userAgent = nil;
lookupName: @"Contacts"
inContext: context
acquire: NO];
certificate = [[contactFolders certificateForEmail: theRecipient] signersFromPKCS7];
p7s = [contactFolders certificateForEmail: theRecipient];
certificate = [p7s signersFromCMS];
algos = [p7s algosFromCMS];
}
else
certificate = [[self mailAccountFolder] certificate];
{
certificate = [[self mailAccountFolder] certificate];
algos = nil;
}
// We check if we have a valid certificate. We can have nil here coming from [[self mailAccountFolder] certificate].
// This can happen if one sends an encrypted mail, but actually never uploaded
// a PKCS#12 file to SOGo for his/her own usage and we're trying to save an encrypted
// version of the message in the current user's Sent folder
if (certificate)
content = [content encryptUsingCertificate: certificate];
content = [content encryptUsingCertificate: certificate andAlgos: algos];
}
finish_smime:

2
UI/Contacts/UIxContactActions.m
View File

@@ -160,7 +160,7 @@
if (pkcs7)
{
data = [[pkcs7 signersFromPKCS7] certificateDescription];
data = [[pkcs7 signersFromCMS] certificateDescription];
if (data)
{
response = [self responseWithStatus: 200 andJSONRepresentation: data];

22
UI/MailPartViewers/UIxMailPartEncryptedViewer.m
View File

@@ -23,7 +23,7 @@
#include <openssl/ssl.h>
#include <openssl/bio.h>
#include <openssl/err.h>
#include <openssl/pkcs7.h>
#include <openssl/cms.h>
#include <openssl/x509.h>
#include <openssl/x509v3.h>
#endif
@@ -101,8 +101,8 @@
STACK_OF(X509) *certs;
X509_STORE *x509Store;
BIO *msgBio, *obio;
PKCS7 *p7;
BIO *msgBio, *obio = NULL;
CMS_ContentInfo *cms;
int err, i;
ERR_clear_error();
@@ -110,21 +110,25 @@
msgBio = BIO_new_mem_buf ((void *) [signedData bytes], [signedData length]);
output = NULL;
p7 = SMIME_read_PKCS7(msgBio, NULL);
cms = SMIME_read_CMS(msgBio, NULL);
certs = NULL;
certificates = [NSMutableArray array];
emails = [NSMutableArray array];
validationMessage = nil;
if (p7)
if (cms)
{
if (OBJ_obj2nid(p7->type) == NID_pkcs7_signed)
if (OBJ_obj2nid(CMS_get0_type(cms)) == NID_pkcs7_signed)
{
NSString *subject, *issuer;
X509 *x;
certs = p7->d.sign->cert;
BIO *dummybio = BIO_new(BIO_s_mem());
CMS_verify(cms, NULL, NULL, dummybio, NULL, CMS_NO_SIGNER_CERT_VERIFY | CMS_NO_ATTR_VERIFY | CMS_NO_CONTENT_VERIFY);
ERR_clear_error();
BIO_free(dummybio);
certs = CMS_get0_signers(cms);
for (i = 0; i < sk_X509_num(certs); i++)
{
@@ -171,7 +175,7 @@
x509Store = [self _setupVerify];
obio = BIO_new(BIO_s_mem());
validSignature = (PKCS7_verify(p7, NULL, x509Store, NULL,
validSignature = (CMS_verify(cms, NULL, x509Store, NULL,
obio, 0) == 1);
err = ERR_get_error();
@@ -214,7 +218,7 @@
}
}
PKCS7_free(p7);
CMS_ContentInfo_free(cms);
BIO_free (msgBio);
BIO_free (obio);

19
UI/MailPartViewers/UIxMailPartSignedViewer.m
View File

@@ -21,7 +21,7 @@
#if defined(HAVE_OPENSSL) || defined(HAVE_GNUTLS)
#include <openssl/bio.h>
#include <openssl/err.h>
#include <openssl/pkcs7.h>
#include <openssl/cms.h>
#include <openssl/x509.h>
#include <openssl/x509v3.h>
#endif
@@ -99,7 +99,7 @@
STACK_OF(X509) *certs;
X509_STORE *x509Store;
BIO *msgBio, *inData;
PKCS7 *p7;
CMS_ContentInfo *cms;
int err, i;
ERR_clear_error();
@@ -112,21 +112,25 @@
msgBio = BIO_new_mem_buf ((void *) [signedData bytes], [signedData length]);
inData = NULL;
p7 = SMIME_read_PKCS7(msgBio, &inData);
cms = SMIME_read_CMS(msgBio, &inData);
certs = NULL;
certificates = [NSMutableArray array];
emails = [NSMutableArray array];
validationMessage = nil;
if (p7)
if (cms)
{
if (OBJ_obj2nid(p7->type) == NID_pkcs7_signed)
if (OBJ_obj2nid(CMS_get0_type(cms)) == NID_pkcs7_signed)
{
NSString *subject, *issuer;
X509 *x;
certs = PKCS7_get0_signers(p7, NULL, 0);
BIO *dummybio = BIO_new(BIO_s_mem());
CMS_verify(cms, NULL, NULL, dummybio, NULL, CMS_NO_SIGNER_CERT_VERIFY | CMS_NO_ATTR_VERIFY | CMS_NO_CONTENT_VERIFY);
ERR_clear_error();
BIO_free(dummybio);
certs = CMS_get0_signers(cms);
for (i = 0; i < sk_X509_num(certs); i++)
{
@@ -172,7 +176,7 @@
else
{
x509Store = [self _setupVerify];
validSignature = (PKCS7_verify(p7, NULL, x509Store, inData,
validSignature = (CMS_verify(cms, NULL, x509Store, inData,
NULL, PKCS7_DETACHED) == 1);
err = ERR_get_error();
@@ -205,6 +209,7 @@
}
CMS_ContentInfo_free(cms);
BIO_free (msgBio);
if (inData)
BIO_free (inData);