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      1 /* Copyright (c) 2015, Google Inc.
      2  *
      3  * Permission to use, copy, modify, and/or distribute this software for any
      4  * purpose with or without fee is hereby granted, provided that the above
      5  * copyright notice and this permission notice appear in all copies.
      6  *
      7  * THE SOFTWARE IS PROVIDED "AS IS" AND THE AUTHOR DISCLAIMS ALL WARRANTIES
      8  * WITH REGARD TO THIS SOFTWARE INCLUDING ALL IMPLIED WARRANTIES OF
      9  * MERCHANTABILITY AND FITNESS. IN NO EVENT SHALL THE AUTHOR BE LIABLE FOR ANY
     10  * SPECIAL, DIRECT, INDIRECT, OR CONSEQUENTIAL DAMAGES OR ANY DAMAGES
     11  * WHATSOEVER RESULTING FROM LOSS OF USE, DATA OR PROFITS, WHETHER IN AN ACTION
     12  * OF CONTRACT, NEGLIGENCE OR OTHER TORTIOUS ACTION, ARISING OUT OF OR IN
     13  * CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE. */
     14 
     15 #include <gtest/gtest.h>
     16 
     17 #include <openssl/crypto.h>
     18 #include <openssl/err.h>
     19 #include <openssl/pkcs8.h>
     20 #include <openssl/x509.h>
     21 
     22 #include "../internal.h"
     23 
     24 
     25 // kDER is a PKCS#8 encrypted private key. It was generated with:
     26 //
     27 // openssl genrsa 512 > test.key
     28 // openssl pkcs8 -topk8 -in test.key -out test.key.encrypted -v2 des3 -outform der
     29 // hexdump -Cv test.key.encrypted
     30 //
     31 // The password is "testing".
     32 static const uint8_t kDER[] = {
     33   0x30, 0x82, 0x01, 0x9e, 0x30, 0x40, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05,
     34   0x0d, 0x30, 0x33, 0x30, 0x1b, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c,
     35   0x30, 0x0e, 0x04, 0x08, 0x06, 0xa5, 0x4b, 0x0c, 0x0c, 0x50, 0x8c, 0x19, 0x02, 0x02, 0x08, 0x00,
     36   0x30, 0x14, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x03, 0x07, 0x04, 0x08, 0x3a, 0xd0,
     37   0x70, 0x4b, 0x26, 0x50, 0x13, 0x7b, 0x04, 0x82, 0x01, 0x58, 0xa6, 0xee, 0x02, 0xf2, 0xf2, 0x7c,
     38   0x19, 0x91, 0xe3, 0xce, 0x32, 0x85, 0xc5, 0x01, 0xd9, 0xe3, 0x5e, 0x14, 0xb6, 0xb8, 0x78, 0xad,
     39   0xda, 0x01, 0xec, 0x9e, 0x42, 0xe8, 0xbf, 0x0b, 0x46, 0x03, 0xbc, 0x92, 0x6f, 0xe4, 0x0f, 0x0f,
     40   0x48, 0x30, 0x10, 0x10, 0x9b, 0xfb, 0x4b, 0xb9, 0x45, 0xf8, 0xcf, 0xab, 0xa1, 0x18, 0xdd, 0x19,
     41   0xa4, 0xa4, 0xe1, 0xf0, 0xa1, 0x8d, 0xc2, 0x23, 0xe7, 0x0d, 0x7a, 0x64, 0x21, 0x6b, 0xfa, 0x48,
     42   0xb9, 0x41, 0xc1, 0x0c, 0x4b, 0xce, 0x6f, 0x1a, 0x91, 0x9b, 0x9f, 0xdd, 0xcf, 0xa9, 0x8d, 0x33,
     43   0x2c, 0x45, 0x81, 0x5c, 0x5e, 0x67, 0xc6, 0x68, 0x43, 0x62, 0xff, 0x5e, 0x9b, 0x1a, 0x15, 0x3a,
     44   0x9d, 0x71, 0x3f, 0xbe, 0x32, 0x2f, 0xe5, 0x90, 0x65, 0x65, 0x9c, 0x22, 0xf6, 0x29, 0x2e, 0xcf,
     45   0x26, 0x16, 0x7b, 0x66, 0x48, 0x55, 0xad, 0x9a, 0x8d, 0x89, 0xf4, 0x48, 0x4f, 0x1f, 0x9d, 0xb8,
     46   0xfa, 0xe1, 0xf1, 0x3b, 0x39, 0x5c, 0x72, 0xc6, 0xb8, 0x3e, 0x98, 0xe8, 0x77, 0xe8, 0xb6, 0x71,
     47   0x84, 0xa8, 0x6e, 0xca, 0xaf, 0x62, 0x96, 0x49, 0x8a, 0x21, 0x6f, 0x9e, 0x78, 0x07, 0x97, 0x38,
     48   0x40, 0x66, 0x42, 0x5a, 0x1b, 0xe0, 0x9b, 0xe9, 0x91, 0x82, 0xe4, 0xea, 0x8f, 0x2a, 0xb2, 0x80,
     49   0xce, 0xe8, 0x57, 0xd3, 0xac, 0x11, 0x9d, 0xb2, 0x39, 0x0f, 0xe1, 0xce, 0x18, 0x96, 0x38, 0xa1,
     50   0x19, 0x80, 0x88, 0x81, 0x3d, 0xda, 0xaa, 0x8e, 0x15, 0x27, 0x19, 0x73, 0x0c, 0xf3, 0xaf, 0x45,
     51   0xe9, 0x1b, 0xad, 0x6c, 0x3d, 0xbf, 0x95, 0xf7, 0xa0, 0x87, 0x0e, 0xde, 0xf1, 0xd8, 0xee, 0xaa,
     52   0x92, 0x76, 0x8d, 0x32, 0x45, 0xa1, 0xe7, 0xf5, 0x05, 0xd6, 0x2c, 0x67, 0x63, 0x10, 0xfa, 0xde,
     53   0x80, 0xc7, 0x5b, 0x96, 0x0f, 0x24, 0x50, 0x78, 0x30, 0xe5, 0x89, 0xf3, 0x73, 0xfa, 0x40, 0x11,
     54   0xd5, 0x26, 0xb8, 0x36, 0x96, 0x98, 0xe6, 0xbd, 0x73, 0x62, 0x56, 0xb9, 0xea, 0x28, 0x16, 0x93,
     55   0x5b, 0x33, 0xae, 0x83, 0xf9, 0x1f, 0xee, 0xef, 0xc8, 0xbf, 0xc7, 0xb1, 0x47, 0x43, 0xa1, 0xc6,
     56   0x1a, 0x64, 0x47, 0x02, 0x40, 0x3e, 0xbc, 0x0f, 0x80, 0x71, 0x5c, 0x44, 0x60, 0xbc, 0x78, 0x2e,
     57   0xd2, 0x77, 0xf8, 0x6e, 0x12, 0x51, 0x89, 0xdb, 0x90, 0x64, 0xcd, 0x76, 0x10, 0x29, 0x73, 0xc2,
     58   0x2f, 0x94, 0x7b, 0x98, 0xcd, 0xbb, 0x61, 0x16, 0x1d, 0x52, 0x11, 0x73, 0x48, 0xe6, 0x39, 0xfc,
     59   0xd6, 0x2d,
     60 };
     61 
     62 // kNullPassword is a PKCS#8 encrypted private key using the null password.
     63 static const uint8_t kNullPassword[] = {
     64     0x30, 0x81, 0xb0, 0x30, 0x1b, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86, 0xf7,
     65     0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x0d, 0x04, 0x08, 0xb2, 0xfe, 0x68,
     66     0xc2, 0xea, 0x0f, 0x10, 0x9c, 0x02, 0x01, 0x01, 0x04, 0x81, 0x90, 0xe2,
     67     0xf6, 0x1c, 0xca, 0xad, 0x64, 0x30, 0xbf, 0x88, 0x04, 0x35, 0xe5, 0x0f,
     68     0x11, 0x49, 0x06, 0x01, 0x14, 0x33, 0x80, 0xa2, 0x78, 0x44, 0x5b, 0xaa,
     69     0x0d, 0xd7, 0x00, 0x36, 0x9d, 0x91, 0x97, 0x37, 0x20, 0x7b, 0x27, 0xc1,
     70     0xa0, 0xa2, 0x73, 0x06, 0x15, 0xdf, 0xc8, 0x13, 0x9b, 0xc9, 0x8c, 0x9c,
     71     0xce, 0x00, 0xd0, 0xc8, 0x42, 0xc1, 0xda, 0x2b, 0x07, 0x2b, 0x12, 0xa3,
     72     0xce, 0x10, 0x39, 0x7a, 0xf1, 0x55, 0x69, 0x8d, 0xa5, 0xc4, 0x2a, 0x00,
     73     0x0d, 0x94, 0xc6, 0xde, 0x6a, 0x3d, 0xb7, 0xe5, 0x6d, 0x59, 0x3e, 0x09,
     74     0xb5, 0xe3, 0x3e, 0xfc, 0x50, 0x56, 0xe9, 0x50, 0x42, 0x7c, 0xe7, 0xf0,
     75     0x19, 0xbd, 0x31, 0xa7, 0x85, 0x47, 0xb3, 0xe9, 0xb3, 0x50, 0x3c, 0xc9,
     76     0x32, 0x37, 0x1a, 0x93, 0x78, 0x48, 0x78, 0x82, 0xde, 0xad, 0x5c, 0xf2,
     77     0xcf, 0xf2, 0xbb, 0x2c, 0x44, 0x05, 0x7f, 0x4a, 0xf9, 0xb1, 0x2b, 0xdd,
     78     0x49, 0xf6, 0x7e, 0xd0, 0x42, 0xaa, 0x14, 0x3c, 0x24, 0x77, 0xb4,
     79 };
     80 
     81 // kNullPasswordNSS is a PKCS#8 encrypted private key using the null password
     82 // and generated by NSS.
     83 static const uint8_t kNullPasswordNSS[] = {
     84     0x30, 0x81, 0xb8, 0x30, 0x23, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86, 0xf7,
     85     0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x15, 0x04, 0x10, 0x3f, 0xac, 0xe9,
     86     0x38, 0xdb, 0x40, 0x6b, 0x26, 0x89, 0x09, 0x73, 0x18, 0x8d, 0x7f, 0x1c,
     87     0x82, 0x02, 0x01, 0x01, 0x04, 0x81, 0x90, 0x5e, 0x5e, 0x11, 0xef, 0xbb,
     88     0x7c, 0x4d, 0xec, 0xc0, 0xdc, 0xc7, 0x23, 0xd2, 0xc4, 0x77, 0xbc, 0xf4,
     89     0x5d, 0x59, 0x4c, 0x07, 0xc2, 0x8a, 0x26, 0xfa, 0x25, 0x1c, 0xaa, 0x42,
     90     0xed, 0xd0, 0xed, 0xbb, 0x5c, 0xe9, 0x13, 0x07, 0xaa, 0xdd, 0x52, 0x3c,
     91     0x65, 0x25, 0xbf, 0x94, 0x02, 0xaf, 0xd6, 0x97, 0xe9, 0x33, 0x00, 0x76,
     92     0x64, 0x4a, 0x73, 0xab, 0xfb, 0x99, 0x6e, 0x83, 0x12, 0x05, 0x86, 0x72,
     93     0x6c, 0xd5, 0xa4, 0xcf, 0xb1, 0xd5, 0x4d, 0x54, 0x87, 0x8b, 0x4b, 0x95,
     94     0x1d, 0xcd, 0xf3, 0xfe, 0xa8, 0xda, 0xe0, 0xb6, 0x72, 0x13, 0x3f, 0x2e,
     95     0x66, 0xe0, 0xb9, 0x2e, 0xfa, 0x69, 0x40, 0xbe, 0xd7, 0x67, 0x6e, 0x53,
     96     0x2b, 0x3f, 0x53, 0xe5, 0x39, 0x54, 0x77, 0xe1, 0x1d, 0xe6, 0x81, 0x92,
     97     0x58, 0x82, 0x14, 0xfb, 0x47, 0x85, 0x3c, 0xc3, 0xdf, 0xdd, 0xcc, 0x79,
     98     0x9f, 0x41, 0x83, 0x72, 0xf2, 0x0a, 0xe9, 0xe1, 0x2c, 0x12, 0xb0, 0xb0,
     99     0x0a, 0xb2, 0x1d, 0xca, 0x15, 0xb2, 0xca,
    100 };
    101 
    102 // kEmptyPasswordOpenSSL is a PKCS#8 encrypted private key using the empty
    103 // password and generated by OpenSSL.
    104 static const uint8_t kEmptyPasswordOpenSSL[] = {
    105     0x30, 0x82, 0x01, 0xa1, 0x30, 0x1b, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86,
    106     0xf7, 0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x0d, 0x04, 0x08, 0x86, 0xaa,
    107     0xd7, 0xdf, 0x3b, 0x91, 0x97, 0x60, 0x02, 0x01, 0x01, 0x04, 0x82, 0x01,
    108     0x80, 0xcb, 0x2a, 0x14, 0xaa, 0x4f, 0x38, 0x4c, 0xe1, 0x49, 0x00, 0xe2,
    109     0x1a, 0x3a, 0x75, 0x87, 0x7e, 0x3d, 0xea, 0x4d, 0x53, 0xd4, 0x46, 0x47,
    110     0x23, 0x8f, 0xa1, 0x72, 0x51, 0x92, 0x86, 0x8b, 0xeb, 0x53, 0xe6, 0x6a,
    111     0x0a, 0x6b, 0xb6, 0xa0, 0xdc, 0x0f, 0xdc, 0x20, 0xc3, 0x45, 0x85, 0xf1,
    112     0x95, 0x90, 0x5c, 0xf4, 0xfa, 0xee, 0x47, 0xaf, 0x35, 0xd0, 0xd0, 0xd3,
    113     0x14, 0xde, 0x0d, 0xca, 0x1b, 0xd3, 0xbb, 0x20, 0xec, 0x9d, 0x6a, 0xd4,
    114     0xc1, 0xce, 0x60, 0x81, 0xab, 0x0c, 0x72, 0x10, 0xfa, 0x28, 0x3c, 0xac,
    115     0x87, 0x7b, 0x82, 0x85, 0x00, 0xb8, 0x58, 0x9c, 0x07, 0xc4, 0x7d, 0xa9,
    116     0xc5, 0x94, 0x95, 0xf7, 0x23, 0x93, 0x3f, 0xed, 0xef, 0x92, 0x55, 0x25,
    117     0x74, 0xbb, 0xd3, 0xd1, 0x67, 0x3b, 0x3d, 0x5a, 0xfe, 0x84, 0xf8, 0x97,
    118     0x7d, 0x7c, 0x01, 0xc7, 0xd7, 0x0d, 0xf8, 0xc3, 0x6d, 0xd6, 0xf1, 0xaa,
    119     0x9d, 0x1f, 0x69, 0x97, 0x45, 0x06, 0xc4, 0x1c, 0x95, 0x3c, 0xe0, 0xef,
    120     0x11, 0xb2, 0xb3, 0x72, 0x91, 0x9e, 0x7d, 0x0f, 0x7f, 0xc8, 0xf6, 0x64,
    121     0x49, 0x5e, 0x3c, 0x53, 0x37, 0x79, 0x03, 0x1c, 0x3f, 0x29, 0x6c, 0x6b,
    122     0xea, 0x4c, 0x35, 0x9b, 0x6d, 0x1b, 0x59, 0x43, 0x4c, 0x14, 0x47, 0x2a,
    123     0x36, 0x39, 0x2a, 0xd8, 0x96, 0x90, 0xdc, 0xfc, 0xd2, 0xdd, 0x23, 0x0e,
    124     0x2c, 0xb3, 0x83, 0xf9, 0xf2, 0xe3, 0xe6, 0x99, 0x53, 0x57, 0x33, 0xc5,
    125     0x5f, 0xf9, 0xfd, 0x56, 0x0b, 0x32, 0xd4, 0xf3, 0x9d, 0x5b, 0x34, 0xe5,
    126     0x94, 0xbf, 0xb6, 0xc0, 0xce, 0xe1, 0x73, 0x5c, 0x02, 0x7a, 0x4c, 0xed,
    127     0xde, 0x23, 0x38, 0x89, 0x9f, 0xcd, 0x51, 0xf3, 0x90, 0x80, 0xd3, 0x4b,
    128     0x83, 0xd3, 0xee, 0xf2, 0x9e, 0x35, 0x91, 0xa5, 0xa3, 0xc0, 0x5c, 0xce,
    129     0xdb, 0xaa, 0x70, 0x1e, 0x1d, 0xc1, 0x44, 0xea, 0x3b, 0xa7, 0x5a, 0x11,
    130     0xd1, 0xf3, 0xf3, 0xd0, 0xf4, 0x5a, 0xc4, 0x99, 0xaf, 0x8d, 0xe2, 0xbc,
    131     0xa2, 0xb9, 0x3d, 0x86, 0x5e, 0xba, 0xa0, 0xdf, 0x78, 0x81, 0x7c, 0x54,
    132     0x31, 0xe3, 0x98, 0xb5, 0x46, 0xcb, 0x4d, 0x26, 0x4b, 0xf8, 0xac, 0x3a,
    133     0x54, 0x1b, 0x77, 0x5a, 0x18, 0xa5, 0x43, 0x0e, 0x14, 0xde, 0x7b, 0xb7,
    134     0x4e, 0x45, 0x99, 0x03, 0xd1, 0x3d, 0x18, 0xb2, 0x36, 0x00, 0x48, 0x07,
    135     0x72, 0xbb, 0x4f, 0x21, 0x25, 0x3e, 0xda, 0x25, 0x24, 0x5b, 0xc8, 0xa0,
    136     0x28, 0xd5, 0x9b, 0x96, 0x87, 0x07, 0x77, 0x84, 0xff, 0xd7, 0xac, 0x71,
    137     0xf6, 0x61, 0x63, 0x0b, 0xfb, 0x42, 0xfd, 0x52, 0xf4, 0xc4, 0x35, 0x0c,
    138     0xc2, 0xc1, 0x55, 0x22, 0x42, 0x2f, 0x13, 0x7d, 0x93, 0x27, 0xc8, 0x11,
    139     0x35, 0xc5, 0xe3, 0xc5, 0xaa, 0x15, 0x3c, 0xac, 0x30, 0xbc, 0x45, 0x16,
    140     0xed,
    141 };
    142 
    143 // kExplicitHMACWithSHA1 is a PBES2-encrypted private key with an explicit
    144 // hmacWithSHA1 AlgorithmIdentifier in the PBKDF2 parameters.
    145 static const uint8_t kExplicitHMACWithSHA1[] = {
    146     0x30, 0x81, 0xec, 0x30, 0x57, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7,
    147     0x0d, 0x01, 0x05, 0x0d, 0x30, 0x4a, 0x30, 0x29, 0x06, 0x09, 0x2a, 0x86,
    148     0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c, 0x30, 0x1c, 0x04, 0x08, 0x90,
    149     0xcd, 0x1e, 0x47, 0x1d, 0xff, 0x4c, 0xa8, 0x02, 0x02, 0x08, 0x00, 0x30,
    150     0x0c, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x02, 0x07, 0x05,
    151     0x00, 0x30, 0x1d, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03, 0x04,
    152     0x01, 0x02, 0x04, 0x10, 0x34, 0xe7, 0x5b, 0x9b, 0xf9, 0x17, 0xcf, 0x15,
    153     0x59, 0x7c, 0xfd, 0xc1, 0xac, 0xed, 0x6f, 0xdd, 0x04, 0x81, 0x90, 0xe3,
    154     0xd7, 0xfc, 0xbe, 0xe6, 0xe8, 0x92, 0xc1, 0xa2, 0x57, 0x42, 0x4b, 0xf1,
    155     0x35, 0x6c, 0x4f, 0x58, 0x61, 0x14, 0x30, 0x4e, 0xa3, 0x8d, 0x4f, 0xde,
    156     0x2d, 0x0b, 0xa2, 0x62, 0x4b, 0xee, 0x9f, 0xc4, 0xeb, 0x89, 0x33, 0x76,
    157     0x3f, 0x0c, 0x20, 0xad, 0x75, 0x29, 0x42, 0xbc, 0xbd, 0x83, 0x46, 0x1d,
    158     0x5c, 0xae, 0xec, 0x10, 0x05, 0xbb, 0xd3, 0x98, 0xc9, 0x5a, 0x5e, 0x0a,
    159     0x95, 0x12, 0x1e, 0x65, 0x93, 0xdd, 0xdd, 0x51, 0xd5, 0x56, 0xc2, 0xa9,
    160     0xf9, 0x43, 0x0f, 0x68, 0x8a, 0x14, 0x40, 0xe5, 0x62, 0x9e, 0x0d, 0xd7,
    161     0x67, 0x62, 0xf4, 0x49, 0xb1, 0x62, 0x22, 0x42, 0xb1, 0xe1, 0xb2, 0x1d,
    162     0x37, 0x3e, 0x95, 0x52, 0xe9, 0x61, 0x89, 0xc7, 0x62, 0xcc, 0xb1, 0x44,
    163     0x40, 0xef, 0x89, 0xc8, 0xc4, 0x0e, 0xae, 0xa8, 0xf9, 0x17, 0x42, 0x2b,
    164     0x8c, 0x0b, 0x26, 0xf6, 0x07, 0x00, 0xab, 0x25, 0x2b, 0x64, 0xcf, 0xc3,
    165     0x68, 0xf9, 0x5e, 0x01, 0x66, 0x59, 0x5f, 0x3f, 0x05, 0x57, 0xcd,
    166 };
    167 
    168 static void TestDecrypt(const uint8_t *der, size_t der_len,
    169                         const char *password) {
    170   const uint8_t *data = der;
    171   bssl::UniquePtr<X509_SIG> sig(d2i_X509_SIG(NULL, &data, der_len));
    172   ASSERT_TRUE(sig.get());
    173   ASSERT_EQ(der + der_len, data);
    174 
    175   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> keypair(
    176       PKCS8_decrypt(sig.get(), password, -1));
    177   ASSERT_TRUE(keypair);
    178 }
    179 
    180 static void TestRoundTrip(int pbe_nid, const EVP_CIPHER *cipher,
    181                           const char *password, const uint8_t *salt,
    182                           size_t salt_len, int iterations) {
    183   static const uint8_t kSampleKey[] = {
    184       0x30, 0x81, 0x87, 0x02, 0x01, 0x00, 0x30, 0x13, 0x06, 0x07, 0x2a, 0x86,
    185       0x48, 0xce, 0x3d, 0x02, 0x01, 0x06, 0x08, 0x2a, 0x86, 0x48, 0xce, 0x3d,
    186       0x03, 0x01, 0x07, 0x04, 0x6d, 0x30, 0x6b, 0x02, 0x01, 0x01, 0x04, 0x20,
    187       0x8a, 0x87, 0x2f, 0xb6, 0x28, 0x93, 0xc4, 0xd1, 0xff, 0xc5, 0xb9, 0xf0,
    188       0xf9, 0x17, 0x58, 0x06, 0x9f, 0x83, 0x52, 0xe0, 0x8f, 0xa0, 0x5a, 0x49,
    189       0xf8, 0xdb, 0x92, 0x6c, 0xb5, 0x72, 0x87, 0x25, 0xa1, 0x44, 0x03, 0x42,
    190       0x00, 0x04, 0x2c, 0x15, 0x0f, 0x42, 0x9c, 0xe7, 0x0f, 0x21, 0x6c, 0x25,
    191       0x2c, 0xf5, 0xe0, 0x62, 0xce, 0x1f, 0x63, 0x9c, 0xd5, 0xd1, 0x65, 0xc7,
    192       0xf8, 0x94, 0x24, 0x07, 0x2c, 0x27, 0x19, 0x7d, 0x78, 0xb3, 0x3b, 0x92,
    193       0x0e, 0x95, 0xcd, 0xb6, 0x64, 0xe9, 0x90, 0xdc, 0xf0, 0xcf, 0xea, 0x0d,
    194       0x94, 0xe2, 0xa8, 0xe6, 0xaf, 0x9d, 0x0e, 0x58, 0x05, 0x6e, 0x65, 0x31,
    195       0x04, 0x92, 0x5b, 0x9f, 0xe6, 0xc9,
    196   };
    197 
    198   const uint8_t *ptr = kSampleKey;
    199   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key(
    200       d2i_PKCS8_PRIV_KEY_INFO(nullptr, &ptr, sizeof(kSampleKey)));
    201   ASSERT_TRUE(key);
    202   ASSERT_EQ(kSampleKey + sizeof(kSampleKey), ptr);
    203 
    204   bssl::UniquePtr<X509_SIG> encrypted(PKCS8_encrypt(
    205       pbe_nid, cipher, password, -1, salt, salt_len, iterations, key.get()));
    206   ASSERT_TRUE(encrypted);
    207 
    208   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key2(
    209       PKCS8_decrypt(encrypted.get(), password, -1));
    210   ASSERT_TRUE(key2);
    211 
    212   uint8_t *encoded = nullptr;
    213   int len = i2d_PKCS8_PRIV_KEY_INFO(key2.get(), &encoded);
    214   bssl::UniquePtr<uint8_t> free_encoded(encoded);
    215   ASSERT_GE(len, 0);
    216   ASSERT_EQ(static_cast<size_t>(len), sizeof(kSampleKey));
    217   ASSERT_EQ(0, OPENSSL_memcmp(encoded, kSampleKey, sizeof(kSampleKey)));
    218 }
    219 
    220 TEST(PKCS8Test, DecryptString) {
    221   TestDecrypt(kDER, sizeof(kDER), "testing");
    222 }
    223 
    224 TEST(PKCS8Test, DecryptNull) {
    225   TestDecrypt(kNullPassword, sizeof(kNullPassword), NULL);
    226 }
    227 
    228 TEST(PKCS8Test, DecryptNullNSS) {
    229   TestDecrypt(kNullPasswordNSS, sizeof(kNullPasswordNSS), NULL);
    230 }
    231 
    232 TEST(PKCS8Test, DecryptEmptyStringOpenSSL) {
    233   TestDecrypt(kEmptyPasswordOpenSSL, sizeof(kEmptyPasswordOpenSSL), "");
    234 }
    235 
    236 TEST(PKCS8Test, DecryptExplicitHMACWithSHA1) {
    237   TestDecrypt(kExplicitHMACWithSHA1, sizeof(kExplicitHMACWithSHA1), "foo");
    238 }
    239 
    240 TEST(PKCS8Test, RoundTripPBEWithrSHA1And3KeyTripleDES) {
    241   // Test with different salts.
    242   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
    243                 "password", nullptr, 0, 10);
    244   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
    245                 "password", nullptr, 4, 10);
    246   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
    247                 "password", (const uint8_t *)"salt", 4, 10);
    248   // Test with a different iteration count.
    249   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
    250                 "password", nullptr, 0, 1);
    251 }
    252 
    253 // Test that both "" (empty password, encoded as "\0\0") and nullptr (no
    254 // password, encoded as "") work.
    255 TEST(PKCS8Test, RoundTripPBEWithSHA1And3KeyTripleDESEmptyPassword) {
    256   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr, "",
    257                 nullptr, 0, 1);
    258   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr, nullptr,
    259                 nullptr, 0, 1);
    260 }
    261 
    262 TEST(PKCS8Test, RoundTripPBEWithSHA1And40BitRC2CBC) {
    263   TestRoundTrip(NID_pbe_WithSHA1And40BitRC2_CBC, nullptr, "password",
    264                 nullptr, 0, 10);
    265 }
    266 
    267 TEST(PKCS8Test, RoundTripPBEWithSHA1And128BitRC4) {
    268   TestRoundTrip(NID_pbe_WithSHA1And128BitRC4, nullptr, "password",
    269                 nullptr, 0, 10);
    270 }
    271 
    272 TEST(PKCS8Test, RoundTripPBES2) {
    273   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", nullptr, 0, 10);
    274   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", nullptr, 4, 10);
    275   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", (const uint8_t *)"salt",
    276                 4, 10);
    277   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", nullptr, 0, 1);
    278   TestRoundTrip(-1, EVP_rc2_cbc(), "password", nullptr, 0, 10);
    279 }
    280 
    281 TEST(PKCS8Test, InvalidPBES1NIDs) {
    282   static const uint8_t kSampleKey[] = {
    283       0x30, 0x81, 0x87, 0x02, 0x01, 0x00, 0x30, 0x13, 0x06, 0x07, 0x2a, 0x86,
    284       0x48, 0xce, 0x3d, 0x02, 0x01, 0x06, 0x08, 0x2a, 0x86, 0x48, 0xce, 0x3d,
    285       0x03, 0x01, 0x07, 0x04, 0x6d, 0x30, 0x6b, 0x02, 0x01, 0x01, 0x04, 0x20,
    286       0x8a, 0x87, 0x2f, 0xb6, 0x28, 0x93, 0xc4, 0xd1, 0xff, 0xc5, 0xb9, 0xf0,
    287       0xf9, 0x17, 0x58, 0x06, 0x9f, 0x83, 0x52, 0xe0, 0x8f, 0xa0, 0x5a, 0x49,
    288       0xf8, 0xdb, 0x92, 0x6c, 0xb5, 0x72, 0x87, 0x25, 0xa1, 0x44, 0x03, 0x42,
    289       0x00, 0x04, 0x2c, 0x15, 0x0f, 0x42, 0x9c, 0xe7, 0x0f, 0x21, 0x6c, 0x25,
    290       0x2c, 0xf5, 0xe0, 0x62, 0xce, 0x1f, 0x63, 0x9c, 0xd5, 0xd1, 0x65, 0xc7,
    291       0xf8, 0x94, 0x24, 0x07, 0x2c, 0x27, 0x19, 0x7d, 0x78, 0xb3, 0x3b, 0x92,
    292       0x0e, 0x95, 0xcd, 0xb6, 0x64, 0xe9, 0x90, 0xdc, 0xf0, 0xcf, 0xea, 0x0d,
    293       0x94, 0xe2, 0xa8, 0xe6, 0xaf, 0x9d, 0x0e, 0x58, 0x05, 0x6e, 0x65, 0x31,
    294       0x04, 0x92, 0x5b, 0x9f, 0xe6, 0xc9,
    295   };
    296 
    297   const uint8_t *ptr = kSampleKey;
    298   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key(
    299       d2i_PKCS8_PRIV_KEY_INFO(nullptr, &ptr, sizeof(kSampleKey)));
    300   ASSERT_TRUE(key);
    301   ASSERT_EQ(kSampleKey + sizeof(kSampleKey), ptr);
    302 
    303   bssl::UniquePtr<X509_SIG> encrypted(PKCS8_encrypt(
    304       NID_pbes2, nullptr, "password", -1, nullptr, 0, 0, key.get()));
    305   EXPECT_FALSE(encrypted);
    306 
    307   encrypted.reset(PKCS8_encrypt(NID_undef, nullptr, "password", -1, nullptr, 0,
    308                                 0, key.get()));
    309   EXPECT_FALSE(encrypted);
    310 
    311   encrypted.reset(PKCS8_encrypt(NID_rsaEncryption, nullptr, "password", -1,
    312                                 nullptr, 0, 0, key.get()));
    313   EXPECT_FALSE(encrypted);
    314 }
    315