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 <stdio.h>
16 #include <stdlib.h>
17 #include <string.h>
18 
19 #include <openssl/crypto.h>
20 #include <openssl/err.h>
21 #include <openssl/pkcs8.h>
22 #include <openssl/x509.h>
23 
24 #include "../internal.h"
25 
26 
27 /* kDER is a PKCS#8 encrypted private key. It was generated with:
28  *
29  * openssl genrsa 512 > test.key
30  * openssl pkcs8 -topk8 -in test.key -out test.key.encrypted -v2 des3 -outform der
31  * hexdump -Cv test.key.encrypted
32  *
33  * The password is "testing".
34  */
35 static const uint8_t kDER[] = {
36   0x30, 0x82, 0x01, 0x9e, 0x30, 0x40, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05,
37   0x0d, 0x30, 0x33, 0x30, 0x1b, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c,
38   0x30, 0x0e, 0x04, 0x08, 0x06, 0xa5, 0x4b, 0x0c, 0x0c, 0x50, 0x8c, 0x19, 0x02, 0x02, 0x08, 0x00,
39   0x30, 0x14, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x03, 0x07, 0x04, 0x08, 0x3a, 0xd0,
40   0x70, 0x4b, 0x26, 0x50, 0x13, 0x7b, 0x04, 0x82, 0x01, 0x58, 0xa6, 0xee, 0x02, 0xf2, 0xf2, 0x7c,
41   0x19, 0x91, 0xe3, 0xce, 0x32, 0x85, 0xc5, 0x01, 0xd9, 0xe3, 0x5e, 0x14, 0xb6, 0xb8, 0x78, 0xad,
42   0xda, 0x01, 0xec, 0x9e, 0x42, 0xe8, 0xbf, 0x0b, 0x46, 0x03, 0xbc, 0x92, 0x6f, 0xe4, 0x0f, 0x0f,
43   0x48, 0x30, 0x10, 0x10, 0x9b, 0xfb, 0x4b, 0xb9, 0x45, 0xf8, 0xcf, 0xab, 0xa1, 0x18, 0xdd, 0x19,
44   0xa4, 0xa4, 0xe1, 0xf0, 0xa1, 0x8d, 0xc2, 0x23, 0xe7, 0x0d, 0x7a, 0x64, 0x21, 0x6b, 0xfa, 0x48,
45   0xb9, 0x41, 0xc1, 0x0c, 0x4b, 0xce, 0x6f, 0x1a, 0x91, 0x9b, 0x9f, 0xdd, 0xcf, 0xa9, 0x8d, 0x33,
46   0x2c, 0x45, 0x81, 0x5c, 0x5e, 0x67, 0xc6, 0x68, 0x43, 0x62, 0xff, 0x5e, 0x9b, 0x1a, 0x15, 0x3a,
47   0x9d, 0x71, 0x3f, 0xbe, 0x32, 0x2f, 0xe5, 0x90, 0x65, 0x65, 0x9c, 0x22, 0xf6, 0x29, 0x2e, 0xcf,
48   0x26, 0x16, 0x7b, 0x66, 0x48, 0x55, 0xad, 0x9a, 0x8d, 0x89, 0xf4, 0x48, 0x4f, 0x1f, 0x9d, 0xb8,
49   0xfa, 0xe1, 0xf1, 0x3b, 0x39, 0x5c, 0x72, 0xc6, 0xb8, 0x3e, 0x98, 0xe8, 0x77, 0xe8, 0xb6, 0x71,
50   0x84, 0xa8, 0x6e, 0xca, 0xaf, 0x62, 0x96, 0x49, 0x8a, 0x21, 0x6f, 0x9e, 0x78, 0x07, 0x97, 0x38,
51   0x40, 0x66, 0x42, 0x5a, 0x1b, 0xe0, 0x9b, 0xe9, 0x91, 0x82, 0xe4, 0xea, 0x8f, 0x2a, 0xb2, 0x80,
52   0xce, 0xe8, 0x57, 0xd3, 0xac, 0x11, 0x9d, 0xb2, 0x39, 0x0f, 0xe1, 0xce, 0x18, 0x96, 0x38, 0xa1,
53   0x19, 0x80, 0x88, 0x81, 0x3d, 0xda, 0xaa, 0x8e, 0x15, 0x27, 0x19, 0x73, 0x0c, 0xf3, 0xaf, 0x45,
54   0xe9, 0x1b, 0xad, 0x6c, 0x3d, 0xbf, 0x95, 0xf7, 0xa0, 0x87, 0x0e, 0xde, 0xf1, 0xd8, 0xee, 0xaa,
55   0x92, 0x76, 0x8d, 0x32, 0x45, 0xa1, 0xe7, 0xf5, 0x05, 0xd6, 0x2c, 0x67, 0x63, 0x10, 0xfa, 0xde,
56   0x80, 0xc7, 0x5b, 0x96, 0x0f, 0x24, 0x50, 0x78, 0x30, 0xe5, 0x89, 0xf3, 0x73, 0xfa, 0x40, 0x11,
57   0xd5, 0x26, 0xb8, 0x36, 0x96, 0x98, 0xe6, 0xbd, 0x73, 0x62, 0x56, 0xb9, 0xea, 0x28, 0x16, 0x93,
58   0x5b, 0x33, 0xae, 0x83, 0xf9, 0x1f, 0xee, 0xef, 0xc8, 0xbf, 0xc7, 0xb1, 0x47, 0x43, 0xa1, 0xc6,
59   0x1a, 0x64, 0x47, 0x02, 0x40, 0x3e, 0xbc, 0x0f, 0x80, 0x71, 0x5c, 0x44, 0x60, 0xbc, 0x78, 0x2e,
60   0xd2, 0x77, 0xf8, 0x6e, 0x12, 0x51, 0x89, 0xdb, 0x90, 0x64, 0xcd, 0x76, 0x10, 0x29, 0x73, 0xc2,
61   0x2f, 0x94, 0x7b, 0x98, 0xcd, 0xbb, 0x61, 0x16, 0x1d, 0x52, 0x11, 0x73, 0x48, 0xe6, 0x39, 0xfc,
62   0xd6, 0x2d,
63 };
64 
65 /* kNullPassword is a PKCS#8 encrypted private key using the null password. */
66 static const uint8_t kNullPassword[] = {
67     0x30, 0x81, 0xb0, 0x30, 0x1b, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86, 0xf7,
68     0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x0d, 0x04, 0x08, 0xb2, 0xfe, 0x68,
69     0xc2, 0xea, 0x0f, 0x10, 0x9c, 0x02, 0x01, 0x01, 0x04, 0x81, 0x90, 0xe2,
70     0xf6, 0x1c, 0xca, 0xad, 0x64, 0x30, 0xbf, 0x88, 0x04, 0x35, 0xe5, 0x0f,
71     0x11, 0x49, 0x06, 0x01, 0x14, 0x33, 0x80, 0xa2, 0x78, 0x44, 0x5b, 0xaa,
72     0x0d, 0xd7, 0x00, 0x36, 0x9d, 0x91, 0x97, 0x37, 0x20, 0x7b, 0x27, 0xc1,
73     0xa0, 0xa2, 0x73, 0x06, 0x15, 0xdf, 0xc8, 0x13, 0x9b, 0xc9, 0x8c, 0x9c,
74     0xce, 0x00, 0xd0, 0xc8, 0x42, 0xc1, 0xda, 0x2b, 0x07, 0x2b, 0x12, 0xa3,
75     0xce, 0x10, 0x39, 0x7a, 0xf1, 0x55, 0x69, 0x8d, 0xa5, 0xc4, 0x2a, 0x00,
76     0x0d, 0x94, 0xc6, 0xde, 0x6a, 0x3d, 0xb7, 0xe5, 0x6d, 0x59, 0x3e, 0x09,
77     0xb5, 0xe3, 0x3e, 0xfc, 0x50, 0x56, 0xe9, 0x50, 0x42, 0x7c, 0xe7, 0xf0,
78     0x19, 0xbd, 0x31, 0xa7, 0x85, 0x47, 0xb3, 0xe9, 0xb3, 0x50, 0x3c, 0xc9,
79     0x32, 0x37, 0x1a, 0x93, 0x78, 0x48, 0x78, 0x82, 0xde, 0xad, 0x5c, 0xf2,
80     0xcf, 0xf2, 0xbb, 0x2c, 0x44, 0x05, 0x7f, 0x4a, 0xf9, 0xb1, 0x2b, 0xdd,
81     0x49, 0xf6, 0x7e, 0xd0, 0x42, 0xaa, 0x14, 0x3c, 0x24, 0x77, 0xb4,
82 };
83 
84 /* kNullPasswordNSS is a PKCS#8 encrypted private key using the null password
85  * and generated by NSS. */
86 static const uint8_t kNullPasswordNSS[] = {
87     0x30, 0x81, 0xb8, 0x30, 0x23, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86, 0xf7,
88     0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x15, 0x04, 0x10, 0x3f, 0xac, 0xe9,
89     0x38, 0xdb, 0x40, 0x6b, 0x26, 0x89, 0x09, 0x73, 0x18, 0x8d, 0x7f, 0x1c,
90     0x82, 0x02, 0x01, 0x01, 0x04, 0x81, 0x90, 0x5e, 0x5e, 0x11, 0xef, 0xbb,
91     0x7c, 0x4d, 0xec, 0xc0, 0xdc, 0xc7, 0x23, 0xd2, 0xc4, 0x77, 0xbc, 0xf4,
92     0x5d, 0x59, 0x4c, 0x07, 0xc2, 0x8a, 0x26, 0xfa, 0x25, 0x1c, 0xaa, 0x42,
93     0xed, 0xd0, 0xed, 0xbb, 0x5c, 0xe9, 0x13, 0x07, 0xaa, 0xdd, 0x52, 0x3c,
94     0x65, 0x25, 0xbf, 0x94, 0x02, 0xaf, 0xd6, 0x97, 0xe9, 0x33, 0x00, 0x76,
95     0x64, 0x4a, 0x73, 0xab, 0xfb, 0x99, 0x6e, 0x83, 0x12, 0x05, 0x86, 0x72,
96     0x6c, 0xd5, 0xa4, 0xcf, 0xb1, 0xd5, 0x4d, 0x54, 0x87, 0x8b, 0x4b, 0x95,
97     0x1d, 0xcd, 0xf3, 0xfe, 0xa8, 0xda, 0xe0, 0xb6, 0x72, 0x13, 0x3f, 0x2e,
98     0x66, 0xe0, 0xb9, 0x2e, 0xfa, 0x69, 0x40, 0xbe, 0xd7, 0x67, 0x6e, 0x53,
99     0x2b, 0x3f, 0x53, 0xe5, 0x39, 0x54, 0x77, 0xe1, 0x1d, 0xe6, 0x81, 0x92,
100     0x58, 0x82, 0x14, 0xfb, 0x47, 0x85, 0x3c, 0xc3, 0xdf, 0xdd, 0xcc, 0x79,
101     0x9f, 0x41, 0x83, 0x72, 0xf2, 0x0a, 0xe9, 0xe1, 0x2c, 0x12, 0xb0, 0xb0,
102     0x0a, 0xb2, 0x1d, 0xca, 0x15, 0xb2, 0xca,
103 };
104 
105 /* kEmptyPasswordOpenSSL is a PKCS#8 encrypted private key using the empty
106  * password and generated by OpenSSL. */
107 static const uint8_t kEmptyPasswordOpenSSL[] = {
108     0x30, 0x82, 0x01, 0xa1, 0x30, 0x1b, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86,
109     0xf7, 0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x0d, 0x04, 0x08, 0x86, 0xaa,
110     0xd7, 0xdf, 0x3b, 0x91, 0x97, 0x60, 0x02, 0x01, 0x01, 0x04, 0x82, 0x01,
111     0x80, 0xcb, 0x2a, 0x14, 0xaa, 0x4f, 0x38, 0x4c, 0xe1, 0x49, 0x00, 0xe2,
112     0x1a, 0x3a, 0x75, 0x87, 0x7e, 0x3d, 0xea, 0x4d, 0x53, 0xd4, 0x46, 0x47,
113     0x23, 0x8f, 0xa1, 0x72, 0x51, 0x92, 0x86, 0x8b, 0xeb, 0x53, 0xe6, 0x6a,
114     0x0a, 0x6b, 0xb6, 0xa0, 0xdc, 0x0f, 0xdc, 0x20, 0xc3, 0x45, 0x85, 0xf1,
115     0x95, 0x90, 0x5c, 0xf4, 0xfa, 0xee, 0x47, 0xaf, 0x35, 0xd0, 0xd0, 0xd3,
116     0x14, 0xde, 0x0d, 0xca, 0x1b, 0xd3, 0xbb, 0x20, 0xec, 0x9d, 0x6a, 0xd4,
117     0xc1, 0xce, 0x60, 0x81, 0xab, 0x0c, 0x72, 0x10, 0xfa, 0x28, 0x3c, 0xac,
118     0x87, 0x7b, 0x82, 0x85, 0x00, 0xb8, 0x58, 0x9c, 0x07, 0xc4, 0x7d, 0xa9,
119     0xc5, 0x94, 0x95, 0xf7, 0x23, 0x93, 0x3f, 0xed, 0xef, 0x92, 0x55, 0x25,
120     0x74, 0xbb, 0xd3, 0xd1, 0x67, 0x3b, 0x3d, 0x5a, 0xfe, 0x84, 0xf8, 0x97,
121     0x7d, 0x7c, 0x01, 0xc7, 0xd7, 0x0d, 0xf8, 0xc3, 0x6d, 0xd6, 0xf1, 0xaa,
122     0x9d, 0x1f, 0x69, 0x97, 0x45, 0x06, 0xc4, 0x1c, 0x95, 0x3c, 0xe0, 0xef,
123     0x11, 0xb2, 0xb3, 0x72, 0x91, 0x9e, 0x7d, 0x0f, 0x7f, 0xc8, 0xf6, 0x64,
124     0x49, 0x5e, 0x3c, 0x53, 0x37, 0x79, 0x03, 0x1c, 0x3f, 0x29, 0x6c, 0x6b,
125     0xea, 0x4c, 0x35, 0x9b, 0x6d, 0x1b, 0x59, 0x43, 0x4c, 0x14, 0x47, 0x2a,
126     0x36, 0x39, 0x2a, 0xd8, 0x96, 0x90, 0xdc, 0xfc, 0xd2, 0xdd, 0x23, 0x0e,
127     0x2c, 0xb3, 0x83, 0xf9, 0xf2, 0xe3, 0xe6, 0x99, 0x53, 0x57, 0x33, 0xc5,
128     0x5f, 0xf9, 0xfd, 0x56, 0x0b, 0x32, 0xd4, 0xf3, 0x9d, 0x5b, 0x34, 0xe5,
129     0x94, 0xbf, 0xb6, 0xc0, 0xce, 0xe1, 0x73, 0x5c, 0x02, 0x7a, 0x4c, 0xed,
130     0xde, 0x23, 0x38, 0x89, 0x9f, 0xcd, 0x51, 0xf3, 0x90, 0x80, 0xd3, 0x4b,
131     0x83, 0xd3, 0xee, 0xf2, 0x9e, 0x35, 0x91, 0xa5, 0xa3, 0xc0, 0x5c, 0xce,
132     0xdb, 0xaa, 0x70, 0x1e, 0x1d, 0xc1, 0x44, 0xea, 0x3b, 0xa7, 0x5a, 0x11,
133     0xd1, 0xf3, 0xf3, 0xd0, 0xf4, 0x5a, 0xc4, 0x99, 0xaf, 0x8d, 0xe2, 0xbc,
134     0xa2, 0xb9, 0x3d, 0x86, 0x5e, 0xba, 0xa0, 0xdf, 0x78, 0x81, 0x7c, 0x54,
135     0x31, 0xe3, 0x98, 0xb5, 0x46, 0xcb, 0x4d, 0x26, 0x4b, 0xf8, 0xac, 0x3a,
136     0x54, 0x1b, 0x77, 0x5a, 0x18, 0xa5, 0x43, 0x0e, 0x14, 0xde, 0x7b, 0xb7,
137     0x4e, 0x45, 0x99, 0x03, 0xd1, 0x3d, 0x18, 0xb2, 0x36, 0x00, 0x48, 0x07,
138     0x72, 0xbb, 0x4f, 0x21, 0x25, 0x3e, 0xda, 0x25, 0x24, 0x5b, 0xc8, 0xa0,
139     0x28, 0xd5, 0x9b, 0x96, 0x87, 0x07, 0x77, 0x84, 0xff, 0xd7, 0xac, 0x71,
140     0xf6, 0x61, 0x63, 0x0b, 0xfb, 0x42, 0xfd, 0x52, 0xf4, 0xc4, 0x35, 0x0c,
141     0xc2, 0xc1, 0x55, 0x22, 0x42, 0x2f, 0x13, 0x7d, 0x93, 0x27, 0xc8, 0x11,
142     0x35, 0xc5, 0xe3, 0xc5, 0xaa, 0x15, 0x3c, 0xac, 0x30, 0xbc, 0x45, 0x16,
143     0xed,
144 };
145 
146 // kExplicitHMACWithSHA1 is a PBES2-encrypted private key with an explicit
147 // hmacWithSHA1 AlgorithmIdentifier in the PBKDF2 parameters.
148 static const uint8_t kExplicitHMACWithSHA1[] = {
149     0x30, 0x81, 0xec, 0x30, 0x57, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7,
150     0x0d, 0x01, 0x05, 0x0d, 0x30, 0x4a, 0x30, 0x29, 0x06, 0x09, 0x2a, 0x86,
151     0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c, 0x30, 0x1c, 0x04, 0x08, 0x90,
152     0xcd, 0x1e, 0x47, 0x1d, 0xff, 0x4c, 0xa8, 0x02, 0x02, 0x08, 0x00, 0x30,
153     0x0c, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x02, 0x07, 0x05,
154     0x00, 0x30, 0x1d, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03, 0x04,
155     0x01, 0x02, 0x04, 0x10, 0x34, 0xe7, 0x5b, 0x9b, 0xf9, 0x17, 0xcf, 0x15,
156     0x59, 0x7c, 0xfd, 0xc1, 0xac, 0xed, 0x6f, 0xdd, 0x04, 0x81, 0x90, 0xe3,
157     0xd7, 0xfc, 0xbe, 0xe6, 0xe8, 0x92, 0xc1, 0xa2, 0x57, 0x42, 0x4b, 0xf1,
158     0x35, 0x6c, 0x4f, 0x58, 0x61, 0x14, 0x30, 0x4e, 0xa3, 0x8d, 0x4f, 0xde,
159     0x2d, 0x0b, 0xa2, 0x62, 0x4b, 0xee, 0x9f, 0xc4, 0xeb, 0x89, 0x33, 0x76,
160     0x3f, 0x0c, 0x20, 0xad, 0x75, 0x29, 0x42, 0xbc, 0xbd, 0x83, 0x46, 0x1d,
161     0x5c, 0xae, 0xec, 0x10, 0x05, 0xbb, 0xd3, 0x98, 0xc9, 0x5a, 0x5e, 0x0a,
162     0x95, 0x12, 0x1e, 0x65, 0x93, 0xdd, 0xdd, 0x51, 0xd5, 0x56, 0xc2, 0xa9,
163     0xf9, 0x43, 0x0f, 0x68, 0x8a, 0x14, 0x40, 0xe5, 0x62, 0x9e, 0x0d, 0xd7,
164     0x67, 0x62, 0xf4, 0x49, 0xb1, 0x62, 0x22, 0x42, 0xb1, 0xe1, 0xb2, 0x1d,
165     0x37, 0x3e, 0x95, 0x52, 0xe9, 0x61, 0x89, 0xc7, 0x62, 0xcc, 0xb1, 0x44,
166     0x40, 0xef, 0x89, 0xc8, 0xc4, 0x0e, 0xae, 0xa8, 0xf9, 0x17, 0x42, 0x2b,
167     0x8c, 0x0b, 0x26, 0xf6, 0x07, 0x00, 0xab, 0x25, 0x2b, 0x64, 0xcf, 0xc3,
168     0x68, 0xf9, 0x5e, 0x01, 0x66, 0x59, 0x5f, 0x3f, 0x05, 0x57, 0xcd,
169 };
170 
TestDecrypt(const uint8_t * der,size_t der_len,const char * password)171 static bool TestDecrypt(const uint8_t *der, size_t der_len,
172                         const char *password) {
173   const uint8_t *data = der;
174   bssl::UniquePtr<X509_SIG> sig(d2i_X509_SIG(NULL, &data, der_len));
175   if (sig.get() == NULL || data != der + der_len) {
176     fprintf(stderr, "d2i_X509_SIG failed or did not consume all bytes.\n");
177     return false;
178   }
179 
180   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> keypair(
181       PKCS8_decrypt(sig.get(), password, -1));
182   if (!keypair) {
183     fprintf(stderr, "PKCS8_decrypt failed.\n");
184     ERR_print_errors_fp(stderr);
185     return false;
186   }
187 
188   return true;
189 }
190 
TestRoundTrip(int pbe_nid,const EVP_CIPHER * cipher,const char * password,const uint8_t * salt,size_t salt_len,int iterations)191 static bool TestRoundTrip(int pbe_nid, const EVP_CIPHER *cipher,
192                           const char *password, const uint8_t *salt,
193                           size_t salt_len, int iterations) {
194   static const uint8_t kSampleKey[] = {
195       0x30, 0x81, 0x87, 0x02, 0x01, 0x00, 0x30, 0x13, 0x06, 0x07, 0x2a, 0x86,
196       0x48, 0xce, 0x3d, 0x02, 0x01, 0x06, 0x08, 0x2a, 0x86, 0x48, 0xce, 0x3d,
197       0x03, 0x01, 0x07, 0x04, 0x6d, 0x30, 0x6b, 0x02, 0x01, 0x01, 0x04, 0x20,
198       0x8a, 0x87, 0x2f, 0xb6, 0x28, 0x93, 0xc4, 0xd1, 0xff, 0xc5, 0xb9, 0xf0,
199       0xf9, 0x17, 0x58, 0x06, 0x9f, 0x83, 0x52, 0xe0, 0x8f, 0xa0, 0x5a, 0x49,
200       0xf8, 0xdb, 0x92, 0x6c, 0xb5, 0x72, 0x87, 0x25, 0xa1, 0x44, 0x03, 0x42,
201       0x00, 0x04, 0x2c, 0x15, 0x0f, 0x42, 0x9c, 0xe7, 0x0f, 0x21, 0x6c, 0x25,
202       0x2c, 0xf5, 0xe0, 0x62, 0xce, 0x1f, 0x63, 0x9c, 0xd5, 0xd1, 0x65, 0xc7,
203       0xf8, 0x94, 0x24, 0x07, 0x2c, 0x27, 0x19, 0x7d, 0x78, 0xb3, 0x3b, 0x92,
204       0x0e, 0x95, 0xcd, 0xb6, 0x64, 0xe9, 0x90, 0xdc, 0xf0, 0xcf, 0xea, 0x0d,
205       0x94, 0xe2, 0xa8, 0xe6, 0xaf, 0x9d, 0x0e, 0x58, 0x05, 0x6e, 0x65, 0x31,
206       0x04, 0x92, 0x5b, 0x9f, 0xe6, 0xc9,
207   };
208 
209   const uint8_t *ptr = kSampleKey;
210   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key(
211       d2i_PKCS8_PRIV_KEY_INFO(nullptr, &ptr, sizeof(kSampleKey)));
212   if (!key || ptr != kSampleKey + sizeof(kSampleKey)) {
213     return false;
214   }
215 
216   bssl::UniquePtr<X509_SIG> encrypted(PKCS8_encrypt(
217       pbe_nid, cipher, password, -1, salt, salt_len, iterations, key.get()));
218   if (!encrypted) {
219     fprintf(stderr, "Failed to encrypt private key.\n");
220     return false;
221   }
222 
223   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key2(
224       PKCS8_decrypt(encrypted.get(), password, -1));
225   if (!key2) {
226     fprintf(stderr, "Failed to decrypt private key.\n");
227     return false;
228   }
229 
230   uint8_t *encoded = nullptr;
231   int len = i2d_PKCS8_PRIV_KEY_INFO(key2.get(), &encoded);
232   bssl::UniquePtr<uint8_t> free_encoded(encoded);
233   if (len < 0 ||
234       static_cast<size_t>(len) != sizeof(kSampleKey) ||
235       OPENSSL_memcmp(encoded, kSampleKey, sizeof(kSampleKey)) != 0) {
236     fprintf(stderr, "Decrypted private key did not round-trip.");
237     return false;
238   }
239 
240   return true;
241 }
242 
main(int argc,char ** argv)243 int main(int argc, char **argv) {
244   CRYPTO_library_init();
245 
246   if (!TestDecrypt(kDER, sizeof(kDER), "testing") ||
247       !TestDecrypt(kNullPassword, sizeof(kNullPassword), NULL) ||
248       !TestDecrypt(kNullPasswordNSS, sizeof(kNullPasswordNSS), NULL) ||
249       !TestDecrypt(kEmptyPasswordOpenSSL, sizeof(kEmptyPasswordOpenSSL), "") ||
250       !TestDecrypt(kExplicitHMACWithSHA1, sizeof(kExplicitHMACWithSHA1),
251                    "foo") ||
252       !TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
253                      "password", nullptr, 0, 10) ||
254       // Vary the salt
255       !TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
256                      "password", nullptr, 4, 10) ||
257       !TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
258                      "password", (const uint8_t *)"salt", 4, 10) ||
259       // Vary the iteration count.
260       !TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
261                      "password", nullptr, 0, 1) ||
262       // Vary the password.
263       !TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr, "",
264                      nullptr, 0, 1) ||
265       !TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr, nullptr,
266                      nullptr, 0, 1) ||
267       // Vary the PBE suite.
268       !TestRoundTrip(NID_pbe_WithSHA1And40BitRC2_CBC, nullptr, "password",
269                      nullptr, 0, 10) ||
270       !TestRoundTrip(NID_pbe_WithSHA1And128BitRC4, nullptr, "password", nullptr,
271                      0, 10) ||
272       // Test PBES2.
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     return 1;
280   }
281 
282   printf("PASS\n");
283   return 0;
284 }
285