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 // kEncryptedPBES2WithDESAndSHA1 is a PKCS#8 encrypted private key using PBES2
26 // with DES-EDE3-CBC and HMAC-SHA-1. It was generated with:
27 //
28 // openssl genrsa 512 > test.key
29 // openssl pkcs8 -topk8 -in test.key -out test.key.encrypted -v2 des3 -v2prf hmacWithSHA1 -outform der
30 // hexdump -Cv test.key.encrypted
31 //
32 // The password is "testing".
33 static const uint8_t kEncryptedPBES2WithDESAndSHA1[] = {
34   0x30, 0x82, 0x01, 0x9e, 0x30, 0x40, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05,
35   0x0d, 0x30, 0x33, 0x30, 0x1b, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c,
36   0x30, 0x0e, 0x04, 0x08, 0x06, 0xa5, 0x4b, 0x0c, 0x0c, 0x50, 0x8c, 0x19, 0x02, 0x02, 0x08, 0x00,
37   0x30, 0x14, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x03, 0x07, 0x04, 0x08, 0x3a, 0xd0,
38   0x70, 0x4b, 0x26, 0x50, 0x13, 0x7b, 0x04, 0x82, 0x01, 0x58, 0xa6, 0xee, 0x02, 0xf2, 0xf2, 0x7c,
39   0x19, 0x91, 0xe3, 0xce, 0x32, 0x85, 0xc5, 0x01, 0xd9, 0xe3, 0x5e, 0x14, 0xb6, 0xb8, 0x78, 0xad,
40   0xda, 0x01, 0xec, 0x9e, 0x42, 0xe8, 0xbf, 0x0b, 0x46, 0x03, 0xbc, 0x92, 0x6f, 0xe4, 0x0f, 0x0f,
41   0x48, 0x30, 0x10, 0x10, 0x9b, 0xfb, 0x4b, 0xb9, 0x45, 0xf8, 0xcf, 0xab, 0xa1, 0x18, 0xdd, 0x19,
42   0xa4, 0xa4, 0xe1, 0xf0, 0xa1, 0x8d, 0xc2, 0x23, 0xe7, 0x0d, 0x7a, 0x64, 0x21, 0x6b, 0xfa, 0x48,
43   0xb9, 0x41, 0xc1, 0x0c, 0x4b, 0xce, 0x6f, 0x1a, 0x91, 0x9b, 0x9f, 0xdd, 0xcf, 0xa9, 0x8d, 0x33,
44   0x2c, 0x45, 0x81, 0x5c, 0x5e, 0x67, 0xc6, 0x68, 0x43, 0x62, 0xff, 0x5e, 0x9b, 0x1a, 0x15, 0x3a,
45   0x9d, 0x71, 0x3f, 0xbe, 0x32, 0x2f, 0xe5, 0x90, 0x65, 0x65, 0x9c, 0x22, 0xf6, 0x29, 0x2e, 0xcf,
46   0x26, 0x16, 0x7b, 0x66, 0x48, 0x55, 0xad, 0x9a, 0x8d, 0x89, 0xf4, 0x48, 0x4f, 0x1f, 0x9d, 0xb8,
47   0xfa, 0xe1, 0xf1, 0x3b, 0x39, 0x5c, 0x72, 0xc6, 0xb8, 0x3e, 0x98, 0xe8, 0x77, 0xe8, 0xb6, 0x71,
48   0x84, 0xa8, 0x6e, 0xca, 0xaf, 0x62, 0x96, 0x49, 0x8a, 0x21, 0x6f, 0x9e, 0x78, 0x07, 0x97, 0x38,
49   0x40, 0x66, 0x42, 0x5a, 0x1b, 0xe0, 0x9b, 0xe9, 0x91, 0x82, 0xe4, 0xea, 0x8f, 0x2a, 0xb2, 0x80,
50   0xce, 0xe8, 0x57, 0xd3, 0xac, 0x11, 0x9d, 0xb2, 0x39, 0x0f, 0xe1, 0xce, 0x18, 0x96, 0x38, 0xa1,
51   0x19, 0x80, 0x88, 0x81, 0x3d, 0xda, 0xaa, 0x8e, 0x15, 0x27, 0x19, 0x73, 0x0c, 0xf3, 0xaf, 0x45,
52   0xe9, 0x1b, 0xad, 0x6c, 0x3d, 0xbf, 0x95, 0xf7, 0xa0, 0x87, 0x0e, 0xde, 0xf1, 0xd8, 0xee, 0xaa,
53   0x92, 0x76, 0x8d, 0x32, 0x45, 0xa1, 0xe7, 0xf5, 0x05, 0xd6, 0x2c, 0x67, 0x63, 0x10, 0xfa, 0xde,
54   0x80, 0xc7, 0x5b, 0x96, 0x0f, 0x24, 0x50, 0x78, 0x30, 0xe5, 0x89, 0xf3, 0x73, 0xfa, 0x40, 0x11,
55   0xd5, 0x26, 0xb8, 0x36, 0x96, 0x98, 0xe6, 0xbd, 0x73, 0x62, 0x56, 0xb9, 0xea, 0x28, 0x16, 0x93,
56   0x5b, 0x33, 0xae, 0x83, 0xf9, 0x1f, 0xee, 0xef, 0xc8, 0xbf, 0xc7, 0xb1, 0x47, 0x43, 0xa1, 0xc6,
57   0x1a, 0x64, 0x47, 0x02, 0x40, 0x3e, 0xbc, 0x0f, 0x80, 0x71, 0x5c, 0x44, 0x60, 0xbc, 0x78, 0x2e,
58   0xd2, 0x77, 0xf8, 0x6e, 0x12, 0x51, 0x89, 0xdb, 0x90, 0x64, 0xcd, 0x76, 0x10, 0x29, 0x73, 0xc2,
59   0x2f, 0x94, 0x7b, 0x98, 0xcd, 0xbb, 0x61, 0x16, 0x1d, 0x52, 0x11, 0x73, 0x48, 0xe6, 0x39, 0xfc,
60   0xd6, 0x2d,
61 };
62 
63 // kEncryptedPBES2WithAESAndSHA256 is a PKCS#8 encrypted private key using PBES2
64 // with AES-128-CBC and HMAC-SHA-256. It was generated with:
65 //
66 // openssl genrsa 512 > test.key
67 // openssl pkcs8 -topk8 -in test.key -out test.key.encrypted -v2 aes-128-cbc -v2prf hmacWithSHA256 -outform der
68 // hexdump -Cv test.key.encrypted
69 //
70 // The password is "testing".
71 static const uint8_t kEncryptedPBES2WithAESAndSHA256[] = {
72     0x30, 0x82, 0x01, 0xbd, 0x30, 0x57, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86,
73     0xf7, 0x0d, 0x01, 0x05, 0x0d, 0x30, 0x4a, 0x30, 0x29, 0x06, 0x09, 0x2a,
74     0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c, 0x30, 0x1c, 0x04, 0x08,
75     0xd0, 0x39, 0xb7, 0x6d, 0xd0, 0xff, 0x85, 0xa8, 0x02, 0x02, 0x08, 0x00,
76     0x30, 0x0c, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x02, 0x09,
77     0x05, 0x00, 0x30, 0x1d, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03,
78     0x04, 0x01, 0x02, 0x04, 0x10, 0x95, 0xc6, 0x49, 0xc1, 0x61, 0x70, 0x74,
79     0x36, 0xfe, 0xc0, 0x98, 0x19, 0x26, 0x32, 0x9e, 0x1a, 0x04, 0x82, 0x01,
80     0x60, 0x87, 0xe3, 0x4d, 0xff, 0x33, 0x2b, 0x25, 0x07, 0x5f, 0x99, 0x24,
81     0x70, 0x40, 0x29, 0xb4, 0xaa, 0xce, 0xdd, 0x93, 0x60, 0x5c, 0x65, 0xec,
82     0xba, 0xee, 0xf8, 0x5e, 0xc7, 0x8f, 0x3e, 0x49, 0x00, 0xdf, 0xa7, 0xb2,
83     0xbb, 0xa7, 0xf7, 0x74, 0x56, 0xe0, 0xeb, 0x33, 0xe2, 0x30, 0x60, 0x3b,
84     0xd3, 0x34, 0x7b, 0xb0, 0x76, 0xc0, 0xed, 0xa2, 0x7d, 0x51, 0x99, 0x4d,
85     0x52, 0x1c, 0x9e, 0xd7, 0x28, 0x58, 0x32, 0xcf, 0x55, 0xf0, 0x19, 0x87,
86     0x5e, 0x66, 0x69, 0x00, 0x75, 0xd7, 0x68, 0x98, 0x64, 0x6a, 0x1e, 0x8c,
87     0xef, 0x7b, 0xbc, 0x9e, 0xed, 0xaf, 0x67, 0xcf, 0xc4, 0x6c, 0x40, 0x8a,
88     0x23, 0x73, 0xe6, 0x79, 0x5f, 0x7a, 0x15, 0x53, 0x2c, 0x70, 0x3b, 0x69,
89     0xba, 0x3d, 0xfb, 0x6e, 0xb9, 0x27, 0x78, 0x9b, 0xc3, 0x4b, 0xb8, 0xe3,
90     0xe7, 0x31, 0x82, 0x43, 0xee, 0x81, 0x5b, 0x01, 0x3b, 0x7e, 0x23, 0xb1,
91     0xcc, 0x20, 0xc9, 0xe0, 0xca, 0x9d, 0xaa, 0x9c, 0xe9, 0x47, 0x96, 0x0d,
92     0xc4, 0x1e, 0x1b, 0x1f, 0xb1, 0xee, 0x2b, 0x99, 0xaf, 0x2a, 0xb4, 0x9f,
93     0x29, 0xb5, 0x9b, 0x83, 0x5e, 0xe5, 0x7e, 0xf7, 0xf7, 0x58, 0x31, 0x54,
94     0xf6, 0x29, 0x6b, 0xfc, 0x85, 0x1d, 0x8a, 0x5f, 0x22, 0x03, 0xed, 0xce,
95     0x06, 0x5b, 0x93, 0x57, 0x23, 0x4e, 0x0e, 0x5b, 0xf8, 0x29, 0x29, 0x7c,
96     0x2d, 0x4a, 0xc6, 0x9a, 0x97, 0x64, 0x4c, 0x15, 0x72, 0xee, 0xaa, 0xd9,
97     0xed, 0xfd, 0x8f, 0xa2, 0x36, 0xf5, 0xf8, 0xe7, 0xf7, 0xfe, 0x67, 0x4b,
98     0xbe, 0x85, 0xe3, 0xda, 0x3a, 0xcc, 0x5f, 0x17, 0xbe, 0xa6, 0x1a, 0x38,
99     0xed, 0x85, 0x4a, 0xd6, 0x05, 0x4b, 0x5f, 0x54, 0x0e, 0xfd, 0xdc, 0x32,
100     0x9a, 0x0d, 0xca, 0xec, 0x02, 0x3f, 0x78, 0x23, 0x6e, 0x6a, 0xfa, 0x2c,
101     0x04, 0x86, 0xc8, 0x74, 0xa6, 0xf7, 0x2f, 0x1a, 0xf1, 0x1a, 0x51, 0x09,
102     0x2b, 0x04, 0xdc, 0x53, 0xaf, 0x39, 0x85, 0x35, 0x81, 0xc3, 0x11, 0xf0,
103     0x7d, 0xb7, 0xb3, 0x77, 0x0e, 0x8e, 0x22, 0xda, 0x1f, 0xb0, 0x3d, 0x59,
104     0xca, 0xa9, 0x70, 0xc3, 0x33, 0x66, 0xcb, 0x81, 0xfc, 0x85, 0x2a, 0xf0,
105     0xbc, 0xd0, 0x30, 0x85, 0x1b, 0xe6, 0x9b, 0x76, 0x88, 0xca, 0xf1, 0xf5,
106     0xc8, 0x19, 0x8a, 0x62, 0x16, 0x7b, 0x01, 0xc1, 0x1d, 0x80, 0xc0, 0xf7,
107     0xc2, 0x0b, 0xe3, 0xbf, 0x83, 0x9a, 0x3c, 0xc0, 0x0f, 0x5e, 0xea, 0xf7,
108     0xb2, 0x4c, 0xcd, 0x5e, 0xf0, 0xad, 0xa5, 0x98, 0x25, 0x62, 0x69, 0xba,
109     0xd7, 0xab, 0x78, 0x59, 0xd0,
110 };
111 
112 // kNullPassword is a PKCS#8 encrypted private key using the null password.
113 static const uint8_t kNullPassword[] = {
114     0x30, 0x81, 0xb0, 0x30, 0x1b, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86, 0xf7,
115     0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x0d, 0x04, 0x08, 0xb2, 0xfe, 0x68,
116     0xc2, 0xea, 0x0f, 0x10, 0x9c, 0x02, 0x01, 0x01, 0x04, 0x81, 0x90, 0xe2,
117     0xf6, 0x1c, 0xca, 0xad, 0x64, 0x30, 0xbf, 0x88, 0x04, 0x35, 0xe5, 0x0f,
118     0x11, 0x49, 0x06, 0x01, 0x14, 0x33, 0x80, 0xa2, 0x78, 0x44, 0x5b, 0xaa,
119     0x0d, 0xd7, 0x00, 0x36, 0x9d, 0x91, 0x97, 0x37, 0x20, 0x7b, 0x27, 0xc1,
120     0xa0, 0xa2, 0x73, 0x06, 0x15, 0xdf, 0xc8, 0x13, 0x9b, 0xc9, 0x8c, 0x9c,
121     0xce, 0x00, 0xd0, 0xc8, 0x42, 0xc1, 0xda, 0x2b, 0x07, 0x2b, 0x12, 0xa3,
122     0xce, 0x10, 0x39, 0x7a, 0xf1, 0x55, 0x69, 0x8d, 0xa5, 0xc4, 0x2a, 0x00,
123     0x0d, 0x94, 0xc6, 0xde, 0x6a, 0x3d, 0xb7, 0xe5, 0x6d, 0x59, 0x3e, 0x09,
124     0xb5, 0xe3, 0x3e, 0xfc, 0x50, 0x56, 0xe9, 0x50, 0x42, 0x7c, 0xe7, 0xf0,
125     0x19, 0xbd, 0x31, 0xa7, 0x85, 0x47, 0xb3, 0xe9, 0xb3, 0x50, 0x3c, 0xc9,
126     0x32, 0x37, 0x1a, 0x93, 0x78, 0x48, 0x78, 0x82, 0xde, 0xad, 0x5c, 0xf2,
127     0xcf, 0xf2, 0xbb, 0x2c, 0x44, 0x05, 0x7f, 0x4a, 0xf9, 0xb1, 0x2b, 0xdd,
128     0x49, 0xf6, 0x7e, 0xd0, 0x42, 0xaa, 0x14, 0x3c, 0x24, 0x77, 0xb4,
129 };
130 
131 // kNullPasswordNSS is a PKCS#8 encrypted private key using the null password
132 // and generated by NSS.
133 static const uint8_t kNullPasswordNSS[] = {
134     0x30, 0x81, 0xb8, 0x30, 0x23, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86, 0xf7,
135     0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x15, 0x04, 0x10, 0x3f, 0xac, 0xe9,
136     0x38, 0xdb, 0x40, 0x6b, 0x26, 0x89, 0x09, 0x73, 0x18, 0x8d, 0x7f, 0x1c,
137     0x82, 0x02, 0x01, 0x01, 0x04, 0x81, 0x90, 0x5e, 0x5e, 0x11, 0xef, 0xbb,
138     0x7c, 0x4d, 0xec, 0xc0, 0xdc, 0xc7, 0x23, 0xd2, 0xc4, 0x77, 0xbc, 0xf4,
139     0x5d, 0x59, 0x4c, 0x07, 0xc2, 0x8a, 0x26, 0xfa, 0x25, 0x1c, 0xaa, 0x42,
140     0xed, 0xd0, 0xed, 0xbb, 0x5c, 0xe9, 0x13, 0x07, 0xaa, 0xdd, 0x52, 0x3c,
141     0x65, 0x25, 0xbf, 0x94, 0x02, 0xaf, 0xd6, 0x97, 0xe9, 0x33, 0x00, 0x76,
142     0x64, 0x4a, 0x73, 0xab, 0xfb, 0x99, 0x6e, 0x83, 0x12, 0x05, 0x86, 0x72,
143     0x6c, 0xd5, 0xa4, 0xcf, 0xb1, 0xd5, 0x4d, 0x54, 0x87, 0x8b, 0x4b, 0x95,
144     0x1d, 0xcd, 0xf3, 0xfe, 0xa8, 0xda, 0xe0, 0xb6, 0x72, 0x13, 0x3f, 0x2e,
145     0x66, 0xe0, 0xb9, 0x2e, 0xfa, 0x69, 0x40, 0xbe, 0xd7, 0x67, 0x6e, 0x53,
146     0x2b, 0x3f, 0x53, 0xe5, 0x39, 0x54, 0x77, 0xe1, 0x1d, 0xe6, 0x81, 0x92,
147     0x58, 0x82, 0x14, 0xfb, 0x47, 0x85, 0x3c, 0xc3, 0xdf, 0xdd, 0xcc, 0x79,
148     0x9f, 0x41, 0x83, 0x72, 0xf2, 0x0a, 0xe9, 0xe1, 0x2c, 0x12, 0xb0, 0xb0,
149     0x0a, 0xb2, 0x1d, 0xca, 0x15, 0xb2, 0xca,
150 };
151 
152 // kEmptyPasswordOpenSSL is a PKCS#8 encrypted private key using the empty
153 // password and generated by OpenSSL.
154 static const uint8_t kEmptyPasswordOpenSSL[] = {
155     0x30, 0x82, 0x01, 0xa1, 0x30, 0x1b, 0x06, 0x0a, 0x2a, 0x86, 0x48, 0x86,
156     0xf7, 0x0d, 0x01, 0x0c, 0x01, 0x03, 0x30, 0x0d, 0x04, 0x08, 0x86, 0xaa,
157     0xd7, 0xdf, 0x3b, 0x91, 0x97, 0x60, 0x02, 0x01, 0x01, 0x04, 0x82, 0x01,
158     0x80, 0xcb, 0x2a, 0x14, 0xaa, 0x4f, 0x38, 0x4c, 0xe1, 0x49, 0x00, 0xe2,
159     0x1a, 0x3a, 0x75, 0x87, 0x7e, 0x3d, 0xea, 0x4d, 0x53, 0xd4, 0x46, 0x47,
160     0x23, 0x8f, 0xa1, 0x72, 0x51, 0x92, 0x86, 0x8b, 0xeb, 0x53, 0xe6, 0x6a,
161     0x0a, 0x6b, 0xb6, 0xa0, 0xdc, 0x0f, 0xdc, 0x20, 0xc3, 0x45, 0x85, 0xf1,
162     0x95, 0x90, 0x5c, 0xf4, 0xfa, 0xee, 0x47, 0xaf, 0x35, 0xd0, 0xd0, 0xd3,
163     0x14, 0xde, 0x0d, 0xca, 0x1b, 0xd3, 0xbb, 0x20, 0xec, 0x9d, 0x6a, 0xd4,
164     0xc1, 0xce, 0x60, 0x81, 0xab, 0x0c, 0x72, 0x10, 0xfa, 0x28, 0x3c, 0xac,
165     0x87, 0x7b, 0x82, 0x85, 0x00, 0xb8, 0x58, 0x9c, 0x07, 0xc4, 0x7d, 0xa9,
166     0xc5, 0x94, 0x95, 0xf7, 0x23, 0x93, 0x3f, 0xed, 0xef, 0x92, 0x55, 0x25,
167     0x74, 0xbb, 0xd3, 0xd1, 0x67, 0x3b, 0x3d, 0x5a, 0xfe, 0x84, 0xf8, 0x97,
168     0x7d, 0x7c, 0x01, 0xc7, 0xd7, 0x0d, 0xf8, 0xc3, 0x6d, 0xd6, 0xf1, 0xaa,
169     0x9d, 0x1f, 0x69, 0x97, 0x45, 0x06, 0xc4, 0x1c, 0x95, 0x3c, 0xe0, 0xef,
170     0x11, 0xb2, 0xb3, 0x72, 0x91, 0x9e, 0x7d, 0x0f, 0x7f, 0xc8, 0xf6, 0x64,
171     0x49, 0x5e, 0x3c, 0x53, 0x37, 0x79, 0x03, 0x1c, 0x3f, 0x29, 0x6c, 0x6b,
172     0xea, 0x4c, 0x35, 0x9b, 0x6d, 0x1b, 0x59, 0x43, 0x4c, 0x14, 0x47, 0x2a,
173     0x36, 0x39, 0x2a, 0xd8, 0x96, 0x90, 0xdc, 0xfc, 0xd2, 0xdd, 0x23, 0x0e,
174     0x2c, 0xb3, 0x83, 0xf9, 0xf2, 0xe3, 0xe6, 0x99, 0x53, 0x57, 0x33, 0xc5,
175     0x5f, 0xf9, 0xfd, 0x56, 0x0b, 0x32, 0xd4, 0xf3, 0x9d, 0x5b, 0x34, 0xe5,
176     0x94, 0xbf, 0xb6, 0xc0, 0xce, 0xe1, 0x73, 0x5c, 0x02, 0x7a, 0x4c, 0xed,
177     0xde, 0x23, 0x38, 0x89, 0x9f, 0xcd, 0x51, 0xf3, 0x90, 0x80, 0xd3, 0x4b,
178     0x83, 0xd3, 0xee, 0xf2, 0x9e, 0x35, 0x91, 0xa5, 0xa3, 0xc0, 0x5c, 0xce,
179     0xdb, 0xaa, 0x70, 0x1e, 0x1d, 0xc1, 0x44, 0xea, 0x3b, 0xa7, 0x5a, 0x11,
180     0xd1, 0xf3, 0xf3, 0xd0, 0xf4, 0x5a, 0xc4, 0x99, 0xaf, 0x8d, 0xe2, 0xbc,
181     0xa2, 0xb9, 0x3d, 0x86, 0x5e, 0xba, 0xa0, 0xdf, 0x78, 0x81, 0x7c, 0x54,
182     0x31, 0xe3, 0x98, 0xb5, 0x46, 0xcb, 0x4d, 0x26, 0x4b, 0xf8, 0xac, 0x3a,
183     0x54, 0x1b, 0x77, 0x5a, 0x18, 0xa5, 0x43, 0x0e, 0x14, 0xde, 0x7b, 0xb7,
184     0x4e, 0x45, 0x99, 0x03, 0xd1, 0x3d, 0x18, 0xb2, 0x36, 0x00, 0x48, 0x07,
185     0x72, 0xbb, 0x4f, 0x21, 0x25, 0x3e, 0xda, 0x25, 0x24, 0x5b, 0xc8, 0xa0,
186     0x28, 0xd5, 0x9b, 0x96, 0x87, 0x07, 0x77, 0x84, 0xff, 0xd7, 0xac, 0x71,
187     0xf6, 0x61, 0x63, 0x0b, 0xfb, 0x42, 0xfd, 0x52, 0xf4, 0xc4, 0x35, 0x0c,
188     0xc2, 0xc1, 0x55, 0x22, 0x42, 0x2f, 0x13, 0x7d, 0x93, 0x27, 0xc8, 0x11,
189     0x35, 0xc5, 0xe3, 0xc5, 0xaa, 0x15, 0x3c, 0xac, 0x30, 0xbc, 0x45, 0x16,
190     0xed,
191 };
192 
193 // kExplicitHMACWithSHA1 is a PBES2-encrypted private key with an explicit
194 // hmacWithSHA1 AlgorithmIdentifier in the PBKDF2 parameters.
195 static const uint8_t kExplicitHMACWithSHA1[] = {
196     0x30, 0x81, 0xec, 0x30, 0x57, 0x06, 0x09, 0x2a, 0x86, 0x48, 0x86, 0xf7,
197     0x0d, 0x01, 0x05, 0x0d, 0x30, 0x4a, 0x30, 0x29, 0x06, 0x09, 0x2a, 0x86,
198     0x48, 0x86, 0xf7, 0x0d, 0x01, 0x05, 0x0c, 0x30, 0x1c, 0x04, 0x08, 0x90,
199     0xcd, 0x1e, 0x47, 0x1d, 0xff, 0x4c, 0xa8, 0x02, 0x02, 0x08, 0x00, 0x30,
200     0x0c, 0x06, 0x08, 0x2a, 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x02, 0x07, 0x05,
201     0x00, 0x30, 0x1d, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03, 0x04,
202     0x01, 0x02, 0x04, 0x10, 0x34, 0xe7, 0x5b, 0x9b, 0xf9, 0x17, 0xcf, 0x15,
203     0x59, 0x7c, 0xfd, 0xc1, 0xac, 0xed, 0x6f, 0xdd, 0x04, 0x81, 0x90, 0xe3,
204     0xd7, 0xfc, 0xbe, 0xe6, 0xe8, 0x92, 0xc1, 0xa2, 0x57, 0x42, 0x4b, 0xf1,
205     0x35, 0x6c, 0x4f, 0x58, 0x61, 0x14, 0x30, 0x4e, 0xa3, 0x8d, 0x4f, 0xde,
206     0x2d, 0x0b, 0xa2, 0x62, 0x4b, 0xee, 0x9f, 0xc4, 0xeb, 0x89, 0x33, 0x76,
207     0x3f, 0x0c, 0x20, 0xad, 0x75, 0x29, 0x42, 0xbc, 0xbd, 0x83, 0x46, 0x1d,
208     0x5c, 0xae, 0xec, 0x10, 0x05, 0xbb, 0xd3, 0x98, 0xc9, 0x5a, 0x5e, 0x0a,
209     0x95, 0x12, 0x1e, 0x65, 0x93, 0xdd, 0xdd, 0x51, 0xd5, 0x56, 0xc2, 0xa9,
210     0xf9, 0x43, 0x0f, 0x68, 0x8a, 0x14, 0x40, 0xe5, 0x62, 0x9e, 0x0d, 0xd7,
211     0x67, 0x62, 0xf4, 0x49, 0xb1, 0x62, 0x22, 0x42, 0xb1, 0xe1, 0xb2, 0x1d,
212     0x37, 0x3e, 0x95, 0x52, 0xe9, 0x61, 0x89, 0xc7, 0x62, 0xcc, 0xb1, 0x44,
213     0x40, 0xef, 0x89, 0xc8, 0xc4, 0x0e, 0xae, 0xa8, 0xf9, 0x17, 0x42, 0x2b,
214     0x8c, 0x0b, 0x26, 0xf6, 0x07, 0x00, 0xab, 0x25, 0x2b, 0x64, 0xcf, 0xc3,
215     0x68, 0xf9, 0x5e, 0x01, 0x66, 0x59, 0x5f, 0x3f, 0x05, 0x57, 0xcd,
216 };
217 
TestDecrypt(const uint8_t * der,size_t der_len,const char * password)218 static void TestDecrypt(const uint8_t *der, size_t der_len,
219                         const char *password) {
220   const uint8_t *data = der;
221   bssl::UniquePtr<X509_SIG> sig(d2i_X509_SIG(NULL, &data, der_len));
222   ASSERT_TRUE(sig.get());
223   ASSERT_EQ(der + der_len, data);
224 
225   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> keypair(
226       PKCS8_decrypt(sig.get(), password, -1));
227   ASSERT_TRUE(keypair);
228 }
229 
TestRoundTrip(int pbe_nid,const EVP_CIPHER * cipher,const char * password,const uint8_t * salt,size_t salt_len,int iterations)230 static void TestRoundTrip(int pbe_nid, const EVP_CIPHER *cipher,
231                           const char *password, const uint8_t *salt,
232                           size_t salt_len, int iterations) {
233   static const uint8_t kSampleKey[] = {
234       0x30, 0x81, 0x87, 0x02, 0x01, 0x00, 0x30, 0x13, 0x06, 0x07, 0x2a, 0x86,
235       0x48, 0xce, 0x3d, 0x02, 0x01, 0x06, 0x08, 0x2a, 0x86, 0x48, 0xce, 0x3d,
236       0x03, 0x01, 0x07, 0x04, 0x6d, 0x30, 0x6b, 0x02, 0x01, 0x01, 0x04, 0x20,
237       0x8a, 0x87, 0x2f, 0xb6, 0x28, 0x93, 0xc4, 0xd1, 0xff, 0xc5, 0xb9, 0xf0,
238       0xf9, 0x17, 0x58, 0x06, 0x9f, 0x83, 0x52, 0xe0, 0x8f, 0xa0, 0x5a, 0x49,
239       0xf8, 0xdb, 0x92, 0x6c, 0xb5, 0x72, 0x87, 0x25, 0xa1, 0x44, 0x03, 0x42,
240       0x00, 0x04, 0x2c, 0x15, 0x0f, 0x42, 0x9c, 0xe7, 0x0f, 0x21, 0x6c, 0x25,
241       0x2c, 0xf5, 0xe0, 0x62, 0xce, 0x1f, 0x63, 0x9c, 0xd5, 0xd1, 0x65, 0xc7,
242       0xf8, 0x94, 0x24, 0x07, 0x2c, 0x27, 0x19, 0x7d, 0x78, 0xb3, 0x3b, 0x92,
243       0x0e, 0x95, 0xcd, 0xb6, 0x64, 0xe9, 0x90, 0xdc, 0xf0, 0xcf, 0xea, 0x0d,
244       0x94, 0xe2, 0xa8, 0xe6, 0xaf, 0x9d, 0x0e, 0x58, 0x05, 0x6e, 0x65, 0x31,
245       0x04, 0x92, 0x5b, 0x9f, 0xe6, 0xc9,
246   };
247 
248   const uint8_t *ptr = kSampleKey;
249   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key(
250       d2i_PKCS8_PRIV_KEY_INFO(nullptr, &ptr, sizeof(kSampleKey)));
251   ASSERT_TRUE(key);
252   ASSERT_EQ(kSampleKey + sizeof(kSampleKey), ptr);
253 
254   bssl::UniquePtr<X509_SIG> encrypted(PKCS8_encrypt(
255       pbe_nid, cipher, password, -1, salt, salt_len, iterations, key.get()));
256   ASSERT_TRUE(encrypted);
257 
258   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key2(
259       PKCS8_decrypt(encrypted.get(), password, -1));
260   ASSERT_TRUE(key2);
261 
262   uint8_t *encoded = nullptr;
263   int len = i2d_PKCS8_PRIV_KEY_INFO(key2.get(), &encoded);
264   bssl::UniquePtr<uint8_t> free_encoded(encoded);
265   ASSERT_GE(len, 0);
266   ASSERT_EQ(static_cast<size_t>(len), sizeof(kSampleKey));
267   ASSERT_EQ(0, OPENSSL_memcmp(encoded, kSampleKey, sizeof(kSampleKey)));
268 }
269 
TEST(PKCS8Test,DecryptString)270 TEST(PKCS8Test, DecryptString) {
271   TestDecrypt(kEncryptedPBES2WithDESAndSHA1,
272               sizeof(kEncryptedPBES2WithDESAndSHA1), "testing");
273   TestDecrypt(kEncryptedPBES2WithAESAndSHA256,
274               sizeof(kEncryptedPBES2WithAESAndSHA256), "testing");
275 }
276 
TEST(PKCS8Test,DecryptNull)277 TEST(PKCS8Test, DecryptNull) {
278   TestDecrypt(kNullPassword, sizeof(kNullPassword), NULL);
279 }
280 
TEST(PKCS8Test,DecryptNullNSS)281 TEST(PKCS8Test, DecryptNullNSS) {
282   TestDecrypt(kNullPasswordNSS, sizeof(kNullPasswordNSS), NULL);
283 }
284 
TEST(PKCS8Test,DecryptEmptyStringOpenSSL)285 TEST(PKCS8Test, DecryptEmptyStringOpenSSL) {
286   TestDecrypt(kEmptyPasswordOpenSSL, sizeof(kEmptyPasswordOpenSSL), "");
287 }
288 
TEST(PKCS8Test,DecryptExplicitHMACWithSHA1)289 TEST(PKCS8Test, DecryptExplicitHMACWithSHA1) {
290   TestDecrypt(kExplicitHMACWithSHA1, sizeof(kExplicitHMACWithSHA1), "foo");
291 }
292 
TEST(PKCS8Test,RoundTripPBEWithrSHA1And3KeyTripleDES)293 TEST(PKCS8Test, RoundTripPBEWithrSHA1And3KeyTripleDES) {
294   // Test with different salts.
295   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
296                 "password", nullptr, 0, 10);
297   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
298                 "password", nullptr, 4, 10);
299   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
300                 "password", (const uint8_t *)"salt", 4, 10);
301   // Test with a different iteration count.
302   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr,
303                 "password", nullptr, 0, 1);
304 }
305 
306 // Test that both "" (empty password, encoded as "\0\0") and nullptr (no
307 // password, encoded as "") work.
TEST(PKCS8Test,RoundTripPBEWithSHA1And3KeyTripleDESEmptyPassword)308 TEST(PKCS8Test, RoundTripPBEWithSHA1And3KeyTripleDESEmptyPassword) {
309   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr, "",
310                 nullptr, 0, 1);
311   TestRoundTrip(NID_pbe_WithSHA1And3_Key_TripleDES_CBC, nullptr, nullptr,
312                 nullptr, 0, 1);
313 }
314 
TEST(PKCS8Test,RoundTripPBEWithSHA1And40BitRC2CBC)315 TEST(PKCS8Test, RoundTripPBEWithSHA1And40BitRC2CBC) {
316   TestRoundTrip(NID_pbe_WithSHA1And40BitRC2_CBC, nullptr, "password",
317                 nullptr, 0, 10);
318 }
319 
TEST(PKCS8Test,RoundTripPBEWithSHA1And128BitRC4)320 TEST(PKCS8Test, RoundTripPBEWithSHA1And128BitRC4) {
321   TestRoundTrip(NID_pbe_WithSHA1And128BitRC4, nullptr, "password",
322                 nullptr, 0, 10);
323 }
324 
TEST(PKCS8Test,RoundTripPBES2)325 TEST(PKCS8Test, RoundTripPBES2) {
326   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", nullptr, 0, 10);
327   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", nullptr, 4, 10);
328   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", (const uint8_t *)"salt",
329                 4, 10);
330   TestRoundTrip(-1, EVP_aes_128_cbc(), "password", nullptr, 0, 1);
331   TestRoundTrip(-1, EVP_rc2_cbc(), "password", nullptr, 0, 10);
332 }
333 
TEST(PKCS8Test,InvalidPBES1NIDs)334 TEST(PKCS8Test, InvalidPBES1NIDs) {
335   static const uint8_t kSampleKey[] = {
336       0x30, 0x81, 0x87, 0x02, 0x01, 0x00, 0x30, 0x13, 0x06, 0x07, 0x2a, 0x86,
337       0x48, 0xce, 0x3d, 0x02, 0x01, 0x06, 0x08, 0x2a, 0x86, 0x48, 0xce, 0x3d,
338       0x03, 0x01, 0x07, 0x04, 0x6d, 0x30, 0x6b, 0x02, 0x01, 0x01, 0x04, 0x20,
339       0x8a, 0x87, 0x2f, 0xb6, 0x28, 0x93, 0xc4, 0xd1, 0xff, 0xc5, 0xb9, 0xf0,
340       0xf9, 0x17, 0x58, 0x06, 0x9f, 0x83, 0x52, 0xe0, 0x8f, 0xa0, 0x5a, 0x49,
341       0xf8, 0xdb, 0x92, 0x6c, 0xb5, 0x72, 0x87, 0x25, 0xa1, 0x44, 0x03, 0x42,
342       0x00, 0x04, 0x2c, 0x15, 0x0f, 0x42, 0x9c, 0xe7, 0x0f, 0x21, 0x6c, 0x25,
343       0x2c, 0xf5, 0xe0, 0x62, 0xce, 0x1f, 0x63, 0x9c, 0xd5, 0xd1, 0x65, 0xc7,
344       0xf8, 0x94, 0x24, 0x07, 0x2c, 0x27, 0x19, 0x7d, 0x78, 0xb3, 0x3b, 0x92,
345       0x0e, 0x95, 0xcd, 0xb6, 0x64, 0xe9, 0x90, 0xdc, 0xf0, 0xcf, 0xea, 0x0d,
346       0x94, 0xe2, 0xa8, 0xe6, 0xaf, 0x9d, 0x0e, 0x58, 0x05, 0x6e, 0x65, 0x31,
347       0x04, 0x92, 0x5b, 0x9f, 0xe6, 0xc9,
348   };
349 
350   const uint8_t *ptr = kSampleKey;
351   bssl::UniquePtr<PKCS8_PRIV_KEY_INFO> key(
352       d2i_PKCS8_PRIV_KEY_INFO(nullptr, &ptr, sizeof(kSampleKey)));
353   ASSERT_TRUE(key);
354   ASSERT_EQ(kSampleKey + sizeof(kSampleKey), ptr);
355 
356   bssl::UniquePtr<X509_SIG> encrypted(PKCS8_encrypt(
357       NID_pbes2, nullptr, "password", -1, nullptr, 0, 0, key.get()));
358   EXPECT_FALSE(encrypted);
359 
360   encrypted.reset(PKCS8_encrypt(NID_undef, nullptr, "password", -1, nullptr, 0,
361                                 0, key.get()));
362   EXPECT_FALSE(encrypted);
363 
364   encrypted.reset(PKCS8_encrypt(NID_rsaEncryption, nullptr, "password", -1,
365                                 nullptr, 0, 0, key.get()));
366   EXPECT_FALSE(encrypted);
367 }
368