2 files changed, 200 insertions, 2 deletions

diff --git a/src/regress/lib/libcrypto/x509/Makefile b/src/regress/lib/libcrypto/x509/Makefile
index 8b659b7f09..6e4c35f550 100644
--- a/src/regress/lib/libcrypto/x509/Makefile
+++ b/src/regress/lib/libcrypto/x509/Makefile
@@ -1,7 +1,7 @@
-#       $OpenBSD: Makefile,v 1.16 2023/03/02 21:15:14 tb Exp $
+#       $OpenBSD: Makefile,v 1.17 2023/04/25 21:51:44 job Exp $
 
 PROGS = constraints verify x509attribute x509name x509req_ext callback
-PROGS += expirecallback callbackfailures
+PROGS += expirecallback callbackfailures dercache 
 LDADD = -lcrypto
 DPADD = ${LIBCRYPTO}
 
@@ -24,6 +24,9 @@ CLEANFILES +=	x509name.result callback.out
 . endif
 .endif
 
+run-regress-dercache: dercache
+        ./dercache
+
 run-regress-verify: verify
         perl ${.CURDIR}/make-dir-roots.pl ${.CURDIR}/../certs .
         ./verify ${.CURDIR}/../certs
diff --git a/src/regress/lib/libcrypto/x509/dercache.c b/src/regress/lib/libcrypto/x509/dercache.c
new file mode 100644
index 0000000000..d84cb0831f
--- /dev/null
+++ b/src/regress/lib/libcrypto/x509/dercache.c
@@ -0,0 +1,195 @@
+/* $OpenBSD: dercache.c,v 1.1 2023/04/25 21:51:44 job Exp $ */
+/*
+ * Copyright (c) 2023 Job Snijders <job@openbsd.org>
+ *
+ * Permission to use, copy, modify, and distribute this software for any
+ * purpose with or without fee is hereby granted, provided that the above
+ * copyright notice and this permission notice appear in all copies.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS" AND THE AUTHOR DISCLAIMS ALL WARRANTIES
+ * WITH REGARD TO THIS SOFTWARE INCLUDING ALL IMPLIED WARRANTIES OF
+ * MERCHANTABILITY AND FITNESS. IN NO EVENT SHALL THE AUTHOR BE LIABLE FOR
+ * ANY SPECIAL, DIRECT, INDIRECT, OR CONSEQUENTIAL DAMAGES OR ANY DAMAGES
+ * WHATSOEVER RESULTING FROM LOSS OF USE, DATA OR PROFITS, WHETHER IN AN
+ * ACTION OF CONTRACT, NEGLIGENCE OR OTHER TORTIOUS ACTION, ARISING OUT OF
+ * OR IN CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE.
+ */
+
+/*
+ * This program tests whether the presence of "->enc.modified = 1;"
+ * in select X509 setter functions properly triggers invalidation of cached
+ * DER.
+ */
+
+#include <err.h>
+#include <stdio.h>
+#include <string.h>
+
+#include <openssl/evp.h>
+#include <openssl/rsa.h>
+#include <openssl/x509.h>
+
+#define SETUP()                                                 \
+        derp = der;                                             \
+        if ((a = d2i_X509(NULL, &derp, dersz)) == NULL)         \
+                errx(1, "d2i_X509");                            \
+        if ((der2sz = i2d_X509(a, &der2)) <= 0)                 \
+                errx(1, "i2d_X509");                            \
+        der2p = der2;
+
+#define CLEANUP()                                               \
+        X509_free(a);                                           \
+        a = NULL;                                               \
+        free(der2);                                             \
+        der2 = NULL;
+
+#define CLEANUPSETUP()                                          \
+        CLEANUP()                                               \
+        SETUP()
+
+#define SETX509NAME(fname, value, cert)                         \
+        if ((xn = X509_NAME_new()) == NULL)                     \
+                err(1, NULL);                                   \
+        if (!X509_NAME_add_entry_by_txt(xn, "C", MBSTRING_ASC,  \
+            (const unsigned char*) value, -1, -1, 0))           \
+                errx(1, "X509_NAME_add_entry_by_txt");          \
+        if (!fname(cert, xn))                                   \
+                errx(1, "fname");                               \
+        X509_NAME_free(xn);                                     \
+        xn = NULL;
+
+#define SETASN1TIME(fname, value, cert)                         \
+        if ((at = ASN1_TIME_new()) == NULL)                     \
+                err(1, NULL);                                   \
+        if ((at = X509_gmtime_adj(NULL, value)) == NULL)        \
+                errx(1, "X509_gmtime_adj");                     \
+        if (!fname(cert, at))                                   \
+                errx(1, "fname");                               \
+        ASN1_TIME_free(at);                                     \
+        at = NULL;
+
+#define SETINTEGER(fname, value, cert)                          \
+        if ((ai = ASN1_INTEGER_new()) == NULL)                  \
+                err(1, NULL);                                   \
+        if (!ASN1_INTEGER_set(ai, value))                       \
+                errx(1, "ASN1_INTEGER_set");                    \
+        if (!fname(cert, ai))                                   \
+                errx(1, "fname");                               \
+        ASN1_INTEGER_free(ai);                                  \
+        ai = NULL;
+
+
+static int
+x509_compare(char *f, X509 *a, const unsigned char *der, long dersz)
+{
+        unsigned char *der_test = NULL;
+        long der_testsz;
+        int rc = 0;
+
+        if ((der_testsz = i2d_X509(a, &der_test)) <= 0)
+                errx(1, "i2d_X509");
+
+        if (dersz == der_testsz) {
+                if (memcmp(der, der_test, dersz) == 0) {
+                        warnx("%s() didn't invalidate DER cache", f);
+                        rc = 1;
+                } else
+                        warnx("%s() OK", f);
+        } else
+                warnx("%s() OK", f);
+
+        free(der_test);
+        return rc;
+}
+
+int
+main(void)
+{
+        ASN1_INTEGER *ai = NULL;
+        ASN1_TIME *at = NULL;
+        EVP_PKEY *pkey = NULL;
+        EVP_PKEY_CTX *pkey_ctx = NULL;
+        X509_NAME *xn = NULL;
+        X509 *a, *x;
+        const unsigned char *derp, *der2p;
+        unsigned char *der = NULL, *der2 = NULL;
+        long dersz, der2sz;
+        int ret = 0;
+        
+        if ((x = X509_new()) == NULL)
+                err(1, NULL);
+
+        if ((pkey_ctx = EVP_PKEY_CTX_new_id(EVP_PKEY_RSA, NULL)) == NULL)
+                errx(1, "EVP_PKEY_CTX_new_id");
+        if (EVP_PKEY_keygen_init(pkey_ctx) != 1)
+                errx(1, "EVP_PKEY_keygen_init");
+        if (EVP_PKEY_CTX_set_rsa_keygen_bits(pkey_ctx, 2048) <= 0)
+                errx(1, "EVP_PKEY_CTX_set_rsa_keygen_bits");
+        if (EVP_PKEY_keygen(pkey_ctx, &pkey) <= 0)
+                errx(1, "EVP_PKEY_keygen");
+        if (X509_set_pubkey(x, pkey) != 1)
+                errx(1, "X509_set_pubkey");
+
+        SETINTEGER(X509_set_serialNumber, 1, x)
+        SETASN1TIME(X509_set_notBefore, 0, x)
+        SETASN1TIME(X509_set_notAfter, 60, x)
+        SETX509NAME(X509_set_issuer_name, "NL", x)
+        SETX509NAME(X509_set_subject_name, "BE", x)
+
+        // one time creation of the original DER
+        if (!X509_sign(x, pkey, EVP_sha256()))
+                errx(1, "X509_sign");
+        if ((dersz = i2d_X509(x, &der)) <= 0)
+                errx(1, "i2d_X509");
+
+        SETUP()
+
+        // test X509_set_version
+        if (!X509_set_version(a, 2))
+                errx(1, "X509_set_version");
+        ret += x509_compare("X509_set_version", a, der2p, der2sz);
+
+        CLEANUPSETUP()
+
+        // test X509_set_serialNumber
+        SETINTEGER(X509_set_serialNumber, 2, a)
+        ret += x509_compare("X509_set_serialNumber", a, der2p, der2sz);
+
+        CLEANUPSETUP()
+
+        // test X509_set_issuer_name
+        SETX509NAME(X509_set_issuer_name, "DE", a)
+        ret += x509_compare("X509_set_issuer_name", a, der2p, der2sz);
+
+        CLEANUPSETUP()
+
+        // test X509_set_subject_name
+        SETX509NAME(X509_set_subject_name, "FR", a)
+        ret += x509_compare("X509_set_subject_name", a, der2p, der2sz);
+
+        CLEANUPSETUP()
+
+        // test X509_set_notBefore
+        SETASN1TIME(X509_set_notBefore, 120, a)
+        ret += x509_compare("X509_set_notBefore", a, der2p, der2sz);
+
+        CLEANUPSETUP()
+
+        // test X509_set_notAfter
+        SETASN1TIME(X509_set_notAfter, 180, a)
+        ret += x509_compare("X509_set_notAfter", a, der2p, der2sz);
+
+        CLEANUPSETUP()
+
+        // test X509_set_pubkey
+        if (EVP_PKEY_keygen(pkey_ctx, &pkey) <= 0)
+                errx(1, "EVP_PKEY_keygen");
+        if (X509_set_pubkey(a, pkey) != 1)
+                errx(1, "X509_set_pubkey");
+        ret += x509_compare("X509_set_pubkey", a, der2p, der2sz);
+
+        CLEANUP()
+
+        if (ret)
+                return 1;
+}