diff -r -u ruby-1.8.5-p231/ext/openssl/extconf.rb ruby-1.8.5-p231-fixed/ext/openssl/extconf.rb
--- ruby-1.8.5-p231/ext/openssl/extconf.rb	2007-02-13 08:01:19.000000000 +0900
+++ ruby-1.8.5-p231-fixed/ext/openssl/extconf.rb	2010-07-13 02:18:18.000000000 +0800
@@ -1,5 +1,5 @@
 =begin
-= $RCSfile: extconf.rb,v $ -- Generator for Makefile
+= $RCSfile$ -- Generator for Makefile
 
 = Info
   'OpenSSL for Ruby 2' project
@@ -11,7 +11,7 @@
   (See the file 'LICENSE'.)
 
 = Version
-  $Id: extconf.rb,v 1.21.2.9 2006/06/20 11:18:15 gotoyuzo Exp $
+  $Id: extconf.rb 12572 2007-06-18 09:03:15Z technorama $
 =end
 
 require "mkmf"
@@ -36,8 +36,6 @@
 message "=== Checking for system dependent stuff... ===\n"
 have_library("nsl", "t_open")
 have_library("socket", "socket")
-have_header("unistd.h")
-have_header("sys/time.h")
 have_header("assert.h")
 
 message "=== Checking for required stuff... ===\n"
@@ -61,6 +59,8 @@
   exit 1
 end
 
+%w"rb_str_set_len rb_block_call".each {|func| have_func(func, "ruby.h")}
+
 message "=== Checking for OpenSSL features... ===\n"
 have_func("ERR_peek_last_error")
 have_func("BN_mod_add")
@@ -83,6 +83,8 @@
 have_func("HMAC_CTX_copy")
 have_func("HMAC_CTX_init")
 have_func("PEM_def_callback")
+have_func("PKCS5_PBKDF2_HMAC")
+have_func("PKCS5_PBKDF2_HMAC_SHA1")
 have_func("X509V3_set_nconf")
 have_func("X509V3_EXT_nconf_nid")
 have_func("X509_CRL_add0_revoked")
@@ -92,6 +94,7 @@
 have_func("X509_STORE_get_ex_data")
 have_func("X509_STORE_set_ex_data")
 have_func("OBJ_NAME_do_all_sorted")
+have_func("SSL_SESSION_get_id")
 have_func("OPENSSL_cleanse")
 if try_compile("#define FOO(a, ...) foo(a, ##__VA_ARGS__)\n int x(){FOO(1);FOO(1,2);FOO(1,2,3);}\n")
   $defs.push("-DHAVE_VA_ARGS_MACRO")
diff -r -u ruby-1.8.5-p231/ext/openssl/openssl_missing.c ruby-1.8.5-p231-fixed/ext/openssl/openssl_missing.c
--- ruby-1.8.5-p231/ext/openssl/openssl_missing.c	2007-02-13 08:01:19.000000000 +0900
+++ ruby-1.8.5-p231-fixed/ext/openssl/openssl_missing.c	2010-07-13 02:22:10.000000000 +0800
@@ -1,5 +1,5 @@
 /*
- * $Id: openssl_missing.c,v 1.2.2.4 2006/06/02 10:02:56 gotoyuzo Exp $
+ * $Id: openssl_missing.c 16467 2008-05-19 03:00:52Z knu $
  * 'OpenSSL for Ruby' project
  * Copyright (C) 2001-2002  Michal Rokos <m.rokos@sh.cvut.cz>
  * All rights reserved.
@@ -22,17 +22,15 @@
 #include "openssl_missing.h"
 
 #if !defined(HAVE_HMAC_CTX_COPY)
-int
+void
 HMAC_CTX_copy(HMAC_CTX *out, HMAC_CTX *in)
 {
-    if (!out || !in) return 0;
+    if (!out || !in) return;
     memcpy(out, in, sizeof(HMAC_CTX));
 
-    if (!EVP_MD_CTX_copy(&out->md_ctx, &in->md_ctx)
-	    || !EVP_MD_CTX_copy(&out->i_ctx, &in->i_ctx)
-	    || !EVP_MD_CTX_copy(&out->o_ctx, &in->o_ctx))
-	return 0;
-    return 1;
+    EVP_MD_CTX_copy(&out->md_ctx, &in->md_ctx);
+    EVP_MD_CTX_copy(&out->i_ctx, &in->i_ctx);
+    EVP_MD_CTX_copy(&out->o_ctx, &in->o_ctx);
 }
 #endif /* HAVE_HMAC_CTX_COPY */
 #endif /* NO_HMAC */
diff -r -u ruby-1.8.5-p231/ext/openssl/openssl_missing.h ruby-1.8.5-p231-fixed/ext/openssl/openssl_missing.h
--- ruby-1.8.5-p231/ext/openssl/openssl_missing.h	2007-02-13 08:01:19.000000000 +0900
+++ ruby-1.8.5-p231-fixed/ext/openssl/openssl_missing.h	2010-07-13 02:22:10.000000000 +0800
@@ -1,5 +1,5 @@
 /*
- * $Id: openssl_missing.h,v 1.2.2.2 2005/04/15 19:16:18 gotoyuzo Exp $
+ * $Id: openssl_missing.h 18335 2008-08-04 04:44:17Z shyouhei $
  * 'OpenSSL for Ruby' project
  * Copyright (C) 2001-2002  Michal Rokos <m.rokos@sh.cvut.cz>
  * All rights reserved.
@@ -15,6 +15,10 @@
 extern "C" {
 #endif
 
+#ifndef TYPEDEF_D2I_OF
+typedef char *d2i_of_void();
+#endif
+
 /*
  * These functions are not included in headers of OPENSSL <= 0.9.6b
  */
@@ -56,14 +60,33 @@
 	(char *(*)())d2i_PKCS7_RECIP_INFO, (char *)ri)
 #endif
 
+#if !defined(HAVE_EVP_MD_CTX_INIT)
 void HMAC_CTX_init(HMAC_CTX *ctx);
-int HMAC_CTX_copy(HMAC_CTX *out, HMAC_CTX *in);
+#endif
+
+#if !defined(HAVE_HMAC_CTX_COPY)
+void HMAC_CTX_copy(HMAC_CTX *out, HMAC_CTX *in);
+#endif
+
+#if !defined(HAVE_HMAC_CTX_CLEANUP)
 void HMAC_CTX_cleanup(HMAC_CTX *ctx);
+#endif
 
+#if !defined(HAVE_EVP_MD_CTX_CREATE)
 EVP_MD_CTX *EVP_MD_CTX_create(void);
+#endif
+
+#if !defined(HAVE_EVP_MD_CTX_INIT)
 void EVP_MD_CTX_init(EVP_MD_CTX *ctx);
+#endif
+
+#if !defined(HAVE_EVP_MD_CTX_CLEANUP)
 int EVP_MD_CTX_cleanup(EVP_MD_CTX *ctx);
+#endif
+
+#if !defined(HAVE_EVP_MD_CTX_DESTROY)
 void EVP_MD_CTX_destroy(EVP_MD_CTX *ctx);
+#endif
 
 #if !defined(HAVE_EVP_CIPHER_CTX_COPY)
 int EVP_CIPHER_CTX_copy(EVP_CIPHER_CTX *out, EVP_CIPHER_CTX *in);
@@ -107,19 +130,54 @@
 #define OPENSSL_cleanse(p, l) memset(p, 0, l)
 #endif
 
+#if !defined(HAVE_X509_STORE_SET_EX_DATA)
 void *X509_STORE_get_ex_data(X509_STORE *str, int idx);
 int X509_STORE_set_ex_data(X509_STORE *str, int idx, void *data);
+#endif
+
+#if !defined(HAVE_X509_CRL_SET_VERSION)
 int X509_CRL_set_version(X509_CRL *x, long version);
+#endif
+
+#if !defined(HAVE_X509_CRL_SET_ISSUER_NAME)
 int X509_CRL_set_issuer_name(X509_CRL *x, X509_NAME *name);
+#endif
+
+#if !defined(HAVE_X509_CRL_SORT)
 int X509_CRL_sort(X509_CRL *c);
+#endif
+
+#if !defined(HAVE_X509_CRL_ADD0_REVOKED)
 int X509_CRL_add0_revoked(X509_CRL *crl, X509_REVOKED *rev);
+#endif
+
+#if !defined(HAVE_BN_MOD_SQR)
 int BN_mod_sqr(BIGNUM *r, const BIGNUM *a, const BIGNUM *m, BN_CTX *ctx);
+#endif
+
+#if !defined(HAVE_BN_MOD_ADD)
 int BN_mod_add(BIGNUM *r, const BIGNUM *a, const BIGNUM *b, const BIGNUM *m, BN_CTX *ctx);
+#endif
+
+#if !defined(HAVE_BN_MOD_SUB)
 int BN_mod_sub(BIGNUM *r, const BIGNUM *a, const BIGNUM *b, const BIGNUM *m, BN_CTX *ctx);
+#endif
+
+#if !defined(HAVE_BN_RAND_RANGE)
 int BN_rand_range(BIGNUM *r, BIGNUM *range);
+#endif
+
+#if !defined(HAVE_BN_PSEUDO_RAND_RANGE)
 int BN_pseudo_rand_range(BIGNUM *r, BIGNUM *range);
+#endif
+
+#if !defined(HAVE_CONF_GET1_DEFAULT_CONFIG_FILE)
 char *CONF_get1_default_config_file(void);
+#endif
+
+#if !defined(HAVE_PEM_DEF_CALLBACK)
 int PEM_def_callback(char *buf, int num, int w, void *key);
+#endif
 
 #if defined(__cplusplus)
 }
diff -r -u ruby-1.8.5-p231/ext/openssl/ossl_hmac.c ruby-1.8.5-p231-fixed/ext/openssl/ossl_hmac.c
--- ruby-1.8.5-p231/ext/openssl/ossl_hmac.c	2007-02-13 08:01:19.000000000 +0900
+++ ruby-1.8.5-p231-fixed/ext/openssl/ossl_hmac.c	2010-07-13 02:18:36.000000000 +0800
@@ -1,5 +1,5 @@
 /*
- * $Id: ossl_hmac.c,v 1.4.2.2 2004/12/15 01:54:39 matz Exp $
+ * $Id: ossl_hmac.c 16467 2008-05-19 03:00:52Z knu $
  * 'OpenSSL for Ruby' project
  * Copyright (C) 2001-2002  Michal Rokos <m.rokos@sh.cvut.cz>
  * All rights reserved.
@@ -57,6 +57,12 @@
     return obj;
 }
 
+
+/*
+ *  call-seq:
+ *     HMAC.new(key, digest) -> hmac
+ *
+ */
 static VALUE
 ossl_hmac_initialize(VALUE self, VALUE key, VALUE digest)
 {
@@ -81,12 +87,15 @@
     GetHMAC(self, ctx1);
     SafeGetHMAC(other, ctx2);
 
-    if (!HMAC_CTX_copy(ctx1, ctx2)) {
-	ossl_raise(eHMACError, NULL);
-    }
+    HMAC_CTX_copy(ctx1, ctx2);
     return self;
 }
 
+/*
+ *  call-seq:
+ *     hmac.update(string) -> self
+ *
+ */
 static VALUE
 ossl_hmac_update(VALUE self, VALUE data)
 {
@@ -104,9 +113,7 @@
 {
     HMAC_CTX final;
 
-    if (!HMAC_CTX_copy(&final, ctx)) {
-	ossl_raise(eHMACError, NULL);
-    }
+    HMAC_CTX_copy(&final, ctx);
     if (!(*buf = OPENSSL_malloc(HMAC_size(&final)))) {
 	HMAC_CTX_cleanup(&final);
 	OSSL_Debug("Allocating %d mem", HMAC_size(&final));
@@ -116,6 +123,11 @@
     HMAC_CTX_cleanup(&final);
 }
 
+/*
+ *  call-seq:
+ *     hmac.digest -> aString
+ *
+ */
 static VALUE
 ossl_hmac_digest(VALUE self)
 {
@@ -131,6 +143,11 @@
     return digest;
 }
 
+/*
+ *  call-seq:
+ *     hmac.hexdigest -> aString
+ *
+ */
 static VALUE
 ossl_hmac_hexdigest(VALUE self)
 {
@@ -151,6 +168,27 @@
     return hexdigest;
 }
 
+/*
+ *  call-seq:
+ *     hmac.reset -> self
+ *
+ */
+static VALUE
+ossl_hmac_reset(VALUE self)
+{
+    HMAC_CTX *ctx;
+
+    GetHMAC(self, ctx);
+    HMAC_Init_ex(ctx, NULL, 0, NULL, NULL);
+
+    return self;
+}
+
+/*
+ *  call-seq:
+ *     HMAC.digest(digest, key, data) -> aString
+ *
+ */
 static VALUE
 ossl_hmac_s_digest(VALUE klass, VALUE digest, VALUE key, VALUE data)
 {
@@ -191,6 +234,10 @@
 void
 Init_ossl_hmac()
 {
+#if 0 /* let rdoc know about mOSSL */
+    mOSSL = rb_define_module("OpenSSL");
+#endif
+
     eHMACError = rb_define_class_under(mOSSL, "HMACError", eOSSLError);
 	
     cHMAC = rb_define_class_under(mOSSL, "HMAC", rb_cObject);
@@ -202,6 +249,7 @@
     rb_define_method(cHMAC, "initialize", ossl_hmac_initialize, 2);
     rb_define_copy_func(cHMAC, ossl_hmac_copy);
 
+    rb_define_method(cHMAC, "reset", ossl_hmac_reset, 0);
     rb_define_method(cHMAC, "update", ossl_hmac_update, 1);
     rb_define_alias(cHMAC, "<<", "update");
     rb_define_method(cHMAC, "digest", ossl_hmac_digest, 0);