Why is it that when I try to use a certificate/key pair generated from phpseclib, the OpenSSL server code errors out? Certs/Keys generated from OpenSSL work fine. How do I fix this?

Certificate/Key Generation taken straight from phpseclib documentation:

<?php
include('File/X509.php');
include('Crypt/RSA.php');

// create private key / x.509 cert for stunnel / website
$privKey = new Crypt_RSA();
extract($privKey->createKey());
$privKey->loadKey($privatekey);

$pubKey = new Crypt_RSA();
$pubKey->loadKey($publickey);
$pubKey->setPublicKey();

$subject = new File_X509();
$subject->setDNProp('id-at-organizationName', 'phpseclib demo cert');
//$subject->removeDNProp('id-at-organizationName');
$subject->setPublicKey($pubKey);

$issuer = new File_X509();
$issuer->setPrivateKey($privKey);
$issuer->setDN($subject->getDN());

$x509 = new File_X509();
//$x509->setStartDate('-1 month'); // default: now
//$x509->setEndDate('+1 year'); // default: +1 year

$result = $x509->sign($issuer, $subject);
echo "the stunnel.pem contents are as follows:\r\n\r\n";
echo $privKey->getPrivateKey();
echo "\r\n";
echo $x509->saveX509($result);
echo "\r\n";
?>

OpenSSL sample SSL server taken straight from OpenSSL example code:

#include <stdio.h>
#include <unistd.h>
#include <stdlib.h>
#include <memory.h>
#include <errno.h>
#include <sys/types.h>
#include <sys/socket.h>
#include <netinet/in.h>
#include <arpa/inet.h>
#include <netdb.h>

#include <openssl/rsa.h>       /* SSLeay stuff */
#include <openssl/crypto.h>
#include <openssl/x509.h>
#include <openssl/pem.h>
#include <openssl/ssl.h>
#include <openssl/err.h>

#define CHK_NULL(x) if ((x)==NULL) exit (1)
#define CHK_ERR(err,s) if ((err)==-1) { perror(s); exit(1); }
#define CHK_SSL(err) if ((err)==-1) { ERR_print_errors_fp(stderr); exit(2); }

int main (int argc, char *argv[])
{
  int err;
  int listen_sd;
  int sd;
  struct sockaddr_in sa_serv;
  struct sockaddr_in sa_cli;
  size_t client_len;
  SSL_CTX* ctx;
  SSL*     ssl;
  X509*    client_cert;
  char*    str;
  char     buf [4096];
  SSL_METHOD *meth;

  /* SSL preliminaries. We keep the certificate and key with the context. */

  SSL_load_error_strings();
  SSLeay_add_ssl_algorithms();
  meth = SSLv23_server_method();
  ctx = SSL_CTX_new (meth);
  if (!ctx) {
    ERR_print_errors_fp(stderr);
    exit(2);
  }

  if (SSL_CTX_use_certificate_file(ctx, argv[1], SSL_FILETYPE_PEM) <= 0) {
    ERR_print_errors_fp(stderr);
    exit(3);
  }
  if (SSL_CTX_use_PrivateKey_file(ctx, argv[2], SSL_FILETYPE_PEM) <= 0) {
    ERR_print_errors_fp(stderr);
    exit(4);
  }

  if (!SSL_CTX_check_private_key(ctx)) {
    fprintf(stderr,"Private key does not match the certificate public key\n");
    exit(5);
  }

  /* ----------------------------------------------- */
  /* Prepare TCP socket for receiving connections */

  listen_sd = socket (AF_INET, SOCK_STREAM, 0);   CHK_ERR(listen_sd, "socket");

  memset (&sa_serv, '\0', sizeof(sa_serv));
  sa_serv.sin_family      = AF_INET;
  sa_serv.sin_addr.s_addr = INADDR_ANY;
  sa_serv.sin_port        = htons (1111);          /* Server Port number */

  err = bind(listen_sd, (struct sockaddr*) &sa_serv,
         sizeof (sa_serv));                   CHK_ERR(err, "bind");

  /* Receive a TCP connection. */

  err = listen (listen_sd, 5);                    CHK_ERR(err, "listen");

  client_len = sizeof(sa_cli);
  sd = accept (listen_sd, (struct sockaddr*) &sa_cli, (unsigned int*)&client_len);
  CHK_ERR(sd, "accept");
  close (listen_sd);

  printf ("Connection from %lx, port %x\n",
      sa_cli.sin_addr.s_addr, sa_cli.sin_port);

  /* ----------------------------------------------- */
  /* TCP connection is ready. Do server side SSL. */

  ssl = SSL_new (ctx);                           CHK_NULL(ssl);
  SSL_set_fd (ssl, sd);
  err = SSL_accept (ssl);                        CHK_SSL(err);

  /* Get the cipher - opt */

  printf ("SSL connection using %s\n", SSL_get_cipher (ssl));

  /* Get client's certificate (note: beware of dynamic allocation) - opt */

  client_cert = SSL_get_peer_certificate (ssl);
  if (client_cert != NULL) {
    printf ("Client certificate:\n");

    str = X509_NAME_oneline (X509_get_subject_name (client_cert), 0, 0);
    CHK_NULL(str);
    printf ("\t subject: %s\n", str);
    OPENSSL_free (str);

    str = X509_NAME_oneline (X509_get_issuer_name  (client_cert), 0, 0);
    CHK_NULL(str);
    printf ("\t issuer: %s\n", str);
    OPENSSL_free (str);

    /* We could do all sorts of certificate verification stuff here before
       deallocating the certificate. */

    X509_free (client_cert);
  } else
    printf ("Client does not have certificate.\n");

  /* DATA EXCHANGE - Receive message and send reply. */

  err = SSL_read (ssl, buf, sizeof(buf) - 1);                   CHK_SSL(err);
  buf[err] = '\0';
  printf ("Got %d chars:'%s'\n", err, buf);

  err = SSL_write (ssl, "I hear you.", strlen("I hear you."));  CHK_SSL(err);

  /* Clean up. */

  close (sd);
  SSL_free (ssl);
  SSL_CTX_free (ctx);
  return 1;
}
/* EOF - serv.cpp */

This program errors with: (the error is printed out on the call to SSL_write)

Connection from 100007f, port a7ff
SSL connection using (NONE)
Client does not have certificate.
Got 0 chars:''
82673:error:1409E0E5:SSL routines:SSL3_WRITE_BYTES:ssl handshake failure:/SourceCache/OpenSSL098/OpenSSL098-44/src/ssl/s3_pkt.c:539:

Here is the relevant code referenced by the error:

int ssl3_write_bytes(SSL *s, int type, const void *buf_, int len)
    {
    const unsigned char *buf=buf_;
    unsigned int tot,n,nw;
    int i;

    s->rwstate=SSL_NOTHING;
    tot=s->s3->wnum;
    s->s3->wnum=0;

    if (SSL_in_init(s) && !s->in_handshake)
        {
        i=s->handshake_func(s);
        if (i < 0) return(i);
        if (i == 0)
            {
            SSLerr(SSL_F_SSL3_WRITE_BYTES,SSL_R_SSL_HANDSHAKE_FAILURE);
            return -1;
            }
        }
         ...etc