I resolved this problem. It did not involve the fact that the machine
was 64-bit. I had to re-install openssl, before ruby would install
well enough to run rails. Here are my steps.

[EMAIL PROTECTED] uname -a
Linux ???.???.??? 2.6.9-67.0.15.ELsmp #1 SMP Tue Apr 22 13:50:33 EDT
2008 i686 i686 i386 GNU/Linux

#install openssl from source
http://www.openssl.org/source/openssl-0.9.8h.tar.gz
./config shared
make
make test
make install
cp /usr/local/ssl/lib/libssl.so.0.9.8 /lib
rm /lib/libssl.so.4
ln -s /lib/libssl.so.0.9.8 /lib/libssl.so.4
ldconfig

#install and configure zlib
cd /apps
tar xjvf zlib-1.2.3.tar.bz2
./configure --shared
make
make test
make install
vi /etc/ld.so.conf.d/zlib-1.2.3.conf
#insert the value, /usr/local/lib, in the file, on a single line
ldconfig
cp /apps/zlib-1.2.3/zutil.h /usr/local/include
cp /apps/zlib-1.2.3/zutil.c /usr/local/include

#install ruby
cd /apps/ruby-1.8.6
make clean
./configure --prefix=/usr --with-openssl-dir=/usr/local/ssl --with-
openssl-include=/usr/lo\cal/ssl/include
make
make test
make install

#install rubygems
cd /apps/rubygems-1.2.0
ruby setup.rb

#update your gems
gem update
gem install rails

#run a basic rails server to verify that it works
cd /apps
mkdir test
rails /apps/test
cd /apps/test
script/server

# open a browser to localhost:3000 to verify the WebBrick rails server
is running

# installing gems for mongrel...
gem install activesupport
gem install activerecord
gem install actionpack
gem install actionmailer
gem install activeresource
gem install gem_plugin
gem install rails
gem install daemons
gem install fastthread
gem install cgi_multipart_eof_fix
gem install mongrel

# running mongrel...
cd /apps/test
mongrel_rails start


On Aug 8, 10:18 am, bishop <[EMAIL PROTECTED]> wrote:
> I believe my openssl headers are here:
> ls -1 /usr/local/include/openssl
> aes.h
> asn1.h
> asn1_mac.h
> asn1t.h
> bio.h
> blowfish.h
> bn.h
> buffer.h
> cast.h
> comp.h
> conf_api.h
> conf.h
> crypto.h
> des.h
> des_old.h
> dh.h
> dsa.h
> dso.h
> dtls1.h
> ebcdic.h
> ecdh.h
> ecdsa.h
> ec.h
> engine.h
> e_os2.h
> err.h
> evp.h
> hmac.h
> idea.h
> krb5_asn.h
> kssl.h
> lhash.h
> md2.h
> md4.h
> md5.h
> objects.h
> obj_mac.h
> ocsp.h
> opensslconf.h
> opensslv.h
> ossl_typ.h
> pem2.h
> pem.h
> pkcs12.h
> pkcs7.h
> pq_compat.h
> pqueue.h
> rand.h
> rc2.h
> rc4.h
> ripemd.h
> rsa.h
> safestack.h
> sha.h
> ssl23.h
> ssl2.h
> ssl3.h
> ssl.h
> stack.h
> store.h
> symhacks.h
> tls1.h
> tmdiff.h
> txt_db.h
> ui_compat.h
> ui.h
> x509.h
> x509v3.h
> x509_vfy.h
>
> I call configure this way:
> ./configure --with-openssl=/usr/local/include/openssl --with-zlib
> make
> # above make invocation fails because I need to hand-modify the
> Makefiles for:
> # ext/digest/md5
> # ext/digest/rmd160
> # ext/digest/sha1
> # ext/openssl
> # I modify these Makefiles to look for .so files rather than .a files
> for crypt and crypto libraries, and the make succeeds
> make install
>
> Unfortunately, ruby still cannot find openssl:
> ruby -ropenssl -e "puts :success"
> /usr/local/lib/ruby/1.8/x86_64-linux/openssl.so: /usr/local/lib/ruby/
> 1.8/x86_64-linux/openssl.so: undefined symbol: d2i_PKCS7_SIGNER_INFO
> - /usr/local/lib/ruby/1.8/x86_64-linux/openssl.so (LoadError)
>         from /usr/local/lib/ruby/1.8/openssl.rb:17
>
> ...and the web server fails to run:
> ruby -d script/server
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems.rb:
> 772 - no such file to load -- rubygems/defaults/operating_system/usr/
> local/lib/ruby/gems/1.8/gems/rails-2.1.0/lib/initializer.rb:241:
> warning: `&' interpreted as argument prefix
> /usr/local/lib/ruby/gems/1.8/gems/rails-2.1.0/lib/rails/
> gem_dependency.rb:32: warning: `*' interpreted as argument prefix
> Exception `Gem::LoadError' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems.rb:578 - Could not find RubyGem builder (~> 2.1.2)
>
> Exception `Gem::LoadError' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems.rb:578 - Could not find RubyGem xml-simple (~> 1.0.11)
>
> Exception `Gem::LoadError' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems.rb:578 - Could not find RubyGem memcache-client (~> 1.5.0)
>
> Exception `Gem::LoadError' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems.rb:578 - Could not find RubyGem tzinfo (~> 0.3.8)
>
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems/
> custom_require.rb:27 - no such file to load -- Win32API
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems/
> custom_require.rb:34 - no such file to load -- Win32API
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:27 - no such file to load -- fast_xs
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:34 - no such file to load -- fast_xs
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:27 - no such file to load --
> utf8proc_native
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:34 - no such file to load --
> utf8proc_native
> Exception `MissingSourceFile' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/dependencies.rb:512 - no such
> file to load -- utf8proc_native
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:27 - no such file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:34 - no such file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/dependencies.rb:512 - no such
> file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:27 - no such file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:34 - no such file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/dependencies.rb:512 - no such
> file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/core_ext/kernel/requires.rb:19
> - no such file to load -- fcgi
> Exception `MissingSourceFile' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems/custom_require.rb:27 - no such file to load -- mongrel
> Exception `MissingSourceFile' at /usr/local/lib/ruby/gems/1.8/gems/
> mongrel-1.1.5/lib/mongrel/gems.rb:7 - no such file to load --
> mongrel_experimental
> Exception `Gem::LoadError' at /usr/local/lib/ruby/site_ruby/1.8/
> rubygems.rb:578 - Could not find RubyGem mongrel_experimental (>=
> 1.1.5)
>
> => Booting Mongrel (use 'script/server webrick' to force WEBrick)
> Exception `Errno::EEXIST' at /usr/local/lib/ruby/1.8/fileutils.rb:243
> - File exists - /home/m31451/project/test/tmp/cache
> Exception `Errno::EEXIST' at /usr/local/lib/ruby/1.8/fileutils.rb:243
> - File exists - /home/m31451/project/test/tmp/pids
> Exception `Errno::EEXIST' at /usr/local/lib/ruby/1.8/fileutils.rb:243
> - File exists - /home/m31451/project/test/tmp/sessions
> Exception `Errno::EEXIST' at /usr/local/lib/ruby/1.8/fileutils.rb:243
> - File exists - /home/m31451/project/test/tmp/sockets
> => Rails 2.1.0 application starting onhttp://0.0.0.0:3000
> => Call with -d to detach
> => Ctrl-C to shutdown server
> /usr/local/lib/ruby/gems/1.8/gems/mongrel-1.1.5/bin/mongrel_rails:188:
> warning: instance variable @host not initialized
> /usr/local/lib/ruby/gems/1.8/gems/mongrel-1.1.5/bin/mongrel_rails:188:
> warning: instance variable @includes not initialized
> ** Starting Mongrel listening at 0.0.0.0:3000
> ** Starting Rails with development environment...
> /usr/local/lib/ruby/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/
> rails.rb:135: warning: instance variable @rails_handler not
> initialized
> /home/m31451/project/test/config/boot.rb:8: warning: method redefined;
> discarding old boot!
> /home/m31451/project/test/config/boot.rb:15: warning: method
> redefined; discarding old booted?
> /home/m31451/project/test/config/boot.rb:19: warning: method
> redefined; discarding old pick_boot
> /home/m31451/project/test/config/boot.rb:23: warning: method
> redefined; discarding old vendor_rails?
> /home/m31451/project/test/config/boot.rb:27: warning: method
> redefined; discarding old preinitialize
> /home/m31451/project/test/config/boot.rb:31: warning: method
> redefined; discarding old preinitializer_path
> /home/m31451/project/test/config/boot.rb:37: warning: method
> redefined; discarding old run
> /home/m31451/project/test/config/boot.rb:44: warning: method
> redefined; discarding old load_initializer
> /home/m31451/project/test/config/boot.rb:51: warning: method
> redefined; discarding old load_initializer
> /home/m31451/project/test/config/boot.rb:57: warning: method
> redefined; discarding old load_rails_gem
> /home/m31451/project/test/config/boot.rb:69: warning: method
> redefined; discarding old rubygems_version
> /home/m31451/project/test/config/boot.rb:73: warning: method
> redefined; discarding old gem_version
> /home/m31451/project/test/config/boot.rb:83: warning: method
> redefined; discarding old load_rubygems
> /home/m31451/project/test/config/boot.rb:96: warning: method
> redefined; discarding old parse_gem_version
> /home/m31451/project/test/config/boot.rb:101: warning: method
> redefined; discarding old read_environment_rb
> /usr/local/lib/ruby/gems/1.8/gems/activerecord-2.1.0/lib/active_record/
> validations.rb:284: warning: `*' interpreted as argument prefix
> /usr/local/lib/ruby/gems/1.8/gems/activerecord-2.1.0/lib/active_record/
> callbacks.rb:187: warning: `*' interpreted as argument prefix
> /usr/local/lib/ruby/gems/1.8/gems/activerecord-2.1.0/lib/active_record/
> connection_adapters/abstract/connection_specification.rb:41: warning:
> method redefined; discarding old allow_concurrency=
> Exception `LoadError' at /usr/local/lib/ruby/1.8/x86_64-linux/digest/
> md5.so:0 - /usr/local/lib/ruby/1.8/x86_64-linux/digest/md5.so:
> undefined symbol: MD5_Init - /usr/local/lib/ruby/1.8/x86_64-linux/
> digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems/
> custom_require.rb:34 - /usr/local/lib/ruby/1.8/x86_64-linux/digest/
> md5.so: undefined symbol: MD5_Init - /usr/local/lib/ruby/1.8/x86_64-
> linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/dependencies.rb:512 - /usr/
> local/lib/ruby/1.8/x86_64-linux/digest/md5.so: undefined symbol:
> MD5_Init - /usr/local/lib/ruby/1.8/x86_64-linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems/
> custom_require.rb:34 - /usr/local/lib/ruby/1.8/x86_64-linux/digest/
> md5.so: undefined symbol: MD5_Init - /usr/local/lib/ruby/1.8/x86_64-
> linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/dependencies.rb:512 - /usr/
> local/lib/ruby/1.8/x86_64-linux/digest/md5.so: undefined symbol:
> MD5_Init - /usr/local/lib/ruby/1.8/x86_64-linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems/
> custom_require.rb:34 - /usr/local/lib/ruby/1.8/x86_64-linux/digest/
> md5.so: undefined symbol: MD5_Init - /usr/local/lib/ruby/1.8/x86_64-
> linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/gems/1.8/gems/
> activesupport-2.1.0/lib/active_support/dependencies.rb:512 - /usr/
> local/lib/ruby/1.8/x86_64-linux/digest/md5.so: undefined symbol:
> MD5_Init - /usr/local/lib/ruby/1.8/x86_64-linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/site_ruby/1.8/rubygems/
> custom_require.rb:34 - /usr/local/lib/ruby/1.8/x86_64-linux/digest/
> md5.so: undefined symbol: MD5_Init - /usr/local/lib/ruby/1.8/x86_64-
> linux/digest/md5.so
> Exception `LoadError' at /usr/local/lib/ruby/gems/1.8/gems/ ...
>
> read more ยป
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