# Resolving OpenSSL version mismatch in OS X 10.5.8

**URL:** <https://www.ruby-forum.com/t/resolving-openssl-version-mismatch-in-os-x-10-5-8/175913>\
**Category:** Ruby\
**Created:** [September 22, 2009, 7:39pm UTC](https://www.ruby-forum.com/t/resolving-openssl-version-mismatch-in-os-x-10-5-8/175913 "2009-09-22T19:39:16Z")\
**Posts on this page:** 4\
**Page:** 1

<div class="post-metadata">

**Author:** ![johnnyrepp](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/j/b77776/32.png) [@johnnyrepp](https://www.ruby-forum.com/u/johnnyrepp)\
**Post date:** [September 22, 2009, 7:39pm UTC](https://www.ruby-forum.com/t/resolving-openssl-version-mismatch-in-os-x-10-5-8/175913/1 "2009-09-22T19:39:16Z")

</div>

In a Rails app I have built, the Amazon Web Services Product Advertising  
API is used to retrieve book information. Recently, AWS changed their  
API and now requires that requests be signed with a SHA256 key. I’m in  
the process of updating my code to reflect this change, but quickly ran  
into a problem with mismatched versions of OpenSSL on my system.  
Specifically, the AWS API requires a SHA256 key, but I believe the  
version of OpenSSL I am running (0.9.7l) only provides for SHA1.

So I downloaded the latest stable release of OpenSSL (0.9.8k), compiled  
it, and installed it at /usr/local/ssl.

I set my PATH to include this directory:

Macintosh-266:~ root# env  
MANPATH=/usr/share/man:/usr/local/share/man:/usr/X11/man  
TERM=xterm-color  
SHELL=/bin/sh  
USER=root  
PATH=/usr/local/ssl:/usr/local/bin:/usr/local/sbin:/usr/local/mysql/bin:/bin:/usr/bin:/usr/sbin:/sbin:/usr/local/bin:/usr/X11/bin  
PWD=/var/root  
SHLVL=1  
HOME=/var/root  
\_=/usr/bin/env

I’m running Mac OS X 10.5.8. Leopard ships with OpenSSL installed at  
/System/Library/OpenSSL, and this appears to be what is being included  
by ruby when I “require ‘openssl’”:

Macintosh-266:~ Home$ openssl version -a  
OpenSSL 0.9.7l 28 Sep 2006  
built on: Tue Feb 10 19:04:40 PST 2009  
platform: darwin-i386-cc  
options: bn(64,32) md2(int) rc4(ptr,char) des(idx,cisc,16,long)  
blowfish(ptr)  
compiler: cc -arch ppc -arch ppc64 -arch i386 -arch x86\_64 -g -Os -pipe  
-arch ppc -arch ppc64 -arch i386 -arch x86\_64 -pipe -DOPENSSL\_NO\_IDEA  
-DFAR=  
OPENSSLDIR: “/System/Library/OpenSSL”

My installation of ruby (1.8.5) is running at /usr/local/lib/ruby.

Macintosh-266:~ root# irb  
irb(main):001:0\> require ‘openssl’  
=\> true  
irb(main):002:0\> OpenSSL::OPENSSL\_VERSION  
=\> “OpenSSL 0.9.7i 14 Oct 2005”

In /usr/local/lib/ruby/1.8/openssl/digest.rb:

module OpenSSL  
module Digest

```
alg = %w(DSS DSS1 MD2 MD4 MD5 MDC2 RIPEMD160 SHA SHA1)
if OPENSSL_VERSION_NUMBER > 0x00908000
  alg += %w(SHA224 SHA256 SHA384 SHA512)
end
...

```

end  
end

So, as you can see, I need to be running OpenSSL \> v.0.9.8 in order to  
use SHA256 hashing.

I have been scouring the forums and google for about three hours and  
cannot figure out how to make my ruby install use/load the newer version  
of OpenSSL. If anyone can point me in the right direction, I would  
greatly appreciate it.

Thank you very much for your help.  
Cheers, JR

---

<div class="post-metadata">

**Author:** ![johnnyrepp](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/j/b77776/32.png) [@johnnyrepp](https://www.ruby-forum.com/u/johnnyrepp)\
**Post date:** [September 22, 2009, 7:49pm UTC](https://www.ruby-forum.com/t/resolving-openssl-version-mismatch-in-os-x-10-5-8/175913/2 "2009-09-22T19:49:27Z")

</div>

After re-reading my post, I realized that when I’m requiring openssl in  
Ruby, I’m actually getting an even older version (0.9.7i) than the one  
installed at /System/Library/OpenSSL (which is 0.9.7l). I don’t even  
know where that version is on my system, so the problem may be worse  
than I thought. How can I determine where this version ‘lives’, and  
then set Ruby to point to the newer version I’ve installed (0.9.8k)?

Johnny Rodgers wrote:

> Macintosh-266:~ root# irb  
> irb(main):001:0\> require ‘openssl’  
> =\> true  
> irb(main):002:0\> OpenSSL::OPENSSL\_VERSION  
> =\> “OpenSSL 0.9.7i 14 Oct 2005”

---

<div class="post-metadata">

**Author:** ![johnnyrepp](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/j/b77776/32.png) [@johnnyrepp](https://www.ruby-forum.com/u/johnnyrepp)\
**Post date:** [September 22, 2009, 10:38pm UTC](https://www.ruby-forum.com/t/resolving-openssl-version-mismatch-in-os-x-10-5-8/175913/3 "2009-09-22T22:38:01Z")

</div>

On Sep 22, 2009, at 10:39 AM, Johnny Rodgers wrote:

> USER=root
> 
> OPENSSLDIR: “/System/Library/OpenSSL”
> 
> So, as you can see, I need to be running OpenSSL \> v.0.9.8 in order to  
> use SHA256 hashing.
> 
> I have been scouring the forums and google for about three hours and  
> cannot figure out how to make my ruby install use/load the newer  
> version  
> of OpenSSL. If anyone can point me in the right direction, I would  
> greatly appreciate it.

You’ll have to recompile ruby. You might consider just installing  
ruby via macports. I think that would be the quickest path to success.

* * *

Aaron P.  
[http://tenderlovemaking.com](http://tenderlovemaking.com)

---

<div class="post-metadata">

**Author:** ![johnnyrepp](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/j/b77776/32.png) [@johnnyrepp](https://www.ruby-forum.com/u/johnnyrepp)\
**Post date:** [December 3, 2009, 1:27am UTC](https://www.ruby-forum.com/t/resolving-openssl-version-mismatch-in-os-x-10-5-8/175913/4 "2009-12-03T01:27:02Z")

</div>

Just got a bump from another reader asking if I had resolved this issue,  
so I decided to post my reply here for any future readers in the same  
situation. Aaron’s suggestion above got me going in the right  
direction: “You’ll have to recompile ruby.”

I followed the excellent instructions at

> **[Dan Benjamin](https://danbenjamin.com)**
>
> Dan Benjamin's personal website.

to do this, as I took this opportunity to upgrade my ruby dev setup for  
Snow Leopard. To resolve my specific situation, I had to add the path  
to my desired OpenSSL version into my PATH (Step 1 of the Hivelogic  
instructions) before compiling the latest version of Ruby:

export  
PATH=“/usr/local/bin:/usr/local/sbin:/usr/local/mysql/bin:/usr/local/ssl:$PATH”

Though in my case the path to my MySQL install was different because I  
use MAMP. As an aside, for anyone upgrading to Snow Leopard and using  
MAMP as their local web server, this solution resolved issues I ran into  
with the MySQL gem:  
[http://boonedocks.net/mike/archives/175-MAMP-and-the-Ruby-MySQL-Gem.html](http://boonedocks.net/mike/archives/175-MAMP-and-the-Ruby-MySQL-Gem.html)

Thanks for the suggestion, Aaron. I now have a fresh compile of Ruby  
running OpenSSL v.0.9.8k.

Aaron P. wrote:

> On Sep 22, 2009, at 10:39 AM, Johnny Rodgers wrote:
> 
> > USER=root
> > 
> > OPENSSLDIR: “/System/Library/OpenSSL”
> > 
> > So, as you can see, I need to be running OpenSSL \> v.0.9.8 in order to  
> > use SHA256 hashing.
> > 
> > I have been scouring the forums and google for about three hours and  
> > cannot figure out how to make my ruby install use/load the newer  
> > version  
> > of OpenSSL. If anyone can point me in the right direction, I would  
> > greatly appreciate it.
> 
> You’ll have to recompile ruby. You might consider just installing  
> ruby via macports. I think that would be the quickest path to success.
> 
> * * *
> 
> Aaron P.  
> [http://tenderlovemaking.com](http://tenderlovemaking.com)