I decided today to try to get 1.8.3 and readline working on my Mac.
It turns out that there was on OSX update yesterday bringing
the system up to 10.4.3.  And it looks like it updated libcrypto:

-rwxr-xr-x   1 root  wheel  1199188 Nov  5 01:55 /usr/lib/libcrypto. 
0.9.7.dylib
-rwxr-xr-x   1 root  wheel   920352 Nov  5 01:55 /usr/lib/libcrypto. 
0.9.dylib

Can someone who hasn't run the update verify this?

In any case I had a lot of trouble getting readline and OpenSSL to work.
I had to build a static version of the readline extension because of
difficulties getting a dynamic library constructed and I had change a  
call in
ext/ossl.c from OpenSSL_add_all_algorithms() to  
OPENSSL_add_all_algorithms_noconf()
as well as changing calls for BN_mod(...) to BN_div(NUL,...).  There  
was still
some buried call to BN_mod that I could locate with grep (probaby  
some crazy
macro stuff) so I just put a definition in openssl_missing.c

I cobbled all this together from various postings around the net.  I  
have no
idea if all this is the *correct* way to solve these problems, but I  
did get
everything to compile and irb now has readline support and require  
'openssl'
doesn't die with an unresolved symbol.

Perhaps this will help someone else...

RCS file: RCS/ossl.c,v
retrieving revision 1.1
diff -r1.1 ossl.c
385c385
<     OpenSSL_add_all_algorithms();
---
 >     OPENSSL_add_all_algorithms_noconf();



RCS file: RCS/openssl_missing.c,v
retrieving revision 1.1
diff -r1.1 openssl_missing.c
201c201
<     return BN_mod(r, r, m, ctx);
---
 >     return BN_div(NULL, r, r, m, ctx);
204a205,209
 > int   BN_mod(BIGNUM *rem, const BIGNUM *m, const BIGNUM *d, BN_CTX  
*ctx)
 > {
 >       BN_div(NULL, rem, m, d, ctx);
 > }
 >
208c213
<     if (!BN_mod(r,m,d,ctx)) return 0;
---
 >     if (!BN_div(NULL, r,m,d,ctx)) return 0;


Gary Wright