If you just install 2.18 from the repository, OpenSSL works right out the box. 
If you must compile from source for whatever reason, I think I can help you. I 
was having the same issue as you yesterday, but finally managed to do it.

First, make sure you have OpenSSL and libssl-dev installed. Remove any previous 
attempts of freeradius you installed (/usr/local/freeradius). I would also 
remove the folder where you extracted 2.1.9 and extract it again. When you run 
./configure you must add the openssl arguments

./configure --with-openssl-includes=/usr/local/openssl/include 
--with-openssl-libraries=/usr/local/openssl/lib --prefix=/usr/local/freeradius

Please note, I installed openssl from source and that is the directory where I 
installed openssl. You can pipe grep -i OpenSSL to see if there are any errors 
regarding OpenSSL. Now, just run make and make install like you normally do.  
Once done, go to /usr/local/freeradius/sbin to run radius (./radius -X). I got 
an error during this step complaining about not being able to find some OpenSSL 
libraries. You need to make a script to tell radiusd where the file is.

vi run-radius

#!/bin/sh -x

LD_LIBRARY_PATH=/usr/local/openssl/lib
LD_PRELOAD=/usr/local/openssl/lib/libcrypto.so

export LD_LIBRARY_PATH LD_PRELOAD

/usr/local/freeradius/sbin/radiusd $@

Save and exit.
Next, you must make the script executable.

chmod u=rwx run-radius

Now you can run the script and everything should work (./run-radius -X). You 
will always have to execute to script to run freeradius.

I got most of my information from this link: 
http://text.dslreports.com/forum/remark,9286052~mode=flat

I am new to freeradius, so if I am doing something wrong, or inefficiently, 
please tell me.

Thai Ha
From: [email protected] 
[mailto:[email protected]] On 
Behalf Of David Peterson
Sent: Tuesday, June 15, 2010 9:50 AM
To: 'FreeRadius users mailing list'
Subject: Ubuntu OpenSSL

I  know there is probably something easy I am missing but I cannot for the life 
of me get FR to compile with OpenSSL for EAP-TTLS support.  Are there any 
how-to's on getting Ubuntu to compile OpenSSL support into FR2.1.9

David Peterson

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