OT: Security question (openssl vs openssh)

2011-05-03 Thread Mark Moellering

Everyone,
I am looking into setting up a webserver to hold some very sensitive 
information.  I am trying to figure out which is more secure, forcing 
any web connections to be done using an ssh tunnel or forcing ssl.
I have not been able to figure out if one is definitively much more 
secure than another or if they are close to the same.  I would have 
initially thought the ssh tunnel was more secure but knowing that ssl 
can use AES-256, I am now wondering if that isn't adding a complexity 
for little extra security.


Thanks in advance

Mark Moellering
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Re: OT: Security question (openssl vs openssh)

2011-05-03 Thread Maxim Khitrov
On Tue, May 3, 2011 at 10:22 AM, Mark Moellering m...@msen.com wrote:
 Everyone,
 I am looking into setting up a webserver to hold some very sensitive
 information.  I am trying to figure out which is more secure, forcing any
 web connections to be done using an ssh tunnel or forcing ssl.
 I have not been able to figure out if one is definitively much more secure
 than another or if they are close to the same.  I would have initially
 thought the ssh tunnel was more secure but knowing that ssl can use AES-256,
 I am now wondering if that isn't adding a complexity for little extra
 security.

 Thanks in advance

 Mark Moellering

I don't think there is any extra security in tunneling an HTTP
connection over SSH. Use authentication is a different matter, but the
encryption algorithms are the same. Most web servers have an option of
configuring what ciphers are allowed (same as OpenSSH, by the way), so
you can easily restrict HTTPS connections to just AES-256 or any other
cipher you prefer.

The bigger issue will be how to prevent MITM attacks. With SSH, you
have to make sure that the clients have the correct public key ahead
of time or provide a way to verify the key during the first
connection.

With HTTPS you can get a certificate from an existing CA, which allows
clients to verify the server identity without any extra work on your
part. As an alternative, you can create your own CA and distribute the
public key to the clients, which is pretty similar to SSH, except that
it's much easier to change the server certificate later on.

- Max
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Re: OT: Security question (openssl vs openssh)

2011-05-03 Thread Jon Radel


On 5/3/11 10:22 AM, Mark Moellering wrote:


Everyone,
I am looking into setting up a webserver to hold some very sensitive
information. I am trying to figure out which is more secure, forcing any
web connections to be done using an ssh tunnel or forcing ssl.
I have not been able to figure out if one is definitively much more
secure than another or if they are close to the same. I would have
initially thought the ssh tunnel was more secure but knowing that ssl
can use AES-256, I am now wondering if that isn't adding a complexity
for little extra security.

Thanks in advance

Mark Moellering


I'd say that that's a really hard problem to answer definitively, but my 
gut reaction is that the less complex solution is less likely to involve 
configuration screw-ups which compromise security.  Particularly if 
other administrators are or will be involved, that which is too clever 
just begs for innocent, even if clueless, changes that compromise 
assumptions upon which the security depends.


In any case, I'd worry more about how I handle user authentication and 
authorization than squeezing the last little drop of warm fuzzies out of 
the encryption setup.  To the extent that if you already have a fully 
trusted infrastructure in place for ssh keys, you might want to consider 
using ssh tunnels for that reason alone.


Or, to put it another way, if your security is going to fall, it's much 
more likely that it's going to involve a poor configuration choice, a 
user that screws up big time, or a back door to the data, than a 
successful technical attack against TSL or SSH.


--Jon Radel
j...@radel.com
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Re: OT: Security question (openssl vs openssh)

2011-05-03 Thread Bill Campbell
On Tue, May 03, 2011, Mark Moellering wrote:
 Everyone,
 I am looking into setting up a webserver to hold some very sensitive  
 information.  I am trying to figure out which is more secure, forcing  
 any web connections to be done using an ssh tunnel or forcing ssl.
 I have not been able to figure out if one is definitively much more  
 secure than another or if they are close to the same.  I would have  
 initially thought the ssh tunnel was more secure but knowing that ssl  
 can use AES-256, I am now wondering if that isn't adding a complexity  
 for little extra security.

Our solution for critical services like this is to run the
service only on a private LAN segment which is available from the
outside world only through an OpenVPN connection.  The OpenVPN
connection requires unique keys for each client which are easily
revoked if a laptop is lost or stolen or on employee termination.

It also isolates the web service from other external attacks via
insecure PHP scripts and such.

Bill
-- 
INTERNET:   b...@celestial.com  Bill Campbell; Celestial Software LLC
URL: http://www.celestial.com/  PO Box 820; 6641 E. Mercer Way
Voice:  (206) 236-1676  Mercer Island, WA 98040-0820
Fax:(206) 232-9186  Skype: jwccsllc (206) 855-5792

If the personal freedoms guaranteed by the Constitution inhibit the
government's ability to govern the people, we should look to limit those
guarantees.  -- President Bill Clinton, August 12, 1993
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