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is ssl secure enough ?

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Subject Author Date
is ssl secure enough ? Peter Baumann 06-15-2005
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Posted by Karl Levinson, mvp on June 17, 2005, 8:10 am
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> assuming that you only allow the SSL to the Exchange OMA front end and you
> follow best practices in locking down the server, its all acceptable.
>
> The weak point in the security model has nothing to do with your question
> (SSL). The weak point is the IIS server that runs OMA. SSL is bullet
> proof.

I agree that SSL is more or less acceptable for most OWA implementations.

However, SSL is definitely NOT bulletproof. There are known
vulnerabilities, some of which are trivial to exploit, especially in the
default browser configuration. Do a google search for ssl-man-in-the-middle
or "dsniff ssl" for some vulnerabilities. There are free tools that can
sniff SSL. You can mitigate man in the middle attacks somewhat by using
client certificates for mutual authentication.

SSL 2.0, which is enabled by default on many popular browsers, has some
other significant vulnerabilities. [I understand SSL 3.0 has some as well.]
If the browser allows SSL 2.0, an attacker in the middle can remotely force
the browser to downshift the connection to SSL 2.0 and attack it via those
vulnerabilities. The user gets no notification.

To prevent hijacking, SSL, PGP and other server identity validation schemes
generally depend on the user to notice when the server's identity has not
been correctly validated, and to do the right thing in response. If a user
clicks "OK," the session continues as if nothing happened.

If FIPS-140 certification is important to you, for example because you are a
US federal government, note that SSL 2.0 and 3.0 are not FIPS certified.
TLS 1.0 is newer and more secure and FIPS certified and should be used in
place of SSL where possible. The strength of the SSL server certificate you
implement theoretically also makes a difference.

One thing is that nowadays it seems less likely that an attacker would be in
a position to be able to sniff traffic passing in between you and the
server. The most likely place to do this sniffing would be if the attacker
is physically near the client or is on the same wired network segment as the
client [or server] [or has remote control of an infected computer on your
wired network segment]. This somewhat reduces the risk of an outsider
performing such an attack, though an insider, someone in your company, would
have an easier time of it.

Given all this, it's curious that users, banks, etc. continue to feel so
secure with the use of SSL. There is some some debate as to whether these
issues should or should not spell the end of SSL. Clearly SSL is still
being happily used, generally without reported incidents, even though most
people don't seem to notice or care or make recommendations whether SSL 2.0,
3.0 or TLS is used. Perhaps this is because there really aren't too many
good alternatives to SSL/TLS, and also because on the Internet you often
don't have the ability to control how the client browser is configured.




Posted by Mark Gamache on June 17, 2005, 2:26 pm
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There is no question, if SSL is used incorrectly or that the PC has been
compromised, then SSL has risks. SSL MITM attacks require a compromised
machine or a user who clicks OK without understanding the implications. I'm
a big fan of tokens and mutual auth for these reasons.

--
Mark Gamache
Certified Security Solutions
http://www.css-security.com



>
>> assuming that you only allow the SSL to the Exchange OMA front end and
>> you
>> follow best practices in locking down the server, its all acceptable.
>>
>> The weak point in the security model has nothing to do with your question
>> (SSL). The weak point is the IIS server that runs OMA. SSL is bullet
>> proof.
>
> I agree that SSL is more or less acceptable for most OWA implementations.
>
> However, SSL is definitely NOT bulletproof. There are known
> vulnerabilities, some of which are trivial to exploit, especially in the
> default browser configuration. Do a google search for
> ssl-man-in-the-middle
> or "dsniff ssl" for some vulnerabilities. There are free tools that can
> sniff SSL. You can mitigate man in the middle attacks somewhat by using
> client certificates for mutual authentication.
>
> SSL 2.0, which is enabled by default on many popular browsers, has some
> other significant vulnerabilities. [I understand SSL 3.0 has some as
> well.]
> If the browser allows SSL 2.0, an attacker in the middle can remotely
> force
> the browser to downshift the connection to SSL 2.0 and attack it via those
> vulnerabilities. The user gets no notification.
>
> To prevent hijacking, SSL, PGP and other server identity validation
> schemes
> generally depend on the user to notice when the server's identity has not
> been correctly validated, and to do the right thing in response. If a
> user
> clicks "OK," the session continues as if nothing happened.
>
> If FIPS-140 certification is important to you, for example because you are
> a
> US federal government, note that SSL 2.0 and 3.0 are not FIPS certified.
> TLS 1.0 is newer and more secure and FIPS certified and should be used in
> place of SSL where possible. The strength of the SSL server certificate
> you
> implement theoretically also makes a difference.
>
> One thing is that nowadays it seems less likely that an attacker would be
> in
> a position to be able to sniff traffic passing in between you and the
> server. The most likely place to do this sniffing would be if the
> attacker
> is physically near the client or is on the same wired network segment as
> the
> client [or server] [or has remote control of an infected computer on your
> wired network segment]. This somewhat reduces the risk of an outsider
> performing such an attack, though an insider, someone in your company,
> would
> have an easier time of it.
>
> Given all this, it's curious that users, banks, etc. continue to feel so
> secure with the use of SSL. There is some some debate as to whether these
> issues should or should not spell the end of SSL. Clearly SSL is still
> being happily used, generally without reported incidents, even though most
> people don't seem to notice or care or make recommendations whether SSL
> 2.0,
> 3.0 or TLS is used. Perhaps this is because there really aren't too many
> good alternatives to SSL/TLS, and also because on the Internet you often
> don't have the ability to control how the client browser is configured.
>
>




Posted by S. Pidgorny on June 19, 2005, 9:26 pm
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Hi Karl:


> I agree that SSL is more or less acceptable for most OWA implementations.

In my opinion, SSL/TLS are a must for Outlook Web Access - if one needs to
access mail from public places. On the other hand, I much more prefer
Outlook and RPC over HTTP - it should be compatible with smart card logon. I
do not consider access to sensitive information from untrusted endpoints a
good idea.

Regards

Slav




Posted by James Butler on June 19, 2005, 11:22 pm
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I think we are really forgetting the point here. The question is SSL good
enough. Not "is SSL perfect". Security is really about managing all threats,
if companies have to find perfect security solution for every
implementation, we'll never get anywhere. The question is what is the
vulnerability severity of using SSL together with OWA, I would say the
severity is quite low. Let be more pragmatic. Yes, there will always be risk
with any thing you design,but as long as you manage those risk properly and
routinely then you should be ok.


What are the chances of somebody at an Internet café compromising my SSL
connection to my reverse proxy server that connects to our OWA server. Even
if an attacker has attached a key logger to the usb port at the Internet
café computer. The fact that I am using a two factor authentication should
suffice. Because the keyloger would have only captured that session at the
most, they wouldn't be able to logon to my email account since I am using a
strong authentication method. Like I said we are here to manage security not
implement perfect security, no such thing, unless ofcause you work for the
Army or Navy, people and industries want convenience and security.


Using SSL to connect to an OWA through a reverse proxy together with a 2
factor authentication method is an industry standard design, it's best
practice and is sufficient for banks, and most companies.

If you really want to start being impractical then stop using TCP/IP period.
since the whole TCP/IP is inheritably flawed by design, why not go back to
using X25 or x400 which uses the whole 7 layer of the OSI model. We have
to make the most of what we have, by managing the risk associated with
TCP/IP.



Posted by S. Pidgorny on June 20, 2005, 8:19 pm
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You are not not right - but I still prefer not to access corporate
infrastructure from untrusted and potentially hostile endpoints. Even if
you're using two-factor authentication (guess in your case that's one of the
proprietary one-time password generators, right?), you are still exposing
the session. That's fine in most cases (secrets are just not there or
sensitivity of information is greatly exaggerated) but in some cases it is
not. Mobile devices are ubiquitous nowadays so I don't see much need for
Internet kiosks accessing my network anyway.

--
Svyatoslav Pidgorny, MS MVP - Security, MCSE
-= F1 is the key =-

> I think we are really forgetting the point here. The question is SSL good
> enough. Not "is SSL perfect". Security is really about managing all
threats,
> if companies have to find perfect security solution for every
> implementation, we'll never get anywhere. The question is what is the
> vulnerability severity of using SSL together with OWA, I would say the
> severity is quite low. Let be more pragmatic. Yes, there will always be
risk
> with any thing you design,but as long as you manage those risk properly
and
> routinely then you should be ok.
>
>
> What are the chances of somebody at an Internet café compromising my SSL
> connection to my reverse proxy server that connects to our OWA server.
Even
> if an attacker has attached a key logger to the usb port at the Internet
> café computer. The fact that I am using a two factor authentication should
> suffice. Because the keyloger would have only captured that session at the
> most, they wouldn't be able to logon to my email account since I am using
a
> strong authentication method. Like I said we are here to manage security
not
> implement perfect security, no such thing, unless ofcause you work for the
> Army or Navy, people and industries want convenience and security.
>
>
> Using SSL to connect to an OWA through a reverse proxy together with a 2
> factor authentication method is an industry standard design, it's best
> practice and is sufficient for banks, and most companies.
>
> If you really want to start being impractical then stop using TCP/IP
period.
> since the whole TCP/IP is inheritably flawed by design, why not go back to
> using X25 or x400 which uses the whole 7 layer of the OSI model. We have
> to make the most of what we have, by managing the risk associated with
> TCP/IP.
>




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