Re: strong TLS connections

2011-10-31 Thread Eric S. Eberhard
Our monolithic program (which runs in well under a meg including 
the program and all memory it uses) is monitored for correct hash (an 
algorithm we have to give a 21 byte hash total of files for which I 
have never seen two different files with the same hash) from an 
off-site program AND onsite cron processes.  It also has calls within 
itself to validate it has not been de-compiled and modified.  It has 
timing alerts that make using gdb/dbx with break points virtually 
impossible.  It is also tied to the serial number of the AIX box or 
network card address on others.  If even one byte does not match what 
was sent, email alerts are sent, the program is removed (after 
document user ids dates and times), the port is disabled, and so 
forth.  Nothing is impenetrable, but an ordinary patching is not 
going to do the job.


Secondly, dynamic libraries if shared by say 10 programs could be 
modified for some purpose OTHER than my program.  They may be 
debugging their software, and hence write a log file of data, not 
realizing that they are logging my raw credit card data.  My software 
then becomes non-compliant due to the innocent actions of others.  Or 
their software may require a certain version that has a vulnerability 
that I can't live with.  And I don't want to have to monitor this.


Third, I certify my software with the static link.  I know -- and the 
PCI compliance auditors know -- that it is compliant.  If I have no 
control over dynamic libraries I have no way of KNOWING I am 
compliant in that environment.  Neither does the customer or the 
auditor.  Stray debug logging is, in fact, one of the primary causes 
of non-PCI compliance.


Fourth, I use different compiler switches than the open source 
(different thread choices, different one-char default behavior, 
etc).  How that works without a static link is an open question (and 
there are many other issues).


The point of a static link is that ... it is static.  You know what 
your program will do and you know how it will behave and you have 
tested, certified, and deployed in that manner.  It is easy to 
validate that it has not been harassed.  The point of a dynamic link 
is to allow O/S updates that fix perceived bugs/holes.  In some 
situations this may not be a good thing (like say in my stray debug 
example).  And usually not relevant.  I might be using only one 
particular encryption.  The fixes might be for others.  And ... as 
usual with all software, sometimes fixes also have unintended consequences.


I still think that the highest security is achieved with a static 
link.  The easiest to keep current and updated is obviously the 
dynamic link.  So that balance should be what decides.


E


At 12:13 PM 10/30/2011, you wrote:

 There are taste issues on this -- but you may be happier with a
 static link.  It will load a giga-blip faster too with static link,
 and you won't even notice :-)  A lot will depend on what your
 software is and how much of it.  We have thousands of customers.  We
 do credit cards which requires certification and you cannot (should
 not) allow the customer to change your software by installing a
 dynamic library.  In fact, what if they built themselves their own
 libraries that wrote the unencrypted text out to a file?  Then they
 could steal credit card numbers.  BAD BAD BAD.  It is a security hole
 to allow dynamic libraries because you have no control on what is
 really there.

If the code is running at the customer site, you have no control over
it, whether it's static or dynamic linked.  It might be a giga-blip
easier for your customer/attacker to patch a dll, put it's still
trivial to patch your monolithic program.



Eric S. Eberhard
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Re: strong TLS connections

2011-10-28 Thread Kristen J. Webb

After all my wrangling, I'm leaning towards just using client certs.

Is it a reasonable assumption that on UNIX'es these days I can
expect to find libssl.so AND the openssl command line?

If not, is it reasonable to assume that A sysadmin will
install openssl to get my app to work?

Otherwise, it would seem that something as easy and well
documented as creating a CSR could be a lot more coding...

Many thanks for all the useful comments!
Kris

On 10/27/11 7:20 AM, Michael S. Zick wrote:

On Wed October 26 2011, Kristen J. Webb wrote:

Having an app that can use certs, it
appears, is nothing compared with how to deploy it and manage those certs ;)




A general truism not specific to certs.

Recognizing (or implementing) a need for trust is one thing;
Determining (or establishing) what is to be trusted is quite another.

Consider:
Your roof leaks.
Its easy to find a contractor who claims they will fix it.
Its an entirely different matter to find one you can __trust__ to do
the job correctly and to your satisfaction.

Mike

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--
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Teradactyl LLC.

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EMAIL: kw...@teradactyl.com
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Re: strong TLS connections

2011-10-28 Thread Eric S. Eberhard
I have an easy solution I use because not only do you have the 
problem with admins not having the library installed, you have the 
problem of them having the wrong version installed for something they 
need.  Your app or theirs won't work.  Or yours will, and they update 
openssl and it no longer does.  And some places with strict security 
policies won't let you install things like openssl (but if they want 
your app they have to install it!).  I simply build the static 
libraries and link them in.  This means nothing need exist on the 
target machine and that you have a more stable product because you 
have tested against the library version you have static linked. You 
could argue it makes the program bigger and my answer is -- say 
what?  My iPod could handle my entire business suite and data (for 
disk space, not actually running) -- so who cares.  I have found this 
is often the easiest way to go.  I also make a small wrapper that 
only builds certs from openssl and uses a different name, again 
making it appear to be my software.  I also allow them to use a Web 
interface to my site to make a cert and download it.  Eric


At 11:09 AM 10/28/2011, Kristen J. Webb wrote:

After all my wrangling, I'm leaning towards just using client certs.

Is it a reasonable assumption that on UNIX'es these days I can
expect to find libssl.so AND the openssl command line?

If not, is it reasonable to assume that A sysadmin will
install openssl to get my app to work?

Otherwise, it would seem that something as easy and well
documented as creating a CSR could be a lot more coding...

Many thanks for all the useful comments!
Kris

On 10/27/11 7:20 AM, Michael S. Zick wrote:

On Wed October 26 2011, Kristen J. Webb wrote:

Having an app that can use certs, it
appears, is nothing compared with how to deploy it and manage those certs ;)


A general truism not specific to certs.

Recognizing (or implementing) a need for trust is one thing;
Determining (or establishing) what is to be trusted is quite another.

Consider:
Your roof leaks.
Its easy to find a contractor who claims they will fix it.
Its an entirely different matter to find one you can __trust__ to do
the job correctly and to your satisfaction.

Mike

__
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--
Mr. Kristen J. Webb
Teradactyl LLC.

PHONE: 1-505-242-1091
EMAIL: kw...@teradactyl.com
VISIT: http://www.teradactyl.com

Home of the

 True incremental Backup System
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Eric S. Eberhard
(928) 567-3727  Voice
(928) 567-6122  Fax
(928) 301-7537   Cell

Vertical Integrated Computer Systems, LLC
Metropolis Support, LLC

For Metropolis support and VICS MBA Supporthttp://www.vicsmba.com

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(You can see why we love this state :-) )  


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Re: strong TLS connections

2011-10-28 Thread Kristen J. Webb



On 10/28/11 12:39 PM, Eric S. Eberhard wrote:

I have an easy solution I use because not only do you have the problem with
admins not having the library installed, you have the problem of them having the
wrong version installed for something they need. Your app or theirs won't work.
Or yours will, and they update openssl and it no longer does. And some places
with strict security policies won't let you install things like openssl (but if
they want your app they have to install it!). I simply build the static
libraries and link them in. This means nothing need exist on the target machine
and that you have a more stable product because you have tested against the
library version you have static linked. You could argue it makes the program
bigger and my answer is -- say what? My iPod could handle my entire business
suite and data (for disk space, not actually running) -- so who cares. I have
found this is often the easiest way to go. I also make a small wrapper that only
builds certs from openssl and uses a different name, again making it appear to
be my software. I also allow them to use a Web interface to my site to make a
cert and download it. Eric

Static linking is something that we looked at a while back.  Some other
folks have convinced me that static linking may not the best way to go.

- You have to keep up with security updates.  If you link against
the system libraries, then security vulnerabilities can be handled
at the OS level.  OS vendors try hard not to break backward
compatibility, but I suppose time will tell if this will come
back to bite us ;)

- I don't have a complete answer on this yet, but it would seem
to me that dynamic linking against crypto libraries instead of
shipping those bits (static link) would make life easier from a
US export side, but I am no lawyer!

- If I am not mistaken, linking against system OpenSSL libraries
allows you to work around the GNU licensing conflict which
had me worried early on as I looked to adopting OpenSSL.
Again, I'm no lawyer!

Relying on OS configuration is more difficult, especially for Linux, as I need
to now build against many linux distro's to get things right.  Thanks
to virtual environments, this is at least manageable.



At 11:09 AM 10/28/2011, Kristen J. Webb wrote:

After all my wrangling, I'm leaning towards just using client certs.

Is it a reasonable assumption that on UNIX'es these days I can
expect to find libssl.so AND the openssl command line?

If not, is it reasonable to assume that A sysadmin will
install openssl to get my app to work?

Otherwise, it would seem that something as easy and well
documented as creating a CSR could be a lot more coding...

Many thanks for all the useful comments!
Kris

On 10/27/11 7:20 AM, Michael S. Zick wrote:

On Wed October 26 2011, Kristen J. Webb wrote:

Having an app that can use certs, it
appears, is nothing compared with how to deploy it and manage those certs ;)


A general truism not specific to certs.

Recognizing (or implementing) a need for trust is one thing;
Determining (or establishing) what is to be trusted is quite another.

Consider:
Your roof leaks.
Its easy to find a contractor who claims they will fix it.
Its an entirely different matter to find one you can __trust__ to do
the job correctly and to your satisfaction.

Mike

__
OpenSSL Project http://www.openssl.org
User Support Mailing List openssl-users@openssl.org
Automated List Manager majord...@openssl.org


--
Mr. Kristen J. Webb
Teradactyl LLC.

PHONE: 1-505-242-1091
EMAIL: kw...@teradactyl.com
VISIT: http://www.teradactyl.com

Home of the

True incremental Backup System
__
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Automated List Manager majord...@openssl.org



Eric S. Eberhard
(928) 567-3727 Voice
(928) 567-6122 Fax
(928) 301-7537 Cell

Vertical Integrated Computer Systems, LLC
Metropolis Support, LLC

For Metropolis support and VICS MBA Support http://www.vicsmba.com

For pictures: http://www.vicsmba.com/ourpics/index.html

(You can see why we love this state :-) )
__
OpenSSL Project http://www.openssl.org
User Support Mailing List openssl-users@openssl.org
Automated List Manager majord...@openssl.org



--
Mr. Kristen J. Webb
Teradactyl LLC.

PHONE: 1-505-242-1091
EMAIL: kw...@teradactyl.com
VISIT: http://www.teradactyl.com

Home of the

 True incremental Backup System
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Re: strong TLS connections

2011-10-28 Thread Eric S. Eberhard

Kristen,

Your points are all good.  However, I have found the compatibility 
not good with customer installed versions versus my own.  One of the 
problems, for example, could be that openssl compiles with a certain 
type of threads, not the same as your application.  Same with 
semaphores and who knows what else. It could be many features like 
that.  It could be changes in product I have found.  Also, if they 
install in a different location than you, the header of your program 
will not find it (which can be solved with links on the user's 
system, sometimes).  Sometimes the user installs a version with other 
dependencies (for example I use libxml2 but not the libzip ... and 
when a customer put the libzip version in, my application had problems).


So then what I was doing was putting my versions of the dynamic 
libraries in my own location  /usr/local/application_name/lib


And linking that way and installing that way.

But then when the security changes came ... I had to again install 
something and I realized it was easier to just install the static 
linked software.  You also get tighter testing because it will force 
you to get the latest version, compile it, link it, test it, then 
install it.  I do a LOT of cross-platform (AIX, Linux, OS/X, SCO, 
HP/UX, Windows, etc) work and have found that I am always safer 
linking exactly what I want and releasing that.  I guess I feel I 
have more control over quality this way.


BUT THIS IS JUST A DUMB OPINION -- most people disagree.  I have 
found in practice that the dream of the O/S level updates magically 
making security updates work for your software is a dream that is 
more nightmare than pleasant.  But that is just me.  There are others 
who do agree, I am not alone, but I would guess a minority.


As for the export question -- if they are not allowed certain things 
they are not allowed.  Depending on your application, it may be 
OK.  So if you require the illegal export of strong encryption and 
you install or ask them to install, you and they are in trouble.


If your application is, say, a credit card application -- and it is 
static linked and can ONLY be used to process credit cards (and you 
let them generate keys through you) you are in fact able to export 
without legal complication.  I export, had legal advise.


I am not sure what you mean by the GNU licensing conflict.  You are 
still only charging for your application, whether you static or 
dynamic link.  I do always include the proper copyright files and put 
them in /usr/local/lib ... even though my link is static.  I checked 
this as well.


I will tell you that both my legal checks were cursory but I am 
confident they were sufficient.  If you are really worried, check 
with a lawyer.  On the GNU I think it is pretty much a matter of the 
intent of the license anyway.  If you disclose it's use, include the 
proper copyright/license files, and don't charge for it, I think you are fine.


There are taste issues on this -- but you may be happier with a 
static link.  It will load a giga-blip faster too with static link, 
and you won't even notice :-)  A lot will depend on what your 
software is and how much of it.  We have thousands of customers.  We 
do credit cards which requires certification and you cannot (should 
not) allow the customer to change your software by installing a 
dynamic library.  In fact, what if they built themselves their own 
libraries that wrote the unencrypted text out to a file?  Then they 
could steal credit card numbers.  BAD BAD BAD.  It is a security hole 
to allow dynamic libraries because you have no control on what is 
really there.  You cannot look at a customer or credit card auditor 
and say with a straight face that you control the encryption and 
there is no security leak.  If you statically link something in and 
certify it ... it is what is is.  Under current credit card rules you 
may do minor updates just by notifying them -- so if you find a 
security patch that applies to your application (most don't for me) 
then you download, link statically, report to everyone who needs to 
know, and install your app again.


Eric





At 12:13 PM 10/28/2011, Kristen J. Webb wrote:



On 10/28/11 12:39 PM, Eric S. Eberhard wrote:

I have an easy solution I use because not only do you have the problem with
admins not having the library installed, you have the problem of 
them having the
wrong version installed for something they need. Your app or theirs 
won't work.

Or yours will, and they update openssl and it no longer does. And some places
with strict security policies won't let you install things like 
openssl (but if

they want your app they have to install it!). I simply build the static
libraries and link them in. This means nothing need exist on the 
target machine

and that you have a more stable product because you have tested against the
library version you have static linked. You could argue it makes the program
bigger and my answer is 

Re: strong TLS connections

2011-10-27 Thread Jakob Bohm

On 10/27/2011 2:14 AM, Kristen J. Webb wrote:



On 10/8/11 1:16 AM, Michael Sierchio wrote:
On Fri, Oct 7, 2011 at 7:40 PM, Kristen J. 
Webbkw...@teradactyl.com  wrote:


My understanding is that a TLS connection with a server cert
only identifies the server to the client.  This leads to a MiTM
attack, where the mitm can impersonate the client because the server
has not verified the client.


Your understanding is flawed - while in the scenario you mention there
is no binding of a client identity to a public key, SSLv3/TLS are not
vulnerable to MITM - no third party can manipulate the stream without
being detected.

Yes, thank you.  Upon further investigation I find that not using
client certs means that the server cannot prove the identity of the
client.  So I think that the attack I am looking at is more of a
client impersonation, where a rouge client pretends to be the real
client.  All it takes (I think) is for the rouge client to have
enough information about the server (e.g. our application installed)
and be able to present itself to the server as the client under attack.
Since the server cannot distinguish, then the rouge client could use
our application to manipulate the server.  It seems that the only
way to help prevent this is to use client certificates to prove the
identity of the client.  The problem I am having with this is that
managing certs for a few servers is easy, while managing it for
1000's of clients is not.  I'm looking for the way around this
and still keep things secure, but maybe there is not?

There are two possible solutions to this problem:

A. Once the client has verified the identity of the server and checked that
  a strong enough encryption has been chosen (not something like the
  old 40 bit stuff, but there are others that are no longer considered 
safe),

  it can use the encrypted channel to prove itself using any old method,
  such as a plaintext password (randomly generated for each non-human
  client).  This is how many Internet sites use TLS with https.

B. With appropriate attributes, the same certificate could be used as both
  server and client certificate.  However you must be careful not to do 
this
  with a public key algorithm that is not secure in that scenario, 
others on

  this list can tell you which ones are safe and which ones not.

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Re: strong TLS connections

2011-10-27 Thread Michael S. Zick
On Wed October 26 2011, Kristen J. Webb wrote:
 Having an app that can use certs, it
 appears, is nothing compared with how to deploy it and manage those certs ;)
 

A general truism not specific to certs.

Recognizing (or implementing) a need for trust is one thing;
Determining (or establishing) what is to be trusted is quite another.

Consider:
Your roof leaks.
Its easy to find a contractor who claims they will fix it.
Its an entirely different matter to find one you can __trust__ to do
the job correctly and to your satisfaction.

Mike

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Re: strong TLS connections

2011-10-26 Thread Kristen J. Webb



On 10/8/11 1:16 AM, Michael Sierchio wrote:

On Fri, Oct 7, 2011 at 7:40 PM, Kristen J. Webbkw...@teradactyl.com  wrote:


My understanding is that a TLS connection with a server cert
only identifies the server to the client.  This leads to a MiTM
attack, where the mitm can impersonate the client because the server
has not verified the client.


Your understanding is flawed - while in the scenario you mention there
is no binding of a client identity to a public key, SSLv3/TLS are not
vulnerable to MITM - no third party can manipulate the stream without
being detected.

Yes, thank you.  Upon further investigation I find that not using
client certs means that the server cannot prove the identity of the
client.  So I think that the attack I am looking at is more of a
client impersonation, where a rouge client pretends to be the real
client.  All it takes (I think) is for the rouge client to have
enough information about the server (e.g. our application installed)
and be able to present itself to the server as the client under attack.
Since the server cannot distinguish, then the rouge client could use
our application to manipulate the server.  It seems that the only
way to help prevent this is to use client certificates to prove the
identity of the client.  The problem I am having with this is that
managing certs for a few servers is easy, while managing it for
1000's of clients is not.  I'm looking for the way around this
and still keep things secure, but maybe there is not?

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EMAIL: kw...@teradactyl.com
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Re: strong TLS connections

2011-10-26 Thread Wim Lewis

On 7 Oct 2011, at 7:40 PM, Kristen J. Webb wrote:
 I'm exploring the security of TLS for TCP/IP connections.
 I would like to establish TLS connections using server certificates
 (managing client certs via external or internal PKI is painful).
 My understanding is that a TLS connection with a server cert
 only identifies the server to the client.  This leads to a MiTM
 attack, where the mitm can impersonate the client because the server
 has not verified the client.
 
 My question is, if multiple servers are used, can this attack
 (and possibly others) be avoided?
 
 Example:
 initiate_server: TLS connect with client
 initiate_server: send encrypted data over TLS to client (including 
 target_server:port)
 initiate server: TLS connect with target_server
 initiate_server: send encrypted data over TLS to target_server (including 
 listen port, client, etc)
 client: attempt TLS connection to target_server:port
 target_server: accept TLS connection from client
 client/target_server: verify additional encrypted data (from initiate_server)
 to establish a connection

If I understand this, you're trying to use 'initiate_server' to introduce the 
other two machines to each other, and relying on those two machines' server 
certificates to allow initiate_server to verify that it's talking to the right 
machine?

I see two problems with this. One is that initiate_server isn't authenticated 
to the other machines--- evil_server could connect to target_server, give it 
fake encrypted data and client info, and then impersonate the client.

The other problem is that this isn't really avoiding having a certificate on 
the client machine. If you have a trustowrthy certificate on client, which 
initiate_server can use to authenticate the connection, why not use that 
certificate as a client certificate when client connects to target_server (and 
eliminate the role of initiate_server entirely)?

Apologies if I don't understand your original motivation, but I don't see how 
the introducer scheme helps you any.


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Re: strong TLS connections

2011-10-26 Thread Kristen J. Webb



On 10/26/11 6:35 PM, Wim Lewis wrote:


On 7 Oct 2011, at 7:40 PM, Kristen J. Webb wrote:

I'm exploring the security of TLS for TCP/IP connections.
I would like to establish TLS connections using server certificates
(managing client certs via external or internal PKI is painful).
My understanding is that a TLS connection with a server cert
only identifies the server to the client.  This leads to a MiTM
attack, where the mitm can impersonate the client because the server
has not verified the client.

My question is, if multiple servers are used, can this attack
(and possibly others) be avoided?

Example:
initiate_server: TLS connect with client
initiate_server: send encrypted data over TLS to client (including 
target_server:port)
initiate server: TLS connect with target_server
initiate_server: send encrypted data over TLS to target_server (including 
listen port, client, etc)
client: attempt TLS connection to target_server:port
target_server: accept TLS connection from client
client/target_server: verify additional encrypted data (from initiate_server)
to establish a connection


If I understand this, you're trying to use 'initiate_server' to introduce the 
other two machines to each other, and relying on those two machines' server 
certificates to allow initiate_server to verify that it's talking to the right 
machine?

Not exactly, I was trying to develop a method where the transaction could occur 
securely w/o a client certificate.  I am beginning to believe that this is not 
possible.  The original idea I had is starting to look like a twisted/reverse
way that Kerberos does these things (I have implemented GSSAPI using host 
principles, which takes the need of the client cert out of the process).

I see two problems with this. One is that initiate_server isn't authenticated 
to the other machines--- evil_server could connect to target_server, give it 
fake encrypted data and client info, and then impersonate the client.

I was assuming that the clients (and servers) would have the longer term trust 
of the initiate_server via a PEM file that has it's identity.

The other problem is that this isn't really avoiding having a certificate on 
the client machine. If you have a trustowrthy certificate on client, which 
initiate_server can use to authenticate the connection, why not use that 
certificate as a client certificate when client connects to target_server (and 
eliminate the role of initiate_server entirely)?

Yeah, I wish I did not need to manage the client certificates.  I am interested 
in setting up a local CA for client certs.  One of my stumbling blocks is

how to manage the install of a new client with libssl.so, but not openssl
installed (so openssl req not there).

Apologies if I don't understand your original motivation, but I don't see how 
the introducer scheme helps you any.
If my understanding is up to speed you need to manage client certs to do this 
right.  Which brings me to my next set of questions about how to manage

this from install to revocation.  Having an app that can use certs, it
appears, is nothing compared with how to deploy it and manage those certs ;)



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Teradactyl LLC.

PHONE: 1-505-242-1091
EMAIL: kw...@teradactyl.com
VISIT: http://www.teradactyl.com

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 True incremental Backup System
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Re: strong TLS connections

2011-10-08 Thread Michael Sierchio
On Fri, Oct 7, 2011 at 7:40 PM, Kristen J. Webb kw...@teradactyl.com wrote:

 My understanding is that a TLS connection with a server cert
 only identifies the server to the client.  This leads to a MiTM
 attack, where the mitm can impersonate the client because the server
 has not verified the client.

Your understanding is flawed - while in the scenario you mention there
is no binding of a client identity to a public key, SSLv3/TLS are not
vulnerable to MITM - no third party can manipulate the stream without
being detected.
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strong TLS connections

2011-10-07 Thread Kristen J. Webb

Hi All,
I'm exploring the security of TLS for TCP/IP connections.
I would like to establish TLS connections using server certificates
(managing client certs via external or internal PKI is painful).
My understanding is that a TLS connection with a server cert
only identifies the server to the client.  This leads to a MiTM
attack, where the mitm can impersonate the client because the server
has not verified the client.

My question is, if multiple servers are used, can this attack
(and possibly others) be avoided?

Example:
initiate_server: TLS connect with client
initiate_server: send encrypted data over TLS to client (including 
target_server:port)

initiate server: TLS connect with target_server
initiate_server: send encrypted data over TLS to target_server (including listen 
port, client, etc)

client: attempt TLS connection to target_server:port
target_server: accept TLS connection from client
client/target_server: verify additional encrypted data (from initiate_server)
to establish a connection

My apologies if this is obviously weak.  I could not find much info on
the web related to this type of multi-connection approach using TLS.

Kris
--
Mr. Kristen J. Webb
Teradactyl LLC.

PHONE: 1-505-242-1091
EMAIL: kw...@teradactyl.com
VISIT: http://www.teradactyl.com

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