[isapros] Re: OT: Requiring client-side certs for RDP

  • From: "Thor (Hammer of God)" <thor@xxxxxxxxxxxxxxx>
  • To: <isapros@xxxxxxxxxxxxx>
  • Date: Fri, 13 Jul 2007 13:12:05 -0700

And just to be pedantic, Terminal Services Gateway uses RDP over SLL
from the gateway to the back end TS clients.  You are confusing the
*publishing of TSG to the internet* with TSG itself. When published via
ISA, RDP is indeed tunneled over RPC/HTTPS.  At the TSGateway, The RPC
headers are stripped, and the TS Gateway contacts the back end TS server
via RDP/SSL.  You can contact Alex Balcanquall internally at MSFT
(Product Manager) and he'll confirm this for you ;)

t




> -----Original Message-----
> From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-
> bounce@xxxxxxxxxxxxx] On Behalf Of Jim Harrison
> Sent: Friday, July 13, 2007 12:36 PM
> To: isapros@xxxxxxxxxxxxx
> Subject: [isapros] Re: OT: Requiring client-side certs for RDP
> 
> It's true that the client *can* connect, but not until the user has
> acknowledged the popups that are produced whtn the cert isn't trusted,
> fails to match the connection, etc.  This is my point.
> In fact, anyone programming against the TS COM will have to make sure
> they handle this event properly.
> 
> Correct - TSG is not "TS Server using SSL" - that's RDP over SSL (no
> HTTP involved).
> TSG OTOH, is RPC/HTTP - you'll have to web-publish it to see the URLs
> used, but when you do, the /rpc/rpcproxy.dll?<servername>:3388 request
> will clarify this for ya.
> 
> -----Original Message-----
> From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-
> bounce@xxxxxxxxxxxxx]
> On Behalf Of Thor (Hammer of God)
> Sent: Friday, July 13, 2007 12:04 PM
> To: isapros@xxxxxxxxxxxxx
> Subject: [isapros] Re: OT: Requiring client-side certs for RDP
> 
> Actually, yes, it is *completely* wrong.  But let's make sure we're
not
> letting you launch one of your famous misdirection threads ;)
> 
> I'm not talking about TSG (Terminal Services Gateway).  I'm talking
> about Win2k3 Terminal Services configured to require TLS/SSL: The
> client
> does *not* have to trust the CA at all - it does not have to trust the
> cert, the ca, or the entire chain for that matter, even though the
> articles say it must. It doesn't.  The client can connect anyway...
> That's what is wrong with the articles.
> 
> I'm asking if Longhorn terminal services will fix this natively.
Tom's
> point about using ISA's SSL Client Certificate Authorization for this
> is
> a great suggestion for TSG, but that is a different animal.
> 
> t
> 
> 
> > -----Original Message-----
> > From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-
> > bounce@xxxxxxxxxxxxx] On Behalf Of Jim Harrison
> > Sent: Friday, July 13, 2007 11:31 AM
> > To: isapros@xxxxxxxxxxxxx
> > Subject: [isapros] Re: OT: Requiring client-side certs for RDP
> >
> > It's not completely wrong; "..the client must trust the root
> > certificate
> > authority.." actually means "the client must trust the CA that
issues
> > the TSG server certificate", but I agree that it's less than clear.
> >
> > Whether TSG will do this natively, I don't know (and kinda doubt),
> but
> > I
> > can certainly ask.
> > As with OL, the question is more client- than server-based; IIS and
> any
> > application that operates within it can use user cert auth, but so
> far,
> > no RPC/HTTP client is capable of responding to a server that
requires
> > user cert auth.
> >
> > -----Original Message-----
> > From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-
> > bounce@xxxxxxxxxxxxx]
> > On Behalf Of Thor (Hammer of God)
> > Sent: Friday, July 13, 2007 10:41 AM
> > To: isapros@xxxxxxxxxxxxx
> > Subject: [isapros] Re: OT: Requiring client-side certs for RDP
> >
> > While dude's article is clearly wrong, the MSFT KB's should be
> amended
> > as well.  Saying "the client must trust the root certificate
> authority"
> > is simply incorrect and misleading.
> >
> > But, more to the core question, since the ts gateway is not the
place
> > to
> > enforce this, are there plans in place for longhorn terminal
services
> > to
> > support client certificate requirements like IIS does?
> >
> > t
> >
> > > -----Original Message-----
> > > From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-
> > > bounce@xxxxxxxxxxxxx] On Behalf Of Jim Harrison
> > > Sent: Friday, July 13, 2007 10:26 AM
> > > To: isapros@xxxxxxxxxxxxx
> > > Subject: [isapros] Re: OT: Requiring client-side certs for RDP
> > >
> > > I just love it when "tribal knowledge" becomes "documented fact".
> > > It's clear from the "article" that the author never tested any of
> the
> > > configuration or application statements he makes.
> > > Even the dialog for his "attempt authentication" screenshot
clearly
> > > states "Authentication will confirm the identity of the remote
> > computer
> > > to which you connect" - NOT "Authentication will confirm the
> identity
> > > of
> > > the user/machine **from which you connect**".
> > >
> > > In theory you *could* require user cert auth,  but I don't know if
> > the
> > > TSG client will respond appropriately.  Since TSG is "just"
> RPC/HTTP,
> > > it's rpcrt4.dll that handles the translation between RPC and HTTP
> and
> > > AFAIK, it only handles Basic and NTLM.
> > >
> > > Because TSG is RPC/HTTP, you can configure the /RPC vroot to
> require
> > > user certs and thus impose this requirement on your connecting
> > clients
> > > to test this theory.  Of course, if you also share this vroot with
> > > Exchange RPC/HTTP you'll break OL connections, since they can't
> > handle
> > > cert auth.
> > >
> > > -----Original Message-----
> > > From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-
> > > bounce@xxxxxxxxxxxxx]
> > > On Behalf Of Thor (Hammer of God)
> > > Sent: Friday, July 13, 2007 9:29 AM
> > > To: isapros@xxxxxxxxxxxxx
> > > Subject: [isapros] OT: Requiring client-side certs for RDP
> > >
> > > Greets:
> > >
> > >
> > >
> > > Windows Server 2003 SP1 allows one to configure
> server-authentication
> > > via certificate for RDP over TLS/SSL.   The MSFT articles say
> things
> > > like "the client must trust the certificate" etc in their
> > > client-configuration notes, and other articles specify that you
can
> > > control access to RDP by issuing self signed certs and controlling
> > > distribution.
> > >
> > >
> > >
> > > This presents the illusion that one can limit connections to RDP
on
> a
> > > Win2k3 server via this method.  See:
> > >
> > > http://support.microsoft.com/kb/895433
> > >
> > >
> http://technet2.microsoft.com/windowsserver/en/Library/a92d8eb9-f53d-
> > > 4e8
> > > 6-ac9b-29fd6146977b1033.mspx
> > >
> > > http://www.windowsecurity.com/articles/Secure-remote-desktop-
> > > connections
> > > -TLS-SSL-based-authentication.html
> > >
> > >
> > >
> > > Win2k3 Terminal Services allows one to require security levels,
but
> > > only
> > > provides "server" authentication - it does not allow you to
require
> a
> > > particular certification to be requested of the client (as IIS
> does).
> > >
> > >
> > >
> > > Snips from the windowsecurity article compound this perception:
> > >
> > > <snip>
> > > The threat becomes even bigger, when the server running Microsoft
> > > Windows Terminal Services is accessible from the Internet through
> an
> > > RDP
> > > connection on port 3389, even though you have an advanced firewall
> > such
> > > as ISA Server in front of it. A scenario that is common especially
> > for
> > > Microsoft Small Business Server users.
> > >
> > > The good news however, is that you can prevent these attacks. The
> > > solution is certificate based computer authentication. If the
> > computer
> > > cannot authenticate itself by presenting a valid certificate to
the
> > > terminal server it is trying to connect to, then the RDP
connection
> > > will
> > > be dropped before the user has a chance to attempt to log on.
> > >
> > > </snip>
> > >
> > >
> > >
> > > This is simply untrue.  The client does not "present a valid
> > > certificate" at all.  It either trusts the server or not, and it
is
> > up
> > > to the client to make that decision.  While RDP clients 6 and
below
> > > only
> > > allow "No auth, attempt, or require" which do provide the expected
> > > behavior, updated or alternate clients (like Vista) allow you to
> > > connect
> > > anyway.
> > >
> > >
> > >
> > > This being said, does anyone know if the current longhorn/ts
> gateway
> > > features will actually allow enforcement of client certificates
> such
> > a
> > > requiring client certs that are signed by particular authorities?
> > >
> > >
> > >
> > > Sorry for all the detail, but I wanted to avoid people saying
> "Sure,
> > > just require TLS for RDP".
> > >
> > >
> > >
> > > t
> > >
> > >
> > >
> > >
> > >
> > >
> > >
> > >
> > >
> > >
> > >
> > >
> > > All mail to and from this domain is GFI-scanned.
> > >
> >
> >
> >
> > All mail to and from this domain is GFI-scanned.
> >
> 
> 
> 
> All mail to and from this domain is GFI-scanned.
> 


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