[isapros] Re: ISA and SAN Certs

  • From: "Greg Mulholland" <gmulholland@xxxxxxxxxxxx>
  • To: <isapros@xxxxxxxxxxxxx>
  • Date: Tue, 9 Oct 2007 07:18:51 +1000

And you will be wrong again... you must learn patience!

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Steve Moffat
Sent: Tuesday, 9 October 2007 7:07 AM
To: ISAPros Mailing List
Subject: [isapros] Re: ISA and SAN Certs

I reckon it's because they are wrong and I am right....but I've been wrong
before.....

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Monday, October 08, 2007 5:50 PM
To: ISAPros Mailing List
Subject: [isapros] Re: ISA and SAN Certs

Geez, not even just for testing!!!! What I was getting at was to see if you
get errors when you access Exch2k7 web services.

So explain the magic, just how have you got autodiscover working with a
single IP and cert as everyone else seems to think it is not possible...even
with CNAMEs.

JJ

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Steve Moffat
Sent: 08 October 2007 18:18
To: ISAPros Mailing List
Subject: [isapros] Re: ISA and SAN Certs

No, I don't condone the use of OOF....:P~~

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Monday, October 08, 2007 1:54 PM
To: ISAPros Mailing List
Subject: [isapros] Re: ISA and SAN Certs

Steve,

Have you tried configuring Out of Office settings whilst using Outlook
Anywhere externally?

Cheers

JJ

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Steve Moffat
Sent: 08 October 2007 14:22
To: ISAPros Mailing List
Subject: [isapros] Re: ISA and SAN Certs

Because they didn't know?

:)

Because they never tried it??

:)

Because they like making things harder than they need tp?

:)

S

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Monday, October 08, 2007 4:55 AM
To: ISAPros Mailing List
Subject: [isapros] Re: ISA and SAN Certs

Ok, now I am confused. If you can simply add a CNAME to redirect
autodiscover.domain.com to your chosen URL, why did the Outlook team bother
to create the hotfix to use SRV records???

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Steve Moffat
Sent: 06 October 2007 20:51
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

Just to muddy the waters...:)

I pass this information on, that it may be of help to others (including
myself in remembering what i did!)

Preamble: This is my setup, so i cannot guarantee that this will work for
you, I have for this setup, 1 server running Windows 2003 x64. If you want
to install Exchange 2007 you will need it on either Windows 2003 x64 or 2007
x64 bit versions, the 32bit (x86) will not work. I also have one static
public (external) IP. Most of the configurations i came across for Exchange
will talk about multiple web sites (with different internal IPs) the thing
they rarely mention is that you will need multiple external IPs to map to
these internal IPs. If you have multiple external IPs then it is probably
better that you assign 1 for autodiscover.domain.com so that you have more
choices down the road instead of locking it to the same IP as your main CAS
IP. If however you are restricted to 1 external IP this may help you.
A little note about SSL certificates, Exchange 2007 is a bit of a nightmare
for SSL certificates, by default you have a self-signed certificate made by
exchange, which is ok if you have no one accessing any external services
like OWA, activesync, RPC over HTTP (OutlookAnywhere). However this scenario
is probably unlikely. If you do have these services then you either can
install this self-signed certificate on every computer that needs to access
these services not to mention telling people to click through the IE7 stupid
"There is a problem with this website's security certificate", needless to
say this is really not a viable option for most people. So pretty much the
only real option is a commercial SSL certificate. Trying to find the most
economical way to do things, i tried StartCom's free (yes really free, not
trial) SSL certificate, problem is that it is trusted by almost everyone
INCEPT Internet Explorer, needless to say it becomes a pain to teach people
the same thing about untrusted certificates. OK - other choices - for
Exchange 2007 you are talking about 2 SSL (I'll show you the bypass to get
it to 1 later), one for mail.domain.com and another for
autodiscover.domain.com, that means if you've done any research on the
subject that you need an SSL cert that supports SAN (Subject Alternative
Name). At present the cheapest one is $200/year, others are considerably
more expensive. Better but even $200/year i find a little steep if all you
need is just a CAS certificate (exchange 2003 front-end certs are easily
<$100). On top of this you may already have a mail.domain.com cert that
would now be useless. I have a mail.domain.com cert from GoDaddy which cost
$20/year (or less) and that is the one that i will be using.
Getting Started:
To start off I did a clean install of windows 2003 x64, setup DNS, WINS (if
necessary), DHCP, IIS in that order, a fairly typical PDC. Then a standard
install of Exchange 2007, there a few extra programs and hotfixes to install
but the install program is good about telling you what you need. A little
note, you can install the Exchange tools on a 32 bit machine to do most of
the administration from a client machine. Ok so you have a clean Exchange
install, let's configure it.
To allow Exchange to accept connections from other mail server, open
Exchange Management Shell (EMS)
Run the following command;
Set-RecieveConnector -Identity "Default <ServerName>" -PermissionGroups
"AnonymousUsers"
Replace <ServerName> with your CAS name. Close the EMS
To allow Exchange to send mail to other mail servers, open Exchange
Management Console (EMC), open Organization Configuration->Hub Transport,
click on 'Send Connectors', Right click (RC) in the 'Send Connectors' box
and select 'New Send Connector', choose a name, for example 'All Outgoing
Connector', leave the 'Select the intended...' as Custom, for the Address
Space click the 'Add' button and enter * in the Add Address Space window
marked Domain, to accept SMTP connections from all domains, leave the
'Include all subdomains' unchecked. In Network settings leave all values at
their default settings, in 'Source Server' again leave the default values,
and finally in 'New Connector' click on 'New' to create the connector.
At this point Exchange should be able to send & receive mail.
At this point if you are going to support Outlook with RPC over HTTP you
will need to install that service, go to Control Panel->Add/Remove
Programs->Add/Remove Windows Components, Select Networking Services, click
on details, click the 'RPC over HTTP Proxy', click 'ok', Click 'next', make
sure Windows has access to the install source, after the proxy is installed,
click 'Next'.
Now you need to remove the Exchange self-signed cert, Open up IIS manager
(Administrative Tools->Internet Information Services (IIS) Manager), Open
the Server subfolder, open the 'Web Sites' folder, and open the 'Default Web
Site', there will be several virtual directories (VD) below the DWS
including owa, and Autodiscover. RC the DWS and select Properties, then
click the 'Directory Security' tab, then click 'Server Certificate' and then
click 'Next' at the SSL welcome wizard. The next step depends if you already
have an SSL certificate for mail.domain.com or not. If you do then click
'Replace the current certificate' and follow the instructions. If you do not
have an SSL certificate then select the 'Remove the current certificate'.
The latter will only remove the certificate from the DWS, it will stay in
the windows certificate store so if you ever need it in the future you can
always get it back. After you remove the certificate, re-run the wizard and
it should ask you to go through the process of asking for an SSL
certificate, follow the wizard which will create an certreq.txt file which
you will need to make the application at a Certification Authority (CA)
company, such as GoDaddy or others. I will leave this to you to follow since
the process varies a bit from CA to CA (ie for GoDaddy you need to install
an intermediate certificate, which may not be necessary for more expensive
CAs. I am using a turbo ssl cert which is registered for mail.domain.com and
costs $20/year.
At this point you should have your mail.domain.com cert on the DWS, and any
other intermediate certs installed.
Next lets change owa so you need to just enter your username and not
domain\username; In EMC go to Server Configuration->Client Access, RC the
owa (DWS) click Properties, click the authentication tab, select the 'use
forms-based authentication:' and then select the 'User name only', then
click on Browse and choose your logon domain. Click 'Ok' to exit.
To install Outlook Anywhere in EMC go to Server Configuration->Client
Access, RC the server and select 'Enable Outlook Anywhere', for the External
host name use: mail.domain.com , External authentication methods: choose
NTLM authentication, do not select 'Allow secure channel (SSL) offloading',
click Finish to exit.
Next we need to change the URLs used autodiscover so that all services point
to mail.domain.com.
In EMC go to Server Configuration->Client Access choose the Offline Address
Book (OAB) Distribution tab, RC the OAB (DWS) and select properties, Click
on the URLs tab and put in: https://mail.domain.com/oab for both both
internal and external URLs. Click 'Ok' to accept and exit.
Do the same for owa by going to Server Configuration->Client Access (Outlook
Web Access tab) andRC the owa (DWS) and choose properties, on the General
tab change the Internal and External URLs to: https://mail.domain.com/owa ,
click 'Apply', an extra feature you may want to give is access to network
shares through owa, this is available on the Documents box in owa, if you do
then go to the 'Remote File Servers' tab and click the 'Configure' button on
the bottom, enter the domain you are using, ie for mail.domain.com you would
put domain.com, click 'add' then click 'ok' to exit. Then click on the
'Allow' button and enter the FQDN of your CAS, ie if the CAS computer name
is mx1.domain.com, then enter mx1.domain.com and click 'add' then 'ok'. This
will give owa users access to any network shares that exist on mx1. Click
'ok' to save and exit. If you do not want this then disregard that previous
procedure and click 'ok' to exit.
Next we'll change the URLs for the Unified Messaging, while this step is
probably not necessary for most people, it will look better at the end.
However to change the URLs we need to go to the EMS.
Open the EMS and enter the following command;
Set-UMVirtualDirectory "UnifiedMessaging (Default Web Site)" -InternalURL
https://mail.domain.com/Unifiedmessaging/Service.asmx -ExternalURL
https://mail.domain.com/Unifiedmessaging/Service.asmx
Next we change the URLs of the Availability service which will also be the
same for OOF, in EMS enter the following command;
Set-WebServicesVirtualDirectory -Identity "EWS*" -InternalURL
https://mail.domain.com/EWS/Exchange.asmx -ExternalURL
https://mail.domain.com/EWS/Exchange.asmx
Finally we set the autodiscover URL, now this is a little special since it
is not possible to set the external URL of autodiscover. Outlook 2007 is set
to look for autodiscover.domain.com or domain.com/autodiscover, and this is
in my opinion where all the security alert mess comes from. Anyways in the
EMS enter the following command;
Set-ClientAccessServer -Identity "your CAS server name (ie mx1)"
-AutoDiscoverServiceInternalUri
https://mail.domain.com/autodiscover/autodiscover.xml
Ok all done with EMS, you can close it and go to your DNS management,
Administrative tools->DNS. First in the Foward Lookup Zone (FLZ) for
domain.com, RC the domain.com and select 'New Host (A)', enter: mail ,for
the name and input the Internal IP of your CAS. Next RC the FLZ under your
server and select 'New Zone', click 'Next' at the wizard introduction, leave
the zone type as Primary and ActiveDirectory integrated, click 'Next', leave
the zone replication on the default, which is to all domain dns servers,
click 'Next', For the name enter: autodiscover.domain.com , click 'Next',
for the dynamic updates change the setting to 'Allow both unsecure and
secure dynamic updates, click 'next then click 'Finish'. Now RC the new
autodiscover.domain.com and select 'New Alias (CNAME)', leave the name field
blank and just click on the Browse button, In the new browse window,
double-click (DC) the server name, DC the FLZ folder, DC domain.com and then
select the mail entry, click 'ok' to complete. You can now close DNS.
I would recommend restarting the server to insure that the new settings are
accepted. One thing you will want to check after the restart is to go to
EMC->Server Configuration->Mailbox, RC the mailbox database, select
properties, click on the 'Client Settings' tab and verify that you have the
'Default Offline Address Book' listed in the Offline address Book window, if
not click on the Browse button and select it. If it was not there then
restart the server again after you have selected it.
Ok almost done! You should be able to start up a Outlook 2007 client and
when adding an exchange mail account it should use the autodiscover feature
to get all the URLs. Hopefully everything should work, if you do get a
Security Alert windows then try restarting the client and server, also
verify that the SSL cert is accepted on the client. If everything did go
well then Outlook can connect and send/receive from exchange. Now you can
check that all the URLs are pointing to mail.domain.com, while holding down
the left 'Ctrl' button RC the Outlook icon in the system tray, this should
give you a menu which has 'Test e-mail Autoconfiguration' in the test
window, enter your email (ie user@xxxxxxxxxx), unselect the "use guesssmart"
and "secure guesssmart authentication" then click 'Test'
If everything goes well then you should have 2 sections after the results
come in, one for Exchange RPC and the other Exchange HTTP. The RPC is for
LAN connections and HTTP is for HTTP connections. In both sections all the
URLs should start https://mail.domain.com
If this is not the case then go back and find the problem.
Another test to do is to verify that your OWA is working internally. If you
open Internet Explorer (IE) and enter https://mail.domain.com/owa , don't
forget to change domain to whatever your domain is. This should give you the
OWA login webpage, if not then go back and find the problem. You should not
have any Security Alerts with the OWA.
 If this is ok then your 200x Outlook clients should be working ok
internally and your 2003 clients should be ok externally. However if you try
your Outlook 2007 clients from the internet you will probably find that they
give a Security Alert, and that is because they are looking for either an
SSL with a name of autodiscover.domain.com or domain.com. Since yours is for
mail.domain.com it will give a name mismatch error. To resolve this you must
access your external dns entries which are usually handled by your hosting
provider. For your external DNS you will have a MX record for where your
mail is sent and probably entries for www, ftp, etc. These are the way that
computers on the internet find domain.com resources. Usually it takes 4 to
24 hours for adding or changing the external DNS entries to actually start
redirecting clients, so don't expect just because you changed the MX record
that your email will be redirected right away. The setup is very similar to
the DNS entries for the internal network, for the external DNS entries you
will have the MX record to point to mail.domain.com (MX cannot point to an
IP), you will need a Host record (A) that is for mail.domain.com which
points to your external IP and finally an Alias (CNAME) entry for
autodiscover.domain.com which will point to mail.domain.com.
This way when Outlook 2007 is on the internet and asks joeblow_nameserver
for autodiscover.domain.com it will be sent to your external DNS entries
where it will find autodiscover.domain.com which is an alias for
mail.domain.com, the exact details of why outlook accepts it i am not sure,
but it doesn't give me any complaints. So this way you don't need multiple
external IPs (expensive), nor SAN SSL certificates (unnecessary and
expensive), nor create multiple internal websites (unnecessary).
I have been using this for a few weeks now and everything appears normal and
stable, i have been using Outlook 2007, i have not tested this on Outlook
2003 however i do not think there should be any problems. The OWA and
Outlook clients have no problems connecting, the only thing which i find a
bit un-normal is that it seems to take about 2 minutes for Outlook to
connect and synchronize, with Exchange 2003 and Outlook 2003 it seems to be
quite a bit faster, if anyone can comment on this I'd appreciate any
insight.
I have tested this also with Windows Mobile 2003SE and the activesync works
well, if you have the GoDaddy cert you will need to add the CA cert to the
WM2003 trusted root store, then after that it connects fine.
Most of this information is around the internet but I thought this would be
useful to write down in one place since i didn't find much information about
external DNS settings. I did leave out some extra information about
redirecting the OWA URL, which allows users to log into the port 80 http owa
url and then get redirected to the 443 https url, however i am not really
satisfied with the current method of the redirect html page. If i find
something i'll post back. Anyways i hope this give some insight for some and
will help with the installation.

Heh heh...Steve


-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Thursday, September 20, 2007 11:16 AM
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

The fact is you just can't be sure, in my book, that makes is useless if you
want to provide a robust solution and not have to worry about use
location/infrastucture...anyhow, just testing my logic before I decide what
to tell customers...

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jim Harrison
Sent: 20 September 2007 15:05
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

That's kinda myopic...
Your statement suggests that you think all OL clients will be found behind
CERN or SOCKS proxies.  That just ain't true.
Most folks at home use some CompIsUs $25 toy that barely qualifies as a NAT
device; much less a firewall or proxy.  In this case, the SRV record lookup
will (may?) work.


-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Thursday, September 20, 2007 7:00 AM
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

How about we look at it like this; the SRV solution, in reality, is useless!
:-P

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jim Harrison
Sent: 20 September 2007 14:48
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

I see what you mean.
Look at it this way - the benefit for a SRV record in this case is to
specify a non-standard port if one is required.

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Thursday, September 20, 2007 3:29 AM
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

From what I can tell, OA looks for the A record first, this is the bit that
seems silly...especially when combined with the issues of SRV and CERN
proxies.

Quote from KB:

In this example, the Autodiscover service does the following when the client
tries to contact the Autodiscover service:

1. Autodiscover posts to https://contoso.com/Autodiscover/Autodiscover.xml.
This fails.
2. Autodiscover posts to
https://autodiscover.contoso.com/Autodiscover/Autodiscover.xml. This fails.
3. Autodiscover performs the following redirect check:
GET http://autodiscover.contoso.com/Autodiscover/Autodiscover.xml
This fails.
4. Autodiscover uses DNS SRV lookup for _autodiscover._tcp.contoso.com, and
then "mail.contoso.com" is returned.
5. Outlook asks permission from the user to continue with Autodiscover to
post to https://mail.contoso.com/autodiscover/autodiscover.xml.
6. Autodiscover's POST request is successfully posted to
https://mail.contoso.com/autodiscover/autodiscover.xml.

The Outlook 2007 "Test E-Mail Auto Configuration" utility also follows the
same sequence of doing A records first.

JJ

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jim Harrison
Sent: 20 September 2007 01:03
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

Actually, what I'm saying is that if OL 2003/7 is operating as a CERN proxy
client, it performs absolutely no name queries at all; regardless of whether
the name is listed as an A, SRV, TXT, CNAME, etc. record.  This is the basic
nature of a CERN proxy client; it sends a "gimme this, wouldya?" request
without regard for how the endpoint might be resolved.  Thus, OL will never
communicate with a DNS server in this scenario.

The egress proxy will seek an A record, since there is no way for the CERN
proxy client to specify how the proxy should resolve the destination (it's
just not part of the protocol).

You're correct that you have to maintain A as well as SRV records if you
intend to support CERN proxy as well as direct-connected clients.  I'm not
sure how "silly" this is, since CERN proxy mechanisms existed long before OL
started using autodiscover.  AFAIK, OL will seek the SRV record first, since
this is much more informative than the A record.

Jim

-----Original Message-----
From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jason Jones
Sent: Tuesday, September 18, 2007 3:42 PM
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs

Hi Jim,



So, in reality, we are saying that you can never be sure Outlook 2007 will
work correctly with SRV records if you are unsure if the client will ever be
working from behind a CERN proxy??



This seems a little silly as the SRV check is the last in the list, so
therefore you will always need an A record for autodiscover.domain.com to
cater to clients that *may* be behind a proxy. If this A record exists,
surely Outlook will never actually use the SRV record (as it is only used if
the A record cannot be found) and you still need ISA publishing and certs
for autodiscover.domain.com to allow for "behind proxy" outlook clients...



As we provide solution for customers, I cannot really afford to deploy a
solution that may or may not work depending on whether the Outlook client is
behind a proxy or not. So I feel forced to have to go with the A record
method (reluctantly) to avoid potentially embarrassing questions when a CEO
cannot get OA to work when at an internet café that uses a CERN proxy...



Am I way off base here or does the logic seem wrong to you???



Cheers



JJ



From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jim Harrison
Sent: 31 August 2007 15:00
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs



The problem is that many applications operating behind CERN, SOCKS or Socket
proxies can't use SRV records.

1.      CERN proxy clients *never* perform name resolution for themselves
other than to determine if a host is local or remote.  When it comes time to
make the connection, OL (for instance), will simple send a "GET
http://autodiscover.domain.tld/autodiscover.xml"; via its local CERN proxy.
The proxy assumes that it should resolve "autodiscover.domain.tld" using an
A record query and continues on that basis  If all you build is a SRV
record, this connection will fail.

2.      SOCKS proxy clients *may* self-resolve names; it depends on the
SOCKS version in use by the application and SOCKS proxy.  For the record,
ISA operates as SOCKS 4.3A, meaning that it is capable of performing name
resolution on behalf of the client.  If the application knows that it is
speaking to a SOCKS4.3a proxy, it will make the connection request using the
hostname.  In this case, the proxy handles name resolution in the same way
that a CERN proxy does.  If the SOCKS proxy is operating as SOCKS4 or
earlier and the application knows this, the application is required to
perform its own name resolution.

3.      Socket proxy (think FWC) clients will perform name resolution as if
they had access to the 'Net.  How this process is handled depends on how the
client makes the name lookup request.  If it (as OL does) makes a Winsock
GetHostByname or GetAddrInfo call, they don't specify the type of record
they want, and Winsock (and the Winsock LSP/BSP) will send it to the proxy
as received.



IOW, it's a rare case where a proxy-served client will even seek; much less
receive the SRV record.



Jim



From: isapros-bounce@xxxxxxxxxxxxx [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Thomas W Shinder
Sent: Friday, August 31, 2007 6:42 AM
To: isapros@xxxxxxxxxxxxx
Subject: [isapros] Re: ISA and SAN Certs



Hi Jason,



OK, that makes perfect sense and it's the scenario I'm testing today. One
listener, one rule for Outlook Anywhere and one rule for Autodiscovery,
correct?



So I was right that you can't use the /AutoDiscover path that is included in
the Outlook Anywhere rule since the Outlook Anywhere rule doesn't respond to
the public name autodiscover.domain.com. The Outlook Autodiscover rule would
respond to autodiscover.domain.com and forward to the /AutoDiscover path.



The SRV record solution will solve ALL of this complexity because it will
bypass the need for a second URL and second IP address and second
certificate. However, its a hotfix that you have to call PSS to download and
will be included with Office 2007 SP1.

















Thanks!

Tom



Thomas W Shinder, M.D.
Site: www.isaserver.org <http://www.isaserver.org/>
Blog: http://blogs.isaserver.org/shinder/
Book: http://tinyurl.com/3xqb7
MVP -- Microsoft Firewalls (ISA)





________________________________

        From: isapros-bounce@xxxxxxxxxxxxx
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Jason Jones
        Sent: Friday, August 31, 2007 8:15 AM
        To: isapros@xxxxxxxxxxxxx
        Subject: [isapros] Re: ISA and SAN Certs

        Yep - one listener, two IPs, each IP assigned a different SSL cert.



        Not sure if the SRV record will negate the need for the autodiscover
URL and hence allow us to get away with a single SSL cert - have to check
this...



        From: isapros-bounce@xxxxxxxxxxxxx
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Thomas W Shinder
        Sent: 31 August 2007 14:13
        To: isapros@xxxxxxxxxxxxx
        Subject: [isapros] Re: ISA and SAN Certs



        Hi Jason,



        One Web listener, but two IP addresses are being used by the Web
listener, correct?



        Thanks!

        Tom



        Thomas W Shinder, M.D.
        Site: www.isaserver.org <http://www.isaserver.org/>
        Blog: http://blogs.isaserver.org/shinder/
        Book: http://tinyurl.com/3xqb7
        MVP -- Microsoft Firewalls (ISA)





________________________________

                From: isapros-bounce@xxxxxxxxxxxxx
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Jason Jones
                Sent: Friday, August 31, 2007 6:50 AM
                To: isapros@xxxxxxxxxxxxx
                Subject: [isapros] Re: ISA and SAN Certs

                Hi Tom,



                Managed to get this working today too, although I am using
two individual certs on the same external web listener. The internal cert on
Exchange is SAN'd up and ISA publishes everything to the internal cert
common name irrespective of the public URL.



                The key to most of it working is defining correct URLs in
Exchange where is defines "External URLs" for things like OOF, OAB, EWS etc.



                Now we have all exchange 2k7 services (and all the new funky
stuff) working externally...had to do a lot of it by investigation and
cobbling blog entries together, not ideal, but go there at last.



                We currently have it working without SRV records, but just
waiting for the ISP to add these records to test if that is a better
solution...



                Cheers



                JJ



                From: isapros-bounce@xxxxxxxxxxxxx
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Thomas W Shinder
                Sent: 31 August 2007 00:32
                To: isapros@xxxxxxxxxxxxx
                Subject: [isapros] Re: ISA and SAN Certs



                I'd think that Jim might need to update his SAN article. The
article implies that ISA doesn't support SANs on the Web listener, however I
have a guy who has the autodiscover FQDN as a second SAN on the certificate
bound to his Web listener and he's shown me strong evidence that it actually
works, even though it shouldn't.



                I wish the Exchange or ISA UE teams could get it together to
explain how to get autodiscovery working correctly and more importantly,
show us how it works with and without DNS SRV records. It looks like once
you have DNS SRV records, its a no brainer.



                Tom



                Thomas W Shinder, M.D.
                Site: www.isaserver.org <http://www.isaserver.org/>
                Blog: http://blogs.isaserver.org/shinder/
                Book: http://tinyurl.com/3xqb7
                MVP -- Microsoft Firewalls (ISA)





________________________________

                        From: isapros-bounce@xxxxxxxxxxxxx
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Thomas W Shinder
                        Sent: Wednesday, August 29, 2007 2:38 PM
                        To: isapros@xxxxxxxxxxxxx
                        Subject: [isapros] Re: ISA and SAN Certs

                        Never mind :)



                        I found it:



                        http://support.microsoft.com/kb/940881



                        Thomas W Shinder, M.D.
                        Site: www.isaserver.org <http://www.isaserver.org/>
                        Blog: http://blogs.isaserver.org/shinder/
                        Book: http://tinyurl.com/3xqb7
                        MVP -- Microsoft Firewalls (ISA)





________________________________

                                From: isapros-bounce@xxxxxxxxxxxxx
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Thomas W Shinder
                                Sent: Wednesday, August 29, 2007 2:35 PM
                                To: isapros@xxxxxxxxxxxxx
                                Subject: [isapros] Re: ISA and SAN Certs

                                OK, that's an interesting sentence in a KB
OL update article. But there's no mention of this anywhere else on the
ms.com site.



                                In addition, how do we configure the SRV
records?



                                Service?

                                Protocol?

                                Priority?

                                Weight?

                                Port number?

                                Host offering this service?



                                cid:image001.jpg@01C7F522.ABDB5600



                                I try to read minds best as I can, but I'm
flailing on this one :))







                                Thomas W Shinder, M.D.
                                Site: www.isaserver.org
                                Blog: http://blogs.isaserver.org/shinder/
                                Book: http://tinyurl.com/3xqb7
                                MVP -- Microsoft Firewalls (ISA)



                                > -----Original Message-----
                                > From: isapros-bounce@xxxxxxxxxxxxx
                                > [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jim Harrison
                                > Sent: Wednesday, August 29, 2007 2:27 PM
                                > To: isapros@xxxxxxxxxxxxx
                                > Subject: [isapros] Re: ISA and SAN Certs
                                >
                                > DatzDeWun!  O'curse it works in real life;
I tested it.
                                >
                                > http://support.microsoft.com/kb/939184
                                > OL 2K7 seeks a "autodiscovery" SRV record
first, and only if
                                > that fails,
                                > it'll seek the A record.  This is based on
the same domain suffix as
                                > specified in the mail domain.
                                > If your OL client is behind a CERN proxy
(and it knows it), it can't
                                > specify that the proxy should look up a
SRV record for
                                > autodiscover.sfx.
                                > The proxy assumes that any CERN request
will be for a "host"
                                > and makes a
                                > DNS query for an A record.
                                >
                                > OL 2K7 uses the SRV record to discover the
host
                                >
                                > -----Original Message-----
                                > From: isapros-bounce@xxxxxxxxxxxxx
                                > [mailto:isapros-bounce@xxxxxxxxxxxxx]
                                > On Behalf Of Thomas W Shinder
                                > Sent: Wednesday, August 29, 2007 12:15 PM
                                > To: isapros@xxxxxxxxxxxxx
                                > Subject: [isapros] Re: ISA and SAN Certs
                                >
                                > BAM!!!!
                                >
                                > I think I get it. On the TO tab for the
autodiscover.msfirewall.org, I
                                > can still use owa.msfirewall.org since it
resolves to the same IP
                                > address as autodiscover.msfirewall.org on
the internal network -- and
                                > the path is going to /autodiscover, so
that's cool. It's all making
                                > sense on paper -- now to see if it works
in real life :)
                                >
                                > BTW -- why do I need a SRV record for OL
autodiscovery? I haven't seen
                                > any documentation on that requirement on
the Exchange side.
                                >
                                > Thanks!
                                > Tom
                                >
                                > Thomas W Shinder, M.D.
                                > Site: www.isaserver.org
                                > Blog: http://blogs.isaserver.org/shinder/
                                > Book: http://tinyurl.com/3xqb7
                                > MVP -- Microsoft Firewalls (ISA)
                                >
                                >
                                >
                                > > -----Original Message-----
                                > > From: isapros-bounce@xxxxxxxxxxxxx
                                > > [mailto:isapros-bounce@xxxxxxxxxxxxx] On
Behalf Of Jim Harrison
                                > > Sent: Wednesday, August 29, 2007 2:09 PM
                                > > To: isapros@xxxxxxxxxxxxx
                                > > Subject: [isapros] Re: ISA and SAN Certs
                                > >
                                > > Yes; I'd forgotten about the OL client's
"SAN problem".
                                > > It amazed me how much noise the Exch
folks make about the same
                                > > limitation for ISA..  ..but I digress.
                                > >
                                > > "Web Publishing Rule that is publishing
the
                                > > autodiscover.msfirewall.org/autodiscover
path must be
                                > > configured on the
                                > > TO tab to use
autodiscover.msfirewall.org " - how do you
                                > cone to that
                                > > contusion?
                                > > Why do you think you need to use
"autodiscover" in the ISA rule
                                > > published hostname?  Use whatever works
for ISA and let the
                                > > client be as
                                > > stupid as you want.
                                > >
                                > > -----Original Message-----
                                > > From: isapros-bounce@xxxxxxxxxxxxx
                                > > [mailto:isapros-bounce@xxxxxxxxxxxxx]
                                > > On Behalf Of Thomas W Shinder
                                > > Sent: Wednesday, August 29, 2007 12:05
PM
                                > > To: isapros@xxxxxxxxxxxxx
                                > > Subject: [isapros] Re: ISA and SAN Certs
                                > >
                                > > Hi Jim,
                                > >
                                > > CIL...
                                > >
                                > > Thomas W Shinder, M.D.
                                > > Site: www.isaserver.org
                                > > Blog:
http://blogs.isaserver.org/shinder/
                                > > Book: http://tinyurl.com/3xqb7
                                > > MVP -- Microsoft Firewalls (ISA)
                                > >
                                > >
                                > >
                                > > > -----Original Message-----
                                > > > From: isapros-bounce@xxxxxxxxxxxxx
                                > > > [mailto:isapros-bounce@xxxxxxxxxxxxx]
On Behalf Of Jim Harrison
                                > > > Sent: Wednesday, August 29, 2007 1:49
PM
                                > > > To: isapros@xxxxxxxxxxxxx
                                > > > Subject: [isapros] Re: ISA and SAN
Certs
                                > > >
                                > > > All good points, but really orthogonal
to the question of how ISA
                                > > > handles SAN certs.  Actually, I wrote
that because some folks were
                                > > > whining about how ISA handled SAN
certs in general.  In
                                > > fact, I tried
                                > > > not to delve into the variant forms of
self-inflicted ISA
                                > manglement
                                > > > pain that were filling other blogs.
                                > > >
                                > > > Q1 - Why do you need a second
listener?  Use your DNS to point
                                > > > autodiscover to the same Exch
listener.  The public name is a
                                > > > rule; not
                                > > > a listener arttribute.
                                > >
                                > > TOM: We need a second listener because
we can't have two
                                > certificates
                                > > with different common names listening on
the same listener using the
                                > > same IP address. OK, in ISA 2006 I *can*
use multiple
                                > > certificates using
                                > > the same listener, but each of the
certificates must be
                                > assigned to a
                                > > different IP address, so no big deal
there -- so I create two
                                > > different
                                > > Web Publishing Rules -- one for
owa.msfirewall.org and a second Web
                                > > Publishing Rule for
autodiscover.msfirewall.org. So far so
                                > > good and SANs
                                > > aren't even an issue.
                                > >
                                > > > Q2 - why does the external OL client
give a rats bahootie
                                > > > what's listed
                                > > > in the cert used at the CAS?  It never
sees it.
                                > >
                                > > TOM: That's true and I didn't mean to
imply that it did. The
                                > > concern is
                                > > that common name and the first SAN on
the Web site
                                > > certificate bound to
                                > > the Client Access Server site is
owa.msfirewall.org. The
                                > second SAN is
                                > > autodiscover.msfirewall.org
                                > >
                                > >
                                > > > Q3 - why is the lack of the
autodiscover.suffix public
                                > name make the
                                > > > /autodiscover path "useless"?
"Incomplete" perhaps, but
                                > > > hardly useless.
                                > >
                                > > TOM: Because the OWA publishing rule is
listening for
                                > > owa.msfirewall.org, NOT
autodiscover.msfirewall.org. Since
                                > > there are two
                                > > certificates involved here, one with the
common name
                                > > owa.msfirewall.org
                                > > and a second with
autodiscover.msfirewall.org -- we have to use two
                                > > different IP addresses, and
owa.msfirewall.org is NOT going
                                > to resolve
                                > > to the same IP address as
autodiscover.msfirewall.org. Thus,
                                > > adding the
                                > > /autodiscover path to the
owa.msfirewall.org Web Publishing
                                > Rule won't
                                > > work and is extraneous. The
/autodiscover path only applies to the
                                > > autodiscover.msfirewall.org Web
Publishing Rule.
                                > >
                                > > >
                                > > > IOW, create your SRV and A records for
autodiscover.suffix, add
                                > > > "autodiscover.suffix" to the public
names (ISA 2006 only) and
                                > > > make sure
                                > > > the cert used in the ISA web listener
includes
                                > > > "autodiscover.suffix" in
                                > > > the SAN.
                                > >
                                > > Again, the issue isn't with the Web
listeners, I have no
                                > problem with
                                > > that. The issue is with the connection
between the ISA
                                > > Firewall and the
                                > > Client Access Server. The Web site
certificate bound to the Client
                                > > Access Server has a common name and a
first SAN name of
                                > > owa.msfirewall.org and a second SAN name
of
                                > > autodiscover.msfirewall.org.
                                > >
                                > > Given that, the Web Publishing Rule that
is publishing the
                                > > autodiscover.msfirewall.org/autodiscover
path must be
                                > > configured on the
                                > > TO tab to use
autodiscover.msfirewall.org -- HOWEVER, and
                                > this is THE
                                > > QUESTION -- with the ISA Firewall when
establishing the SSL channel
                                > > between itself and the Client Access
Server, be able to use
                                > the SECOND
                                > > SAN on the Client Access Server Web site
certificate to allow the
                                > > connection?
                                > >
                                > > Make sense?
                                > >
                                > >
                                > > >
                                > > > Jim
                                > > >
                                > > > -----Original Message-----
                                > > > From: isapros-bounce@xxxxxxxxxxxxx
                                > > > [mailto:isapros-bounce@xxxxxxxxxxxxx]
                                > > > On Behalf Of Thomas W Shinder
                                > > > Sent: Wednesday, August 29, 2007 11:33
AM
                                > > > To: isapros@xxxxxxxxxxxxx
                                > > > Subject: [isapros] Re: ISA and SAN
Certs
                                > > >
                                > > > This is a good step in understanding
some of the issues,
                                > > but I suspect
                                > > > the major problems people are running
into relates to
                                > publishing the
                                > > > autodisocvery site. You'll notice that
when you run the Exchange
                                > > > Publishing Wizard in ISA 2006 that is
includes an
                                > > /autodiscover path,
                                > > > which is completely useless, since the
client is looking for
                                > > > autodiscover.domain.com/autodiscover
and not the Client
                                > > Access Server
                                > > > Public Name, which would be something
like owa.domain.com.
                                > > >
                                > > > OK, easy problem to solve, right? All
we need to do is
                                > > create a second
                                > > > Web listener on a second IP address
and configure it to listen for
                                > > > public name autodiscover.company.com.
HOWEVER, the Client Access
                                > > > Server's common/subject name and first
SAN is owa.company.com. The
                                > > > second SAN is
autodiscover.company.com.
                                > > >
                                > > > So, if we put on the TO tab
autodiscover.company.com, will
                                > > ISA 2006 be
                                > > > able to "consume" the second SAN to
support to the Outlook 2007
                                > > > autodiscovery service?
                                > > >
                                > > > Thanks!
                                > > > Tom
                                > > >
                                > > > Thomas W Shinder, M.D.
                                > > > Site: www.isaserver.org
                                > > > Blog:
http://blogs.isaserver.org/shinder/
                                > > > Book: http://tinyurl.com/3xqb7
                                > > > MVP -- Microsoft Firewalls (ISA)
                                > > >
                                > > >
                                > > >
                                > > > > -----Original Message-----
                                > > > > From: isapros-bounce@xxxxxxxxxxxxx
                                > > > >
[mailto:isapros-bounce@xxxxxxxxxxxxx] On Behalf Of Jim Harrison
                                > > > > Sent: Wednesday, August 29, 2007
1:10 PM
                                > > > > To: isapros@xxxxxxxxxxxxx
                                > > > > Subject: [isapros] ISA and SAN Certs
                                > > > >
                                > > > >
                                > > > > Another isablog for your reading
pleasure.
                                > > > >
                                > > > >
                                > > > >
http://blogs.technet.com/isablog/archive/2007/08/29/certificat
                                > > > > es-with-mu
                                > > > >
ltiple-san-entries-may-break-isa-server-web-publishing.aspx
                                > > > >
                                > > > > 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.
                                > >
                                > >
                                > >
                                > >
                                >
                                >
                                > 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.





All mail to and from this domain is GFI-scanned.





All mail to and from this domain is GFI-scanned.
















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