Question

Cannot get RPC over HTTPS working, Exchange 2007 SBS 2008

Asked by: UplandSystems

Hi All,

I have recently set up a SBS 2008 running Exchange 2007 with the intention of getting Outlook Anywhere to work, something which I have very quickly found out is easier said than done...

Setup: Single server domain, SBS 2008, Exchange 2007, IIS7, Clients - Outlook 2007 SP2, Windows XP SP3, not joined to the domain, Firewall - ports 443, 80 and 25 open

Installed SBS 2008 clean install, installed Exchange, enabled Outlook Anywhere with basic authentication and hostname remote.domain.co.uk, installed self signed certificate*, checked and set permissions for virtual directories in IIS, pointed remote.domain.co.uk and autodiscover.domain.co.uk to the external static IP address

*I have read that self signed certificates will not work, or at least the default self signed will not work, I have requested a SAN certificate using Exchange PowerShell and issued with my server so that it contains; hostname, hostname.local; domain.co.uk, remote.domain.co.uk, autodiscover.domain.co.uk, assigned in IIS and installed to the clients trusted root CA folder*

I do think the problem may lie with the certificate, however until I know it will solve the issue I am unable to spend the £250 required for a SAN certificate. I also believe there may be another problem as OWA accepts the certificate without a problem when browsing to https://remote.domain.co.uk/owa

Here is how far I can get:
OWA works without a problem, as long as the certificate is installed on the client (cert error if not)
Autodiscover passes a test (the one which ignores SSL authentication) on testexchangeconnectivity.com
When setting up a profile on an external client and entering the email address and password, it brings back the internal name of the server but says 'you must be connected/online to complete this operation'
When setting up a profile on an internal client (not joined to the domain, just in the same switch) it comes back with the correct information, connects and shows emails, but when send/receive is pressed it crashes on receiving when trying to download either the OAB or public folders.

Here is what I have tried from various forums (including this one):
Disabling IPv6
Editing hosts file to hash out #;;1 and add hostname, hostname.local to internal IP
Browsing directly to https://remote.domain.co.uk/rpc  (this prompts for a un/pw and shows a blank page when entered correctly, whichI believe is what it should do)
Switching between NTLM and Basic authentication in Outlook Anywhere
Inserting registry entries to manually assign ports 6001-6004 (which may be redundant but it was worth a shot)
rpcping from client computer (passes tests on ports 6001-6004)
Using a free trial certificate for remote.domain.co.uk from Comodo (unable to find trial SAN certificate)
Manually setting the clients to use https://remote.domain.co.uk rather than using autodiscover
Removing and reinstalling RPC over HTTP
Disabling and re-enabling Outlook Anywhere
Breaking a keyboard (not much good to the server but relieved a little stress)

I apologise if this seems a little scrambled, I have spent the last few days on this same problem so it is possible I have missed a few steps out..! Any suggestions would be greatly appreciated

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Asked On
2009-08-11 at 10:36:58ID24643953
Tags

SBS 2008

,

Exchange 2007

,

RPC

,

HTTPS

,

Outlook 2007

Topic

Exchange Email Server

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Answers

 

by: lastlostlastPosted on 2009-08-11 at 11:23:53ID: 25071842

run a test for Outlook RPC over HTTPS at https://testexchangeconnectivity.com and let us know the results...

 

by: esmith69Posted on 2009-08-11 at 12:13:15ID: 25072311

run the powershell command "get-outlookprovider" and report the results...

 

by: UplandSystemsPosted on 2009-08-11 at 12:44:23ID: 25072601

Get-OutlookProvider

name     server          certprincipalname     TTL
EXCH     hostname                                       1
EXPR     hostname                                        1
WEB     hostname                                         1

Outlook Anywhere With AutoDiscover test:

Attempting to Resolve the host name autodiscover.domain.co.uk in DNS.
  Host successfully Resolved
 Additional Details
  IP(s) returned: [correct IP]  
 
 Testing TCP Port 443 on host autodiscover.domain.co.uk to ensure it is listening/open.
  The port was opened successfully.
 
 Testing SSL Certificate for validity.
  The SSL Certificate failed one or more certificate validation checks.
 Test Steps
   Validating certificate name
  Successfully validated the certificate name
 Additional Details
  Found hostname autodiscover.domain.co.uk in Certificate Subject Alternative Name entry  
 
 Validating certificate trust
  Certificate trust validation failed
 Additional Details
  Certificate chain could not be built. You may be missing required intermediate certificates.

Outlook Provider AutoDiscover (Ignore Trust For SSL)

Attempting to test potential AutoDiscover URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml
  Testing AutoDiscover URL succeeded
 Test Steps
   Attempting to Resolve the host name autodiscover.domain.co.uk in DNS.
  Host successfully Resolved
 Additional Details
  IP(s) returned: [correct IP]
 
 Testing TCP Port 443 on host autodiscover.domain.co.uk to ensure it is listening/open.
  The port was opened successfully.
 
 Testing SSL Certificate for validity.
  The certificate passed all validation requirements.
 Test Steps
   Validating certificate name
  Successfully validated the certificate name
 Additional Details
  Found hostname autodiscover.domain.co.uk in Certificate Subject Alternative Name entry  
 
 Testing certificate date to ensure validity
  Date Validation passed. The certificate is not expired.
 Additional Details
  Certificate is valid: NotBefore = 8/5/2009 8:09:00 AM, NotAfter = 8/5/2011 8:09:00 AM  
 
 
 
 Attempting to Retrieve XML AutoDiscover Response from url https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml for user user.account@domain.co.uk
  Successfully Retrieved AutoDiscover XML Response
 Additional Details
  AutoDiscover Account Settings - XML Response:<?xml version="1.0"?>
<Autodiscover xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
<Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
<User>
<DisplayName>User Account</DisplayName>
<LegacyDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=user.account</LegacyDN>
<DeploymentId>c19e45e1-ed14-4f9c-bb06-143ea2acee51</DeploymentId>
</User>
<Account>
<AccountType>email</AccountType>
<Action>settings</Action>
<Protocol>
<Type>EXCH</Type>
<Server>hostname.local</Server>
<ServerDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=hostname</ServerDN>
<ServerVersion>720180F0</ServerVersion>
<MdbDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=hostname/cn=Microsoft Private MDB</MdbDN>
<ASUrl>https://remote.domain.co.uk/EWS/Exchange.asmx</ASUrl>
<OOF
Url>https://remote.domain.co.uk/EWS/Exchange.asmx</OOFUrl>
<OAB
Url>https://remote.domain.co.uk/OAB/efcc9f04-76ae-490b-b976-e62a11e055f9/</OABUrl>
<UMU
rl>https://remote.domain.co.uk/UnifiedMessaging/Service.asmx</UMUrl>
<Por
t>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<PublicFolderServer>hostname.local</PublicFolderServer>
<AD>hostname.local</AD>
<EwsUrl>https://remote.domain.co.uk/EWS/Exchange.asmx</EwsUrl>
</Pr
otocol>
<Protocol>
<Type>EXPR</Type>
<Server>hostname</Server>
<ASUrl>https://remote.domain.co.uk/EWS/Exchange.asmx</ASUrl>
<OOF
Url>https://remote.domain.co.uk/EWS/Exchange.asmx</OOFUrl>
<OAB
Url>https://remote.domain.co.uk/OAB/efcc9f04-76ae-490b-b976-e62a11e055f9/</OABUrl>
<UMU
rl>https://remote.domain.co.uk/UnifiedMessaging/Service.asmx</UMUrl>
<Por
t>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<EwsUrl>https://remote.domain.co.uk/EWS/Exchange.asmx</EwsUrl>
</Pr
otocol>
<Protocol>
<Type>WEB</Type>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<External>
<OWAUrl AuthenticationMethod="Fba">https://remote.domain.co.uk/owa/</OWAUrl>
<Pro
tocol>
<Type>EXPR</Type>
<ASUrl>https://remote.domain.co.uk/EWS/Exchange.asmx</ASUrl>
</Pr
otocol>
</External>
<Internal>
<OWAUrl AuthenticationMethod="Basic, Fba">https://remote.domain.co.uk/owa/</OWAUrl>
<Pro
tocol>
<Type>EXCH</Type>
<ASUrl>https://remote.domain.co.uk/EWS/Exchange.asmx</ASUrl>
</Pr
otocol>
</Internal>
</Protocol>
</Account>
</Response>
</Autodiscover>

 

by: UplandSystemsPosted on 2009-08-11 at 12:49:18ID: 25072646

Outlook 2003 RPC/HTTP (manual entry of server name etc)

Testing RPC/HTTP connectivity
  RPC/HTTP test failed
 Test Steps
   Attempting to Resolve the host name remote.domain.co.uk in DNS.
  Host successfully Resolved
 Additional Details
  IP(s) returned: [correct IP]
 
 Testing TCP Port 443 on host remote.domain.co.uk to ensure it is listening/open.
  The port was opened successfully.
 
 Testing SSL Certificate for validity.
  The SSL Certificate failed one or more certificate validation checks.
 Test Steps
   Validating certificate name
  Successfully validated the certificate name
 Additional Details
  Found hostname remote.domain.co.uk in Certificate Subject Common name  
 
 Validating certificate trust
  Certificate trust validation failed
 Additional Details
  Certificate chain could not be built. You may be missing required intermediate certificates.  

 

by: esmith69Posted on 2009-08-11 at 12:54:20ID: 25072692

I believe you might need to recreate the certificate using the SBS wizards.

Another thing I might mention...we had a SBS 2008 implementation not too long ago where one of the first things we tried doing (just because of issues when we had Exchange 2007 on Server 2008 boxes) was to disable IPv6.  This ended up causing all sorts of wierd issues with non-Exchange services on the SBS 2008 box, so we ended up turning it back on.

 

by: lastlostlastPosted on 2009-08-11 at 13:43:20ID: 25073213

It is not recommended to disable IPv6 on an SBS 2008 Server.

Also did you have the internal Certificate installed on the computer from where you ran this test?

 

by: UplandSystemsPosted on 2009-08-12 at 00:10:04ID: 25076280

lastlostlast: I will re-enable IPv6, the internal certificate was not installed on the computer I ran the test from, would this make a difference?

esmith69: What would be the best way to create the certificate via SBS? The current certificate I have I requested via Exchange PowerShell, I also tried via IIS but I have not used an SBS certificate wizard before

Thank you both for your assistance in this

 

by: esmith69Posted on 2009-08-12 at 09:15:24ID: 25080190

Try Network->Connectivity->Fix My Network.  From what I've read, this is supposed to recreate the certs.

http://sbs.editme.com/sbs2008certprobs

 

by: UplandSystemsPosted on 2009-08-13 at 04:59:41ID: 25087191

Running Fix My Network found and fixed a few errors, the new log I receive from exchangeconnectivity is:
Attempting to Resolve the host name autodiscover.domain.co.uk in DNS.
  Host successfully Resolved
 Additional Details
  IP(s) returned: [Correct IP]
 
 Testing TCP Port 443 on host autodiscover.domain.co.uk to ensure it is listening/open.
  The port was opened successfully.
 
 Testing SSL Certificate for validity.
  The SSL Certificate failed one or more certificate validation checks.
 Test Steps
   Validating certificate name
  Certificate name validation failed
   Tell me more about this issue and how to resolve it
 
 Additional Details
  Host name autodiscover.cobaltenergy.co.uk does not match any name found on the server certificate CN=remote.domain.co.uk

I have tested it with clients anyway, installing the certificate using the install package in Public\downloads and I get the following results:

Creating a profile whilst on the same network allows me in but (after giving a certificate error, autodiscover.domain.co.uk is not valid on this certificate) it uses TCP/IP rather than HTTPS (even when selected on fast networks). Also, in the field "use this url to connect to my proxy" it has the local hostname rather than the external, if i attempt to change this it changes it back...
When I re-open this profile it seems to attempt to connect to HTTPS (i get the certificate error again) but quickly gives up and uses TCP/IP

Creating a profile manually whilst not on the network results in the "this server must be online / connected" error message.

The only way which seems to half work is if the client is on the same network using TCP/IP, but even then if you send/receive it sticks on receiving and you have to click cancel all

Is there another wizard I am missing?

 

by: esmith69Posted on 2009-08-13 at 06:18:50ID: 25087844

So what is common name of the certificate in use by IIS right now?

 

by: esmith69Posted on 2009-08-13 at 12:21:50ID: 25091842

sorry, I re-read your last post and think I answered my own question.

Check out the following link for some more information about how this whole process works with SBS:  http://blogs.technet.com/sbs/archive/2008/12/03/how-outlook-2007-and-windows-mobile-6-1-use-autodiscover-with-sbs-2008.aspx

 

by: esmith69Posted on 2009-08-13 at 12:22:31ID: 25091848

Essentially it looks like you need to run the internet address management wizard...

 

by: UplandSystemsPosted on 2009-08-14 at 00:47:07ID: 25095901

I've run the wizard as suggested: I already have a domain > I want to manage the domain name myself > [domain.co.uk]. The Remote Web Workplace Site (https://remote.domain.co.uk) gets a tick, Exchange e-mail gets a X, cannot configure email - run Fix My Network to resolve. Fix my network finds no errors but Exchange has already been set up and is working so not sure that is too big a problem.

Still no joy though I'm afraid, I read through the link provided and the only thing I'm not sure about is the SRV record so I have sent an email to our DNS guy

 

by: UplandSystemsPosted on 2009-08-17 at 04:50:39ID: 25113345

Points increase, could really do with a solution this week or t's going to be a server rebuild over the weekend, which I really don't want to do...!

Thanks

 

by: UplandSystemsPosted on 2009-08-17 at 10:28:16ID: 25116438

Update: Since running the internet connection wizard (and possibly the import certificate wizard) the 'rpc' and 'rpcwithcert' virtual directories within IIS have moved from 'SBS Web Applications' to 'Default Website'. OWA, OAB, Exchange etc. are all still in 'SBS Web Applications'.
Now if i browse to https://remote.domain.co.uk/rpc it obviously doesn't work as port 443 is not bound to 'Default Website'.
I realise I could change this back in IIS but am unwilling due to so many reports of 'use the wizards, only the wizards, and nothing but the wizards...!'

 

by: esmith69Posted on 2009-08-17 at 10:42:11ID: 25116559

I think you can export a directory to a backup file, then restore it into the location that you desire in IIS.  I know this is how it was done in 2003 but I'm not 100% sure the process is identical in 2007.  I'd imagine you could at least copy the OWA, OAB, Exchange, etc. directories into the default website though and maybe that would do the trick?

 

by: esmith69Posted on 2009-08-17 at 10:43:09ID: 25116565

just a followup--I haven't done this process in IIS7 but in IIS6 you would right click the directory and do something like export->configuration to a file.  Then you would go to the new web site and then choose "new->virtual directory from a configuration file".

 

by: hottipsPosted on 2009-08-24 at 05:21:09ID: 25167539

i too am having similiar problems. I noticed on my setup that the /Rpc and /RpcwithCert folders are under Default Website and not SBS Web Applications. I beleive this is a result of installing TS Gateway on the SBS 2008 Server which set a binding on port 443 on the Default Website. Given that two websites cannot listen on port 443, the default website does not start.

 

by: UplandSystemsPosted on 2009-08-24 at 07:11:40ID: 25168451

Finally managed to get this working!! Just as I was about to open a support call to Microsoft I stumbled across this forum:

http://social.technet.microsoft.com/Forums/en-US/exchangesvrdeploy/thread/c8a2179c-39f3-4859-aca2-b1f6b529098b

The part that worked for me was the following:

On our exchange server:

-       We added another registry key: HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\lanmanserver\parameters

Value Name: MaxWorkItems

Data Type: REG_DWORD

Value data: 8192 (decimal)

-       Ran IISRESET and restarted the System Attendant service.

-       Now, the username resolves while configuring a profile and Outlook connects on HTTPS without errors.

This is the only place i have even seen this key mentioned, and I have no idea why it works but am very happy it does. Hopefully this will help with anybody else having this problem.

hottips: please see the below link for how I managed to move my /rpc and /rpcwithcert virtual directories;

http://www.experts-exchange.com/OS/Microsoft_Operating_Systems/Server/SBS_Small_Business_Server/Q_24466155.html

Thanks everyone for the suggestions

 

by: esmith69Posted on 2009-08-24 at 08:35:55ID: 25169388

Yikes, I've never even heard of that key.  Thanks for the tip!

 

by: djpattoPosted on 2009-09-01 at 05:16:06ID: 25230707

I had a similar error I followed the link below it may help
http://sbs.editme.com/sbs2008certprobs

20120131-EE-VQP-002

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