Question

SSL Certificate for Exchange Server 2007

Asked by: chouckham

Hi,

Does anyone know whether you need to have an SSL Certificate for Outlook Anywhere (which connects over https)
Is it a special type of SSL Cert? or will any do?
Ive managed SSL's in the past but for websites only.


Cheers,

Craig

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Asked On
2007-11-13 at 08:42:11ID22957564
Tags

exchange

,

ssl

,

2007

,

certificate

Topics

Secure Socket Layer (SSL) & HTTPS

,

Exchange Email Server

Participating Experts
2
Points
500
Comments
18

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Answers

 

by: victorjones1Posted on 2007-11-13 at 08:50:25ID: 20272909

Yes, you need to either create one yourself or purchase one.

 

by: victorjones1Posted on 2007-11-13 at 08:53:50ID: 20272945

If you create your own you will always get a certificate error when accessing OWA and will not be able to connect any exchange active sync PDAs to the email.

godaddy.com is the cheapest I've seen lately, $14.99 per year for an SSL

 

by: SembeePosted on 2007-11-13 at 13:57:10ID: 20275565

The thing with Exchange 2007 is that the certificates are used for more than just Outlook Anywhere. They are used for a lot of the core functionality. If you go down the Microsoft route then you should be purchasing SAN certificates. However these are still very expensive - close to US$500 and there are limited suppliers.

The method I am using (which for some reason Microsoft don't recommend) is the multiple certificates method. I have blogged about it here: http://www.sembee.co.uk/archive/2007/01/21/34.aspx

You have to install the certificates within Exchange to get them accepted correctly. I need to update my article or post again to indicate that. I have been using PowerGui to do that . http://www.powergui.org/

As pointed out, Go Daddy do the cheapest certificates, but if you have a co.uk domain they struggle to issue them. For co.uk you will need to spend a little more and go to RapidSSL, which are US$60 if bought direct, but I have seen them for less on reseller web sites.

Simon.

 

by: victorjones1Posted on 2007-11-13 at 14:19:41ID: 20275773

I purchased a godaddy SSL yesterday for this specific purpose.  I followed their directions to install and it works perfectly on my .com domain

 

by: victorjones1Posted on 2007-11-13 at 14:37:39ID: 20275927

I purchased & installed a Microsoft IIS SSL Cert for mail.mydomain.com

 

by: SembeePosted on 2007-11-13 at 15:01:48ID: 20276136

So how are you handling auto discover?
That is the major issue with the SSL certificate support. If you are using Outlook 2003 it is not so much of a problem, but Outlook 2007 doesn't like it.

Simon.

 

by: victorjones1Posted on 2007-11-13 at 15:18:54ID: 20276259

I am currently using MS Office 2003 in my environment, so i have not had any problems at all.  I also tested this SSL setup with a free SSL from Startcom for several months before paying for one that is recognized by Microsoft & Mozilla.

 I will have to cross the auto discover bridge when i upgrade to Office 2007.  Unless you can give me the solution.  I'm sure that when the time comes i will have to post it as an EE question.

 

by: victorjones1Posted on 2007-11-13 at 15:26:07ID: 20276313

According to http://technet.microsoft.com/en-us/library/bb332063.aspx

Autodiscover and Certificates

One of the most important aspects of a successful Exchange messaging deployment is how you configure your SSL certificates for securing client communication to your Exchange infrastructure. This is because all communication between Outlook clients and the Autodiscover service endpoint, in addition to communication between the Outlook client and Exchange services, occurs over an SSL channel. For this communication to occur without failing, you must have a valid SSL certificate installed. For a certificate to be considered valid, it must meet the following criteria for the Autodiscover service:

The client can follow the certificate chain up to the trusted root.

The name matches the URL that the client is trying to communicate with.

The certificate is current and has not expired.


My SSL meets the above 3 criteria, so i am not sure what would cause the Cert support issue you mention.

 

by: SembeePosted on 2007-11-13 at 15:36:57ID: 20276404

The issues are around the name on the SSL certificate and getting it trusted. If you look at what Autodiscover works on, without some heavy hacking around it work on a limited number of URLs and will generate errors.
If you haven't deployed Outlook 2007 then you will not have seen the errors, but anyone who has will be well aware of the problems. If you look at expert ATIG's blog he has a big article on Autodiscover which is probably the biggest pain point for Exchange 2007 admins with Outlook 2007.

Simon.

 

by: victorjones1Posted on 2007-11-13 at 15:47:38ID: 20276498

Thanks i will keep that in mind

 

by: chouckhamPosted on 2007-11-14 at 13:20:30ID: 20283976

Hi Simon and Victor

If i want to have OWA and Outlook Anywhere working.
do i need to get 2 x ssl certs?
or do i just get one that covers: mail.mydoman.com?


thanks :-)

 

by: SembeePosted on 2007-11-14 at 13:39:41ID: 20284147

If you don't have any Outlook 2007 clients then you can use one certificate for whatever name you want to use. It is only when autodiscover comes in to play that things get complicated.

Simon.

 

by: victorjones1Posted on 2007-11-14 at 13:43:48ID: 20284185

From Microsoft:
http://technet.microsoft.com/en-us/library/9026d461-ec6a-4ef5-ba9d-de33030858f3.aspx

Benefits of Using Outlook Anywhere

There are several benefits to using Outlook Anywhere to enable Outlook 2003 and Outlook 2007 clients to access your Exchange messaging infrastructure. The benefits are as follows:

Remote access to Exchange servers from the Internet.

You can use the same URL and namespace that you use for Microsoft Exchange ActiveSync and Outlook Web Access.

You can use the same Secure Sockets Layer (SSL) server certificate that you use for both Outlook Web Access and Exchange ActiveSync.

Unauthenticated requests from Outlook cannot access Exchange servers.

Clients must trust the certification authority that issues the certificate.

You do not have to use a virtual private network (VPN) to access Exchange servers across the Internet.

You must allow only port 443 through your firewall, because Outlook requests use HTTP over SSL. If you already use Outlook Web Access with SSL or Exchange ActiveSync with SSL, you do not have to open any additional ports from the Internet.

 

by: chouckhamPosted on 2007-11-15 at 03:07:42ID: 20288135

thanks so much for all your information guys!
im gonna test all this out with a Verisign 14 day trial ssl cert.

Im having a little trouble generating a key that verisign will accept:

New-ExchangeCertificate -GenerateRequest -DomainName mail.mydomain.com,autodiscover.mydomain.com,exchange,exchange.mydomain.local -FriendlyName mail.mydomain.com -PrivateKeyExportable:$true -Path c:\cert_exchange.txt

is there something wrong with my request command above?

thanks,

 

by: victorjones1Posted on 2007-11-15 at 06:24:49ID: 20289044

Do you mean a Certificate Signing Request (CSR), and if so, what application are generating it from?

 

by: chouckhamPosted on 2007-11-15 at 08:30:35ID: 20290178

sorted guys thanks

 

by: victorjones1Posted on 2007-11-15 at 09:39:01ID: 20290767

Is there anything else we can help you with regarding this issue?

 

by: chouckhamPosted on 2007-11-16 at 08:24:00ID: 31409078

Thanks guys!

20120131-EE-VQP-002

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