Resetting Self-Signed Certs in Exchange 2007/SBS 2008

Good Day Experts,

I have a fairly challenging issue here that im hoping you guys will be able to help with.


-      Windows 2008 SBS
-      Exchange 2007
-      Self-Signed Certificates

I have taken over management of this particular server from a previous IT and it seems to be a great mess!

The issue I’m having is around Certs, Active Sync (for iPhones) and RPC.

The server seems to have valid self-signed certificates installed but only for OWA works ok if you bypass the Cert error, installing it into Trusted Root Container doesn’t seem to work, I guess the Certificate is for and not

They will need Hosts for the following:

- (for VPN)
- (for OWA)
- (For Autodiscover)

How do I go about removing these certs and installing new ones (Self-Signed for the moment). Im fairly new to Exchange 2007 so a noddy guide would be GREAT :)

Let me know any info you may need to help further.
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You should hav 1 certificate attached to IIS, with Subject Alternative names.


You will need at least

Justin DurrantSr. Engineer - Windows Server/VirtualizationCommented:
You need a SAN or UC certificate.  I recommend GoDaddy  or

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:

- 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.

Remember,  the cert request needs to be generated by Exchange using PowerShell.

When you get the response back from the CA, use the import-certificate command to process  and enable it for SMTP, IIS, etc.

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Satya PathakLead Technical ConsultantCommented:
Suppose we want to create a UCC self-signed certificate. We will require the following names:

#NETBIOS name of Exchange: EX-2k7 (example)
#Internal FQDN: (example)
#External FQDN (Public name): (example) (use nslookup/ping to verify the external FQDN)
#Autodiscover name: (example)
#SubjectName: (example)

In EMS, run the following command to generate the new self-signed certificate:

New-ExchangeCertificate -FriendlyName "SelfSigned Cert" -SubjectName "" -DomainName EX-2k7,,, -PrivateKeyExportable $True

Next enable the certificate with Enable-ExchangeCertificate cmdlet. Enable atleast IIS and SMTP.

Enable-ExchangeCertificate -Thumbprint xxxxxxxxxxxxxxx -Services POP,IMAP,SMTP,IIS

Next verify certificate has been installed using EMS/IIS Manager or both. (Sometimes you may have to remove the certificate and then install/enable certificate again).

Some important points:

1. If you are creating a self-signed certificate, it is always better to create one that has all the subject alternative names specified above. This will prevent any certificate security warnings related to name mismatch. If you are creating single-name self-signed certificate, you would have to modify internal URIs of multiple virtual directories as explained in KB940726. The other benefit of multiple SANs is avoiding event 12014 and similar events.

2. Autodiscover for non-domain joined machines will work only after record is created in external DNS

3. You will have to install the certificate in the trusted root on client machines else you will receive a certificate warning. On Vista machines, you will have to run IE with elevated privileges to be able to install the certificate when you open OWA.

4. You can use group policy to install the certificate in trusted root (applicable only to domain joined machines). Copy to file the self-signed certificate (ideally in .p7b format) and then edit the default domain policy and import the certificate into "Computer Settings\Windows Settings\Security Settings\Public Key Policies\Trusted Root Certification Authorities". No user intervention is required once you do this. (Users would have to install the certificate themselves on non-domain joined machines).

5. SBS2008 Information: When you install SBS 2008, setup Internet Address wizard uses self-issued certificate by default. You will find it is "Issued to" "external FQDN" of the server and "Issued by" would be "Internal FQDN-CA" (SBS setup configures CA by default). When the wizard generates the self-signed certificate, it also generates a Certificate distribution package. The package (Install Certificate is located under one of the default shares named Public (C:\Users\Public). Another point to remember about SBS2008 is that the default certificate is single-name certificate and if you create a new one with multiple subject alternative names using the procedure above, you will receive a warning while enabling SMTP on the certificate. This warning can be ignored. You can verify availability of STARTTLS verb using Telnet.

6. In Exchange 2007 SP2, validity of self-signed certificate has been increased to 5 years (earlier it was one year)

7. You can use Fix My Network Wizard in the SBS 2008 Console to renew self-signed certificate
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dt3itsteamAuthor Commented:
Right, i have bought a UCC SSL certificate from GoDaddy.

Ive imported and enabled it and when i browse to it works perfectly.

Working with 3rd party Certs is about 200% easier, so i thank you for all your suggestions!

SatyaPathak: that information will be invaluable to me for another couple of servers so i will hang on to that! Thanks very much!

The issue im now having is Active Sync for iphone syncing. When i check the URL ActiveSync is using in EMC

Internal URL:
External URL:

Outlok anywhere is enabled and set to (basic authentication set)

Do i need to change the URL for Active SYnc, and if so how? Surely its not just changing that External URL field, that just seems way to simple!
Justin DurrantSr. Engineer - Windows Server/VirtualizationCommented:
It is that simple... you need to change the URI in exchange with ActiveSync properties or get a new cert that includes
dt3itsteamAuthor Commented:
mmm strange!

my cert does include

Still doesnt work tho!
Shreedhar EtteCommented:

Go to and perform a ActiveSync test and post result.

Justin DurrantSr. Engineer - Windows Server/VirtualizationCommented:
Should work..
dt3itsteamAuthor Commented:
Hi all,

Turns out that i had to reset all the authentication types on the virtual directories to Basic Authentication, they were all mixed up for some reason.

All working ok now!
dt3itsteamAuthor Commented:
Easiest way to end result
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