Exchange 2010 OutLook anyhwere troubelshooting

Hi Experts,

My situation is like below;

I have email servers hosted outside of my network:
I have internal win2k8 AD domain: mydomain.local
Exchange server 2010 deployed in a separate win2k8 server and "accepted domain" has been changed to:

Now email sending is fine, receiving using the POP configured in the Out Look Client.

From my internal network OutLook anywhere is connecting to the Exchange server and working any without issue.

I have created "A" record and pointed in to the Exchange server via 443. And I'm trying to connect OutLook Anywhere from a public network. It's detects the SLL certificate too (it's an expired self singed one by the win2k8 server) but not connecting.

What could be the reason ? Thanks a lot for your time !
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Patrick BogersDatacenter platform engineer LindowsCommented:

Sounds like you enforce the use of SSL instead of allow the use of SSL. (which is best practice)

To ensure this policy:

In IIS Manager, select Default Web site or the Web site on which you're hosting your Outlook Web App virtual directories.
2. In the Web site Home pane, double-click SSL Settings in the IIS area.
3. In SSL Settings, select the Require SSL check box.

In your case you could try, allow SSL instead of require (meaning there must be a valid one in place)

Simon Butler (Sembee)ConsultantCommented:
The self signed SSL certificate is not supported for use with Outlook Anywhere. Furthermore if the SSL certificate has expired then I would expect Outlook to fail to connect.
You need to use switch to a trusted valid SSL certificate before you test any further.


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First of all,

Self-signed certificate is only use of Internal purpose, even we can use it for external, but it is not trusted.

If you want to use activesync, then you need to purchase thirdparty TLS certificate, which is more secure over the network, as compare to self-signed.

Little bit info about Certificates:

Self-Signed certificate:

1. Self-signed certificate which we create using powershell command, encrypt strenght is ony 128 bits.
Self-signed certificate we have to install manually on the client machine.

Thirdparty certificate:

1. Thirdparty certificate which is trusted and encryption strenght is 128 to 2048 bits.

2. Thirdparty certificate does not requires to install manually, its inbuit with browser.

So, you need switch to thirdparty certificate and with all the service should be enable, especially IIS for ActiveSync.

Thank You!
Shakthi777Author Commented:
Tnx !
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