Outlook Anywhere Nightmare

Ok, We have been at this for over a week now and still no luck.

What we want:
We want to be able to use Outlook Anywhere, with external clients using Outlook 2007.

The Problem:
Some Users are unable to connect to Outlook Anywhere.

Right now we have 4 Users testing out Outlook Anywhere, out of the 4 of us, only 1 can connect to Outlook Anywhere. The others get error messages saying Exchange is unavailable, or Exchange is offline, error messages like that. These error messages appear before the user gets a chance to input a username and password.

Just recently we have tested out the Outlook Anywhere proxy settings in the "More Settings" when we add our accounts to Outlook, and that has got us a little further, those 3 users are now asked for their usernames and passwords. But when they put them in it then gives them one of the previous errors, and everything fails.

These users are able to use OWA without a problem.

We are using Windows Server 2008 with Exchange 2007 SP1

We've tried almost everything we can think of, and still no luck.

Any Help would be Appreciated!


Who is Participating?
MesthaConnect With a Mentor Commented:
The self signed certificate is not supported for use with Outlook Anywhere, so switch to a commercial certificate. You should do that anyway, as the self signed certificate is just a place holder.

You need a SAN/UC certificate. I have gone through the full process on my blog here:

first of all please try and use the tool to test the outlook anywhere connectivity www.testexchangeconnectivity.com this will give you a lot f information
and after that please go through these articles

i hope this will answer all your questions. if not let us know the results of the connectivity test.

svellutoAuthor Commented:
Ok First off - Thanks for the quick response.

The first link the connectivity tool is really nice, I'm running it now as I type, so I'll be able to find out what's wrong shortly.

Also - those articles you posted, the links are the same, did you mean to provide different articles?

Free tool for managing users' photos in Office 365

Easily upload multiple users’ photos to Office 365. Manage them with an intuitive GUI and use handy built-in cropping and resizing options. Link photos with users based on Azure AD attributes. Free tool!

i am sorry my mistake i wanted to give you another article
svellutoAuthor Commented:
It looks as though it fails on testing the SSL Certificate Validity.

We are using a self-signed certificate.

The 1 person that can connect, is able to connect over the internet to the exchange server, without any problems, or certificate errors. (This is where I'm confused, I think if 1 person can connect they all should be able to, or if 1 person can't connect no one should be able to).

The one person who can connect, is just reporting a Security warning to me, it is saying autodiscover.mydomain.com is not on the SSL Certificate. And then he is still able to connect.

svellutoAuthor Commented:
I asked everyone to run the rpcping utility, and everyone (even the client that Can connect to exchange via outlook 2007) gets the exception 1722.
are u using autodiscover to connect or you are using manual configuration of outlook anywhere.
and first of all please try to connect manuely,
please have the certificate installed on the machine
what is the authentication method you have selected while enabling the outlookanywhere you need to selece the same authentication method while creating the OL profile
svellutoAuthor Commented:
We have always been using Manual Configuration.

I only brought the autodiscover address up because the link to test RPC out said that is where the error occurred.

We have been using Basic Authentication.

As for the certificate, we currently have a self-signed one installed - and it is working for the 1 client. So we assumed a new certificate was not needed.

But if the certificate will solve our problem, we will purchase a UCC certificate, and test it out.

Please confirm this is correct type of certificate we should purchase.

good morning,
i aggree with Mestha

you can create a new internal certificate for testing and after that you can go for a third party certificate
All Courses

From novice to tech pro — start learning today.