Autodiscover-SSLCert-Activesync Issue

Hello. I have odd issue. So first of all we are on Exchange 2010 and have host our email and that of 2 other companies. The other companies mailboxes are setup in our domain but we change their SMTP alias to that of their domain name. We then setup their
Outlook to point to us via Outlook Anywhere using our OWA address (owa.mydomain.com) and set their phones up for activesync with the same address. Now, we do have an external autodiscover namespace for our domain and one for one of the other domains and that
domain along with ours auto discover.mydomain.com and theirs auto discover.theirdomain.com are both on our SSL cert, these are both A Records. The third company does not have an external auto discover namespace setup nor is that on our SSL Cert. 
So a couple of things. 
First, why are we having to manually type in the server when setting up email on phones for the two companies that have auto discover namespaces (shouldn't auto discover do this automatically)?
Secondly, how can I setup the third company to use this without having to add an additional entry to the SSL Cert?
Now the weird thing, for some reason the second company (the one with the autoautodiscover namespace), if I remove their external autodiscover.theirdomain.com namespace then all of their Outlook client start throwing up a "Allow this website to configure
server settings" and it is some other namespace like cpanelmaildiscovery.cpanel.net or they get the SSL Cert message :The name on your SSL Cert is not same as" and it lists some other namespace. You get that same type of thing when setting up the
phones with their external namespace in place too, but not in Outlook, only when you remove the external auto discover.theirdomainname.com entry. All of this and the third company with no external autodiscover namespace and no entry to the SSL Cert does not
have this problem. 
If someone can help me make heads or tails out of this mess I would appreciate it.
Thank you. 

The following is the answer to both your questions, I think.  For autodiscover for someone in, say, company3.com to work, the ActiveSync client needs to be able to contact autodiscover.company3.com, which will point to the server they connect to. 
If you have configured company1.com on the certs for your Exchange servers, the client will fail on this step, and you will need to manually configure the server.  For autodiscover to work properly for all companies you host, you need to have your certificate
configured to support all of them.
So, to support the three companies you host, you need autodiscover names for each on your certificate - and a wildcard cert won't work, since it's for a single domain.  You need autodiscover.company1.com, autodiscover.company2.com, and autodiscover.company3.com
on your certificate.
As for your "weird thing", I think I'd need more detail of what is on your certificate SAN and what your SMTP namespaces are before I'd be able to guess why it does and doesn't work.

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    ▲ Vote if Helpful / Mark if Answer
    MCSE: Messaging 2013 Charter / Private Cloud / Server Infrastructure
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    Exchange 2010 will proxy ActiveSync for Exchange 2003.  For OWA, it will redirect, so you need a legacy redirect URL.  You can test all of this internally without changing your Internet connection.  For ActiveSync you can use a WiFi connection.
    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

  • Microsoft Exchange ActiveSync issues

    I am unable to add my office's Microsoft Exchange to my email acounts. 
    I get the following message: "There was an unexpected error and the operation was canceled"
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    "What modelof blackberry is it? From my understanding blackberry doesn’t support exchange based webmail without an intermediate server or a desktop application set up to sync to outlook. That’s the main reason they are going out of business. We have an entire BES server here at GQ just so that our one blackberry user is able to work.
    Id have to do some research if it’s a newer phone, but in all of my past experiences android and apple have been doing phone email better for the last 8 or so years."
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    Your IT guy has no clue about the new BlackBerry 10 devices (and no clue about BB going out of business either for that matter.) Your Q10 should connect EXACTLY like an iPhone or Android device using Exchange Active Sync. Do they have Active Sync enabled on your account? I've seen the same error message reported when people don't have AS enabled for their account.
    They need a new BES10 server for BB10 devices. Your Q10 will not connect to their old BES 5 or older BES server. Have them contact BlackBerry for more info. Right now BES10 migrations are free from BlackBerry.
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