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Possible workaround for Outlook Mac remote problem

A reader reports in our Forum a problem where Outlook Mac doesn't work outside his network. Our guess is that it has to do with Outlook's Autodiscover feature not working correctly, and that turning off this feature and manually setting the location of Exchange Server could fix it. Here's the problem:

I'm running a 2008 SBS & have a handful of sales people using MacBook Pro laptops & Outlook 2011 for Mac. Outlook seems to either work good inside or outside the office, but not both. In trying to emulate the problem on my own mac, I went to office & set up Outlook. When getting back home, I get the alternating message in lower right corner, connecting to mydomain / not connected to mydomain. When checking my advanced settings, under Accounts>Advanced>Server, I see; https://sites/EWS/Exchange.asmx, which was automatically put in there when setting up the account while in office.

If I'm out of the office and I change this to https://mailserver.mydomain.com/EWS/Exchange.asmx , it works fine, but once I'm back in the office this changes back to the https://sites... setting. I can change it to https://mailserver.mydomain.com... & it will work fine - in or out of the office, so is there a way to keep this setting in there or can someone tell me what's wrong with this picture?

On a possibly unrelated note, smart phones or Windows laptops have no problems in or out of the office.

It could be that Autodiscovery is turned on in the Mac, but is not working when outside of the his office. Without addressing the Autodiscover issue itself, one workaround would be to can turn off Autodiscovery off on the Mac and have it access the URL you specify. Microsoft has information here.

If you've seen this issue

TIP: SMTP, DNS sources of remote Outlook Mac problem

Two readers sent in two different fixes for the problem of Outlook 2011 for Mac not being able to remotely access Exchange Server. Our suggestion was to disable AutoDiscover in Outlook, but the readers fixed their problems with DNS (related to the Autodiscover feature) and with SMTP settings.

Israel Adame altered the Autodiscover's proxy setting for DNS:

Yes, we used to have the same issue. Our problem was related to DNS, so because we cannot makes changes to our DNS we decided to try and bypass in the proxy settings autodiscover, and so far it has been almost two years since Office 2011 was released that our users do not have that problem anymore. So our solution is to add in the Proxies Tab for each network interface inside the "Bypass proxy settings for these Hosts & Domains", autodiscover.domain.com .

The original poster of the message solved the problem by specifying a new SMTP server in Outlook:

It is fixed now, I had recently changed Internet network and I now apparently have to use their outgoing server details and not my third party SMTP! It took me a week to fix that, what a nightmare. Thanks for your advice though.

If you've seen this problem

(This problem was first reported in our forums.)

For more help with Outlook troubleshooting, see Outlook 2011 for Mac Tips and Reports.