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dbasplus
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Outlook Anywhere - SBS 2011 & Outlook 2013

I'm trying to set up Outlook Anywhere for some remote users we have. They will be running Outlook 2013 on their workstations. Our server is running SBS 2011 (which contains Exchange 2010), and everything internally is working fine.

Outlook Web Access works fine, but the users are required to use the full version of Outlook on a regular basis.

I've followed the steps in this article - https://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_27725666.html - but still can't get it to work. I suspect the main difference is that I'm using Outlook 2013 which I don't think was available when that article was published.

We are using the SBS 2011 self-signed certificate which has been installed on the workstations. The workstations have never been part of the domain (and are unlikely to be as they are physically located in another state).

The error message I'm getting is "Cannot start Microsoft Outlook. Cannot open the Outlook window. The set of folders cannot be opened. The attempt to log on to Microsoft Exchange has failed."

Can anyone help please?
ExchangeOutlookSBS

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dbasplus

8/22/2022 - Mon
ASKER CERTIFIED SOLUTION
Alan Hardisty

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dbasplus

ASKER
Will get a 3rd party certificate later (before allowing all the users to start using it), but by the sounds of it I should be able to prove that it technically works with just the self-signed certificate, correct? This was already installed on the client by using the "Install Certificate Package" - would this have done everything I need, or do I need to do a further step? Certificates aren't my strong point I must admit.
Alan Hardisty

I've only ever installed 3rd party certs with the public FQDN in them and it's always worked 1st time.

Never tried it with the self-issued cert and if the name of the cert is something.internaldomain.local, then it won't work because it can't be resolved in DNS.
dbasplus

ASKER
Ok I might have to bite the bullet and buy one then.

Any suggestions as to where I can find instructions for the process for obtaining/installing the certificate on the server & workstations?
Experts Exchange is like having an extremely knowledgeable team sitting and waiting for your call. Couldn't do my job half as well as I do without it!
James Murphy
pgm554

Just go to Godaddy.

They're easy to obtain(cheap) and easy to install.
They have step by step animation flash..

Because they are 3rd party ,you don't need to install on anything but server.

Also a no brainer on smart devices.

Word of advice,when you request SSL common name ,use
remote.yourdomain.com and mail.yourdomain.com

yourdomain meaning your registered domain name.

two ways to do it,you can generate from the SSL wizard in SBS or use IIS to generate cert.
Gareth Gudger

Will need autodiscover in there as well.

You will need to purchase a UC / SAN certificate.

Do a quick Google search for GoDsddy.com Promo Codes for additional savings. They usually offer multi-years discounts as well.

This article is focused on migrating from Exchange 2003 to 2010, but it does discuss designing an Exchange namespace, how to configure split brain DNS, and how to generate and apply a certificate.
http://supertekboy.com/2014/04/07/migrating-exchange-2003-2010-part-iii/
dbasplus

ASKER
Seem to have got it working now with a 3rd party certificate. I didn't end up getting a UC/SAN certificate as we don't need autodiscover, but I will keep it in mind for the future.

I did use the RPCnofrontend fixup tool to make sure that the registry settings on the server were correct.

Thanks for your help!
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