Assistance on how to configure Outlook Anywhere on Outlook 2010, as it failed to connect to Exchange Server 2010

We will like to ask for assistance regarding Outlook Anywhere unable to connect to Exchange Server 2010,

We faced some problems and the errors messages are shown in the attached screenshots.

We will like to check with you, whether this error is due to the Certificate issues or whether does the PC that we want to configure Outlook Anywhere need to be a domain computer 1st before it is able to use the Outlook Anywhere feature.

The PC that we are trying to configure Outlook Anywhere is not part of the Domain which the Exchange Server is residing. The PC is in a standalone workgroup.

We need some technical advices.

For your assistance and advice please.

Thanks and Regards

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Madan SharmaConsultantCommented:
to work outlook anywhere you must have to buy a SSL certificate from a trusted authority with multiple SAN names like:-
your outlookanywhereurl
youcasFQDN name etc.

once you will have this certificate installed on your server you will be able to use the outlook anywhere on any pc whatever pc is in domain network or not

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You can definitely connect to Outlook Anywhere from non-domain computers, the problem you have is that your certificate isn't trusted by the client machine.

You can either import the root certificate for the certificate authority you have received the certificate from onto the client or obtain a certificate from one of the main certificate authorities which will already be trusted by the client.
Md. MojahidExchange server admin Commented:
you have to purchase SSL certificate and install then you can able to configure outlook anywhere.

Follow these step for installation certificate

then you can get try certificate on this website and when your problem will resolved you can buy the same.  
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