Connecting Outlook 2013 for a local user

Question

We’re having trouble connecting a users connecting a domain user’s Outlook 2013 to our Exchange 2013 server. The user has a domain user account, and an Exchange mailbox.
However;
 The user in question uses a PC that is physically connected to the network, but isn’t a domain-joined machine. The user is using a locally-provisioned account on the PC.
The machine can query internal DNS servers, and has network connectivity through to the Exchange server.
The user can successfully log in to OWA, where everything functions as normal. The user wishes to use Outlook 2013 for archiving of PST files.
We are having issues creating a mail profile for the user, whether manually configuring or utilising autodiscover.
With autodiscover, the user enters her name, email address and password in the initial wizard in Outlook 2013. 2 of the 3 steps succeed, before ‘The action cannot be completed. The name cannot be matched to a name in the address list’ error window is displayed.
Is this because Exchange is having issues with the account being used to create the profile (the local user account on the PC)?
Now what’s really odd, is that when using Outlook 2013 away from the network (at home), with any PC, the autodiscover method succeeds. What is causing it to fail internally?
So, with the autodiscover method out of the window, we turned to manually configuring the profile.
The local name of the Exchange server is entered for the server name, with the user’s email address for the username.
In ‘More Settings’, the connection tab is configured to ‘Connect to Microsoft Exchange using HTTP’.
The URL used to connect the proxy server for Exchange, is the external name used for OWA. This is the same address used when the user is using OWA internally/externally, which works without issue.
Options ‘Connect using SSL only’, along with ‘Only connect to proxy servers that have this principal name in their certificate’ are selected with
msstd:<external FQDN name> being entered.
Basic Authentication is selected for the proxy authentication settings section.
The user is then prompted for credentials. The following formats have been attempted;
Domain.local\username
Email Address
[email protected]
The correct password is used, but nothing is accepted.
How can we get Outlook 2013 configured for this non-domain joined PC?
Many thanks.

Answer 1

We’re having trouble connecting a users connecting a domain user’s Outlook 2013 to our Exchange 2013 server. The user has a domain user account, and an Exchange mailbox.
However;
 The user in question uses a PC that is physically connected to the network, but isn’t a domain-joined machine. The user is using a locally-provisioned account on the PC.
The machine can query internal DNS servers, and has network connectivity through to the Exchange server.
The user can successfully log in to OWA, where everything functions as normal. The user wishes to use Outlook 2013 for archiving of PST files.
We are having issues creating a mail profile for the user, whether manually configuring or utilising autodiscover.
With autodiscover, the user enters her name, email address and password in the initial wizard in Outlook 2013. 2 of the 3 steps succeed, before ‘The action cannot be completed. The name cannot be matched to a name in the address list’ error window is displayed.
Is this because Exchange is having issues with the account being used to create the profile (the local user account on the PC)?
Now what’s really odd, is that when using Outlook 2013 away from the network (at home), with any PC, the autodiscover method succeeds. What is causing it to fail internally?
So, with the autodiscover method out of the window, we turned to manually configuring the profile.
The local name of the Exchange server is entered for the server name, with the user’s email address for the username.
In ‘More Settings’, the connection tab is configured to ‘Connect to Microsoft Exchange using HTTP’.
The URL used to connect the proxy server for Exchange, is the external name used for OWA. This is the same address used when the user is using OWA internally/externally, which works without issue.
Options ‘Connect using SSL only’, along with ‘Only connect to proxy servers that have this principal name in their certificate’ are selected with
msstd:<external FQDN name> being entered.
Basic Authentication is selected for the proxy authentication settings section.
The user is then prompted for credentials. The following formats have been attempted;
Domain.local\username
Email Address
[email protected]
The correct password is used, but nothing is accepted.
How can we get Outlook 2013 configured for this non-domain joined PC?
Many thanks.
The first problem is, if this Exchange 2013 then the server name in Outlook isn't really a server name, it is in actuality the ExchangeGUID of the mailbox.  
Since you are trying to access the mailbox from a machine that is not on the domain you will need to make sure the externalURLs resolve properly internally.  Meaning either the user can access them by going out to the internet and getting routed back
in (not ideal) or you configure them to resolve to the internal IPs on your internal DNS servers.
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Thank you for your reply.
As I mentioned, this machine can query internal DNS servers without issue. Autodiscover is working in a fashion, as the name of the mail server is hashed. 
In an update to the post, I have exported a working profile from the registry of the machine for a domain user, and have imported for a local user. This actually works, but I'd still like to know the reason for not being able to configure it in the first
instance.