Help joining an SBS 2011 domain across a VPN

Posted on 2014-03-11
Last Modified: 2014-03-17
Working on an SBS 2011 domain.  Several machines are remote from the office using a watchguard VPN  - office subnet is, remote location is

Trying to join a new win 7 machine to this network.

Added entries for server in hosts file on win 7:


all point to the of the server

we can ping it
added domain.local to the advanced DNS tab

when we try


we get a message that security cert is invalid, then when we click continue, we get a 404 message.

When we try or

we get:

Server Error in '/' Application.

Runtime Error
Description: An application error occurred on the server. The current custom error settings for this application prevent the details of the application error from being viewed remotely (for security reasons). It could, however, be viewed by browsers running on the local server machine.

Details: To enable the details of this specific error message to be viewable on remote machines, please create a <customErrors> tag within a "web.config" configuration file located in the root directory of the current web application. This <customErrors> tag should then have its "mode" attribute set to "Off".

<!-- Web.Config Configuration File -->

        <customErrors mode="Off"/>

Notes: The current error page you are seeing can be replaced by a custom error page by modifying the "defaultRedirect" attribute of the application's <customErrors> configuration tag to point to a custom error page URL.

<!-- Web.Config Configuration File -->

        <customErrors mode="RemoteOnly" defaultRedirect="mycustompage.htm"/>
we haven't added a computer in a while, but the server seems to be working OK?

Any advice?
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LVL 13

Assisted Solution

by:Andy M
Andy M earned 500 total points
ID: 39921400
I believe your SBS server will be using a self-signed certificate that the remote computer is unaware of.

If you look on the server in Public user documents/downloads (can never remember which) you should find a certificate installation package, copy this to the remote system somehow, run it and restart the remote computer.

Then check to see if you still get the same certificate error.

The other option is to join the domain via the system properties dialog on the remote computer - assuming dns is working fine it should allow you to join the domain through tha way as well.

Author Comment

ID: 39921426
join through the sys properties - that doesn't do all that http://connect does, right?

and we are using a Godaddy cert (at least when out on the web).
LVL 13

Assisted Solution

by:Andy M
Andy M earned 500 total points
ID: 39921444
Personally I've never really used the web method of joining to the domain so not sure what else it actually does differently - always used the sys properties and providing that there's no dns issues I've never had a  problem doing it that way.

When it brings up the cert warning on the remote computer does it let you view the certificate it's trying to use and see if it is the GoDaddy certificate or something else?

Is this the first machine you've joined in this method? If not I take it the other machines worked fine?
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Author Comment

ID: 39921472
I am used to being able to click on the lock or similar to see the cert details.

all it says is:  The security certificate presented by this website was issued for a different website's address.

Security certificate problems may indicate an attempt to fool you or intercept any data you send to the server.

which makes sense since the cert isn't for https://connect : )

I've joined other machines over the vpn a long time ago and remember it wasn't easy.  Of course, I didn't take notes on how to do it to avoid this.  reinventing the wheel....

Author Comment

ID: 39921479
actually now, when I type https://connect

I get the cert message, click continue then get to the IIS 7 page.

anyone know what another address would be for the connect computer page for sbs 2011 or how to tell if that part of the server is working OK?
LVL 13

Accepted Solution

Andy M earned 500 total points
ID: 39921497
Well that would explain why you are getting certificate warnings.

Assuming you have a certificate for something like "" - if you setup an A host record on the remote PC dns for and point it at the server's internal IP (192.168 . . .) do you still get certificate warnings when trying to access

I recall SBS been really funny about certificates - think we spent a while trying to get things like Outlook Anywhere and Remote Web Workplace working correctly which turned out to be certificate issues in the end.

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