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exchange 2010 and outlook 2010 outlook anywhere will not accept user credentials

Posted on 2013-06-12
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Last Modified: 2013-06-13
I have a problem connecting outlook 2010 to exchange 2010 via outlook anywhere, on a computer not connected to the domain (running windows 7 home premium).

I have a certificate generated by local CA, which I know is not ideal.

BUT, the confusing part is, I have 1 machine working with this setup, but I cannot get any other machine to work - I am comparing every setting and I cannot see why one machine is working and not the other - everything SEEMS identical.

Can someone help?
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Question by:davids355
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8 Comments
 
LVL 22

Expert Comment

by:Haresh Nikumbh
ID: 39241863
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LVL 10

Expert Comment

by:tmoore1962
ID: 39241933
Are the network settings the same on the machine that works and those that aren't, may be a name resolution issue so just wondering on the DNS servers information.
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LVL 11

Expert Comment

by:James Hodge
ID: 39241945
Hi Davids,

Run the testexchangeconnectivity tests as suggested by takecoffee and this may give some hints.

Are the non-domain members located internally (on the LAN) or remotely?

It sounds like DNS might be the problem.

James
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Author Comment

by:davids355
ID: 39242608
I havent run the connectivity test yet, I will run that in the morning.

Both computers are in our office (Not the clients network), both connected to the same lan, both win 7 home premium, both outlook 2010.
All settings seem identical, the only thing I can think that I may have done diffrently is the original procedure for installing certificates on the client machines.

I guess the correct way will be to get a proper certificate, but its really bugging me why this wont work.

I will try the connectivity test in the morning and report back.
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LVL 11

Accepted Solution

by:
James Hodge earned 250 total points
ID: 39242623
If you are not sure about how you installed the certificate, open up cert manager and delete the certificate wherever you can see it, then re-install it to the correct location.
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LVL 63

Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 250 total points
ID: 39242896
Test Connectivity is going to be a waste of time because you are using a self signed certificate. Those aren't supported for use with Outlook Anywhere. If you really cannot get the $60 or less for a trusted certificate from GoDaddy, then if your DNS provider supports SRV records get a free certificate from StartSSL.

Simon.
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Author Comment

by:davids355
ID: 39243602
james, the non domain members are located outside of the lan.

I have tried going in and removing all certificates related to the server, then re-adding.

the exchange connectivity test works, but only if I tick the box that says, ignore trust for SSL.

Sembee, we can purchase a certificate, but I really want to get to the bottom of it, mainly because I have one computer working, so it must be possible.
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Author Comment

by:davids355
ID: 39243734
sorted now guys - I started from scratch, then just installed the CA certificate on the client under trusted root certification authorities.

then re-configured outlook anywhere and made sure to change authentication to basic (because they are non domain members).

this seemed to solve it.

I think I had just tried so many things I got confused with what I had and hadn't done.

thanks for the help.
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