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Getting “Security Alert” dialog box - Outlook Certificate error

Posted on 2012-08-14
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Last Modified: 2012-12-12
I have a newly built Windows SBS 2008 server that runs Exchange 2007

I get this “Security Alert” dialog box - Outlook Certificate error every time a user brings up Outlook on their desktop.

I was told that you can self-sign it.  I don’t know what this means
Under the “Windows SBS Console” there’s an option to add a trusted certificate. I don’t know what this is or if it’s the same certificate I need to keep the pop up from re-occurring in Outlook.
-      The option I see is under “Windows SBS Console” > Network > Connectivity tab.  Is this where I create a “self-issued “certificate?

How do I create a self-signed certificate to keep all users from getting this “Security Alert” every time a user opens Outlook 2010 on their desktop
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Question by:agieryic
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Accepted Solution

by:
dlacoste81 earned 1000 total points
ID: 38294237
Self-signing is the default option but users will have to add your certificate to their trusted store and once they do that the error message will go away. Personally I've always preferred using an external certification authority, SSL's can be had for as little as $12 so no point in not getting one.

Back to the original question: If you followed the wizards when you set up SBS it should have created a self-signed certificate automatically. Users can download and install it from \\yourserver\Public\Downloads\
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Assisted Solution

by:Exchange_Geek
Exchange_Geek earned 1000 total points
ID: 38294397
You are getting the alert cause your cert has the following values and this is not in-sync with your server.

When you view the cert - it will give errors that the cert name is mismatch or does not match the site. Read: http://support.microsoft.com/kb/940726

There are few basic setting that you'll need to know and your issue wouldn't cause an issue to any user - no downloading cert etc **only for internal users**

Use the following link to work with installation of certs

http://blog.sembee.co.uk/post/SBS-2008-Certificate-Installation.aspx

Regards,
Exchange_Geek
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Author Comment

by:agieryic
ID: 38334158
I will take a look at this article
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Expert Comment

by:Exchange_Geek
ID: 38338305
Sure, let me know if you need any help.

Regards,
Exchange_Geek
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Author Comment

by:agieryic
ID: 38453033
I am very sorry for not getting back to this Post. I am going onsite tomorrow and will follow up to complete this .
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Author Comment

by:agieryic
ID: 38582407
I am having issues with the workstation accepting th ebuilt-in SBS2008 certificate under the adminitrators profile download folder
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Expert Comment

by:Exchange_Geek
ID: 38583156
What does that mean?

Regards,
Exchange_Geek
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Author Comment

by:agieryic
ID: 38686115
As I looked into this further, it appears that I need to purchase a 3rd party certificate as dlacoste81 mentioned and waht many others are recomending.
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Author Closing Comment

by:agieryic
ID: 38686121
this has been a great learning curve. Thanks for your input - and very sorry for waiting so long
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