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the certificate is not from a trusted certifying authority

Posted on 2016-08-05
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Last Modified: 2016-08-07
Please help!  

I have a simple server that I have enabled RDP on at work.  I go home, fire up Remote Desktop, type in a public IP address, log on with my credentials, and I'm in.  

During the logon process, I get an alert like the one attached: "the certificate is not from a trusted certifying authority".  If I go through the process of installing the certificate, I get the prompt "The server name on the certificate is incorrect".  

I don't want to ignore the prompt (I have to explain the prompt to management).  Is there a way I can get rid of it without having to buy an external certificate, setup an enterprise CA, or setting Remote Desktop to not warn me about it (advanced tab > server authentication option)?  Can I safely ignore it, since I'm using an IP address that I know, and can be fairly certain it's not a man in the middle attack?  I do have NLA enabled on the remote box.  

The remote box is server 2012 and my home computer is Windows 7 with the latest version of Remote Desktop.  

Thank you all, I appreciate any help I can get.
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Question by:npinfotech
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by:Dave Baldwin
ID: 41745179
Self-signed certificates are never 'trusted'.  You have to purchase a certificate from a reputable vendor to get it to be "from a trusted certifying authority".  Only then will there be a certificate chain that leads back to a "trusted certifying authority".
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by:David Johnson, CD, MVP
ID: 41745369
Since you don't want to set up a proper certificate you can elect to ignore it.  If the certificate changes you will have to agree to ignore it in the future.
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by:npinfotech
ID: 41745618
Thank you for the responses, I appreciate them.  

My understanding is that the point of the prompt is to ultimately help prevent man-in-the-middle attacks.  Since I am using NLA and am using an IP address to connect, is a man-in-the-middle still possible, or highly unlikely?
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Assisted Solution

by:Dave Baldwin
Dave Baldwin earned 100 total points
ID: 41745705
I thought your problem was having to explain why you are getting the prompt.  If you use the current cert, each new user will get the prompt and have to accept it.  The only way around that is to buy a cert that is traceable to a "trusted certifying authority".
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by:npinfotech
ID: 41745760
Thanks.  Is there a way I can visually tell if the information on the prompt is actually legitimate (spot if something is wrong)?
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Expert Comment

by:Dave Baldwin
ID: 41745772
Certificate error messages normally give the details of their complaint.  A valid certificate will show in the address bar where you can click on it to get more info about it.
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David Johnson, CD, MVP earned 400 total points
ID: 41745801
With a self-signed certificate ANYONE can create a certificate using ANY name including the expected name that you are expecting. If you are worried about MITM then vpn into the domain then connect your rdp session. MITM isn't that easy to implement without physical access to the internet endpoints.
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by:npinfotech
ID: 41746558
I will be opening another thread based on this
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