MS Exchange certification issue

I have a situation were intermittently, users trying to log into Exchange 2013 or 2010, with an Outlook client, will get a prompt to install the certificate even though the cert was previously installed. This issue occurs most frequently when the access is over VPN
Barry-f4Asked:
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Jose Gabriel Ortega CEE Solution Guide - CEO Faru Bonon ITCommented:
Is it a public Certificate? or a self-signed certificate?.
They are being prompt since outlook detect that there's a change in the network. Every time you got a change of network (you can try it yourself to use the LAN port and then disconnect and connect using wifi) you will be prompt for credentials.

About the certificate if it's self-signed certificate, what is the error you're getting?.
if it's a public certificate you should probably get a different error, but you need to tell us what is the error or message you're getting since we can't see the crystal ball to determine what's going on.
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Jose Gabriel Ortega CEE Solution Guide - CEO Faru Bonon ITCommented:
no follow up given
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Barry-f4Author Commented:
It is a self signed cert. I intermittently get the prompt to install the cert even though the cert has been installed
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Jose Gabriel Ortega CEE Solution Guide - CEO Faru Bonon ITCommented:
Ok In this case if the access is via VPN in a self-signed certificate, you would need to install the certificate over the client so the certificate would be trusted, but you have to repeat the operation for each device that is connecting to the VPN so it can trust the certificate, so the best bet is to get an SSL Comodo wildcard certificate or one SSL with at least 2 domains validated (mail.domain.com and autodiscover.domain.com, for example) and forget about those annoyances.
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Barry-f4Author Commented:
I am not sure what you mean by install the certificate over the client. I have reinstalled the cert more than once. Please explain.
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