Outlook Security msg connecting to Exchange

I have several small and non-profit clients that are getting those dreaded security alert msgs when they open their outlook (2010 and 2013) connected to Exchange 2010.  I have researched this several times and just am not comfortable with the powershell changes everyone recommends. I have tried the various manual adding of certificates and registry entries to supposedly disable - nothing works. These are small clients and do not want them to have to pay $500 for Microsoft to come in and do the work. Is there a surefire way to just disable the alerts via the registry or GPO OR add the certificate in Outlook 2010/2013??
bcp_cnsllcAsked:
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davorinCommented:
What exactly are these security messages saying?
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bcp_cnsllcAuthor Commented:
it is your standard outlook security msgs listed in articles such as these

https://support.microsoft.com/en-us/kb/276597

https://community.spiceworks.com/topic/278039-email-certificate-security-alert-everytime-opening-outlook-2010

etc. There are a hundred of these and short of doing the ECS I am getting nowhere and to chicken to do the ECS. I would rather hack Outlook itself or try to do something based on a GPO which I have read mentioned but never seen any tangible suggestions/settings to try.

I can paste mult versions of these bec have them on 5 different small companies and 1 larger lawyer firm. These are pretty much based on either the .local is no longer allowed in an ssl OR companies doing a pop and dump into Exchange so they dont need an ssl.
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davorinCommented:
First link has nothing to do with your problem.
For sure you have some problems with certificate.
Or certificate is not trusted by clients (have you bought the certificate), or it is created wrongly for configured exchange server settings. In some cases it is the easiest to change outlook providers for autodiscovery. All settings outlook clients gets from autodiscovery and even if you change registry manually the change will be reverted next time you open outlook.
I'm sorry, but if you plan to support exchange servers (and most of other Ms servers) you will need get comfortable with powershell, because there will be more and more stuff you will not be able to configure thru GUI. And using unsupported solutions can bring you more and more problems...

Is the certificate trusted when you try to connect to owa? Do certificate subject name is the same as msstd record used in outlook exchange proxy settings?
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