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MS Outlook - An encrypted connection to your mail server is not available

Right, here we go! When trying to run the wizard using Autodiscovery to connect to a MS Exchange server from Outlook 2010, you may be given this error:

Microsoft Outlook Encrypted connection error

 

Fix 1: Ensure you can 'see' the Exchange server from your computer

The fist thing to do is to visit Microsoft Remote Connectivity Analyzer and run a test. Visit this website https://www.testexchangeconnectivity.com/ and select the "Exchange Server" tab, then click the Outlook Autodiscover from the Microsoft Office Outlook Connectivity Tests. This test will ensure that your Outlook 2010 can actually see Exchange

Microsoft Outlook Encrypted connection error

 

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Fix 2: Ensure you don't have a 'persistant' proxy

Another good tip is to ensure you are not using any "persistant" proxy server, and I mean situations where in the past you had a proxy server configured but then remove it. Internet Explorer and other browsers may connect well to the Internet, but the "persistent" proxy may still be lingering in the background, causing applications or services that go up and down the OSI model to be wrongly re-routed to the Internet

To check if you have a "persistent" proxy:

 

1.- For Windows 7, run the following in CMD with Administrative rights:

 

netsh winhttp show proxy

 

netsh http show proxy

If it shows you that you have a proxy server, use the commnad "netsh winhttp reset proxy" to remove it

2.- For Windows XP, run the following command on CMD:

proxycfg

 

netsh winhttp reset proxy