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Today you're really excited that you have finally moved over to Office 365, and can’t wait to start your day with using the new Microsoft Exchange services. You put in your credentials, and notice that you get the dreaded message saying “An encrypted connection to your mail service is not available”.
Instinctively you click next and try again. Over the next few minutes you repeat the process thinking this was only a hiccup and that your account will finally work after a few tries.
Unfortunately, during this process there is a lot taking place on the back-end. Microsoft Outlook is performing several tests to locate where your mailbox is stored with the Autodiscovery feature for using the products. When it works, it works great!
If you’re ever in a bind and need to start connecting right away, Microsoft does have a solution for you, which bypasses several of these checks taking place in the background and preventing you from connecting!
On Microsoft’s website, you can download and install the software (can be located here), Microsoft Support and Recovery Assistant for Office 365 on the workstation you are working on.
After the Microsoft Support and Recovery Assistant has been installed, go past the license agreements and select the second option, Outlook.
You will be brought to another screen which asks you about the issue you would like to resolve or diagnose. Click on the second option that says “I need help setting up my Office 365 email in Outlook”.
At this point, you will be brought to another screen which asks you about the issue you would like to resolve or diagnose (where several troubleshooting options are available for selection). Click on the second option that says “I need help setting up my Office 365 email in Outlook”.
This option will be directing you to the area which you need to go to resolve the issue with connecting your Office 365 account.
Once you have made the selection, click "Next:
During this portion of the process, you will be prompted for your email address and credentials for your Office 365 account, and a diagnostic will be performed.
Now the tool is certain checks which Outlook does when adding your account, and it bypasses certain ones which may be preventing you from authenticating and adding your Office 365 account.
Once the diagnostic is complete, it will prompt you to add the account to Outlook and provide you with fully functioning email!