8 Standard Ways To Test E-mail Server Availability. 1 Way To Solve It.

"An Encrypted Connection To Your Mail Server Is Not Available"

SIGNS

When setting up an email for an Office 365 user in Outlook, the following error message appears :

An encrypted connection to your mail server is not available. Click next to attempt using an unencrypted connection.

ROOT CAUSE

This error occurs when one or more of the following conditions are true:

• Autodiscover issue prevent Outlook from detecting the correct Exchange Online information for the user account

• Network connectivity issues prevent Outlook from communicating with the Exchange Online servers

RESOLUTION

If the standard solutions stated below are not successful:

• o365 outlook connectivity guided walkthrough
• Software update
• Recreating a new Outlook profile by choosing manual configuration setting
• Unexpected autodiscover behavior 
• Test E-Mail AutoConfiguration
• Remote connectivity Analyzer 
• Check system corruption by running in safe mode the command "sfc /scannow" (with privilege admin)
•  Adding a new UPN suffix to the domain with the external domain in Active Directory Domains and Trusts

 Then the other way is to use the on-cloud existing Outlook profile data in order to regenerate (write back) the on-premise Outlook profile. To use this fix, please verify that you have the following update installed on your machine:

•   MS Office SP2
•    Microsoft Outlook 2010 SP2/Microsoft Outlook 2013/etc..
•    Mailbox OnCloud/OnPremise

Bear in mind that this solution is a workaround.

First of all, open Control Panel, change the view and select «Small icons», and from «Mail (32-bit)», remove the existing profile and click «Apply».

Then rename the ost profile from the Outlook folder as described below :

Start>Computer>Users>username>AppData>Local>Microsoft>Outlook>username@....ost

Rename username@....ost into username@....ost.old for example.

If you can’t see the « AppData » folder, open windows explorer, click on «Organize» and «Folder and search options». Under the tab « view », tick the box «show hidden files, folders and drives».

Afterwards, launch Outlook and click Next to start configuring your profile as described below :

E-mail Account>Manually configure server settings or additional server types>Microsoft Exchange or compatible service>More Settings

In the picture below, the field User Name will be provided automatically

On the « General » tab, enter your Exchange account username@hotmail.com instead of «Private Folders», tick the box «Automatically detect connection state» and the Default connection state is already ticked and leave 30 seconds until server connection timeout.

On the second tab «Advanced», leave the box «Use Cached Exchange Mode» ticked and untick the box «Download shared folders».

On the third tab « Security », untick the box «Encrypt data between Microsoft Outlook and Microsoft Exchange» and in the Logon network security, select the authentication that is based on your cloud settings, on my case it's «Anonymous Authentication» instead of «Negociate Authentication».

On the fourth tab «Connection», tick «Connect using my Local Area Network (LAN)», then tick the box «Connect to Microsoft Exchange using HTTP» and click on «Exchange Proxy Settings».

Enter the URL to connect to your proxy server for Exchange. This information can be retrieved on OWA, so open a browser and type the link that is used to access outlook web access (i.e: outlook.office365.com), in my case it's «email.server.com».

Check the address bar and copy only the name of the node (name of the server where your are located). It should start by office365.server.node.com

Paste it into the «Use this URL to connect to your proxy server for Exchange» field in the fourth tab.

Leave by default the «Connect using SSL only» box ticked», tick the box «Only connect to proxy servers that have this principal name in their certificate» and enter in the field below the principal name registered in your certificate that allow to connect on your proxy server, in my case it's «certificate:*-server.node.com».

Tick the box «On fast networks, connect using http first, then connect using TCP/IP» and leave the box «On slow networks, connect using http first, then connect using TCP/IP» ticked.

Then choose the authentication that is based on your cloud settings, in my case it's «Basic Authentication» instead of «NTLM Authentication» from the Proxy authentication settings and when clicking on Apply, you will be asked to restart Outlook.

Click OK to restart, then you will be prompted to enter your credentials and for the section "Server" of the "Server Setting" window, the information will be regenerated automatically.

If it does not work when you click on OK, instead of the server being generated in the field above, you should enter directly the name of the node you belong to, for example « outlook.office365.server.node.com» (see below):

Outlook will now be able to restart properly. Afterwards, click on «Send/Receive» to update your current mailbox folder as shown below :

These steps works for me when i got stuck trying to configure different existing profile outlook on-premise and on-cloud, so it should definitely work for you too.

Leaving a review only takes 30 seconds and i appreciate it so much!

View Same Topic