An Encrypted Connection to Your Mail Server is Not Available

When Exchange Server 2010 has been introduced to an existing Exchange 2003 organization some Outlook 2010 clients may report the following error when setting up a new mail profile.

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

After trying an unencrypted connection Outlook fails to connect to the user’s mailbox.

This will occur for Outlook 2010 users who still have mailboxes on an Exchange 2003 server, however it should only occur when a new profile is being created, not every time they launch Outlook.

You can create the profile by choosing the “Manually configure server settings” option instead.

About Paul Cunningham

Paul is a Microsoft Exchange Server MVP and publisher of Exchange Server Pro. He also holds several Microsoft certifications including for Exchange Server 2007, 2010 and 2013. Find Paul on Twitter, LinkedIn or Google+, or get in touch for consulting/support engagements.

Comments

  1. HI Paul,
    I have a problem setting up my gmail account with outlook. When I search for the settings It cannot find then and it gives me this message An Encrypted Connection to Your Mail Server is Not Available. How can I get this fixed, Ive also tried to manually confugure the account but stil doesnt work. Can you help me with other alternative ways to fix this or give me the manual config. settings please.

    • You’ll need to check the Gmail help info for that one.

    • Mohammad Faisal Wadood says:

      I had the same problem when I want to make an account in MS Outlook 10. I got a solution that you must get an “APPLICATION SPECIFIC PASSWORD” from your google setting. And than use that new passport only for one tine while entering your email address and password in Outlook.

      That password contains 16 alphabets. And also keep that password in safe place for any other application.

      Gmail Setting ===> Account (Tab) ===> Other Google Account Setting ===> Go to Security (Tab) ===> Click on App Password “Setting” ====> Enter your regular password ====> Enter the name of Application f.e.x “OUTLOOK” and than Click on “Generate Password ====> your will get a password like “ABCD EFGH IJKL MNOP”. =====> now click DONE.

      That 16 alphabet password will be your APPLICATION SPECIFIC PASSWORD.

      Go to OUTLOOK===> ADD NEW ACCOUNT ====> enter your NAME, EMAIL and that 16 ALPHABET PASSWORD instead of your regular password of your Email ===> Click NEXT.

      • Thanks Mr.Mohammad Faisal Wadood.
        I too had the above issue. But Manual configuring didn’t work. Tried your method.great , It really worked.
        Thanks once again.

  2. hi there Paul,
    I am having this problem with outlook 2010 and Exchange Server 2010!!! which is a fresh install on Windows Server 2008 R2.Besides I am having certificates issues and don’t want to buy certificates because the exchange system is for internal use only and I am running a ONE mailbox with popcon to grab pop3 messages online.
    My error is as : http://exchangeengine.wordpress.com/2010/03/18/getting-autodiscover-warning-message-in-outlook-2007-domain-joined-workstations/.
    Thank you for help!!!!

  3. Dear Sir,
    i have problem in out look mail, i cant send & receive any mail after that showing like this ” An encrypted connection to your mail server is not available click next to attempt using an unencrypted connection” please advise us what to do..?

  4. did you even bother testing this?

    manual configuration results in:

    The action connot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.

    all mailboxes have been moved to the 2010 server.

    • Hi Jason,

      Did I even bother testing this? I’m not sure how to respond to that.

      Yes I tested it, that’s why I posted the solution. It deals with the specific scenario described in the post:

      - Exchange 2010 installed into existing Exchange 2003 org
      - Outlook 2010 client creating new Outlook profile for a mailbox still on Exchange 2003

      If you’ve already moved the mailboxes to Exchange 2010 you may have a different underlying issue that presents as the same error. If you’d like to describe your scenario in more detail, including anything you’ve already checked, there might be some more suggestions I can offer.

      • Hi Paul,

        I’m having the same problem except I’m not computer savy enough to have thought about even bothering to testing this. Before I even read your response I was thinking what a cocky POS answer Jason gave. Of course this does not help me but just wanted to say that you took the high road.

        I’m wondering if I reinstall exchange 2003 and use my old settings so I can access my Outlook.

        Thanks,
        Sarah

  5. Aseff Eqbal says:

    -
    I am haing Exchange 2010 in my environment & using outlook 2010 where i faced the subject issue “An Encrypted Connection to Your Mail Server is Not Available”.

    I found out that the user for whom i was trying to configure outlook was LOCKED in AD. I unlocked his account & the problem was resolved.

  6. I noticed you needed to enable imap in your gmail settings using the web.

  7. Another tip is to go http://www.google.com/accounts/DisplayUnlockCaptcha and login using your credentials. After doing that then go back and try your Outlook connection to your gmail account.

  8. I have been racking my brains with what to do and finally came across this which sorted it… hope it helps you guys

    http://support.apple.com/kb/HT1625

  9. Sunny Agarwal says:

    HI Paul,
    I have a problem setting up my gmail account with outlook. When I search for the settings It cannot find then and it gives me this message An Encrypted Connection to Your Mail Server is Not Available. How can I get this fixed, I’ve also tried to manually confugure the account but stil doesnt work. But when I give setup with my brother’s gmail account, it is connected. So can you help me with other alternative ways to fix this or give me the manual config. settings please..

  10. Hi Paul — or anyone who can help —
    We have two email addresses for our company, and set them both up to work with Outlook 2007. This has worked out fine on one of our computers but the other one will not receive mail from the most recent account. It says “an encrypted connection to your mail server is not available.” What are some possible causes of this?
    Thank you so much,
    Erin

  11. I finally solved the problem by configuring my gmail account in Outlook 2007 (An encrypted connection to your mail server is not available. Click Next to attempt using an unencrypted connection.), everything works with what Clay said on January 12, 2012 at 11:35 am, follow the steps in “create an application-specific password” at this link

    http :/ / http://www.google.com / accounts / DisplayUnlockCaptcha

  12. hi paul,

    i have same issue with my user whose exchange mailbox is on 2003 exchange server and he is using outlook 2010.we have introduced Exchange 2010 servers into the environment but user is not yet migrated.

    user has 2 email ID one for domain1.com and another for domain2.com.
    He has a single profile configured with 2 accounts and domain1.com is set as default. domain1 account works fine but domain2 email account in same profile will show the same error as you mentioned above.if i configure domain2 account in separate profile it works fine.
    could you please help me.for domain1 account user uses Https connection to connect for server,wil this cause any issues.
    NOTE: both accounts work when is in office that is domain1.com

  13. Hi,
    I keep getting this error ;

    An encrypted connection to your mail server is not available…

    tried configuring – did not work
    when I use webmail I can read the emails however outlook 2010 doesnot download the emails it used towork fine for about 3 weeks since installed outlook 2010 but now I get
    An encrypted connection to your mail server is not available…
    An encrypted connection to your mail server is not available…

    l. help

  14. Dear All,

    Just in case you are getting this problem post enabling “2-step verification” on your gmail account then its worth reading about “Application-specific passwords” .

    Basically either get rid of “2-step verification” or simply generate a password for your email client called “Application-specific passwords”. This password you should be using to connect to gmail via email client.

    cheers
    Deepak

  15. Hi,

    I have Outlook 2010 and Window 8. When outlook mail was trying to connect to server. There would be a pop-up screen to enter password. But it was strange that it popped up many times. And then it appeared An encrypted connection to your server is not available. Then I tried unencrypted connection, the result was also the same.

    Is it possible that the server of outlook mail doesn’t support Win 8?

  16. Hi.

    I want rediffmail account Configure in outlook 2010 but i am getting some error “Log onto incoming mail server (POP3): Your e-mail server rejected your login.Verify your user name and password for this account in Account setting. Ther server responded:- ERR Authorization failed” Please suggest….

    • Log onto incoming mail server (POP3): Your e-mail server rejected your login.Verify your user name and password for this account in Account setting. Ther server responded:- ERR Authorization failed

  17. I ahve an issue with this error.

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

    worked yesterday, guys gets to work today and gets asked for passwords from both his pcs, nat’d to the same IP. set him up with a new mail account in a differrent domain to test and that has the same issue, auto discover works and so does owa to both accounts.

    no one else is getting the issue in the same office all on the new hosted exchange as he is?

    Any ideas is it encryption? when we remove everything and start again we cannot get even the old one to work !

    Guy

  18. Dave Youkers says:

    We’re a small business. For our regular employees, we’ve converted everyone to Office 365 and migrated our 3rd party hosted IMAP mail server over to MS hosted exchange mail servers. Everything is working fine, however, we have a couple part time employees who need to access our mail system from home using desktop versions of Outlook 2007. We “bought” Exchange licenses for everyone, but when we go to add exchange based accounts to their Outlook, they’re getting the “encrypted connection not available” message. We’ve tried the unencrypted route with no success. Any suggestions?

    • I’d suggest an Outlook upgrade for them. Or use Outlook Web App (webmail) only.

      http://technet.microsoft.com/en-us/library/office-365-system-requirements.aspx

      “Office 365 is not designed to work with Office 2007 because Office 2007 left mainstream support on October 12, 2012. Office 365 does not offer code fixes to resolve problems you encounter when using the service with Office 2007. You should expect the quality of the user experience to diminish over time, and many new Office 365 experiences will not work at all. We recommend that you upgrade as soon as possible to Office 365 ProPlus or Office Professional Plus 2013 for the best experience with Office 365.”

  19. My Office Tools 2007 keep saying that there is no encrypted connection, how can I fix this?

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