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.

An Encrypted Connection to Your Mail Server is Not Available

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

An Encrypted Connection to Your Mail Server is Not Available

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.

An Encrypted Connection to Your Mail Server is Not Available

About the Author

Paul Cunningham

Paul is a former Microsoft MVP for Office Apps and Services. He works as a consultant, writer, and trainer specializing in Office 365 and Exchange Server. Paul no longer writes for Practical365.com.

Comments

  1. Vitalstats

    I don’t know if this will help, but I finally found that the problem was not on the desktop side, but on the server/hosting side. I use exchange server, hosted by Microsoft, and had to turn off “Security Defaults” in my Office portal. Once I had done that, Outlook stopped asking repeatedly for the password. I guess the problem might be the same with other email hosts as well, just try to find out if there is a setting somewhere on gmail/yahoo/outlook or whatever you are using. Gmail have a “support for less secure apps” setting that caused some trouble if it was enabled.

    To fix my Exhange security settings, I just did the “Turn Security defaults on or off” part of https://docs.microsoft.com/en-us/microsoft-365/admin/security-and-compliance/set-up-multi-factor-authentication?view=o365-worldwide

  2. Lal Bahadur Yadav

    an encrypted connection to your mail server in not available click next to attempt using an unencrypted connection. When configured outlook using internal network getting above error. But on external network able to configured working fine.

  3. Julia

    Just is case somebody is still looking for answers.

    I have an older Outlook 2007 and 2-Step Verification on my Google account. I updated my password on Google and my Outlook stopped working. When trying to repair, it would give me an error message: “No encrypted connection to your mail server is not available.”

    I found an answer here from Mr. Mohammad Faisal Wadood that finally helped me. So I want to update the information, because the steps that need to be taken have changed in Google.

    You need to create and App Password. Here is what Google writes about those: “App passwords let you sign in to apps and devices that don’t support 2-Step Verification.”

    Here are the steps:
    > Log-in into your Google Account
    > Go to Manage your Google Account
    > Go to “Security” tab in the left menu
    > Scroll down to “Signing into Google” section
    > Click on “App passwords” and confirm your login information.
    > Select the App (for me Mail worked).
    > Select Device (Windows Computer if that’s what you use)
    > Click on the button “Generate”
    > Follow instructions and use this password for your Outlook Account.

    Worked for me!

    1. Steve

      This worked for me. I have Outlook 2010 running on Windows 10. The only additional thing I had to do was sign up for the 2 step verification before I could see the “Apps passwords” option.

      1. Kevin

        I finally solved this problem using the steps described above too including adding the 2-step verification on my Google account before I could see the Apps Password option. I am using Outlook 2010 running on Windows 7 Ultimate desktop PC.

    2. Anirban Mukherjee

      thank u so much, worked for me as well. I was breaking my head whole morning

    3. Dominique HUGO

      Works like a charm !! thanks Julia.

      Domi.

    4. Heather Stephens

      Thanks, worked for me

  4. Rajat

    Someone pls help me to resolve it.

    Thanks in advance ?

  5. Rajat

    I’m getting in Office 365 Outlook error “An encrypted connection to your mail server is not available. Click Next to attempt using an unencrypted connection.” and Same account is working fine in web outlook

    1. Julia

      Did your email solved? How did you find? I have the same problem with my email?
      Can you please assist me? Tks

  6. Dalene

    Help.. can not find my gmail like above steps

  7. ajmal

    i am using outlook 2013 i have been problem to sent mail, but i am receiving mails.
    when i am sending mail its showing error message.

  8. Noor Habib

    Dear all if some one use the kaspersky antivirus the main causes that prevent connection between your mail to server side that protect your pc to communicate with office 365 just remove the antivirus and delete the old outlook profiles and re configure the outlook also install antivirus again.

  9. Noor Habib

    dear all the main causes is to delete or remove the antivirus from your PC then re configure
    the outlook and re install antivirus.

  10. Harmel

    Hi
    I had multiple email attached to office 365 and connect with Microsoft Outlook 2010 though I connect my gmail account to outlook 2010 now it does not work.
    it is connected but not sending and receiving mail at the point after I connect it.
    would you have any suggestion

  11. Lorrie

    I have several emails in Outlook of which they all worked fine until the first few weeks after the update to 2010. Now one of them (att.net account) doesn’t. None of these accounts were installed after but have exited for a year and a half. I received the message many have: An Encrypted Connection to Your Mail Server is Not Available. I have ran a test email, it works fine, but I still cannot receive any other incoming emails and receive a error report. I can receive emails on my email account at Att online. I have Office Home/Business 13 installed. I’m frustrated in what to do next. Help!

    1. Julua

      I have same problem as you do. Can receive email but unable send it out.
      I received message ” problem connecting to serve. ” An encrypted connection to your email is not available. Click next to attempt using an unencrypted connection”. Where find it?

  12. Laine

    THANK YOU MAHAMMAD FAISAL. REALLY WORK FOR ME. THANKS!

  13. karthik

    thank you soo much it worked for me

  14. Ismini papageorgiou

    Bro, you have just MADE MY DAY!!!!

  15. ginalyn

    hi paul can you help me what should i do i cannot log in my microsoft email account. when i enter my user name pasword still i cannot log in

    1. Paul Cunningham

      Maybe your password is wrong? If it’s for a Microsoft Account you’ll need to contact Microsoft or try a password reset.

  16. tasos

    This must be the most lazy “tutorial” i’ve ever read, given the authors answers to people’s questions as well.

    1. Paul Cunningham

      Thanks! I didn’t know that there were folks trawling the internet and ranking tutorials by laziness, so imagine my delight at being told I rank at the top! You’ve made my day.

  17. Darla

    THANK YOU!!!!!!!!!!!!!!!!!! Mr.Mohammad Faisal Wadood.

    1. Julia

      How did you solved?
      I have the problems of sending email but can receive only.

  18. JLW

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

  19. Dave Youkers

    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?

    1. Paul Cunningham

      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.”

  20. Guy

    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

  21. Bapu Bankar

    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….

    1. Bapu Bankar

      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

  22. Mong

    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?

    1. rakhi

      Hey I am also facing Same isssue do you have any solution

  23. Deepak

    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

  24. sam

    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

  25. sowmya

    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

  26. Ranses

    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

  27. Erin

    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

  28. Sunny Agarwal

    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..

    1. Arnold

      This worked for me perfect.

      Thanks for the poste

      1. Suresh

        This worked me after, almost 1 hour of trying. Thanks so much

    2. Ms Thankful

      Thank you Clay, your suggestion worked straight away 🙂 and I didn’t even have to charge my private information as suggested by Mohammad Faisal Wadood herein.

      Thank You!

  29. Clay

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

  30. Aseff Eqbal


    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.

  31. Jason

    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.

    1. Paul Cunningham

      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.

      1. Sarah

        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

  32. Harish

    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..?

  33. sam

    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!!!!

  34. Mthobisi

    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.

      1. Praveen

        what is the contact details for Gmail ?

    1. Mohammad Faisal Wadood

      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.

      1. Najma

        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. Danish Siddiqui

        Thnx bro,, i m facing that problem so long time but i tried your method i really work,, nd ma prblm solvout,, thnx bro..

      3. naresh

        thanks a lot problem solved

      4. zetra

        OMG thanx a million times bro it work, problem solved.

      5. Fajiq

        Thank you very much. i m facing this problem almost 1 year. But now i tried your method its really work,

      6. Arshad Shaikh

        Thanks a lot…
        Problem solved..

      7. Muthu

        Thank you Mr.Mohammad Faisal Its Great Work Actually, I was Searching For the Solution With many Procedures but Didn’t Work but Your Method Worked out

        once again thank you

      8. Berjang Pun

        Thank you for the post. I have relaxed with this post.
        ………..

        1. deepak sharma

          thanks bro for solve my problem

      9. Rathana

        Thanks Mr.Mohammad Faisal Wadood for your very helpful sharing

      10. Rajakumar

        ji ??? your are great jii… i successfully linked my outlook with ur way… thank u so much… if you have any pages in google plus or facebook., please let me know

        1. MSLover

          overacting in its worst wat

      11. rajendra

        thank u it was worked out

      12. Jojo

        Hello Mohammad Faisal Wadood:

        I tried the steps you outlined and it worked like magic. Thank you very much from the bottom of my heart.

        I had battled with this technical issue for several weeks and it was making me upset. Good to have remained persistent in my quest to get the technical issue fixed.

        Thanks once more.

        Kind regards,

        Jojo

      13. Sanket K

        Dear sir,
        i could not find where is the gmail setting tab.

        i am facing same problem ,i cant configure gmail account in outlook 2010.

        please help me. sir

      14. Vakul Patpatia

        Mohammad Faisal
        Thank you so much Mohammad

        It worked perfectly

        Thanks A lot 🙂

      15. Joe PNG Kange

        Thanks alot it truly does work.

        Thanks man!!!

      16. Praveen

        The encryption error may also occur due to your setting for hacking account. Use the following to remove the setting and the outlook can be configured successfully in Windows 10 also.

        Gmail Setting ==>Account (Tab) ==>Other Google Account Setting ==> My Account
        Use your google account user name and password

        Go to – My Account ==> Sign in and security ==> Device activity & notifications ==> Security alerts settings ==> manage settings ==> Critical security risks ==> Check email and mobile SMS alert

        Now save this setting, come out from gmail / google account setting, then configure the outlook mail box using the standard method.

        Hope this will help somebody.

      17. E Rabi

        Thanks a lot great solution my long day issue solved

      18. Sarathpal

        Wow !!!!
        Amazing dude.
        many thanks,
        Sarathpal

      19. David Yong

        I have connection encryption problem too, I tried Mohmmand Faisal wadood method its work. Thanks

      20. eklas00

        I have connection encryption problem too, I tried this method its work just fine . Thanks

      21. Cindy L

        Yes! Thank you! Finally something that works!!!

      22. Karan

        Just Enable Allow less secure apps: ON option.

      23. Rasheed

        Thanks Its working

      24. Qamar

        Dear

        I am also facing the problem in OUTLOOK EXPRESS 2016.
        I tried as you mentioned but I am not getting the following
        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.

        Could you please explain in detail?
        Thanks
        Qamar

      25. Thanks

        Thank you so very much Mahmoud Faisal, jazak Allah khairan.

      26. Julia

        Thank you so very much, Mr. Mohammad Faisal Wadood! I was so frustrated, because after changing my password in Google my Outlook stopped working. And this helped. So very thankful!

      27. Vinita Wadhwa

        Hi,
        I tried this solution and many more solutions but nothing seems to work for me. I am not able to update my outlook e-mails as it shows password error again and again.

    2. vijay

      Dear Mthobisi says
      ” An Encrypted Connection to Your Mail Server is Not Available. ”

      solution :
      i too faced this problem , from my R & D in this you can try my tricks like following stepls
      step one : change your mail passwords in gmail
      step two : go to microsoft outlook try by new password it will open ,
      by
      vijay
      B.TECH ( T T )

    3. Hugo patrice

      I have the same problem.
      I can access the exchange server via OWA and EAS easily from outside.
      And can connect to outlook from inside, but not from outside.
      I get the following error message: “No encrypted connection to your mail server is not available.”
      I need help please.

    4. Arunkumar

      Same problem will arising me also…if u came to know kindly help me also.

    5. Aadil

      Just google how to allow Less secure apps for your gmail account, after that you are done 😀

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