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How to sync EspoCRM with Office365, especially with SMTP

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  • How to sync EspoCRM with Office365, especially with SMTP

    Hi everyone,

    basically, I know this is not the first question about configuration EspoCRM with Office365, but I couldn't find any solution which can be helpful.

    All I found is a very brief description without any help. I know there is an Outlook extension but I just want to sync e-mails, no calendar, etc., so I can follow up my B2B communication with my customers and exactly what did I sent to my customers in emails, in which period and without filtering or searching. I want to connect leads, customers, tasks, sent and received emails for every customer individually in one place.

    So, my problem is with SMTP or Outgoing email server for Office365. I am sure that I configurated SMTP correctly but every time when I try to test the SMTP connection I got Error 500. My IMAP connection works great but SMTP no way!

    When I look in espo-2020-12-17.log file there is

    [2020-12-17 10:35:05] Espo.ERROR: Email sending error. Could not open socket: stream_socket_client(): unable to connect to ssl:// (Network is unreachable)

    [2020-12-17 10:35:05] Espo.WARNING: Email sending:Email sending error.; 500

    Please, is there any solution how to fix that problem? I will appreciate any kind of help.
    Thank you in advance.


  • #2
    Please provide a screenshot with your SMTP configs.


    • #3
      Originally posted by Maximus View Post
      Please provide a screenshot with your SMTP configs.

      Hi Maximus,
      thank you very much for your fast reply.
      Here is a screenshot of my SMTP configs. This is for my personal e-mail...

      p.s. I changed my email in photoshop...


      • #4
        Hi Doma,

        Welcome to EspoCRM (PS: I'm not a staff member).

        Anyway there is quite a few people that have similar issue to you; I can sum it up as "2FA" (2 factor authentication; e.g login using SMS code or email code, etc).

        Refer to:
        If you already have 2FA disable or whitelist somehow, maybe Post #4 will help.

        Other thread:


        After you manage to get your email working, have a look at this, you might find something useful when you decide to customize your CRM.


        • #5
          Microsoft blockes unknown IP´s

          had the same problem. Sending was possible, but didn´t receive any mail. Microsoft seems to block IP´s they do not know.
          First my settings:
          IMAP, port 993, SSL, user your e-mail adress
          SMTP, port 587, SSL, user your e-mail adress
          1. You have to go to (see below)
          2. There are listed all logins from different devices you did. If there is one Microsoft judges as insecure, this IP is blocked and you cannot receive e-mails, but strange, send them. Declare the login attempt was ok und you will get instantly e-mails in your account.

          Click image for larger version

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          • #6
            Hi everyone, thank you very much for your comments and for trying to solve this problem with your advice!

            I tried everything, really I tried everything, all your advice, also my office 365 does not have 2-factor authentication, I lost my 10 days to find the solution and how to solve this problem but without succeeding... I am disappointed but, I still think that EspoCRM is one of the easiest and logical CRM that I ever tried to use. Also, there is a lot of space for expansion and advancement.

            Also, this is for the owner of EsposCRM, the extensions are a little bit expensive. I believe earning is much better if you sell 1000 extensions for approx 50-100€/per extension than 100 extensions per 240E€, that just my point of view!

            If someone finds some solution, please be free to contact me. Thank you in advance and I wish you all the best.

            Best regards,


            • #7
              hi Doma ,

              I have went through the thread, were you able to successfully test smtp from Administration -> Outbound Emails ?

              Let me know.


              • #8
                Hi everyone,

                first of all, I wish you all the best in 2021. year.
                No, I didn't succeed with the SMTP test. I still have the same problem, same error and I am starting to be a little bit frustrated ...


                • #9
                  Hi everyone,

                  finally, I found the problem and made it work, of course, thanks to technical support staff from my hosting company.

                  On the hosting, there is a local DNS that I did not direct to remote routing and we added permission for the remote SMTP user in the firewall on the server.

                  I hope this maybe help someone who hade the same problem.



                  • espcrm
                    espcrm commented
                    Editing a comment
                    Did they also teach you how you can do it yourself or it is only accessible by the admin/server provider?

                  • Doma
                    Doma commented
                    Editing a comment
                    Unfortunately, it's only accessible by the admin/server provider in my case, it's a shared hosting account... But, if you have WHM or some other access to the server I believe you can do it yourself. Regards, Doma

                • #10
                  Hi everybody
                  This article explains the issue and how to fix it.