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Office365 and old Email Clients and/or Appliances

Discussion in 'Tech Tips and Reviews' started by dlipman, Feb 6, 2019.

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  1. dlipman

    dlipman Thread Starter

    Feb 14, 2013
    First Name:
    Microsoft has moved to TLS and the support for the latest security protocols has left many email clients and appliances behind and unable to access Office365 based email. What I am providing below is a capability to allow email clients and appliances to access Office365 accounts.

    I have found STunnel is beneficial for making software access to TLS compliant systems as STunnel is a SSL/TLS Proxy based upon OpenSSL. STunnel is quite "tweakable" and thus can be used for all sorts of Secure connections and tunneling.

    The Email client connects to the STunnel Proxy and the Proxy makes the secure connection to the Microsoft Servers. The following is for Windows...

    • Install the software for "All users" [ Start Menu --> Programs --> stunnel AllUsers ]
    • When you first install the software, it will guide you in the creation of a PEM certificate [ Through the stunnel Start Menu - "Build a Self-signed stunnel.pem" ]
    • Edit the configuration file; STunnel.conf and append the below referenced settings and save the file. [ Through the stunnel Start Menu - "Edit stunnel.conf" ]
    • Install STunnel as a NT Service. [ Through the stunnel Start Menu - "stunnel Service Install" ]

    On the email client you enter for the Server:
    For the SMTP Port; 13587
    For the IMAP Port; 13993
    Normal authentication
    No SSL/TLS

    client = yes
    accept = 13587
    verify = 2
    CAfile = ca-certs.pem
    protocolDomain = Client_Domain.com
    sslVersion = TLSv1.2
    protocol = smtp
    connect = smtp.office365.com:587
    client = yes
    accept = 13993
    connect = outlook.office365.com:993
    In the above I used; Client_Domain.com
    Reference [1] Option 2 about MX endpoint. In that example the following directive would be set.
    protocolDomain = contoso.com

    The NT Service is called: stunnel
    In an elevated Administrative Command Prompt you can use; net stop stunnel and net start stunnel or SERVICES.MSC to disable/enable the NT service so you can edit and reload the STunnel configuration file.

    Here is an example of how this can work on an Appliance. Let's say that you have a All-in-One Printer/Scanner/Copier ( AIO ) where you can Scan-to-Email. The objective is to use an Office365 email account on the AIO to send the scanned object. This is where you can scan an item and choose to send the scanned object ( as a mutli-page TIFF or PDF ) as an email attachment to your email address.

    Lets us say that this AIO is on IP Address;

    Let us also stipulate that STunnel is installed, tested, and working for Office365 on a PC with a static IP address;

    On the AIO you set the SMTP server to; with the SMTP Port to; 13587 with normal authentication but not enabling SSL/TLS.

    The AIO will then connect to the STunnel Proxy on to send the email and the STunnel proxy makes the secure connection to the Office365 SMTP server.

    I have used this with email clients; Pegasus Mail, Windows Live Mail, Thunderbird and Outlook 2003/2007/2010 and Ricoh AIO.

    I have also used this with appliances that send Administrative Email Notifications such as with Brother Printers.

    Using different configuration settings in STunnel.conf it can be used with any Email Server.

    STunnel has versions for MAC, 'nix, Android and Windows [2]32/64

    1. How to set up a multifunction device or application to send email using Office 365

    2. As of December '18 no new versions of a 32bit STunnel are produced.
    The last 32bit version of STunnel v5.49 can be downloaded from;
    as; stunnel-5.49-win32-installer.exe
    Last edited: Feb 7, 2019
  2. dlipman

    dlipman Thread Starter

    Feb 14, 2013
    First Name:
    Reference: Thunderbird/Outlook/Office365 Email

    This could be applied here but may be too complex for a friend to help a friend.

    However, in that case the protocolDomain directive would be set as...

    protocolDomain = btconnect.com
    protocolDomain = btinternet.com
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