[stunnel-users] Getting incoming Exchange online (Office 365) emails to go to port 110 and not 995

Brent Kimberley brent_kimberley at rogers.com
Fri Jul 24 17:40:56 CEST 2020

 Hi Mel.I can't speak to it either.  (It seems to be a generic issue - across the industry.  And, I'm not aware of any OAUTH2.0 transparent proxy clients - at present.)  

Hopefully someone else can advise?  i.e. How do others connect to Email as a Service providers using OAUTH2.0 for authentication?

Microsoft is going to disable basic/legacy authentication for Exchange Online. What does that actually mean and does that impact me?

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Microsoft is going to disable basic/legacy authentication for Exchange O...

Update: On April 3rd 2020, the Exchange Team announced that due to the COVID019 crisis, they will postpone disab...



<snip>We will continue to disable Basic Authentication for newly created tenants by default and begin to disable Basic Authentication in tenants that have no recorded usage starting October 2020. And of course you can start blocking legacy authentication today, you don’t need us to do anything if you want to get started (and you should).</snip>

    On Thursday, July 23, 2020, 6:09:45 p.m. EDT, Mel Gilbert <m.gilbert at baymedicalgroup.com.au> wrote:  
Mmm I was not aware of the change and my IT skills in this area are not great. Are you able to give me more details how to inject an OAUTH2.0 transparent proxy? I will do some investigation. I only have the need for 1 email address to work within the client app. Kind of like a shared mailbox

Sent from my iPhone

On 24 Jul 2020, at 4:29 am, Brent Kimberley <brent_kimberley at rogers.com> wrote:

Office365 IMAP4S + POP3S is dropping legacy authentication in favour of OAUTH2.0 authentication -- effective October 2020.  (Some may have longer.)

How do you you plan to migrate to authentication?  Do you plan to upgrade your client(s) or inject anOAUTH2.0 transparent proxy ?

Message: 1
Date: Thu, 23 Jul 2020 01:22:06 +0000
From: Mel Gilbert <m.gilbert at baymedicalgroup.com.au>
To: "stunnel-users at stunnel.org" <stunnel-users at stunnel.org>
Subject: Re: [stunnel-users] Getting incoming Exchange online (Office
    365) emails to go to port 110 and not 995
    <SY4P282MB074766F32238B92A3D951499C1760 at SY4P282MB0747.AUSP282.PROD.OUTLOOK.COM>
Content-Type: text/plain; charset="us-ascii"


Trying to get an application with inbuilt email to receive emails using POP and port 110. However we use Office 365 and I have tried below config but it is not working.  I want people to send email to an Exchange Online Account port 995 and it gets forwarded on to the email app on port 110

client = yes
output = stunnel-log.txt

[POP3 Incoming]
accept = 110
connect = Outlook.office365.com:995
cert = stunnel.pem

[SMTP Outgoing]
protocol = smtp
accept = 25
connect = smtp.office365.com:587
cert = stunnel.pem

The outgoing email works fine using SMTP relay that I've set up on Office 365 but cant get the incoming emails to work.

Any help would be appreciated



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