Hi Armand, 

What version of Evo are you running, my understanding is that this is resolved in V10 and higher. The alternate solution you highlighted (enabling legacy support) should work, are you using the legacy smtp server settings - smtp-legacy.office365.com

Thanks for your assistance, Deepak.

Hi Armand, especially if you're on Evolution version 7.20, please refer to the following link for an article about the TLS 1.0 and 1.1 issues and what to do.

https://za-kb.sage.com/portal/app/portlets/results/viewsolution.jsp?solutionid=220210084719360&page=1&position=1&q=E-Mailing%3A%20%E2%80%98Unable%20to%20send%20e-mail!%20Error%20TLS%201.0%20and%201.1%20are%20not%20supported%E2%80%A6%E2%80%99%20E-mailing%20error

Kind Regards

Bennie 

Hi Deepak, 

Thank you for the prompt response.  Yes I tried smtp-legacy but on wireshark it still indicates that we are breaking out via TLS1.2 which is surprising.
What prompted me to post my message was due to the use case being on Evo 7.2.9.  I have not tried V10 which I will do very soon no doubt.
Will post my findings.

Hi Bennie.  Thank you for the link. 

Surprising that I have not found that page before as I have spent so much time on this already. My troubleshooting is aligned with the link though - I tried that solution already but no joy.
I assume it continues to be a problem because we can see even though we use smtp-legacy, it still shows that we are interrogating TLS1.2 when checking the active connection protocols on the client's firewall & Wireshark.

Will check the Evo version relevance, if it turns out that Evo needs an upgrade I guess that would be the most sustainable solution.

Best, 

Armand

My pleasure, Armand

But just to be sure, are you not able to achieve the following portion of the article in the above link?

1. Within the Exchange Server PowerShell (Exchange Management Shell), involving the Set-TransportConfig cmdlet, set the Transport Config to allow Legacy TLS

But I agree, upgrading to the latest Evolution version/build is always the first prize.

In that case, open the following link for a detailed article on how to access and download Evolution version 10.1.3.009

https://za-kb.sage.com/portal/app/portlets/results/viewsolution.jsp?solutionid=220218110020480&page=1&position=1&q=10.1.3.009

Kind Regards

Bennie 

Hi Bennie,

Unfortunately that does not work. I have adjusted the Set-TransportConfig cmdlet etc to allow Legacy TLS but it still does not work.

We did this for multiple clients on various M365 tenants but not gaining anything by doing so.

I will however revise the config to ensure that I have configured as per the guidelines but I don't foresee any other outcome at this stage. For me the giveaway is seeing that the outbound protocol remains TLS1.2 and not TLS1.0 on our monitoring software/devices.

Best,

Armand

Thanks Armand

I can not only foresee the best solution then is to upgrade to Sage Evolution version 10.1.3.009

Hi Bennie,

Just an update.  I tested on Evolution V10.1.3.008 and it worked perfectly.

Interestingly enough when I performed a mail header analysis on the email received from the system I could see and confirm what my hunch was about the TLS level being TLS1.2 and not TLS1.0.  
TLS 1.0 is not used when sending via smtp.office365.com nor smtp-legacy.office365.com; both use TLS1.2. So irrespective of configuring legacy support on the MS Tenant and using smtp-legacy.office365.com; it does not work on Evo V7.20.9.

See below which was extracted from the header whilst using smtp-legacy.office365.com.

"Received: from JNAP275MB0543.ZAFP275.PROD.OUTLOOK.COM (2603:1086:0:28::9) by
 JN1P275MB0411.ZAFP275.PROD.OUTLOOK.COM (2603:1086:0:d::5) with Microsoft SMTP
 Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id
 15.20.5017.23; Thu, 24 Feb 2022 11:16:32 +0000
Received: from JNAP275MB0543.ZAFP275.PROD.OUTLOOK.COM"

At least now we now know what TLS protocol is interrogated which is great.

Thank you for suggesting the later versions.  I am not sure whether it works on all V10 builds as I have only tested on 10.1.3.008.
I may investigate that further to see if we can assist the companies that relies on the builds they are currently on.

Best,

Armand

Thanks for the valuable insights that you shared here, Armand.

Yes, I can confirm that all of the never Evolution versions are making use of TLS 1.2 

The current latest version is 10.1.3.09 and is available on the Sage FTP site