We are getting the same issue now at a second client.  It has to be windows related.. but this is causing customers to be very upset.  Any direct or Idea's anyone has found?  Randomly we are getting the "unable to log into SMTP connection" but it happens randomly like one instance was the 4th invoice and the 17th invoice failed but all the others emailed just fine.

Getting the error details to the Email Support persons has not be helpful.

thanks,

Dawn

I believe we have this resolved at my client.  IT stated this is related to Office 365 and the type of spam/blast-type of controls that Microsoft has in place. So IT is relaying e-mails thru their spam filter of which I updated the Sage 100 e-mail settings in Comp Maint.

Hi , could you share what settings you updated to fix this.  Just started happening to us this week also !

The only setting change I made was in Sage 100 Company Maint > E-mail.  I replaced the Office 365 settings with just the new address/smtp and port provided by IT.  

We have had clients struggling with this also.  One thing to be aware of - when using a relay (IP provided by your IT), its still possible that the relayed emails will fail due to the same issue - but Sage will NOT be aware of it (it simply sends the emails off to the relay so they will always appear successfully sent).  In our testing with the relay, we found that there were still emails that failed to send due to (presumably) the same issue.

We have had 3 customers today with TLS errors on pre version 2019.  

Connection closed by server.

      Failed to read beginning of SSL/TLS record.

      Failed to read incoming handshake messages. (1)

      Client handshake failed.

      Failed to establish TLS connection.

    --SMTP_Connect

    Failed to connect to SMTP server.

Found this article about Microsoft 'road bump' strategy to shutting off TLS 1.0.

https://office365itpros.com/2021/08/19/exchange-online-to-introduce-legacy-smtp-endpoint-in-2022/

There is a workaround to point to smtp-legacy.office365.com as a temporary workaround.   Haven't heard if anyone has been successful in doing this yet.

Anyone have any thoughts on doing that?

I would be interested to hear if anyone has success with the legacy site as well.

It appears to be directly related to TLS 1.2 .  We have setup an email relay at a client and send to that from Sage 100, then have that send to O365 and so far so good.  More testing coming but it's random when it fails since most likely it depends on the data center it's communicating with.

Justin - it did not work.

Thought I'd join the thread.

Client reported this issue last Thursday running 2018.

Sue in the original post says it's happening on 2019, 2020 & 2021.

Another poster said that upgrading to 2019+ will resolve this issue.

Need clarification if doing the upgrade will fix the issue?