During October we have been made aware that some of our customers are experiencing problems reliably sending emails if they use Microsoft 365's email server (SMTP) settings through EQ. During our investigations this appears to be an issue affecting various users across the world using Office 365 and SMTP email sending and is not exclusive to EQ. We have communicated with EQ customers about this issue via email on 22/10/2021.
In addition to the below article, some Microsoft 365 users may experience the error "Invalid authentication response" when sending email. Please see this article for help creating an app password.
Does this affect my EQ?
If your EQ email settings, in System Config, have this address shown below then you could be impacted:
The Symptoms
The symptoms include some emails being delivered normally and some messages, even to the same recipients, not being delivered at all. No error message is apparent when sending messages.
Technical Background
Microsoft 365 customers can send email via third party applications (like EQ) and hardware (like scanners/copiers) using their mail server smtp.office365.com. This supports mail sending using several authentication standards of TLS 1.0, TLS 1.1 and TLS 1.2. During the last quarter of 2021 Microsoft are discontinuing their support for TLS 1.0 and TLS 1.1 meaning that all third party software (like EQ) must send email using TLS 1.2.
Read Microsoft's recent announcement article with more details.
From the article note the strategy is:
"With this in mind, starting in September 2021, we will reject a small percentage of connections that use TLS1.0 for SMTP AUTH. Clients should retry as with any other temporary errors that can occur during submission. Over time we will increase the percentage of rejected connections, causing delays in sending that more and more customers should notice."
We believe this strategy could be responsible for the intermittent delivery of some email messages.
When will this be fixed?
This problem is not the result of a bug or incompatibility in EQ.
Unfortunately there are multiple factors that can be responsible in determining the TLS version used for sending emails. EQ's email sending ability is already able to send emails using TLS 1.2.
The version of Windows operating system, and Windows settings could impact on email sending ability, as well as email servers elsewhere on the Internet.
Compusoft are currently exploring the available options to help our customers fix this intermittent issue to be able to reliably use Office 365 email with EQ.
What can I do?
Based on this, it may be necessary that you encourage your intended recipient to confirm receipt of any emails they receive from you, especially purchase orders, to avoid any unwanted outcomes due to missing or incomplete communication.
Updates
04/11/2021 - This article will be updated with more information as it is available.
16/12/2021 - Added a link at the top of the article regarding an email sending error "invalid authentication response" which is related to enabling the Passwordless account setting in Microsoft 365. Some EQ users are experiencing one or both email related issues.
17/01/2022 - Changes have been made in EQ to allow for the changed Microsoft 365 requirements to improve email sending reliability. They are implemented in EQ version 17.2.1. Please contact support to arrange an upgrade if you are experiencing intermittent email sending using Microsoft 365.
Click the Follow button at the top right of this article to be informed when changes are made.
Further reading:
Sending email "invalid authentication response" (Microsoft 365 email)