I have an ISY 994i PRO/IR with firmware 5.0.16C. It has been stable for years, and has used SMTP smtp.gmail.com to send various status email messages to my gmail email account without problem.

In recent years (2022) I had to get an application-specific password assigned via the two factor verification section of my Google account. This password was then used as the login password, together with my google email address, in the SMTP setting page. Port 587 was specified, timeout set to 10,000, and the Use TLS box was checked.

This worked fine until something changed a few months ago, and the notifications are no longer being sent to my email..

When I try and send a test email now from the SMTP setup page I get the errors:

SSL request not authenticated

Mail server failure

(TLS negotiation failed)

I have no idea what the problem might be, or how to troubleshoot further. I am wondering if it is something to do with expired certificates or ??

I am not familiar with certificates and have never touched them before in the ISY network settings page.

Rather than trying for too long to troubleshoot this problem on this obsolete non-supported hardware/firmware, I am wondering if it makes sense to back up the configuration and then spend the $ to update to a new eisy lite and USB PLM, load the configuration, and then go from there.

Suggestions or recommendations would be appreciated!

You may want to buzz through this thread to see if it helps you.

Your settings look like mine. My "Use Default" box is unchecked.

In going through the thread that @Ross kindly directed me to, I saw many others with the same problem as me, and not solved. I was just about to consider this unsolvable and admit defeat rather than wasting more time trying to solve.

Then I came across the posting by @ters towards the end of that thread with a potential solution using EmailRelay. and which I've excerpted below. The instructions provided are excellent, very clear, and I was able to successfully get this working. Problem solved!

Note that when you do the message test from the Notification page in the Console display you don't get any status confirmation there or error message, so it's not apparent that it worked. But the test message shows up in my Gmail inbox. So all good!

@ters thank you so much !!!

On 4/2/2026 at 7:23 AM, ters said:

Here is a document I put together on how to locally solve the SMTP email problems that crop up with older devices like the ISY994i. It is pretty simple and straight forward to set up, taking only a few minutes to do, and covers installing E-MailRelay SMTP software on 1 (or more) PCs in your home intranet network. Once installed, you can simply configure your devices to SMTP to the Windows relay PC within your intranet, and have the relay PC do all the "modern day" stuff (encryption, sending to gmail/etc. using TLS port 587, etc.). This should "future proof" SMTP errors from just about any device (ISY, Cameras/NVRs, etc.) within your intranet. I tried to make it understandable, so hopefully I succeeded and it helps someone.

*edited: Person reached out regarding a non-ISY device they also have that requires a sender id and password to be entered for the SMTP config on that device. I added a blurb to the page 6 Misc Notes section for that scenario.

EmailRelay and ISY994i Setup.pdf