0 votes

Pretty easy to replicate. image.png

On the Adaxes server, you can use Powershell to send to that SMTP server so we know it's not a firewall issue:

$myCredential = Get-Credential -Username "it-noreply@contoso.com" -Message "Enter your password"
Send-MailMessage -From "it-noreply@contoso.com" -To "ngb@contoso.com" -Subject "test" -body "test" -SmtpServer smtp-hve.office365.com -UseSsl -Port 587 -Credential $myCredential

I've got a packet capture of both the Adaxes attempt and the Powershell success that I can send to you in an email. The packet capture shows the Adaxes server doesn't issue either an EHLO or a STARTTLS command.

by (280 points)

1 Answer

+1 vote
by (279k points)


This behavior is expected. The thing is that you are using Microsoft 365 as SMTP server and it does not support SSL. We cannot comment why the Send-MailMessage works. Most probably, it is using an old library which had a bug making SSL be ignored.

To remedy the issue, clear the The server requires an encrypted connection (SSL) in the Adaxes mail settings. It does not mean your mail will be sent unencrypted. If you specified a secure port (465 or 587), Adaxes will use TLS, which is effectively an upgraded version of SSL with fixed security vulnerabilities.


Thanks - that did the trick!

Related questions

+1 vote
1 answer

Hello All, it is possible to configure SMTP mail setting using Exchange Online with modern authentication and Azure security defaults enabled? Currently I have setup local IIS ... defaults but I would like to connect to my more secured tenant. Regards Ivaylo

asked Dec 6, 2022 by ivaylo.valkov (100 points)
0 votes
1 answer

We have 4 om prem servers to setup Adaxes on, we currently have almost everything on one server but have crashed on several occassions when multiple scheduled jobs are ... way to achieve this configuration without having to buy double the licenses. Thanks' Jay

asked Sep 24, 2021 by willy-wally (3.2k points)
0 votes
0 answers

Hello, Why Adaxes cannot manage email forwarding configured as SMTP address? It works only with email forwarding when forwarding is done to mail contact or other mailbox ... frustrated team members because forwarding exists but is not represented in Adaxes...

asked Dec 6, 2018 by DLe (760 points)
0 votes
1 answer

We are attempting to update from 2021.1 version 3.14.20916.0 to the most current version - 3.14.21404.0. We have two servers in a multiserver configuration once ... Adaxes Service reverts to the previous server that no longer exists and displays the error.

asked Sep 1, 2023 by awooten (60 points)
0 votes
1 answer

Hallo, As a part of my custom command I'd like to create forward from a mailbox to an external SMTP. Unfortunately I cann't use below script because of security policy: ... it by myself but I stuck on bing contact for forward. Could you please help me?

asked Aug 28, 2015 by axmaster (510 points)
3,434 questions
3,130 answers
546,352 users