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Hi Microsoft team, we are facing a serious problem, our company specializes in Cyber Security, we have been asked to carry out a Phishing assessment on the employees of one of our clients, the client uses MS Outlook email service, but we were unable to get our emails from our email service provider to the Client Inbox neither were the mails landing in the spam, so we decided to set up an Azure VM with the Cyberpanel email server, basically we decided to host our own email server, we are unable to send outbound emails from the Azure VM,
This is the error being generated from the Cyberpanel email server
We can ping external resources
But traceroute and telnet fail to connect to external resources
Any help will be greatly appreciated, thanks, regards
Joseph
Hi,
Outgoing port 25 is blocked by default for many Azure subscription types. Please see article below to see if you are eligible to have the block removed:
https://learn.microsoft.com/en-us/azure/virtual-network/troubleshoot-outbound-smtp-connectivity
Thanks.
-TP
Hi,
You cannot send outgoing SMTP email using Azure VM on standard port 25 unless you are under Enterprise Agreement and even then there may be companies that have blocked Azure ips on their email server. What you can do is instead use a service like SendGrid. They have a free plan that allows 100 emails/day and paid plans if that isn't enough. Unsure if SendGrid allows simulated phishing emails so you need to check their terms of service before you try it.
One thing that is concerning from your original post is you said that you attempted to send the emails through some other method and they never reached your client.
Another thing you could do is have your client set up a port address translation (PAT) mapping on their firewall for a custom incoming port, (say, port 4501) and map it to port 25 on their email server. You would set up a static Public ip for your Azure VM and give that to your client so that they could set the firewall to only allow incoming port 4501 from your VM. Then when you send email from your VM you would set it to send out on port 4501 instead of 25.