Sending email from Azure VM app using on-prem SMTP server (exchange 2016 edge relay server) in Hybrid Environment. is it possible?

Hi， zohaib yousuf Thanks for posting your question in the Microsoft Q&A forum. Based on your description, I have a few questions that are not clear to me yet and need your confirmation: Can you describe your current mailbox environment in detail? Is your exchange 2016 built on an Azure VM? What exactly is your Azure VM app? If your environment is hybrid, you can send emails from On-prem or Online. Can you explain in detail what "Sending email from Azure VM app using on-prem SMTP server" means? Your answer is very helpful for us to solve your problem. We hope for your support and understanding.

Sending email from Azure VM app using on-prem SMTP server (exchange edge relay server) in Hybrid Environment

Accepted answer

Bruce Jing-MSFT 4,190 Reputation points Microsoft Vendor

2024-08-27T05:11:15.65+00:00
Hi，zohaib yousuf

Thanks for posting your question in the Microsoft Q&A forum.

Based on your description, I have a few questions that are not clear to me yet and need your confirmation:

Can you describe your current mailbox environment in detail? Is your exchange 2016 built on an Azure VM?

What exactly is your Azure VM app?

If your environment is hybrid, you can send emails from On-prem or Online. Can you explain in detail what "Sending email from Azure VM app using on-prem SMTP server" means?

Your answer is very helpful for us to solve your problem. We hope for your support and understanding.
Please sign in to rate this answer.
zohaib yousuf 21 Reputation points

2024-08-27T09:28:36.1133333+00:00

Hi @Bruce Jing-MSFT

Thanks for your replay. I have hybrid environment. Four on-prem Exchange 2016 Mailbox Server and 2 on-prem Exchange 2016 Edge server (Relay Server). My all on-prem application relay from on-prem Exchange Edge 2016 server and send email properly. but from azure unable to send email from on-prem relay server although we have point to point connectivity with Azure.

i have mixed, 40% mailbox is cloud and 60% mailbox is on-prem,

i want to send email from azure VM using on-prem smtp relay server(Exchange Edge 2016 ). just like my other application which are hosted is on-prem and using on-prem
smtp relay server(Exchange Edge 2016 ).

zohaib yousuf 21 Reputation points

2024-08-27T17:40:44.9733333+00:00

plus send from anonymous ID without MFA and mailbox.

Bruce Jing-MSFT 4,190 Reputation points Microsoft Vendor

2024-08-28T02:38:49.8533333+00:00

Hi，@zohaib yousuf

I'm glad to hear back from you.

According to your description, your all on-prem application relay from on-prem Exchange Edge 2016 server and send email properly, it means your hybrid configuration is fine. Can you please check the configuration of Azure VM with Exchange Edge 2016, including whether the ports and protocols are supported.

Sending email on Port 25 is unsupported for all other Azure Platform-as-a-Service (PaaS)

You can refer to this link for details: Troubleshoot outbound SMTP connectivity in Azure | Microsoft Learn

If my answer is helpful to you, please mark it as the answer so that other users can refer to it. Thank you for your support and understanding.

zohaib yousuf 21 Reputation points

2024-08-29T09:19:30.6266667+00:00

@Bruce Jing-MSFT Thanks for reply, i have test both port 587 and 25 port but no progress. I want to send email from hosted App in azure VM via anonymous ID without MFA and mailbox.

Bruce Jing-MSFT 4,190 Reputation points Microsoft Vendor

2024-08-30T06:18:08.9766667+00:00

Hi,@zohaib yousuf

I'm glad to hear back from you.

I have basically understood your question. Your connector's anonymous connection is fine, I suspect that the Azure VM's are blocking port 587 (currently port 25 is not supported).

Is the system currently reporting any errors? If so, can you provide a screenshot?

zohaib yousuf 21 Reputation points

2024-09-08T18:28:53.08+00:00

Hi @Bruce Jing-MSFT ,

May be, You are right its blocked from network end because when i asked network team so he confirmed that we allowed just limited services from Azure to On-Premise. so i decided to use office 365 Smtp to send email from Azure Host VM.

Bruce Jing-MSFT 4,190 Reputation points Microsoft Vendor

2024-09-09T01:18:35.9233333+00:00

Hi，@zohaib yousuf

I'm glad your problem was solved, and if my answer was helpful, please don't forget to click “Accept Answer” which might be beneficial to other community members reading this thread.
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Sending email from Azure VM app using on-prem SMTP server (exchange edge relay server) in Hybrid Environment

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