SQL Server Database Mail doesn't work 100% of the time

Nadun 1

Hi,

I have set up Database mail with a Microsoft Office 365 email account. It used to work flawlessly for many years and I noticed I am missing some email notifications couple of months ago and it's getting worse. When I do a test email, it delivers. Only fails sometimes which is not good as I use this function to inform me and my clients of events.

Here is an image of the log
https://ibb.co/r7T7WtC

select @@veriosn
Microsoft SQL Server 2017 (RTM-CU22-GDR) (KB4583457) - 14.0.3370.1 (X64)   Nov  6 2020 18:19:52   Copyright (C) 2017 Microsoft Corporation  Standard Edition (64-bit) on Windows Server 2016 Datacenter 10.0 <X64> (Build 14393: ) (Hypervisor)

I am on an Azure Virtual machine with SQL server installed.

Any help would be appreciated.

AmeliaGu-MSFT 13,961 Reputation points Microsoft Vendor

2021-12-22T07:26:44.247+00:00

Hi Nadun-5457,

How are things going? Does the answer help you?
Please feel free to let us know if you have any other question.
If the post in the thread is helpful, you could kindly accept it as answer.

Best Regards,
Amelia
Nadun 1 Reputation point

2022-01-10T03:21:45.78+00:00

Hi Amelia,

Sorry for the late reply. Our company was closed for holidays and also I haven't received approval to install that third-party software on the VM yet. I will let you know if we do.

Thanks,
Nadun

1 answer

AmeliaGu-MSFT 13,961 Reputation points Microsoft Vendor

2021-12-20T03:31:18.717+00:00

Hi Nadun-5457,

Welcome to Microsoft Q&A.
Azure doesn't offer smtp servers by default. You have to use SendGrid email delivery service that supplies your virtual machine with an SMTP relay.
Please refer to SQL Server Database Mail configured with the Send Grid Email Service and Configure Database Mail on SQL Server Azure VM using T-SQL which might help.

Best Regards,
Amelia

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Nadun 1 Reputation point

2021-12-20T22:58:13.813+00:00

Hi Amelia,

Thank you very much for taking the time to reply. I really appreciate it.

I am a bit confused as to how was I able to send email notifications for years (I set it up in 2017) and now only giving me trouble and it's working most of the time but fails 10% of the time but I need it to work 100% because it's very important to get the notifications to clients.

Also, when I right-click on "Database Mail" and "Send Test E-Mail" emails get through 100% of the time.

I also don't think I am using "SQL Server 2016 running on Azure's Infrastructure As A Service (IAAS)" because I remote into the Virtual Machine and use MSSMS to interact with the SQL server.

Do you think I need to implement this "SendGrid email delivery service"?

Thanks,
Nadun

AmeliaGu-MSFT 13,961 Reputation points Microsoft Vendor

2021-12-21T05:51:23.35+00:00

Hi Nadun-5457,

Thanks for your reply.
It is recommended to use authenticated SMTP relay services to send email from Azure VMs or from Azure App Service. SendGrid is one such SMTP relay service.
Please refer this doc and this similar thread.

Best Regards,
Amelia

Tom Phillips 17,716 Reputation points

2022-01-10T13:14:30.937+00:00

MS Office recently disabled non-TLS 1.2 emails. This requires you to upgrade and enable TLS 1.2 on your server. If you do not, you will not be able to send emails to office 365 servers.

See this on the same subject
https://learn.microsoft.com/en-us/answers/questions/682065/sql-server-2016-o365-smtp-34failure-sending-mail34.html

Nadun 1 Reputation point

2022-01-11T00:57:59.217+00:00

Thanks Tom, I have updated the registry entries on the windows server and rebooted it. I'll keep an eye on the DBMail log and see if it helped.

Nadun 1 Reputation point

2022-02-18T04:21:38.807+00:00

I can confirm it's fixed. Thank you very much Tom.
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SQL Server Database Mail doesn't work 100% of the time

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