Hi, Emails are not being sent to users by our API Management Service (e.g. password reset, new user verification, etc). We can't find a way to troubleshoot this on our end. We know this started recently. We're also trying to find the logs of emails sent/not sent in the activities log or somewhere else in the Azure portal. Anyone knows where can I find this? Thanks in advance for your help!

Hi @Alejandro Gomez Rivera Thanks for reaching out. I am unable to reproduce the same at my end. I don't see any problem with my service sending emails. Please do verify your junk mail some email providers (such as Gmail) block or send emails generated by Developer Portal to Junk mail. Most likely APIM is successfully sending emails, but your email system is blocking them. One way to verify this is to create a user with a Microsoft account (Outlook/Hotmail) and see if email arrives in Inbox. If it does, that confirms that your email system is most likely blocking emails. Is your APIM instance is public or deployed inside a VNET? If it is deployed inside a VNET please verify the Network connectivity status If SMTP communication is blocked, the auto generated emails for developer portal won't work. For instance, when a new user signs up to the developer portal, they get an email with a link to activate their account. Similarly, if a developer portal user has to reset their password, they won't be able to do so since APIM won't be able to send emails. you need to allow the following ports 25,587,25028 to Connect to SMTP Relay for sending e-mails - https://learn.microsoft.com/en-us/azure/api-management/api-management-howto-configure-notifications#-configure-notification-templates let me know incase of further queries, I would be happy to assist you. Please 'Accept as answer' and ‘Upvote’ if it helped so that it can help others in the community looking for help on similar topics.

Users not receiving emails from Azure API Management Service

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JananiRamesh-MSFT 26,631 Reputation points

2022-09-20T16:11:29.19+00:00

Hi @Alejandro Gomez Rivera Thanks for reaching out. I am unable to reproduce the same at my end. I don't see any problem with my service sending emails. Please do verify your junk mail some email providers (such as Gmail) block or send emails generated by Developer Portal to Junk mail.

Most likely APIM is successfully sending emails, but your email system is blocking them. One way to verify this is to create a user with a Microsoft account (Outlook/Hotmail) and see if email arrives in Inbox. If it does, that confirms that your email system is most likely blocking emails.

Is your APIM instance is public or deployed inside a VNET? If it is deployed inside a VNET please verify the Network connectivity status

If SMTP communication is blocked, the auto generated emails for developer portal won't work. For instance, when a new user signs up to the developer portal, they get an email with a link to activate their account. Similarly, if a developer portal user has to reset their password, they won't be able to do so since APIM won't be able to send emails.

you need to allow the following ports 25,587,25028 to Connect to SMTP Relay for sending e-mails - https://learn.microsoft.com/en-us/azure/api-management/api-management-howto-configure-notifications#-configure-notification-templates

let me know incase of further queries, I would be happy to assist you.

Please 'Accept as answer' and ‘Upvote’ if it helped so that it can help others in the community looking for help on similar topics.
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Alejandro Gomez Rivera 21 Reputation points

2022-09-20T19:39:01.77+00:00

Thank you for your thorough answer!!

Unfortunately this time that is not the case. It was working properly until a few days ago. We've tried it using multiple email domains and none receives any email, including as junk.

I'm still trying to find the log of emails sent by the service, do you know where can I find those (apart from the network section you show in your email, we have a basic account so no access to that view)?

Thank you!

JananiRamesh-MSFT 26,631 Reputation points

2022-09-22T13:36:46.357+00:00

Hi @Alejandro Gomez Rivera , could you please check the Originating email in the notification template blade? It must contain "apimgmt-noreply@Monique gmx .windowsazure.com" I had a discussion today internally and confirmed that this is currently a limitation.

Previously customers were allowed to change the "From" address for emails auto generated by APIM. That generates an email with "On Behalf Of" in the message as we retain the original "From" address to be apimgmt-noreply@Monique gmx .windowsazure.com. This causes some email systems such as Gmail to completely block the email. It doesn't even appear in Junk mail folder. For Outlook/Hotmail, the email does show up in Junk.

so the solution is to not to change the Originating email address in the Notification template.

let me know incase of further queries, I would be happy to assist you.

Please 'Accept as answer' and ‘Upvote’ if it helped so that it can help others in the community looking for help on similar topics.

Alejandro Gomez Rivera 21 Reputation points

2022-09-22T16:55:20.743+00:00

Thank you so much for looking into it.

The originating email is the same. We did find out that the service is sending the email but service providers like google are rejecting these emails due to the following:

Received from an SMTP server with IP address: .*..** (TLS enabled)
550-5.7.1 [...] Messages missing a valid address in From: header, or 550 5.7.1 having no From: header, are not accepted.

Do you have any insights on how can we fix this "From: header: issue in the API Management service?

JananiRamesh-MSFT 26,631 Reputation points

2022-09-27T03:34:09.797+00:00

Hi @Alejandro Gomez Rivera Thanks for sharing the details, it looks like there is a problem with APIM when the sender's name is a large string (you can change from Azure portal in "Organization Name" field. Current workaround is to use a short name (like an acronym, e.g. MSFT) please let me know if this works.

Please 'Accept as answer' and ‘Upvote’ if it helped so that it can help others in the community looking for help on similar topics.

Alejandro Gomez Rivera 21 Reputation points

2022-09-27T18:51:07.28+00:00

Hi @JananiRamesh-MSFT , thank you very much for your help.

I just found out that the issue was not the length of the string, instead it was that I was using a comma in the Organization Name (E.g., "Acme, Inc"). That comma was causing an incorrect parsing of the headers by gmail and other email providers, causing the rejection.

Once we removed the comma and the APIM service was updated the emails reached their destination.

Thanks a lot for your help.

Ale

JananiRamesh-MSFT 26,631 Reputation points

2022-09-28T09:40:32.513+00:00

Hi @Alejandro Gomez Rivera I am very happy to hear that your issue is resolved. Will now proceed to close this thread. Feel free to reach out to us anytime.

Please "Accept the answer" if the information helped you. This will help us and others in the community as well.
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