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Mail sent from my VPS does not arrive to my Outlook Inbox

Mussab Bin Shahid 0 Reputation points
2023-07-06T07:52:07.81+00:00

Hello,

I am currently using the Gmail API to send emails, and I am experiencing an issue with email delivery. When I run the script locally on my PC, the emails are successfully sent to both Outlook and Gmail. However, when I run the script on a VPS, the emails are only delivered to Gmail, and they do not appear in Outlook. I have thoroughly checked the Junk and Deleted Items folders in Outlook, but the emails are not present. Additionally, I have configured outbound firewall rules to allow the SMTP port, but the issue persists.

I kindly request your support in resolving this matter. I am seeking assistance to ensure that the emails sent through the Gmail API are correctly delivered to both Outlook and Gmail when the script is run on the VPS.

Thank you for your attention to this matter.

Exchange | Exchange Server | Management
Exchange | Exchange Server | Management

The administration and maintenance of Microsoft Exchange Server to ensure secure, reliable, and efficient email and collaboration services across an organization.

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  1. Kai Yao 37,791 Reputation points Moderator
    2023-07-07T01:26:35.7233333+00:00

    Hi @Mussab Bin Shahid

    Kindly note that the tag "Exchange Server Management" is used for Exchange on-premises server questions.

    Since you are using Gmail API on your VPS, which we are not very familiar with, if possible please consider contacting Gmail support and your VPS vendor for better support.

    If "Outlook" in your post refers to an Exchange Online account, and you also have admin access to that organization tenant, from Exchange Online side you can use message trace to check if the message actually reached Exchange Online server, or possibly get quarantined or blocked by Exchange Online Protection.

    More detailed information: Message trace in the modern Exchange admin center in Exchange Online

    Besides, since sending from local PC the email can be received by Outlook, the possible cause may be the VPS's ip address is on some blacklists or blocked by Outlook servers.

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment". 

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