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RichardLabel-7925 avatar image
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RichardLabel-7925 asked JadeLiang-MSFT commented

Why are sent emails from my gmail account in outlook 2016 disappearing for certain recipients?

When I send an email to an ISP non web based email account such as videotron.ca or sympatico.ca from my Gmail account in outlook 2016, the message is sent, Gmail records the message in the sent folder but then it is not sent to the recipient by Gmail. There is no error message that the message could not be delivered. When I try to send the email using another program such as Microsoft Mail or web based Gmail, the message is received by the recipient. There is no problem if I send a message from my Gmail account to another Gmail , Hotmail or other Web based email accounts. This behavior is occurring on both my computers. However when I set up the accounts at my sister's house, again using outlook 2016, there is no problem.
I have reinstalled office ( no change) , allowed less secure apps in Gmail, checked that all the IMAP settings for sending email is correct. I have set up another gmail account in Outlook, and again tried to send a message to a Videotron account. The same problem occurs. While it appears to be an Outlook problem, it may be that another program is affecting how emails are sent.
I am out of ideas. Can you help?

office-outlook-itpro
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JadeLiang-MSFT avatar image
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JadeLiang-MSFT answered JadeLiang-MSFT converted comment to answer

Hi @RichardLabel-7925,

However when I set up the accounts at my sister's house, again using outlook 2016, there is no problem.

According to your description, the issue may be more related to your client itself, are there any difference between your Outlook client and your sister's (such as the detailed client version or install any third-party tools)?

Gmail records the message in the sent folder but then it is not sent to the recipient by Gmail

Have you checked if these messages were in your web mail's sent folder? It would further confirm if they were sent successfully from your client.

If we couldn't find these messages sent from Outlook client, as I know, any sync error between your client and server may cause it, it's suggested to rename your send/receive file (.srs) and restar your Outlook to check if the issue has any difference(File location: C:\Users\Username\AppData\Roaming\Microsoft\Outlook)

If the issue still exists, corrupted Outlook profile may also cause it, it's recommended to create a new Outlook profile and re-add your account to check if the issue would be reproduced in a new Outlook profile(Control Panel>Mail>Show profiles>Add>Readd your imap account)

If it's still invalid or that's not your case, considering any third-party tools may also affect the Outlook client, in order to avoid the interference of them, please try to perform a clean boot in windows and send the message on Outlook for testing.

If your issue has any update, please feel free to post back.


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RichardLabel-7925 avatar image
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RichardLabel-7925 answered JadeLiang-MSFT commented

The reason why the email was not getting through is that gmail was blocking the mail. Apparently, the non profit group that I belong to, and because I send out messages to multiple recipients (100-150) caused gmail to consider me as a spammer and blocked some of the mail to ISPs. I have subsequently purchased a subscription to Microsoft 365 which allows emails of up to 300 recipients. Hopefully this will fix the problem.

Thanks

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Hi @RichardLabel-7925,

Thanks for your update about your issue is caused by the recipients limit, I noticed that you have purchased a subscription to Microsoft 365, does this issue has any update? Based on my research, I found a related article about some sending limits on Microsoft 365, for your reference: Sending limits

If your issue has been resolved after that, would you mind marking your solution as an answer? It would benefit others who also has similar issues find the related information more easier. Also, if you encounter any other issues on Outlook client, please kindly post it in our forum again, we would continue to research it with you.

Have a nice day :)


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