Emails get stuck in Outbox of Gmail IMAP in Outlook for Windows

Question

The emails are only sent after about 8-15 minutes being stuck in the Outbox folder. This only happens in Outlook for Windows connected to Gmail via IMAP. I do not experience the same issue with Outlook for macOS nor Apple Mail in macOS. Have you experienced the same and found a solution or even just a workaround?

Answer 1

Hi @Arvin Dimaculangan ,

What's the version of your Outlook? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.

Is this a problem that has only recently occurred? Did you have this issue right after the first time you configure your Gmail account to Outlook client?
Does this issue happen to all the sent emails? Or specific sent emails such as those with large attachments?

As I know, there are some common possible factors that may cause similar issues of messages stuck in the Outbox, such as large attachments, Outlook rules, corrupted local data fil, etc. In order to conduct further researches on your issue, please try the suggestions in these articles to troubleshot your issue and see if your issue would have any difference:
My messages won't send
Fix messages that are stuck in the Outbox

Any updates, please feel free to let me know.

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Answer 2

Hi @Arvin Dimaculangan and @SteveCBiscemi ,

Thanks for your update.

According to your description, seems that this issue happens to multiple Gmail users in your organization, right? If so, do these problematic users have any similarities?

I do did lots of tests in my Outlook 365 desktop client(Version 2010 Build 13328.20356 and Beta Version 2012 Build 13512.20000), in both versions I can send emails from Gmail account normally.

Can this issue be reproduced if you send same emails from other email account in your Outlook client(Exchange email account for example)? If other email accounts can work fine in the same Outlook client, I'm afraid that your desktop client might not be the key of your issue. As I know, factors from your Network environment and Anti-virus Software may also cause similar issues. So, please check if there is any Internet related settings which might blocked your connection to your Gmail server.