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Emails stuck in Outbox

Anonymous
2019-09-12T23:50:46+00:00

Hi All,

about 6 months ago we migrated our client to Office 365 in a hybrid configuration. After all the mailboxes were migrated we then installed the Office apps on 4 new RDS servers. All went well but we have one niggling problem with a few of the users. Sometimes their emails bank up in the Outbox and if they try to select any of the emails Outlook freezes. We have to end the task and after restarting Outlook the Outbox items are gone. No sign of them in sent items in the client or webmail. What we found as a workaround is to move the Outbox emails to Drafts and restart Outlook. Then we can open the draft emails and send them successfully. We found similar reports to this online, for instance https://community.spiceworks.com/topic/2048361-outlook-2016-didn-t-send-then-dumped-outbox-in-crash

We've tried a few of the suggested fixes but the problem still happens. Any suggestions?

Thanks!

Outlook | Windows | Classic Outlook for Windows | For home

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  1. Anonymous
    2019-09-13T02:32:30+00:00

    Hello Bluefly,

    From your description, seems there are some users share the 4 Outlook clients in your organization. May I know why they can't use their own Outlook client to send messages? Please let us know the more background information if possible. Meanwhile, please also let us know the detailed mail flow in your organization.

    Generally, messages stuck in Outbox may have the following reasons:

    1. Can't connect to server. (Network issue)
    2. The top message's size is bigger than the limitation.
    3. Too many messages need to be sent out in a short time which makes the Outlook client failed response.
    4. The top message had set up the delay delivery.

    According to above possible cause, please check them and let us know the result.

    Looking forward to your update.

    Regards,

    Rudy

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  2. Anonymous
    2019-09-13T04:03:27+00:00

    Hello Tony,

    Never mind. I know you are talking with me, so don't care about it.

    From your information, the Outlook seems isn't using the latest version, please try to update it.

    Meanwhile, we'd lik to know the detailed mail flow like: the message sent from your Office 365 EOP to Internet directly or from your Office 365 EOP to on-premise firstly then sent out to internet, etc.

    Also, can you provide us one of those users' SMTP address for us to check it further? We will send you a private message to collect it.

    Moreover, except creating new profile, what else troubleshooting steps had you done before?

    Regards,

    Rudy

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  3. Anonymous
    2019-09-13T03:34:24+00:00

    Hi Rudy, (apologies for calling you Ron by mistake)

    The Outlook version is 16.0.11328.20390.

    Can you clarify what you mean by you want to know the detailed mail flow please?

    Also, we have tried creating a new Outlook profile but the problem persists.

    Thanks!

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  4. Anonymous
    2019-09-13T03:17:05+00:00

    Hello Tony,

    Thanks for your quick reply.

    Except the above answers, we still want to know the detailed mail flow for those effected users. We would highly appreciate your efforts.

    Meanwhile, had you tried creating a new Outlook profile for those users? If not, please check it. For your reference: https://support.office.com/en-us/article/Create-an-Outlook-profile-F544C1BA-3352-4B3B-BE0B-8D42A540459D 

    Note: Please don't remove any old profile.

    Also, always using the latest Outlook version is strongly suggested. Can you let us know the detailed Outlook version please?

    Regards,

    Rudy

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  5. Anonymous
    2019-09-13T02:56:14+00:00

    Hi Ron,

       Thank you for your prompt reply.

    "seems there are some users share the 4 Outlook clients in your organization"

    No, all the users share four terminal servers and use Outlook in their own session

    "May I know why they can't use their own Outlook client to send messages?"

    They are using Outlook to send messages.

    "Can't connect to server. (Network issue)"

    Not a network issue because other users logged in to the same server don't have a problem

    "The top message's size is bigger than the limitation."

    from the examples I've seen they are just simple emails non exceeding 1 megabyte

    "Too many messages need to be sent out in a short time which makes the Outlook client failed response"

    from the examples I've seen there are only 5 or six emails sent out over a period of time that accumulate in the outbox

    "The top message had set up the delay delivery"

    No, the users did not use the delay delivery option

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