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OhmitFlag for Denmark

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Outlook mails stuck in outbox when externally connected

I'm having a very strange and extremely annoying problem with Outlook remote access via http.

My company has an Exchange 2013 latest build.
All users are running windows10 with Outlook 2016.
All pcs are configured as domain clients and Outlook set up while connected to the domain.

When users connects from outside the office via Outlook http, half of the users are complaining that mails are stuck in OUTBOX for several minutes before send - If a file is attached, this can be up to 20 minutes.
My problem is, that I can't replicate this problem!
No matter where Im located, connected to wifi or via my smart phone it works PERFECT!
Mailflow is fast with no delays.
Is this because these users are connecting from slow wifis or something?
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John
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If the mail is truly in the Outbox, then it is an Exchange issue, not a connection issue.

For one of these users, have them open Outlook, then see the Outbox (should be empty) , send an email and immediately look in the Outbox.  May not be there yet.

So it is most likely a connection issue but check as noted above.
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ASKER

Hello John - Always an honor to receive your inputs! :-) Thank you!

Well, Im not sure if I understand your question.
When these users are connected inside the LAN to the domain, everything works fine, and mail flow is smooth.
When some of these users are on the road they connects from home, hotels, smart phones shared connections, mails are OFTEN BUT NOT ALWAYS stuck in the outbox for a significant amount of time.
You can actually see the mails in the outbox until they are sent.

HOWEVER - as I said, I can't replicate this???? Im sitting at home with a pc from one of the complaining users, but mail flow is excellent.
If the users are on a slow connection, it will take time to get the message to Exchange for sending, especially if there is a big attachment.  

My guess (considering the circumstances) is that the message has not gotten fully to Exchange for sending.
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ASKER

Im sorry but what do you mean by this? "the message has not gotten fully to Exchange for sending."
If the message is large or slow, it takes time to completely get into Outbox for sending.  Exchange will not send until the message is complete.  Slow connections or large attachments take time to send completely from remote user into Exchange.
When you (user) are in Outlook, compose a message and press send, watch the lower right or the dialogue box and see how long it takes for the send process to complete.
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ASKER

It happens INSTANTLY (for me)
So then the answer likely is a slow connection. "Send" at the remote end takes time for the message to traverse to the server (Exchange).
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timgreen7077

This usually happens when user are external and they open outlook in cached mode, but their outlook client actually never connects to exchange. If the outlook client never connects to exchange then the email will sit in the outlook box until the outlook client connects to exchange and then it will send. This is very common issue because the end user doesn't realize they are not connected to exchange, all they know is that they are in outlook and they see their emails, but its very likely even as they are not able to send, they are also not receiving any emails during that time. Just have those user verify they are connected to Exchange because at the bottom of outlook it will show the status of the connection and it should say "Connected to Microsoft Exchange", if they don't see that then they are not connected and the email will stay in the outbox until they get connected. They can also access OWA if they are having connection issues externally, that way they will for sure connect to exchange and they can send and receive emails via the web browser.
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ASKER

Ok guys sorry my late reply. The issue remains!
I cant really say if the status is CONNECTED TO MICROSOFT EXCHANGE because Outlook freezes when you press SEND.

I have tried to uncheck USE CACHED EXCHANGE MODE but that did not solve the problem
ASKER CERTIFIED SOLUTION
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Ohmit
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