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outlook 2013 has mail stuck in outbox and preparing to send and receive

I have 2 machines, W7Pro with Outlook 2013 connecting to office 365.
Both machines are configured with 2 exchange accounts, the same 2 accounts.


One machine works seamlessly.
The second machine has a problem when trying to send from one of the accounts.

If i try to send as janedoe@abc.com "Preparing to Send and receive" is displayed, but the email never leaves the outbox. Or maybe it will eventually but I've let it go for minutes with no good result.

On the other machine both accounts send as expected. The email hits the outbox and is gone almost instantly.

On the machine with the problem, john@abc.com works as expected.

So far I've tried deleting the .ost and doing an office repair. The problem persists.

Anybody seen this problem? Solved it?


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8/22/2022 - Mon

Try this:

1. Switch your account from Exchange Cache mode to Online mode to check the result.

2. Right click the folder and choose Properties, change between the option "the show number of unread items" and "Show total number items"

3. Type "Outlook.exe /resetfolders" in Windows search bar and press Enter.

4. Use MFCMAPI tool to check if there is really any message items leave in the outbox folder.

Manpreet SIngh Khatra

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does the mail go out in OWA?

if you log in to owa with the account, do you get an error?

I haven't tried office online mode yet, but there is another machine in the same office configured the same way that works fine. I set these both up at the same time and are almost identical.

That machine uses the same domain login and has the same two exchange accounts in Outlook. The only difference I can think of is that the primary accounts are reversed

On machine 1 the primary account is johndoe@abc.com, secondary is janedoe@abc.com.
This machine can send with no problems from either.

Machine 2 has janedoe@abc.com as the primary account and johndoe@abc.com as the other.

I think I may delete the windows user profile from machine 1 and recreate it.
One thing worth mentioning that was kind of odd, when I originally setup outlook on machine 2 (I should mention I setup machine 2 first) was that after I setup the first account (during the initial setup of Outlook when opening it for the first time) I noticed that I could add another account, so I did. When outlook opened, the second account was not there (johndoe@abc.com) So I opened control panel-mail-add edit- and added the second account.

That second account never worked properly, even after removing/recreating the outlook profile, and deleting the ost.

When I did machine 1, i purposely did not add the second account during the initial setup of outlook. Instead I configured for one account, opened outlook, closed outlook, went to control panel and added the second account and it has worked perfectly.

So, I think I'll delete the windows user profile, recreate it, then configure outlook in the same manner I did on machine 1.
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Most likely a profile issue.
I haven't had the opportunity to explore an answer since the client decided not being able to send from that account on that pc is an issue.