Hi

In our environment we're using a lot of MacBook Pro's running OSX. These OSX users use Outlook 2011 for Mac, Outlook 2015 for Mac (Office 365) and some use AirMail 2.1. Apart from their local e-mail client, they often also have an active Citrix session in which Windows Outlook 2013 is running. 

We've noticed the following very strange behaviour:

- When OSX users send an e-mail from their local e-mail client AND the Citrix Windows Outlook is closed, e-mails will go out immediately.

- When OSX users send an e-mail from their local e-mail client AND the Citrix Windows Outlook is open, e-mails SEEM to go out of the local e-mail client, but when you look in the Citrix Windows Outlook, the e-mail is stuck in the "SENT" items and has an "draft" icon. It is NOT stuck in "Outbox", it is NOT in "Drafts" but in Sent items. On the local client, it shows as if it has been sent. See pictures attached. When the user then presses SEND in the Citrix Windows Outlook, the e-mail is finally sent.

In the attached image you see in the LOWER half how the e-mail looks like when it is sent from the OSX client. Just a normal e-mail and it looks to be sent. In the top half you see what the e-mail then looks like when I then see it in the Citrix Windows client. Notice the "draft" icon and the option to press "SEND". The e-mail is in the "Sent items" folder.

Hi,

According to your description and research, I find an thread provided by you. For your reference:
http://answers.microsoft.com/en-us/mac/forum/macofficeo365-macoutlook/outlook-for-mac-emails-dont-get-send-but-not-in/17e3c9cd-0d8a-4a6d-9b0e-76859d7bf8d5

I want to double confirm whether any other Outlook client experience this issue, also try to configure other type account in problematic workstation to narrow down issue.
If this issue only occur on OSX, please try to update OSX and Outlook to latest version for troubleshooting. For your reference:
https://support.office.com/en-us/article/Check-for-Office-for-Mac-updates-automatically-bfd1e497-c24d-4754-92ab-910a4074d7c1

Thanks

Hi

I have this with Oulook 2011 for Mac, Outlook 15.9 (and olde versions) and AirMail 2.1 (and had this with 2.x). 

OSX on several versions also the most recent updates.

Regards

Gabrie

Hi,

Sorry for delay.

Please try to confirm whether this issue only occur on Exchange account.
If this issue only occur when Citrix session opening, it seems that theres a software conflict between them.
Would you please contact Citrix to double confirm?

Thanks