Hi Vishy, Given this situation, please create a new profile, and then add this account in this profile to check if the issue persists. Meanwhile, we'd like to confirm when the issue occurs, if the recipient has received the attachments. Moreover, if you are not using the latest version of the Outlook for Mac, please update it to check if the issue persists.
Outlook 2016 for Mac (aka Outlook for Mac for Office 365) has some changes compared to Outlook for Mac 2011 in regards to Junk Email Protection. This blog post will explain how Outlook 2016 for Mac handles Junk Email Protection. Jun 14, 2017 Email attachments are 'grayed out' in Outlook for Mac sent items Split from this thread. Hi, I have the same issue. This happens in some update of outlook, sometimes goes off with the next update. Right now I am on 15.34, Mac OS 10.12.5. This issue has appeared. Outlook / Mac / Office 365 for business.
If it is the latest one, please send us a screenshot about the version.To check it, go to Outlook About Outlook. We need to know if your account type is POP, IMAP or Exchange account for further investidaion.
Please Go to Tools Account. Also, please provide us a screenshot about 'Email attachments are 'grayed out' in Outlook for Mac sent items'. Thanks for your time.
Regards, Rudy.
AutoUpdate will find and install these update. To use start on of the Microsoft Office programs and select Help, then click on Check for Updates. Common name Version Number Release Date & Comments Outlook 2016 15.14.2 September 23 2015 Office 2016 for Mac – September 23, 2015 Update Improves Mac OS X El Capitan compatibility Outlook 2016 15.14 September 15 2015 Outlook 2016 15.13.1 August 12 2015.
Requires OS X 10.10 or newer. Outlook 2016 15.11.2 Office 2011 SP1 April 12, 2011.