Hello, I'm a suscriber of Office 365 home. I use it mainly on my iMac with Yosemite 10.10.5. I have installed the outlook app ver. 15.13.1. I have configured the outlook to manage my work email at home. The company uses a Microsoft Exchange 2010 server. I have web access to my email account thru a browser, in the form mail.company.com. In my iphone, I have the account configured with domain\login and password, using owa1.company.com as server, and have not issues at all. But in outlook for mac it;s a different story. When I had outlook 2011 installed, never had an issue. But now, I have ran into many problems, from "root certificate not found", to be requested by Outlook every few minutes to enter account password. I am not an expert on exchange but am pretty familiar with Microsoft Office and computing systems. After updating my Outlook app to last version and re-configured my email account, the certificate error and password requesting issues have gone. But for some reason Sent Items mailbox never syncs. It only synced when I configured the account for the first time. Now when I want to check if an email was properly sent, I need to go through web access. Your support on this matter would be much appreciated.

I recommend that you post this in the Exchange Online (Office 365) Forum: http://social.technet.microsoft.com/Forums/en-US/onlineservicesexchange/threads

and/or the Outlook for Mac Forum:  http://www.officeformac.com/ProductForums/Outlook/

Hi,

Please confirm whether the Sent Items folder is updated in OWA or not. If everything works fine in OWA, the issue should be narrowed down to Outlook client side. Please ask a question in Outlook 2016 for Mac forum:

http://answers.microsoft.com/en-us/mac/forum/macoffice2016-macoutlook?sort=lastreplydate&dir=desc&tab=threads&status=all&mod=&modAge=&advFil=&postedAfter=&postedBefore=&threadType=all&tm=1439800231855

Regards,