I have an issue where calendars items aren't always posted to Outlook.com.  

I am using Outlook 2013 with an Outlook.com account.  New calendar items are not always posted to Outlook.com and therefore they don't get pushed to my phone.  I have found that if I am not connected to the internet and Outlook 2013 says Disconnected in the bottom right and I create a new calendar item, when I do connect back to the internet, the calendar is not created on Outlook.com.  

For some reason it appears Outlook 2013 won't add items to Outlook.com if they were created while in the disconnected state and then you later connect.  So it makes working offline difficult.  And this is not the issue when working with an Exchange account / backend server.

The work around I found is if I am in disconnected, I must first manually work offline by clicking Work Offline in the Send / Receive, create my calendars items.  Then when I do get back online, I must manually switch to online by clicking the Work Offline.  Then it seems the items are added to Outlook.com and eventually pushed down to my phone.

Any ideas what is going on?