I seem to have encountered a strange issue.  I am using Outlook 2013 connected to my Outlook.com account and been having issues with calendar items getting pushed to Outlook.com.  Sometimes I create a new calendar item on Outlook 2013 and if I check Outlook.com it is there and other times it does not show up.  Very frustrating and since my phone connects to Outlook.com, my calendar has become unreliable.

So I did some digging and this is what I found.  It appears that the calendars items never get pushed up to Outlook.com if they are created while Outlook 2013 is in the Disconnected state such as when I am not connected to the internet.  So even after I reconnect to the internet any newly created items don't get pushed up to Outlook.com.  

I tried something else.  In Outlook 2013, on the Send / Receive tab there is the option to Work Offline.  If I disconnect from the internet, click Work Offline, create a calendar item, reconnect to the internet and the click Work Offline to work online again everything works fine as the items are properly published.

So to me it looks there is an issue when creating calendar items while disconnected from the Outlook.com servers.  Even when you reconnect the items do not get added to Outlook.com.

Any experience this and have a solution?