If the iCloud add-in is not syncing Outlook Calendar and Contacts, verify it is enabled in Options, Add-ins. You may need to edit the registry if it won't stay enabled.
Blocking Mail From New Top-Level Domains
How to block junk mail and spam sent from the new top-level domains in Outlook.
Always Warn Before Downloading Content
How to disable the ability to change the 'Warn me before downloading content when editing, forwarding, or replying to e-mail' option by setting a registry key.
Outlook Calendar & Variable Working Times
Setting the working hours in Outlook's calendar is a problem for anyone who works a mix of full and half days.
Outlook .HOL Error: US Election Day
The HOL file supplied with Outlook 2010 (and in the Outlook 2007 holiday update released in 2012) the 2016 US Election Day event is on the wrong date.
Synchronize Quick Access Toolbar and Ribbons?
How to save Outlook's Quick Access Toolbar or Ribbon customizations to use on another computer.
Category Colors Don't Display in Inbox
Category names but not the colors are displayed in the message list when the category column is moved.
Outlook.com Contact Photos
Several users came to me after their accounts were migrated to the new Outlook.com servers, looking for help restoring their contact photos, which disappeared in the migration.
Rename Account in the Navigation Pane
How to change the Outlook.com or Exchange filename (usually your email address) in the Navigation pane in Outlook 2016.
Outlook 2016 Sept 2016 Updates
This month's security update includes fixes for the following nonsecurity issues. Office subscribers will have these updates installed automatically. Add OST corruption events. Translate some terms so that the meaning is accurate. Fixes an issue with corrupt forms cache. When a message is sent programmatically, the addresses are not added to the autocomplete cache. A