Historically, email accounts dealt with only one type of information – email messages being sent and recieved. At the very core of the process, that is still very much true today for the most part with extensions added to store and retrieve PIM (Personal Information Management) data such as contacts, calendar and tasks.
As things matured, online email servers provided the facility to add this PIM information via a browser interface but there is no universal process to sync that information to the desktop client. For example, you may have an email account associated with your own custom domain used for your website and the online email interface allows you to store varying degrees of PIM information depending on the capabilities provided but there is no way that this information gets automatically sync’d down to the desktop or mobile client unless both the server and the client both support something like Exchange ActiveSync (EAS).
With the exception of the Outlook ‘2013 EAS protocol for Outlook.com accounts, there is no “native built-in” functionality for syncing both Email and PIM information in any version of Outlook. In Outlook ‘2010 and earlier, he Outlook Hotmail Connector does not get included automatically when Outlook is installed.and must be downloaded/installed separately if required. The Outlook Hotmail Connector is not required if the Outlook.com account is going to be configured as either a POP3 or IMAP Account.
Google Gmail also provides extensions for PIM information and originally provided a free Outlook addin to synchronize Google contact and calendar items with Outlook. However, starting in August 2014, Google has removed this option for free Gmail accounts. Synchronization with Google contacts and calendar is only possible if you have a paid Google Gmail business account.
Similarly, Apple also provides it’s own Outlook addin for synchronizating Outlook contacts with its iCloud service. Like the Outlook Hotmail Connector, it must be downloaded and installed separately. The capabilities available with any Apple based sync addin is completely under Apple’s control which must also ensure that it gets updated to function with the version of Outlook for which it’s being installed. Before upgrading from any version of Outlook to another where the Apple addin is essential, it’s imperative that you first verify if the addin has been upgraded to function correctly. It’s not a given that just because a new version of Outlook has been released that Apple has upgraded the addin to work with the new version. The onus is on Apple to complete any updates to function with Outlook and not Microsoft to modify another vendor’s application to make sure it works with Outlook. Microsoft does not have access to third party applications.
There is also an Outlook sync addin provided by Yahoo to synchronize Yahoo accounts with Outlook called <Yahoo Sync>. Like Apple, the capabilities depend solely on what Yahoo incorporates in this addin and it is Yahoo that would provide support should any problems arise through the use of the addin.
One third party product worth reviewing that provides comprehensive sync functionality for PIM related information is CompanionLink for Outlook.