The following table shows the differences and similarities between Outlook for Mac 2016 and Outlook for Mac 2011.
| MAIL FEATURES | Outlook for Mac 2011 | Outlook 2016 for Mac |
| Use different signatures for new messages and replies | No | Yes |
| Imports Outlook for Windows .pst | Yes | Yes |
| Imports Outlook for Mac .olm | Yes | Yes |
| Exports into .pst | No | No |
| Exports into .olm | Yes | Yes |
| Shows conversation view (a threaded view of e-mail messages in an Outlook folder) | Yes | Yes |
| Supports Propose New Time | No | Yes |
| Supports more than one account in one Inbox | Yes | Yes |
| Supports the creation of tables | No Tip: You can copy tables from Word into Outlook. | No Tip: You can copy tables from Word into Outlook. |
| Supports voting buttons | No | No |
| Supports message recall | No | No |
| Supports read receipt | No | No |
| Supports plan text and HTML editing | Yes | Yes |
| Supports Ignore and Clean Up actions | No | No |
| Shows attachment previews in mail messages | Yes | Yes |
| Displays photos of your contacts in your mails, contact lists, and calendar | Yes | Yes |
| Provides the capability to expand distribution lists into individual members when you add a distribution list in the To field, or when you rest the mouse pointer on a distribution list | Yes | Yes |
| EXCHANGE FEATURES | Outlook for Mac 2011 | Outlook 2016 for Mac |
| Use Clutter to sort low priority email messages | No | Yes |
| Synchronizes category list (names and colors) with Exchange server | No | Yes |
| Supports Online Archive | No | Yes Note: Your primary mailbox and archive must both be on-premise or both on Microsoft 365. An on-premise mailbox with a Microsoft 365 archive is not currently supported. |
| Provides access to the Offline Address Book (OAB) | Yes Note: You can search for people in the Global Address List (GAL) but you can't browse the GAL when offline. | Yes Note: You can search for people in the Global Address List (GAL) but you can't browse the GAL when offline. |
| Creates or modifies server-side rules | Yes | Yes |
| Manages Exchange server distribution lists | No | No |
| Synchronizes the personal distribution list with Outlook for Windows | No | No |
| Synchronizes categories with the Exchange server | Yes | Yes |
| Synchronizes contact photos with the Exchange server | Yes | Yes |
| Supports mailtips | No | No |
| Provides mailbox size and quota information, which includes the total mailbox size and space available space | No | No |
| Supports Information Rights Management policies | Yes | Yes |
| CALENDAR FEATURES | Outlook for Mac 2011 | Outlook 2016 for Mac |
| Weather forecast in calendar | No | Yes |
| Share availability (free/busy) information, calendar, or contacts | Yes | Yes |
| Overlay calendars | Yes | Yes |
| Side-by-side calendars | No | Yes |
| Calendar preview in meeting requests When you view a meeting invitation, Outlook automatically displays your calendar alongside the body of the message. This lets you see whether the proposed time works with your schedule, without having to switch back and forth between your messages and calendar. | Yes | Yes |
| Provides the option to enable the calendar to display week numbers | Yes Note: Supported in day and week view but not in mini calendars or month view. | Yes Note: Supported in day and week view but not in mini calendars or month view. |
| MISCELLANEOUS FEATURES | Outlook for Mac 2011 | Outlook 2016 for Mac |
| Supports Skype presence information | Yes | Yes |
| Supports creation of online meetings with Lync for Mac | Yes | Yes |
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