Windows
Skype Conversations can be found in the Conversation History folder in Outlook 2016.
- To delete a conversation, right-click on it and choose Delete from the menu.
- To permananently delete a conversation, hold down the Shift key while right-clicking on it and choose Delete from the menu, then click Yes to confirm.
Mac
Conversations can be deleted in the main Skype window or in Outlook 2016.
- In the main Skype window, you can only delete one message at a time. Go to the Chats section, select the message and press the Delete key or select Delete from the Edit menu.
- In Outlook 2016, go to the Conversation History folder, select the conversation(s) you would like to delete and click Delete in the menu bar at the top. To delete it permanently, you will have to delete it from your Trash folder (click Delete to confirm).