Why does dragging and dropping an attachment from outlook into a record not work



This article will cover the reason why attachments from Outlook are not able to be directly dragged into a ServiceNow record such as an incident.

Drag and Drop of Attachments from Outlook into ServiceNow

The drag and drop functionality is determined by the browser and Outlook, which does not support the file system hooks that a browser must use to grab the file when presented with a file drop event. It's an Outlook design which limits the drop and drag ability that browsers rely on. 
In order to drag-and-drop a file into ServiceNow, you will need to first drag the file to your desktop and then drag it into the SN instance as this converts the file into something that is readable by the platform. 

Additional Information

Here are a couple of sites which discuss this limitation of Outlook: