The DocSend for Outlook add-in puts DocSend right inside your email compose window. You can create links on the fly using the add-in.
Here's how it works:
With the Outlook add-in, we will auto-populate the subdomain of your recipient's email address into the Account name field. The best practice is to make sure your Account names are consistent, so we can tie back separate link activity to your target Accounts in DocSend.
The link settings tie back closely to the link creation settings in the DocSend UI. If you'd like anyone after your first viewer to be asked for their email address in order to view your document, go ahead and check "Require email to view". If you do not require an email, we'll still give you other relevant information on your visitor including viewing stats, operating system and location.
Similarly to the link settings on docsend.com, you are able to allow or disallow downloading and set an expiration date or passcode if relevant.