When you store files in OneDrive they are stored ‘in the cloud’ i.e. in a web location. This means they can be easily shared, at least with people on the school network.

When you attach a file from One Drive to an email, the normal thing is for Outlook 2016 to provide a link, rather than a copy of the file.  This makes it easier for sharing and reduces the number of copies of files floating around the cloud. Still with me? But it will not work for sending files outside of the school network, and so you need to attach a copy instead of sending a link.

If you are using Outlook 2016 on a PC, then the options you need are tucked away behind a drop down menu.

Here’s how to do it:

Manage the items attached to an email

After you’ve attached an item, select the drop down menu next to the attachment to take other actions, such as Open, Remove, Print and so on.

If you’ve attached a file from a shared location, you can also choose:

  • Attach as copy    If you want to send a local copy of a file, instead of the file on a shared location.
  • Change permissions     If you want to select edit or view only permissions on a shared file.

Choose permissions for an attachment

For more info: https://support.office.com/en-gb/article/Attach-a-file-to-an-email-in-Outlook-2016-for-Windows-bdfafef5-792a-42b1-9a7b-84512d7de7fc

I also tried the default mail app on my iPad and it attached a copy by default.

I also tried the Outlook app in Office 365 and it gave me an explicit choice, not hidden from view.