YesYou can configure the 'officeatwork_attachments' column in SharePoint online as a 'Multiple lines of text' field with the option 'Allow unlimited length in document libraries' set to 'Yes'. That way, you can capture multiple file paths, separated with a ; (semicolon), in the officeatwork_attachments field. When choosing that content in Outlook, the Content Chooser will attach all the listed files to your email message.