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This could go either way but since the source system is Sharepoint I will start here. I have a WebDav connection to multiple libraries via the Quick Access menu (Windows 10) in my SP tenant. I am on Outlook 2016. When I try to attach a file to any WebDav connection that is a regular document library the "Insert File" popup shows a Sharepoint reprentation of the library folders meaning you can only choose one file at a time. When I try to attach a file to any WebDav connection that is a picture library the "Insert File" popup shows a Windows Explorer reprentation of the library folders meaning you can choose multiple files. 

 

A) Why is there a difference

B) Anyone know a way to have the regular DocLib allow multiple file uploads.

C) When the heck is Microsoft going to figure out real integration between Outlook and SPO 365?

4 Replies
If the files are in a document library - why are you attaching them and not sharing them?

Because when I have 10 files from 4 different folders I would have to navigate and share each one individually...right? Even if multiple files within a library you can't share all at once. If there is another way please let me know. 

Are you aware of the "cloud attachments" functionality in Outlook?
To your last point about integration between Outlook and SPO - this is exactly what it does. In Outlook I can browse anywhere I want in SharePoint and select the files which will share them with the recipient.
See this post: https://blogs.office.com/en-us/2015/11/09/attachments-in-outlook-2016-ready-for-collaboration/

@Loryan Strant I am aware of that capability but it has always been worthless for us. A) The Browser Web Locations -> Sites only brings up recent sites accessed and there seems to be no rhyme or reason as to which sites are included and B) when you access a Document library using this method you get the Sharepoint view that only allows you to attach 1 document at a time. see pic.

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