So after three hours on the phone and a remote session with an agent, and another 30 minutes on a chat session with different agent, all signs point to this being specifically an Outlook 2016 issue, not an Office 365, or Tenant, or Network issue and I was
directed back to these forums. I can start a new thread back in the Office thread where I placed it, or if possible the thread could be moved back.
However, this issue presents on all installations of Outlook 2016, whether it is an Office 365 Business Plan license, an Office 365 Enterprise license, or an Office 2016 Box License. It occurs regardless of Windows 10 or Windows 7 operating system, and occurs
now tested across 3 different tenants, 3 different domain controlled devices, 2 domains, and 3 non-domain devices.
This issue is with Outlook 2016, nothing else in the environment seems to matter. I went so far as to do a clean installation, within a brand new VM, in which the only things installed were Windows 10 and Office 2016 from a Box license. The same issue happens.
I am unable to save Multiple Attachments to a Network location.
All local drives work, whether it is a permanently mounted drive, or an external media, only Network folders are effected and can not save multiple attachments simultaneously. Using the Save Multiple Attachments system, I can save any attachment individually
to a network location, but not multiple files simultaneous.