In Task Scheduler, in the Task properties, on the General tab, besides "Run whether user is logged on or not", is "Run with highest privileges" also selected? Even for my own custom programs I need to check this box for it to run unattended successfully.

These are greyed out in Windows for the Tasks created by Sage Task Scheduler,  unless I don't have privileges for tasks I create 

Actually the Sage task DOES attempt to check that box when creating the Windows task. Since it cannot, very likely it doesn't have the permission do so. If running on Advanced or Premium, it means the account running Sage App Server (service) doesn't have that permission.

Also, since you cannot yourself directly in Windows Task Scheduler override that setting, I presume that means your own Windows account doesn't have that permission either. Try logging in as Administrator.

I have this issue as well.  Sage 100 2015, Windows Server 2012 R2 (Terminal Server).  I have tried every possible setting for the Tash Scheduler, but unless I am logged into the actual Terminal Server (not a session), the Sage Intelligence reports tasks won't trigger if I am not actually logged in on the Server as Administrator.  I have save the admin login and password in the Task Scheduler, but nothing works.  My workaround works ok, until that time there is a reboot then I have to login to the Server and not ever log out.  

I have this issue as well.  Sage 100 2015, Windows Server 2012 R2 (Terminal Server).  I have tried every possible setting for the Tash Scheduler, but unless I am logged into the actual Terminal Server (not a session), the Sage Intelligence reports tasks won't trigger if I am not actually logged in on the Server as Administrator.  I have save the admin login and password in the Task Scheduler, but nothing works.  My workaround works ok, until that time there is a reboot then I have to login to the Server and not ever log out.  

We have had the same issue with Sage 300. Here are the steps we have used to resolve the issue.

• • Install “Active Directory Module for Windows PowerShell” on Sage Apps server
  • Adjust “AccPac Signon Manager” settings in Component Manager according to article: https://www.greytrix.com/blogs/sageaccpacerp/2018/12/26/additional-task-scheduler-setting-with-sage-300/
  • Create missing directories according to this blog: https://social.technet.microsoft.com/Forums/ie/en-US/c03d6691-b058-4f8d-961c-e8eba25bbaed/task-scheduler-problem-run-whether-user-is-logged-on-or-not?forum=w7itprogeneral
    • C:\Windows\System32\config\systemprofile\Desktop
    • C:\Windows\SysWOW64\config\systemprofile\Desktop