Hi Shelby,
I just tried your workflow and it worked fine for me. Here are the particulars of my test:
License as Concurrent use (connecting to a license manager)
Python script:
import arcpy
p = arcpy.mp.ArcGISProject("C:\\arcgisserver\\documents\\GPService\\ProGPPDS.aprx")
layout = p.listLayouts()[0]
layout.exportToPNG("c:/temp/KEVIN.PNG")
Task scheduler settings:
- Run whether user is logged on or not
- Do not store password is UNCHECKED (I entered my password when I made the task)
- Configured for Windows 2016 (and 2008, I created two tasks)
- Occurs at: just a time I set for today, then logged off before it ran
- Starts program: C:\ArcGIS\bin\Python\envs\arcgispro-py3\python.exe
- Argument: C:\PythonStuff\ExportPNG.py
- No other settings configured
Like I said, I logged out. Let the task run. Came back and have c:\temp\kevin.png waiting for me.
Checking the history of the task I see that it ran successfully.
Task Scheduler successfully finished "{d7f8189f-2cd6-4fb2-b465-95e91a6464c7}" instance of the "\KEVIN - python export PNG" task for user "domain\kevin".
Note - this is using Pro 2.0 (which will be available to you soon). I really dont think there is any difference between 1.4 and 2.0 in regards to this workflow.
If this continues to not work for you, can you provide more information. Such as your script, messages from the task scheduler, task scheduler settings, etc.