Is there a way to stop the error list/output windows from automatically pinning every time I debug a file? There is already too little real estate on the screen to work with as it is.
You can auto hide them and once hidden they will not show up again in next debug session.
Thanks,
Ashok 
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Option 1: Go to Setup → Reset Settings . ( Goes to Default settings)
Option 2 :
please check following.
Go to → \AppData\Local\UiPath → Open layout.xml.
there you can see the below line.
if IsOpen it’s false. Please make a true and save the file , before that close all the UiPath studio window.
( am using RPA platform trial version) you may try on above steps on your end.
@jrhalstead you can try this also, I hope this will solve your issue. you need to disable it.
Still pops back up each debug session and un-autohides or re-pins for lack of a better term
I have found the settings have moved to AppData\Local\UiPath\UiActivities.Settings
A setting for the output window does not exist in the file
What’s the version of UiPath studio you are using?
I’m using latest community version and can confirm that in not able to reproduce the behaviour you are mentioning.
Thanks,
Ashok 
2023.10.6 Enterprise.
But it’s been doing this the entire time I’ve been working with UiPath. Three years at this point.
May be it’s the Studio version. I’m using 2024.2.1 and the issue you are highlighting is fixed in it.
Thanks,
Ashok