1. Remove "skip_save_on_exit", this is very confusing when the Auto Save option is enabled, but the preferences are not saved automatically. Once the factory settings have been loaded, just explicitly turn off the Auto Save option.

2. When loading factory settings, display the "Auto-Save" or "Disable Auto-Save (don't save preferences on exit)" checkbox in the confirmation dialog, so the user can directly see what is happening and what settings he has.
   
   
   

3. Display the "Auto-Save" checkbox in the Preferences so that the user can clearly see that autosave is enabled.
   
   
   
   

@Yevgeny Makarov (jenkm) @Campbell Barton (campbellbarton) I think this one could help as well. Since any save option is just kinda missing when auto-save is enabled. It's all hidden in the popup otherwise.

In T68649#753295, @Yevgeny Makarov (jenkm) wrote:

3. Display the "Auto-Save" checkbox in the Preferences so that the user can clearly see that autosave is enabled.
   
   
   
   

Other than that I think the dialogue is great.

@Yevgeny Makarov (jenkm) Your proposal looks nice, but it's not complete. What would be shown when Auto-Save is turned off by the user? Do you show the checkbox and the save button at the same time? What if the user wants to reset to factory settings, then turn off auto-save, then save the new preferences, what would that look like?

It's the same as it is now, but shows the checkbox instead of the empty space.

By default, Auto Save is enabled:

Auto Save is turned off by the user:

change

if prefs.use_preferences_save and (not bpy.app.use_userpref_skip_save_on_exit):
    pass
else:

to

if prefs.use_preferences_save:
    row.prop(prefs, "use_preferences_save", text="Auto-Save Preferences")
else:

line 45, space_userpref.py

And you need to rename the "Auto Save Temporary Files", "Recover > Auto Save…" to "Auto Backup", so as not to confuse.

Oh, and another thing, "Load Factory Settings" vs "Load Factory Preferences".
The difference is only visible when you see them next to each other.

When you see "Load Factory Settings" in the menu, you don't remember that in the Preferences,
the option is called "Load Factory Preferences" and you think it's the same function.

In T68649#753567, @Yevgeny Makarov (jenkm) wrote:

Auto Save is turned off by the user:

This means they won't be able to turn it on again.

This means they won't be able to turn it on again.

Yes, just like it is now.

Alternatively, it could just be a "Auto Save enabled" label, not a checkbox.
This is only to allow the user to clearly see that the Auto Save feature is enabled.

In T68649#753698, @Yevgeny Makarov (jenkm) wrote:

This means they won't be able to turn it on again.

Yes, just like it is now.

No, that's not how it is now. It's a checkbox that's always available:

@Sybren A. Stüvel (sybren) It's all here, if you mean the menu, I'm not suggesting remove anything, just add a checkbox (or label), see my comment above T68649#753568.

I think having a checkbox that disappears when you un-check it is a bad idea. We've had that before, and it was horribly confusing.

Diff: P1070

Mockup of the dialog box:

I'd rather we not use exclamation marks like that - and since most apps always auto-save preferences, there's no need to draw that much attention to the fact that Blender works the same.

I do like the idea to expose the "Autosave = On" as a checkmark when it's enabled.

and since most apps always auto-save preferences, there's no need to draw that much attention to the fact that Blender works the same.

I agree but but Blender didn't work like that so far. It's a new concept for Blender users so it makes sense to highlight it a bit more. Not necessarily shout it out in the interface but at least showing it prominently when it's enabled instead of always hiding it.

In T68649#753567, @Yevgeny Makarov (jenkm) wrote:

It's the same as it is now, but shows the checkbox instead of the empty space.

By default, Auto Save is enabled:

Auto Save is turned off by the user:

most apps always auto-save preferences, there's no need to draw that much attention

These applications are not able to disable autosave, so the user always knows that autosave will take place.

In Blender autosave is an option and as it is important it should be visible.

Or this option (to disable autosave) should not exist as in other applications. In order not to confuse users.