I have this issue too on my laptop, but its a single monitor and it happens when it turns back on. I don't get a message at all though, I just turn it on and notice it doesn't hide, then check settings and see that the option isn't checked.
Window 11 taskbar auto-hide turning off
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Anonymous
I switched to Windows 11 a few weeks ago, and ever since then, the taskbar auto-hide quits working when the computer comes out of Sleep mode. I have to be away from the computer for a while before it will happen, and I believe it has something to do with me running dual monitors. When I wake my computer, my secondary monitor appears to come up faster than my primary by just a fraction. Once my primary is on, there is a message saying something about the taskbar already being hidden (I think) and the taskbar on my primary monitor has the taskbar up. When I go to Taskbar Behaviors, 'Automatically hide the taskbar' is no longer checked. I'll select it again, and it will work fine until the system goes back into Sleep mode for a while, again.
Windows for home | Windows 11 | Settings
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Anonymous
2022-10-02T02:02:19+00:00 -
Anonymous
2022-10-02T11:18:15+00:00 This is bugged for me when going from sleep to wake, as well as browsers freezing. Has been since Windows 11 launch never had the issue on 10. The auto-hide resets and shows a message that it can only be on one screen. Then I have to dig into settings to reset it ( when windows 10 you could just right click taskbar as it should be still). Fix your &%!# please or stop doing these blanket bad updates that ruin windows for years at a time.
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Anonymous
2022-10-02T16:53:32+00:00 Same issue. I also have a dual monitor setup
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Anonymous
2022-10-06T19:44:02+00:00 I'm on the latest 22H2 and the issue is STILL not fixed! Dual-monitor setup (DP and HDMI) and getting the "a toolbar is already hidden" message on every screen on event.
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Anonymous
2022-10-10T15:57:19+00:00 I have exactly the same problem - two monitor set-up (one HDMI, one VGA) and it is EXCEPTIONALLY IRRITATING - Microsoft please listen and DO SOMETHING ABOUT IT!