Keep Getting "Outlook closed while you had items open. Reopen items from last session?" Even Though It's Not True

Thanks for the coherent walkthrough of all that has not worked in resolving this issue. Given the current environment in big tech (with one notable exception) I am not surprised at what happened to you when you made some "not-nice" comments...I will heed your advice. Much appreciated.

I agree absolutely with you about not mucking about with the registry;

But this did work for me;

If you open Outlook directly from the app menu make a shortcut on your desktop and use that. 

Right click on the Outlook desktop icon, Select Properties and edit the" Target" field by adding a command switch as follows. 

.......\OUTLOOK.EXE" /restore

Adding the command switch /restore will...

The space before the / is needed

I'm just a regular user so I'm not about to go into editing registry values or rolling back versions since I learned the hard way not to do that quite some years ago when I thought I knew what I was doing.

I've got a Dell Inspiron 5510 64bit running Win11 and Office Home and Business 2021, Outlook v2037/Build 16626.20134.

I've gotten this same "Reopen Items" from Outlook 4 out of 5 times I turned on my pc in the morning ever since the latest update from MS (2023-07 Cumulative Update Preview for Windows 11 Version 22H2 for x64-based Systems (KB5028254) came through on 7/26/23 - it was not happening before then, ever. Needless to say it was a bit disconcerting the first or second time it came through but now it's just really annoying, especially if I click "Yes" to reopen those items and get a second Outlook window active...

Reading through this thread I did check "File-Options" whether I could change "Startup Options" and found that there is no drop-down list so that idea is kerplunkt. I also do not/will not allow any storage or backup in 'the cloud' for security reasons.

My routine is I turn on my pc first thing in the morning and wait a couple minutes until it's stopped with the background noise, then open Outlook and keep it open all day long (I found a couple years ago that constantly opening and closing Outlook during the day seemed to mess with the Outlook data file) until beddy-bye time at which point I close Outlook, wait at least 2 minutes, then turn off my pc until the next morning.

After the first or second time I got the "reopen items" message, that night after closing Outlook I found in Task Manager that Outlook was indeed still running after I closed the Outlook window, so did a right-click, close. That next morning I still got the same message, so that night again checked Task Manager and this time Outlook was closed - but I still got that 'reopen' message the next morning. Arrgggghhhh! Yesterday morning I got that 'reopen' message, this morning I did not, and I did absolutely nothing different in between with my usual routine, so what do you do with a sporadic problem???

One might think that this problem might get fixed sooner rather than later, but oh well.

PS - I had a different problem about 5-6 years ago with MS Office and wrote some not-nice comments on this MS Users Forum on that different topic and the day after I posted those comments (I kid you not!!!), I could not log into my pc the next morning because my MS password inexplicably was 'invalid'... so I'm keeping it civil.

Perhaps the Microsoft software folks need to give up on their own intelligence, and just rely on the new AI. :-)