My contact in support just let me know that he repro'd it in both Outlook 2019 and 2021 and submitted a bug report on it ...
Hi Diane Poremsky:
There's speculation in CSG-08's 04-Jul-2023 thread My Outlook 2016 "Start Up Options menu" has no drop down submenu that this problem could be connected to the appearance of the "Try the new Outlook" switch in perpetual editions of MS Outlook 2016 / 2019 / 2021 - see garrybock's 19-Jul-2023 post <here> on page 5 of that thread.
I'm not sure how it happened but the experimental preview of the MS Outlook for Windows PWA (progressive web app) was installed on my system a few months ago - see the images I posted in my 07-May-2023 thread "New" Outlook for Windows UWP App (Preview) Installed Without Permission. I never launched the "new" Outlook app and tried to remove the last traces of it from my system with O&O AppBuster, but perhaps the installation was enough to do permanent damage to my MS Outlook 2019 registry entries and settings.
According to the 04-Apr-2023 Microsoft 365 Insider blog entry Starting to Support Third-party Accounts in New Outlook for Windows if you turn on that "Try the new Outlook" switch to test the preview of the "new" Outlook PWA "You can switch back to your previous Outlook experience . Just slide the toggle off and it will automatically open your previous version with no data or email loss." That might be true for M365 but perhaps that isn't the case for perpetual editions of MS Outlook 2016 / 2019 / 2021 Click-to-Run.
Just to recap, the section at File | Options | General | Start Up Options in my Outlook 2019 settings is now blank (i.e., there is a section header but no check boxes or dropdown lists), there is no section named Cloud Storage Options at File | Options | General, I have no registry entry for ReopenWindowsOption at HKEY_CURRENT_USER | SOFTWARE | Microsoft | Office | 16.0 | Outlook | Preferences (for now, I've decided not to re-create this registry entry manually), and I am still seeing the occasional "Outlook closed while you had items open. Reopen those items from your last session?” prompt when I start Outlook 2019.
Dell Inspiron 5584 * 64-bit Win 10 Pro v22H2 build 19045.3208 * Firefox v115.0.2 * Microsoft Defender v4.18.23050.5-1.1.23060.1005 * Malwarebytes Premium v4.5.33.272-1.0.2069 * Macrium Reflect Free v8.0.7279 * Microsoft Office 2019 Home and Business 2019 Version 2306 / Build 16529.20182 C2R