Using classic Outlook for Windows in business environments
... I was having this same issue on Outlook 2016 and then I used on the ONLINE office repair. It still didn't work until I actually clicked "Open" on the Outlook app in the root folder instead of the shortcut. I didn't even have to "Run as administrator." It seemed as if the online repair actually uninstalled my Outlook and reinstalled it but the old toolbar shortcut had issues. I deleted the old shortcut and once it was open correctly, I "Pinned to the toolbar" and all seems well now....
Hi Photoman2525:
What is your Windows OS (if Win 10 or Win 11 please include the version and build shown at Settings | System | About Windows Specifications or open a Run dialog box and enter winver), the full name of your MS Office 2016 Click-to-Run product (e.g., MS Office Professional 2016 Click-to-Run), and what is your current MS Office version shown beside the "About Outlook" button at File | Office Account | About Outlook? Has your repaired MS Office installation updated back to the current Version 2307 / Build 16626.20134 (rel. 27-Jul-2023), and if so can you confirm that your "When Outlook opens:" dropdown box at File | Options | General | Startup Options is still present after you are patched back to the current MS Office Version 2307 / Build 16626.20134?
Also, when you ran the full ONLINE repair of MS Office (i.e., not the QUICK repair) as instructed in the support article Repair an Office Application do you recall what version and build was originally installed? The ONLINE repair is essentially an uninstall and reinstall of your MS Office installation that should not touch your profile and user data, and it's possible that an ONLINE repair didn't work earlier for users prior to 27-Jul-2023 because they were simply reinstalling a buggy Version 2306 build.
I'm also curious why you had to launch Outlook.exe manually from C:\Program Files\Microsoft Office\root\Office16 (i.e., instead of your toolbar icon) after your repair in order to see the dropdown box at File | Options | General | Startup Options. Just FYI, I tried running Outlook.exe from this folder today without trying the ONLINE repair first and the dropdown box at File | Options | General | Startup Options is still missing from my MS Outlook 2019 settings, so it's not just a corrupted shortcut icon that's causing the problem.
Dell Inspiron 5584 * 64-bit Win 10 Pro v22H2 build 19045.3208 * Firefox v116.0.1 * Microsoft Defender v4.18.23050.9-1.1.23060.1005 * Malwarebytes Premium v4.5.34.275-1.0.2089 * Macrium Reflect Free v8.0.7279 * Microsoft Office 2019 Home and Business 2019 Version 2307 / Build 16626.20134 Click-to-Run