Hi @Andy Brisendine,
Thank you for reaching out to the Microsoft Q&A forum and for clearly outlining your concern.
From your description, Outlook switches to the new version after every restart, and you need Classic Outlook to remain your default. I truly understand how important it is to keep your preferred experience consistent, and I appreciate the time and effort you have already invested in switching it back.
To explain why this happens, the New Outlook for Windows installs as a separate application. As a result, Windows may target that app when you launch Outlook from the Start menu, from a taskbar pin, or from email links. In addition, updates can re-enable the Try the new Outlook control inside Classic Outlook, which can redirect you to the new app again.
To keep Classic Outlook in place for your situation, please try the following options, step by step.
1/ Make Classic Outlook the default everywhere
- Close all Outlook windows.
- Open Start and type Outlook (Classic). Right click it, choose Open file location, then right click the shortcut and select Pin to taskbar.
- If you see an entry named New Outlook or one that opens the Store version, right click it and choose Unpin from taskbar.
- Open Windows Settings, then Apps, then Default apps. Search for Outlook. Set Email to Outlook and set MailTo and MAPI to Outlook.
- Launch Outlook using the pinned Classic shortcut and confirm it stays in Classic after a restart.
2/ Uninstall the New Outlook app so it cannot take over
- Open Windows Settings, then Apps, then Installed apps.
- Search for New Outlook or Outlook from Microsoft Store, select it, and choose Uninstall.
- Restart the device, then open Outlook from your Classic shortcut.
3/ Hide the Try the new Outlook switch through the registry
- Press the Windows key and R, type regedit, and press Enter.
- Navigate to
HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Options\General. - Right click in the right pane, select New, then DWORD value. Name it
HideNewOutlookToggleand set its value to 1. - Close Registry Editor, restart Outlook, and confirm the switch to the new Outlook is no longer shown.
If your device is managed by your organization, your IT administrator can also enforce this using Group Policy so the option to try the new app is hidden and Classic Outlook remains in place.
I hope this information is helpful. Please follow these steps and let me know if it works for you. If you have any updates regarding the issue, please feel free to share them with me.
Thank you for your patience and your understanding. I look forward to continuing the conversation.
If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment”.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.