Hello Marvin the Moon Martian,
Thank you for posting this case in Microsoft Community!
As mentioned, you are unable to open all links in Outlook for Windows which showing 404 error. I would like to cooperate with you working on this case. To clarify this case, please kindly provide us your Outlook version with product details by going to Outlook > File > Office Account and share that entire page screenshot with hide personal information. What version of Outlook do I have?
Please also help to collect following information for further analysis:
- Have you tried to type or copy one link to test it if working via editing one new email?
- Have you tried to access Outlook Web and test if working via default browser? If working fine, this mean that may be related to your Windows system or Outlook client.
If working fine in Outook web, for my suggestion, please try following workaround as shared:
- Firstly, please try to change different default Windows browser if working fine or not such as Microsoft Edge, Firefox and so on.
Change your default browser in Windows
- Please also try to access registry editor with admin level and locate: HKEY_CURRENT_USER\Software\Classes.html, change the default value on the right to:htmlfile.
(Note: You need to backup pervious settings firstly if may change it back to avoid causing any issues.)
- And please go to Search menu to type Run and type Outlook.exe /safeto open it to test it again. If working in safe mode, this may be related to certain add-in caused the issue. Please check the following capture as Microsoft article shared: I can’t start Microsoft Outlook or receive the error “Cannot start Microsoft Outlook. Cannot open the Outlook Window”
- Please try to use SARA tool to fix your issue if possible. About the Microsoft Support and Recovery Assistant
- Please also try to re-configure Outlook profile and test it again.
Steps:Create an Outlook profile - Microsoft Support
(1).In Outlook, select File > Account Settings > Manage Profiles;
(2).Choose Show Profiles > Add.
(3).In the Profile Name box, type a name for the profile, and then choose OK.
- Please try to repair your Office 365 application and test it again.
Steps:Repair an Office application - Microsoft Support
(1).Right-click the Startbutton(lower-left corner), and select Apps and Featureson the pop-up menu.
(2).Select the Microsoft Office product you want to repair, and select Modify.
(3).Select Online Repair>Repairto make sure everything gets fixed.
- If still not working, you may try to re-install the latest version of Office 365 application and check if working or not.
Download and install or reinstall Microsoft 365 or Office 2021 on a PC or Mac - Microsoft Support
If you need further assistance, please feel free to let me know, I will keep assisting you.
Your understanding and patience will be appreciated.
Thank you!