Using classic Outlook for Windows in business environments
Hi Jason Smith
Since you can see everyone's availability in Outlook on the web and in New Outlook, it sounds like your mailbox and calendar permissions are working correctly. The fact that other colleagues using Classic Outlook can also see availability suggests the problem is likely isolated to Classic Outlook on your computer rather than a Microsoft 365 service issue.
Here are some recommendations you can try first:
Check Outlook's connection status
- Hold Ctrl and right-click the Outlook icon in the system tray > Select Connection Status.
- Make sure Outlook is connected successfully and isn't showing any connection errors.
Try a new Outlook profile
You can follow this article: Create a profile in classic Outlook for Windows | Microsoft Support
Try disabling Cached Exchange Mode temporarily
Sometimes a local Outlook cache issue can affect calendar lookups.
- Go to File > Account Settings > Account Settings > Double-click your account.
- Temporarily disable Use Cached Exchange Mode.
- Restart Outlook and test again.
If the issue continues after these steps, I'd suggest reaching out to your IT administrator. They can check a few things that aren't easily visible from the Outlook client, such as:
- Whether Autodiscover is working correctly for your account.
- Whether Exchange Web Services (EWS) is available and functioning properly.
- Whether any Group Policies, security software, or network restrictions are affecting Classic Outlook.
- If your organization has a hybrid Exchange setup, whether there are any free/busy configuration issues.
I hope this information helpful and if you have any further questions, please feel free to ask via comment section.