Hi @Leo Cappello,
Thank you for posting your question in the Microsoft Q&A forum.
It appears you're encountering an issue where the iCal calendar link either shows a “Try again later” error in Classic Outlook or loads as a blank calendar in New Outlook.
Based on Microsoft’s documentation and known behavior across Outlook versions, here are a few insights:
- In Classic Outlook, the error is often related to how Outlook handles authentication with external calendar servers. Some servers may reject the connection, resulting in the “Try again later” message.
- In New Outlook, the calendar may appear but show no events if the server doesn’t respond correctly or if the calendar requires specific permissions or headers that aren’t being sent.
Here are a few suggestions that may help migrate the issue:
1/ Try Outlook web app (OWA):
This method avoids some of the authentication issues seen in desktop apps.
- Go to Outlook Web Calendar.
-  Click Add calendar    
-  Subscribe from web and paste your iCal link.   
2/ Use the correct link format:
-  If your calendar link starts with https://, you can try replacing it with webcal://. This format is specifically designed for calendar subscriptions and may resolve compatibility issues.   
3/ Check permissions:
- Since other employees can access the calendar, it’s worth checking if your account has any restrictions or conditional access policies that might block the sync.
For more technical details, you can refer to Microsoft’s official troubleshooting guide here:
Can't add an Internet calendar - Outlook | Microsoft Learn
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I hope this information is helpful. Please follow these steps and let me know if it works for you. If not, we can work together to resolve this.
Thank you for your patience and your understanding. If you have any questions, please feel free to reach out.
I'm looking forward to your reply.
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