Hi @Lyke, Betheny
Welcome to the Microsoft Q&A forum and thank you for taking the time to share your situation.
I truly understand how inconvenient it is when Outlook suddenly stops adding your airline or hotel confirmations to your calendar. This feature is incredibly helpful when it works consistently
There are a few key reasons and the steps you can try to set up on your calendar:
1. Some airline or hotel email domains are no longer supported by Outlook
Outlook only auto‑creates events from specific, approved sender domains. Recently, several major airlines began using different confirmation email domains that are no longer on Microsoft’s supported list, so Outlook won’t trigger an event from those messages. For example, Delta confirmations using t.delta.com are not recognized by Outlook’s automatic event‑creation system.
2. Outlook settings may have reset after updates
A number of customers have found that their Events from email setting was unintentionally toggled off. To make sure Outlook continues adding travel plans automatically, you can re‑enable it using the steps below:
- Open Outlook on the web
- Go to Settings > View all Outlook settings
- Select Calendar > Events from email
- For Flights, Hotels, and other categories, choose “Show event summaries in email and on my calendar.”

3. Some travel providers changed how they format confirmation emails
Certain airlines have stopped embedding .ics files or structured event data in their emails, so Outlook doesn’t detect them anymore. This means Outlook may still show “Outlook found new events” at the top of the email, but it won’t be able to add anything to the calendar if the data format isn’t supported.
For more information, please refer to the following link:
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I look forward to your thoughts on this.
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