Hi Jim Pritchard,
Thanks for reaching out. I understand how important it is to send emails from the correct address, especially when using multiple accounts or aliases. Outlook usually picks the address based on the folder you're in, unless you've set a default.
To set your default "From" address in Outlook.com, go to Settings > View all Outlook settings > Mail > Sync email, then choose your preferred address and save. In the Outlook desktop app, go to File > Account Settings, select the account, and click Set as Default.
If you're using an alias and it’s not showing up, try sending an email from it once, Outlook should remember it after that.
Which version of Outlook are you using web, desktop, or mobile?
Let me know how it goes. If you found this helpful, marking it as helpful might make it easier for others to find the solution. Thanks!
Regards,
Carlo