Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi, w s4
Good day.
Thank you for posting to the Microsoft Community. We are glad to assist.
According to your description, I understand that you are experiencing issues with multiple attachment file selection in Outlook. I apologize for any inconvenience this may have caused you.
To select multiple contiguous files in Outlook, you can hold down the SHIFT key and click on the first and last file in the range you want to select. If you are experiencing issues with this method, you can try using the CTRL key instead. Hold down the CTRL key and click on each file you want to select.
If the issue persists, I recommend checking for any updates for Outlook and Windows 11 Pro. You can also try repairing your Outlook installation by going to Control Panel > Programs and Features > Microsoft Office > Change > Repair.
If the above suggestions failed to you, would you please share your detailed client version and we will explore other soultions for you.
Ref- What version of Outlook do I have? - Microsoft Support.
Please feel free to contact us if you have any further issue. Looking forward to your new updates.
Thanks for your precious time and your understanding would be highly appreciated.
Hope you all the best!
Microsoft Community Moderator.