Outlook isn't letting me resize an image. Used to click on the pasted image and drag the corner to size. Why make updates that make things more difficult?

Hello Rod45103,

Good day! 
Thank you for posting to the Microsoft Community. We are happy to assist you.

After thorough research and consultations, it has been concluded that the feature you are inquiring about is not yet available in the new Outlook. However, thank you so much
for bringing this to our attention, your suggestion is constructive and I believe it could make the use of Outlook even better. We will surely raise your concerns with our Product Development Team and hopefully, this can be included in future updates. Please note new Outlook is still in active development.
In the meantime, we sincerely recommend you post your concern as an idea to our Outlook in-app feedback site Contact support and provide feedback within the new Outlook for Windows - Microsoft Support

Our Product Development Team is committed to enhancing the customer experience by continually examining suggestions to include in the design and development of future
product upgrades based on your suggestions. Hopefully, your suggestion will help many users in the future.

Thank you for your time and understanding. For other questions, feel free to add your post to the Microsoft Community team.
Stay safe and healthy. Have a good day!

Hi Eleni,

Good day to you as well, and thanks for the quick response.

I can resize with the size command in the ribbon; however, I can no longer click the image and drag with the "corner sizing handles". This is what I was referring to but didn't know the terminology.

These sizing handles no longer activate when clicking on the inserted images.

Hello Rod45103,

Good day!

Thank you for posting to the Microsoft Community. We are glad to assist.

As per your mentioned description about "Outlook isn't letting me resize an image. Used to click on the pasted image and drag the corner to size. Why make updates that make things more difficult?".

In new Outlook for Windows, you can change the display size of an image you've inserted in an email message, but you cannot reduce the file size of that image:

1. Select the image in the body of the email message.
2. On the ribbon, select the Picture format tab.
3. Select Size, then select the size option you want from the menu.
4. If the image still isn't quite the size you want, you can select the image, then click and drag a corner sizing handle inward or outward to adjust the size further.

AS Microsoft article : Reduce the size of pictures and attachments in Outlook email messages

We understand your concern about this feature and how it helps you improve your efficiency in a work schedule. Still, as it is related to Outlook product design, submitting your valuable feedback directly to the Microsoft product development team is strongly recommended by either going to Help from your dedicated App > submit Feedback or posting on Outlook · Community (microsoft.com) for feature requests.
Please note that nobody here is the product developer/decision maker and has no control over the product. Everyone, including us as community moderators, can only assist you with the query for providing available solutions and the feature's availability status within our scope and capability.
To check more details about how to submit feedback, kindly refer to this article Learn about how to provide feedback to Microsoft - Microsoft 365 admin | Microsoft Learn

Thank you for your time and understanding. For other questions, feel free to add your post to the Microsoft Community team.

We are looking forward to your response! Thanks for your precious time. Have a nice day!