Hi Awatts,
Thanks for reaching out. I understand how frustrating this can be when PowerPoint doesn’t behave as expected. I'm here to help!
First, this behavior is actually a known limitation in PowerPoint. The image inside a shape doesn’t truly skew or rotate with the shape, it only aligns within the bounding box. The “Rotate with Shape” option affects rotation but not distortion or skew.
Second, a quick workaround is to insert the image separately, manually rotate or skew it to match the shape, and then group them together.
Third, if you want a more template-friendly solution, you can use the Slide Master. Create a picture placeholder, then change its shape to your desired skewed form. Images inserted into that placeholder will adopt the shape’s skew automatically.
Last, if you need precise distortion, third party tools like Photoshop or GIMP can warp the image before inserting it into PowerPoint. Unfortunately, PowerPoint doesn’t currently support true image skew inside shapes.
I hope you find this information helpful. Please let me know if you have any further questions If the answer is helpful, please click "Accept Answer".
Regards,
Carlo