Hey there, and welcome to Apple Support Communities Ericwalker87,
We can certainly understand your concern and are here to help.
We recommend checking out these steps on how to compress, resize and flip images with Preview and see if it matches up with your procedures.
" Resize, rotate, or flip an image in Preview on Mac
You can resize or rotate an image opened in Preview to fit into a particular spot. You can also reduce the file size to save disk space or to download an image more quickly.
Change an image’s dimensions
- In the Preview app
on your Mac, click the Show Markup Toolbar button 
(if the Markup toolbar isn’t showing), then click the Adjust Size button 
. - Enter new values for width and height, or click the “Fit into” pop-up menu and choose a size.
- Resize the image by a percentage: Choose “percent” from the pop-up menu next to the Width and Height fields, then enter the percentage in those fields.
- Force the image to keep its original proportions: Select “Scale proportionally.” If you change either the width or height, the other value changes to maintain the proportions. If you choose a size from the “Fit into” pop-up menu, the image’s width or height may be smaller than the chosen size to maintain the proportions.
- Make the image’s dimensions smaller without losing any detail: Deselect “Resample image” before changing the width or height.
Tip: To resize multiple images at the same time, display the images in the same window, select them in that window’s sidebar, then choose Tools > Adjust Size.
Rotate or flip an image
- In the Preview app on your Mac, open the file you want to change.
- Do any of the following:
- Rotate an image: Select the image, then click
(or use the Touch Bar) to rotate the image to the left. Continue clicking to keep rotating.- To rotate the image to the right, press and hold the Option key and click
until you’re done rotating the image. - Flip an image: Choose Tools > Flip Horizontal or Flip Vertical.
Tip: To rotate or flip multiple images at the same time, display the images in the same window, choose View > Thumbnails, select them in that window’s sidebar, then choose Tools > [Rotate or Flip].
Reduce an image’s file size
- In the Preview app on your Mac, open the file you want to change.
- Choose Tools > Adjust Size, then select “Resample image.”
- Enter a smaller value in the Resolution field.
- The new size is shown at the bottom.
Tip: To reduce the file size of multiple images at the same time, display the images in the same window, select them in that window’s sidebar, then choose Tools > Adjust Size. "
For additional information, check out this link: Resize, rotate, or flip an image in Preview on Mac - Apple Support
Kindest regards!
