Cloudinary counts all image processing.
For example, if you upload an image, then apply a transformation (e.g.,
w_200,h_200,c_fill), two transformations will be counted towards the transformations quotas. Once for the original image's upload, and an additional one for the initial transformation generation (the first time the 200x200 image's URL is accessed).
After the transformation is generated, the transformed version of the image is stored in your account for quicker recurring accesses. Therefore, for the next requests of the transformed image's URL Cloudinary returns an already generated image which doesn't require further processing and therefore isn't counted as additional transformations.
Another matter that should be taken into account is the media-lib-thumb version which is being automatically processed upon uploads via the media-library or while browsing through your uploaded images.
For more information regards counting of Transformations and other plan limits, see: