UPDATE: WordPress.com reports that they have fixed the issue but it will take time for the images to process as there have been millions of images uploaded during the past 12 hours. They recommend waiting patiently. Some sites may update immediately, some may take 24 hours, though it is likely to be less. Just keep doing what you are doing and the images will appear, as if by magic. 😀
This is also a good time to check to see if you have been adding your ALT (alternative text) description. If you have, the image will appear as an empty box with the words that describe the image for the blind and visually impaired as required by most international countries for compliance with web accessibility laws.
Please be aware that WordPress.com is aware of the issue that images uploaded in the last 12 hours or so are not appearing on your WordPress.com sites.
DO NOT keep deleting and uploading images.
DO NOT blame the Theme, your browser, yourself, or anything else.
DO NOT call, email, or text me with your terror. It’s okay. Relax.
This is just a rare and temporary glitch in the system and they are on it and fixing it.
Go have a cup of tea or take a walk. It will be okay shortly. 😀