In the Calypso (My Sites) interface, you may add such a tooltip, or “text-filled popup,” by giving the image a title as follows:
1. In a post or page editor where the image resides, click on the image to display the image editor toolbar.
2. Click the pencil icon to open the image editor.
3. Insert (type or paste) a title into the title field.
4. Click update to save the change.
5. Update the post or page.
In a WP Admin page or post editor, the process is similar. See the Advanced Options section of the Image Settings support page for relevant information. The Image Title Attribute field is the one to insert the text into that will display in a tooltip when a cursor hovers over the image.
I should have tested those steps first. The instructions I provided above for the Calypso post and page editors didn’t work in tests as I’d expected they would. However, a tooltip can easily be added by inserting text into the Image Title Attribute field of a WP Admin post or page editor Image Settings module, then updating to save the change.
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