I designed my first cover for a print publication in Aldus PageMaker on the original, black-and-white Macintosh computer as a teenager, when I co-edited my high school's annual arts publication. My first cover designs in the professional sphere, however, were for a handful of issues of the Fantagraphics Books long-defunct, monthly, comic-book-sized, newsprint promotional booklet FBI Informant (edited by the late Kim Thompson). The following example was for an issue that had dual front covers promoting two new important comic book projects for the company by Mark Kalesniko and Dave Cooper, with the second of the two front covers being printed upside-down, so that when the reader flipped the pamphlet around to see this cover right-side up, the reader would then find a second section of the publication inside, printed upside-down from the first. This allowed each comic book shop to choose which version of the cover they preferred to display on their shelves.
The following image was the cover of a tiny print run small press anthology comic book called Undercurrent published by a small group of comic book drawing friends I met on the internet (though, unfortunately, never in person). The cover image references a story inside written by Elliot Blake and drawn by Jason Whitley called "100 Guys Named Vinny." The entire cover was created in the Macromedia FreeHand illustration software.
Finally, the following is the cover of the second edition of the autobiography of Portland State University political science professor emeritus Ralph Bunch. Ralph requested this pre-existing NASA starfield image be used on the cover. My goal was to make the text over this complicated image legible and pleasing to the eye.