Esquire wanted a creative way to package its summer reading issue. Slate thought its political coverage could use another outlet. And the Wall Street Journal wanted to further test its ability to sell digital content.

For a variety of reasons, some of journalism's biggest names are entering the e-book market. The format offers one large advantage: in a world of shaky profit models, it gives publications a relatively low-risk opportunity to earn money on content they already own. But several books in, some are finding they've traded one set of problems for another.

Esquire's foray began a year ago, when the publisher gave away about 7,000 copies of an e-book based on its summer reading issue. Last fall, it got more ambitious, as it tried to wring some revenue from e-books with the true-crime anthology Love and Murder. The magazine sold only a fraction of the number of copies it previously gave away. For its third book, a compilation of essays called How to Be a Better Man, the magazine returned to the free-content model, in a move that makes its e-book line look more like brand extension than a potential revenue stream.

"We're in a holding pattern," said online editor Brendan Vaughan. "All the books worked editorially, but we can't seem to find a way to make money on them." Vaughan points to technology as the problem, in the familiar carousel argument between techies and editors over who's responsible for tepid sales.

Perhaps an even more striking example is that of the Wall Street Journal. Despite the newspaper's ability to draw more than half a million paying subscribers to its site, it has had trouble extracting e-book sales. The newspaper's imprint with the Free Press has come out with a half dozen titles adapted from the newspaper's special reports, on topics such as e-commerce and world business. A new title, a guide to business schools, contains far less reconstituted content. But even that book, said Free Press executive editor Bill Rosen, has proven "a success by e-book standards but inconsequential to the bottom line of Simon & Schuster." Still, Rosen points to the ability for the publisher to gain information on the market as a reason not to quit.

As a member of the Microsoft family, Slate is the magazine with arguably the most invested in e-book adoption. Its program has been correspondingly ambitious—repurposing its own content through such books as a fifth anniversary anthology, as well as buying the rights to Nicholas Lemann's New Yorker essays on the presidential race and republishing them as an e-book. (It garnered 28,000 free MS Reader downloads, the only format in which Slate e-books are available.) The future will likely yield more experimentation: the magazine is in talks with New York houses about a possible joint e-book/print imprint.

"We don't want to regurgitate material that doesn't make sense, but the editorial effort that goes into selecting the 'best of' is something we think has value," publisher Scott Moore said of the effort to repackage, adding, "The idea of publishing electronic books is not very different from publishing an online magazine."

Indeed, the smudging of the line between books and magazines may end up being e-books' legacy. In the rush to repackage material, some sites have used the term e-book so loosely that it's hard to pinpoint the difference between an e-book and magazine content that happens to be downloadable.

This smudging also brings problems—such as production costs and sales penetration—familiar to all content providers on the Web. Then there are the issues that relate particularly to e-books. Some suggest that readers are too cynical—or cheap—to buy compilations of stories they can get for free on the Web. (Rosen counters that, in print, anthologies have traditionally done well, in part because of the editorial talent that goes into them and the convenience they offer readers.) Others say a more user-driven model might make the difference.

"As a reader, I'd love to go to an electronic newsstand and just fill my shopping cart with a piece from Vanity Fair, an article from Time, an essay from Slate," Vaughan said. That may end up as e-books' real contribution, though for such a smorgasbord, hungry readers may have to wait.