The EPUB format might get most of the press in the ebook world, but among document-handling professionals in the business world, PDF still reigns supreme, and utilities like Smile’s PDFpen and PDFpenPro remain essential. Smile has now released version 6.0 of both versions of PDFpen, adding the capability to convert PDFs to Word documents, simplifying PDF editing with a new editing bar, providing support for Auto Save and Versions, and more. The updates cost $30 or $40, depending on the version and how you’re upgrading. PDFpen 6.0 requires OS X 10.7 Lion or 10.8 Mountain Lion.

Apple’s Insane Upgrade Dance -- Normally, I’d save upgrade details for the end, but thanks to Apple’s developer-hostile policies surrounding the Mac App Store, it can be a bit confusing. If you purchased directly from Smile and want to upgrade through them, things are simple: the upgrades for either version of PDFpen cost $30, and if you want to jump from PDFpen to PDFpenPro at the same time, it’s $40. However, because PDFpen and PDFpenPro are also sold through the Mac App Store, where Apple doesn’t see fit to allow paid upgrades, Smile has released entirely new apps for PDFpen and PDFpenPro. To be painfully clear, if you bought an earlier version of PDFpen through the Mac App Store, you won’t get any notification or discount pricing — you must buy a new copy to “upgrade.” (Smile offered reduced pricing for 48 hours on the Mac App Store, but that time has now passed.)

But wait, it gets more complicated! Apple also doesn’t allow any apps sold outside of the Mac App Store to use iCloud document syncing, so if you want that feature, you’ll need to purchase PDFpen through the Mac App Store, even if you previously purchased through Smile. Copies purchased through Smile will not be able to open or save or sync documents from iCloud. Luckily, Dropbox syncing is available regardless, so doing business directly with Smile (which also increases their earnings by more than 20 percent) doesn’t prevent you from syncing documents using a cloud-storage service.

If you purchased PDFpen from Smile on or after 15 October 2012, your upgrade through them is free and should be automatic; the internal Check for Updates feature will download the new version and run you through the process to update your serial number.

In theory, you should be able to test the trial version of PDFpen 6.0 and be able to revert if desired, since the automated updater is supposed to retain the previous version of PDFpen in the Applications folder. That didn’t happen in one test here, so I recommend making a Zip archive of the old version of PDFpen 5.x before allowing the upgrade to happen, just in case (Control-click PDFpen in the Applications folder and choose Compress “PDFpen”). Or you can just download another copy from Smile’s Download page.

Export to Word -- Meanwhile, back at why you might want to upgrade from PDFpen 5.x to 6.0, the marquee feature of the new version is its capability to export to Microsoft Word format (either .doc or .docx), after which you can work with the text however you want, although you may not be able to create a new PDF that matches the original version all that well.

This feature uses the Nuance OmniPage Cloud Document Conversion Service, and is available only to licensed users (meaning that it won’t work in trial versions of PDFpen 6.0; Smile has some sample exports you can check out before buying). Perhaps due to the need to accept the license agreement, I found that I had to choose File > Export twice to get it to work, so if you have trouble the first time, give it a second try.

Export is not as quick as a simple Save As — a 7-page test document took 20–30 seconds, and as a torture test, I fed it the 226-page “Take Control of Your iPad, Second Edition,” receiving back an estimate for over 37 minutes. Luckily, it actually took only 7 minutes, and you can tell from the progress bar and the elapsed time counter how long it’s likely to take for real. Although you cannot continue to work in the document that’s being converted, you can open and work in other documents in PDFpen 6.0 while the conversion is taking place.

The real question is how good the conversion is, and, frankly, I was pretty impressed. I’ve tested a lot of conversion programs over the years, and their results are usually so pathetic that I want to either laugh or cry, depending on how badly I want the program to work. In “Take Control of Your iPad, Second Edition,” PDFpen’s conversion did a shockingly good job.

Overall, the document looked “right,” which involved setting tabs and indents correctly, using the proper fonts, bringing screenshots in at the right size and formatting their captions correctly, using tabs instead of spaces for line spacing, and so on. Of course, it wasn’t perfect, with the conversion making some mistakes and non-ideal choices, but none were show-stoppers. Here’s what I found:

• The cover was blank — no text or graphics. That wasn’t entirely surprising, since it’s created in Adobe InDesign using unusual fonts and stacked objects for many of the buttons. The only way to render it in Word would have been to bring it in as a single graphic.

• Some spacing between bordered paragraphs and paragraph borders themselves were wrong on occasion. Again, I wasn’t surprised, since borders are hard to get right even when converting between word-processing formats.

• One of our heading styles is in Eurostile Bold 36-point; without access to that font, the converted document used Arial 31-point. Other heading styles are set in Verdana Bold; the conversion got Verdana right, but lost the bold.

• In a few instances, the text in a box was invisible except for the last line. It was present, and formatted correctly (I could select it, copy it, and paste it into a new document), but nothing I could figure out in Word would make it show up in the converted document.

• Tables had some formatting problems, including some fonts that weren’t quite right, one of which forced a table onto the next page, thus adding a nearly blank page to the document. More problematic was the fact that tables were often broken into multiple table objects in Word, and multi-line cells were often turned into multiple cells. I was amazed that the conversion did even this well — tables are normally nearly impossible for conversion utilities.

• Every page had a section break at the bottom, which made sense, since every page had a page number there, and even though the page numbers were properly formatted and centered, they were normal text, not Word’s page number objects, so text couldn’t flow around them. However, even in documents without page numbers or footers, a section break appears at the bottom of every page. They’re easily found (search for ^b) and deleted in Word if necessary.

• One indented bullet list (but not others with similar formatting) had its bullets replaced with another character.

• Small inline graphics within lines of text were lost.

As long as you start a PDF-to-Word conversion from PDFpen 6.0 with reasonable expectations, you shouldn’t be disappointed. If you need to edit and republish the converted document, you’ll definitely have cleanup work to do, but far less than if you were forced to extract text from a PDF and paste it into Word manually.

Other Features -- Most of the rest of the new features in PDFpen 6.0 are tweaks to existing capabilities or support for underlying Mac technologies. The most notable include:

• A new editing bar provides faster access to common tools and properties.




• Support for Auto Save and Versions has been added, making it easy to revert to a previous version of an automatically saved document.

• Annotations can now be printed as a list at the end of a document (look for an Append Annotations Summary checkbox in the Print dialog), and you can now filter which types of annotations (text, notes, comments, links, and highlights) appear in the left sidebar after you choose View > Annotations.

• The Library now combines user-created text and freehand items into a single view, and lets you drag to rearrange them in the list, which wasn’t previously possible.

• A new View > Highlight Form Fields command makes it easier to see form fields that have a transparent background and are otherwise invisible.

• Smile has added support for Russian language OCR.

• PDFpen 6.0 is now optimized for full resolution on Retina displays.

Finally, two new features are available only in PDFpenPro, which sets itself apart from its little brother mostly through its support for turning Web pages into PDFs, constructing tables of contents, and creating PDF forms. Those who make a lot of forms will particularly appreciate PDFpenPro 6.0’s newfound capability to create form fields by detecting text field areas, checkboxes, and radio buttons and inserting the appropriate form elements automatically.

The other new PDFpenPro 6.0 feature is control over document permissions — if you want to restrict printing, saving, copying, and/or editing of your PDF, that’s now possible. Don’t assume that these PDF permissions are guaranteed, though, since there is software available that can remove those restrictions if someone is sufficiently interested in doing so.

One last comment. Although we can’t predict a specific publication date yet, Michael Cohen is hard at work on “Take Control of PDFpen 6,” and it will be a free upgrade for those who have bought “Take Control of PDFpen 5” after 15 October 2012, so there’s no harm in picking up a copy now, either through us or through Smile, and using it to learn about the features that remain the same in PDFpen 6.0.