Smile History: PDFpen Reaches 14 !

14 Years of PDFpen

On June 12, 2018, Smile celebrates our 15th birthday. In this series we’re looking back at some of our history. Hope you enjoy!

Smile’s 15th Birthday means PDFpen’s 14th Birthday was in January! In our first year as SmileOnMyMac when we embarked on PDFpen, the second product Greg and I were to work on together.

PDFpen was conceived because we were tired of printing and signing and scanning documents we received as electronic faxes from PageSender. By cutting that process completely and signing the fax directly as a PDF, we could send it back by either fax or email. Plus, faxing was slowly ceding ground to email in general.

Next, looking at the PDF editor options in 2003 there appeared a huge gap between Apple’s Preview, in which PDFs were read-only, and Adobe Acrobat, which was much more than most needed for everyday use. We figured we could fit somewhere between those two extremes.

Our first release of PDFpen was focused on document assembly and signing. The goal was to make it easy to use and easy to sign contracts. Our deadline was Macworld 2004, January! We were solving issues and building the product the morning we shipped! I can only remember it was a little hair-raising. Still, ship we did.

PDFpen was even shipped as a physical retail product and appeared on the shelves of the Apple Store in 2006. It was great to have that experience and super exciting at the time! While not super successful financially, it was great advertising. Now retail software is no more and everything is downloaded.

PDFpen retail box
Philip with the retail box


Being able to take a scan, which is normally treated as static image, and turn it into a more editable PDF where you can copy text, seemed a valuable feature to have. That meant adding an Optical Character Recognition (OCR) engine into PDFpen. So we hunted for a decent engine.

First, we used Google’s, which is what we have in PDFpen Scan+ today.

We’ve since updated to use Nuance’s, which has the benefit of higher quality output, though at a higher price tag. A lesson in this case, a higher price does mean higher quality.

On iOS

Once Apple created the iPad, and we gave it a chance to get powerful enough, we launched PDFpen for iPad in time for Macworld 2012. That’s the year IDG re-branded the expo as Macworld/iWorld in order to include the growing iOS presence. I suppose we were on the same page there, as adding iOS apps to our product line prompted us to rebrand as well. We dropped OnMyMac from our company name, shifting from SmileOnMyMac to Smile, so as to encompass our spread to more platforms.

At that Macworld we had two booths, one for our Mac products and another in the iWorld section. I manned that iOS kiosk myself, showing off PDFpen for iPad, the rest of the team took shifts at the Mac booth. I received this question at Macworld in 2012, and our support still receive it occasionally today:

Where’s the “pen?”

There is no “pen.” We are not a developer of styluses for your iPad. We are a developer of software for editing PDFs.

A tradeshow lesson: after our first few years of tradeshows together, Greg and I decided when we set up a booth to include the luxury of extra (read: any) padding under the carpet. Standing on concrete for eight hours a day, it really makes a difference.

I miss Macworld and its camaraderie, but I don’t miss the long tradeshow days.

About 9 months after PDFpen for iPad we launched a version on iPhone. We hadn’t intended to make one, an iPhone screen being quite small, even smaller in 2012. But when customers ask, we deliver.

A bit later Apple came out with universal apps, single app purchases which ran on both iPhone and iPad. So we merged PDFpen for iPhone and PDFpen for iPad into PDFpen for iPad & iPhone.

That upgrade shift was interesting. We used Apple’s gift of bundles and “Complete My Bundle” to offer a version of upgrade discount pricing to customers moving from v1 to the universal v2, as outlined in a blog post on the topic.

In 2013 we launched PDFpen Scan+, the OCR and scanner companion to PDFpen, and the final entry in what became the PDFpen Family.

The Saga of Sync

Pre-iCloud, getting PDFs from Mac to Mac was pretty easy, people just used Dropbox. But how to get them from Mac to iPad?

PDFpen for iPad & iPhone Sync

Initially, we introduced a way to edit PDFs you had in your various sync services, Dropbox, Google Drive, Evernote, and so on. This involved copying a PDF into PDFpen for iPad & iPhone from a sync service, editing, then exporting another copy back into that service. This obviously leads to lots of different version copies everywhere. And this isn’t sync. You can’t effortlessly edit on your Mac and your iPad. You have to track all your copies and know which version you’re editing.

So next we added a way to sync. You could pick a Dropbox folder to be specially linked to PDFpen for iPad & iPhone. You could edit PDFs in that folder “live,” as you were editing the original version of the PDF not imported copies. You could edit a PDF on your Mac and your iPad at the same time. Sync solved!

Not quite.

Not everyone wants Dropbox, what about sync for other services?

So, next, we added Linked PDFs, sort of a proxy sync. You could select a PDF from one of your sync services to have a special status in PDFpen for iPad & iPhone. When you opened the PDF it would sync with the original document. You would then edit the PDF. When you close the PDF it would re-sync. It’s a form of sync, but not quite “live” sync. And it didn’t work for all sync services.

Then in 2017, with iOS 11, came the iOS Files app, which would give us sync for everything the Files app supported. We instituted the Files interface on PDFpen for iPad & iPhone 3.

Finally, sync for everyone.

PDFpen for Mac Sync

As soon as Apple introduced a way to sync iOS and macOS with iCloud in 2011, people wanted it. We could even have PDFpen for Mac share the same iCloud folder as PDFpen for iPad & iPhone and PDFpen Scan+!

But iCloud was limited to apps sold through the App Stores, not sold direct from developers. How to get the iCloud experience to people who bought PDFpen from our Smile store and PDFpen for iPad & iPhone from Apple’s iTunes Store?

We introduced the short-lived PDFpen Cloud Access to be the “iCloud” part of PDFpen for Mac. If you didn’t purchase PDFpen through the Mac App Store, you could purchase PDFpen Cloud Access through the Mac App Store for iCloud access. You can read more about that saga in Greg’s post Smile History: Products That Weren’t. In sum, it didn’t work for long.

Then Apple introduced iCloud Drive. This meant you could use iCloud in the PDFpen iOS apps and access the same PDF on your Mac by opening it from iCloud Drive. This pretty much gave people what they wanted.

iCloud solved!

Except… PDFpen has a Library. You can save up your signature, images, your favorite stamps and proofreading marks to drag and drop into a document. And that Library only syncs thru iCloud.

So we waited, and waited, and joyfully received Apple’s announcement opening iCloud to everything.


PDFpen has changed a lot since 2004, though we’ve kept our focus on making the basics of PDF editing easy to do. PDFpenPro was launched at the same time as PDFpen 2 in 2005, and the product has grown from humble beginnings to a dependable staple as a full featured PDF editor! PDFpen for iPad & iPhone is a solid and powerful PDF editor. I’m quite proud of the whole line.

Here’s a bit of icon history. Just like the products themselves, they’ve come quite a way.

PDFpen Family icons


Smile Founder
Whittler of PDF flavored pens