Have a question? Search our Knowledge Base for answers. 

Here are a few of our other resources:

"Thank you so much for your reply! Everything you told me worked like a charm. To be honest...I didn't even expect a reply. I've emailed companies so many times and as far as I can recall...this is the very first time someone ever even bothered to reply at all. You not only replied...but you replied promptly—and—actually solved my problems!"
—Doug Hoyer, Kailua, Hawaii

Frequently Asked Questions

How do I install PDFpen?

See the installation instructions here.

How do I buy PDFpen?

Buy PDFpen now from our web store. To buy from within the product itself click here for instructions.

PDFpen won't register no matter what! What do I do?

You can find directions on our Activation Help page.

I bought from the Mac App Store and the upgrade isn't working!

Find directions to upgrade PDFpen. If they don't help, contact support.

I purchased on the Mac App Store after August 1, 2014. How do I get a free upgrade?

PDFpen or PDFpen 7 can only be upgraded for free via download of the direct-purchase version of PDFpen or PDFpen 7, not via the Mac App Store version. When you launch the downloaded app, you'll be prompted to locate your PDFpen 6 Mac App Store receipt file, as that can only be read with your permission. Once your receipt is verified, PDFpen or PDFpen 7 will offer to contact our server and issue you a license to the direct purchase version.

Are PDFpen and PDFpenPro compatible with Mac OS X 10.10 (Yosemite)?

The latest versions of PDFpen and PDFpenPro are compatible with the latest version of 10.10. See our Mavericks page to find more details on version support in Mavericks.

(Download the latest version of PDFpen and PDFpenPro here.)

I have more than one computer. Does a single license allow me to install on all of them?

Yes, if you are the only user of those computers. If you have multiple computers used by more than one person in the same household, you can purchase a Family Pack license, which covers 5 computers in the same household. (Click here for more information.)

How does PDFpen compare to Adobe Acrobat and Preview?

See this comparison chart of PDF editing features in other PDF editing software.

What is the difference between PDFpen and PDFpenPro?

PDFpenPro has all the PDF editing features of PDFpen. PDFpenPro also has the ability to:

  • Convert websites to multi-page PDFs, complete with hyperlinks
  • Create cross-platform fillable PDF forms
  • Export to Microsoft® Excel, PowerPoint and PDF/A formats
  • Create and edit PDF document Table of Contents.
  • Create form fields automatically in a non-interactive form
  • Edit document permissions to restrict saving, printing, copying, etc.

More information about PDFpenPro.

What if I don't have Mac OS X 10.10 or later?

For Mac OS X 10.9-10.7 please download PDFpen 6.3.2. Mac OS X 10.6 please download PDFpen 5.9.5. For Mac OS X 10.4 and 10.5, please download PDFpen 4.7.1. For Mac OS X 10.2.5 - 10.3.9, please download PDFpen 2.4.3.

How can I purchase a license for version 6.x or earlier?

We stopped selling v.6 licenses when v.7 was released. A current version license of PDFpen v.7, can be used to register a previous version, like v.6. This license will also work in the future to register PDFpen v.7 should you update beyond Mac OS X 10.9 Mavericks and need to be able to run PDFpen v.7.

Is there an education discount?

Yes, there is a 30% education discount. Please visit our education store for more details.

When are updates available on the Mac App Store?

Smile submits applications for review by the Mac App Store on the day that they are released. Apple must approve the update, and has sole control over when they appear in the Mac App Store.

How do I use PDFpen with iCloud Drive?

Learn more about and iCloud Drive on our blog.


I launched PDFpen, but nothing happened. What's wrong?

Look for the PDFpen icon in the Dock. If you click you'll see that the upper-left text in the menu bar changes to "PDFpen". To proceed, select "File > Open" from the menu. PDFpen needs you to open a PDF file to begin. PDFpen can launch PDFs, Word documents and other image formats such as JPG, TIFF, PNG. If you prefer to start from scratch select "File > New One Page Document".

How can I set up PDFpen as the default PDF program instead of Preview or Adobe Reader?

Select a PDF file in the Finder, and then select File > Get Info. Locate the "Open with" section in the resulting window and change it to PDFpen. Click the Change All button that then appears below and PDFpen will be the default.

Why is there a Smile logo on my PDF when I save it?

Documents saved by the PDFpen demo retain this watermark. The only way to remove the watermark is to purchase  a license for PDFpen and register the application.
When you open a watermarked document with a registered copy of PDFpen, the watermark will be removed automatically and you can simply save again to permanently remove it. Do not save watermarked documents using File > Print > PDF > Save as PDF... or the watermark will remain permanently as though you'd printed to a physical printer.

Export a PDF to Word format, hows and whys.

If you have questions regarding PDFpen's export to Word feature, please see Word Export. If you have PDFpenPro, this is where you can find out more about PDF to Excel, PowerPoint and PDF/A format.

I need the ability to write freehand. Can PDFpen work with my tablet device?

Yes, PDFpen works with pen tablet devices such as Wacom Bamboo, Axiotron's Modbook etc. For quick markups, you can use the "Scribble Tool" for freehand drawing on your PDF. To use this tool simply, launch your PDF with PDFpen, select the Scribble Tool and write away.

Can I use Outlook or another email client for File -> Email Document?

Yes, PDFpen uses your default email client for that function. To set your default email client, launch Apple's Mail application and visit its General preferences. Set your Default email reader to Outlook or another email application then quit Mail. PDFpen will now use your newly-specified email client for File -> Email Document.

Storing and Editing Documents in iCloud

What are the system and version requirements for iCloud?

You will need PDFpen or PDFpenPro 6.0 or later on OS X Lion 10.7.2 or later to access PDFpen documents on iCloud (Mac App Store version only).

Apple restricts iCloud access to applications purchased through the Mac App Store.

You can use iCloud Drive in place of iCloud if you are running OS X Yosemite 10.10. To use iCloud Drive with your iPad or iPhone you need to run iOS 8.

Editing Documents

Can PDFpen do actual text editing: replace or change wording, change paragraph spacing, change font type, etc?

Yes. Select the text you want to modify using the “Select Text” tool, and click the "Correct Text" button in the toolbar. The selected text will be replaced by an editable text block.

How do I get a tool to revert to the Select tool after each use?

By default, a tool will stay selected after each use. To override this, double-click the tool. The Select tool will become active after each use of the Text tool. You can also uncheck the "Keep tools selected after use” option in Preferences.

I started typing some text using the Text tool, but it is too wide. I have resized my text box, but when I try to type in it after resizing, it reverts to its original size. How can I keep the new size?

Select the text box, and choose "Edit > Wrap Text" from the main menu.
Note: If you use the text box tool to drag out a text box, instead of just clicking to create a text box, Wrap Text is the default behavior.

How can I adjust font size and type in PDFpen?

To change the font on your current document, choose Format > Font > Show Fonts and select your font type and size. If the size does not change automatically, go to the Cog dropdown menu and choose "Edit Sizes." To set you default font size for current and future documents, choose PDFpen > Preferences. Then, under "General Preferences," you can select "Default font."

Why can't I print or modify my document in PDFpen?

Is this a document-specific issue? Otherwise, authors of PDF documents may set permissions separate from those in the operating system. These permissions govern the abilities to edit, save and print documents, and PDFpen respects these permissions. To edit you will need to contact the original author of the document and ask for a version without restrictions.

How do I reduce the size of my PDF file?

You can reduce the color depth and resolution of images and scanned pages by choosing Edit > Resample Image. Reducing a color scan to monochrome text will significantly reduce file size. For color images you can recompress them with a selective JPEG quality so they take less space but remain in color. See the PDFpen Help for more details under "Images, Signatures and Imprints" and "Scanning." Another way to reduce file size is to apply a Quartz filter when saving the document.

How do I flatten a PDF so that the elements I've added in PDFpen are no longer editable?

Choose Print from the File menu, and then click Save as PDF. The resulting file will not be editable in most PDF viewers. It will still be editable in PDFpen 3.X / PDFpenPro 3.X and later versions, because these versions allow you to edit any images in a PDF file, including ones that have been added by PDFpen and PDFpenPro.

Why are my pages not rendering in order?

PDFpen draws thumbnail images of document pages in the background, and the most recently requested sequence of images (e.g. where I've just scrolled to) is drawn first. If you have two processors you'll find that pages are frequently rendered out of order as PDFpen utilizes both of them to generate the thumbnails.

Can a PDF roundtrip to Word or other formats?

Yes. In order to open a Word document in PDFpen/Pro, from PDFpen/Pro select File > Open and then locate a DOC or DOCX file on your HD. It will open in PDFpen/Pro as a PDF. In order to export a PDF to a Word document:

  1. Open the PDF you would like to convert and go to File > Export…
  2. An Export to: dialog will open. Select a type of Word document, Word (DOC) or Word 2007 (DOCX).
  3. Click Export. Depending on the size of the PDF this may take a moment. The dialog will change to show a progress bar along with the amount of time elapsed since the conversion started, and the estimated amount of time the conversion will take.
  4. Once the conversion is finished a Save dialog appears. Choose where on your hard drive to save this new Word document. Open After Saving is checked by default. Find this at the bottom of the dialog box.
  5. Click Save to finish.

Scanning & OCR

I want to Import from Scanner. How can I get my scanner to appear under Devices?

We use Apple's Image Capture framework for our scanning support, so your scanner should appear in the Image Capture application. If you do not see your scanner, you might try contacting Apple (AppleCare for your Mac) to see if they can help get your scanner working with Image Capture. Once that's sorted, it should also work with PDFpen.

What is OCR, and what happens to a document post-OCR?

OCR (Optical Character Recognition) is the process of converting a bitmap image of text (like a scanned document) into text that can be selected, copied and searched by PDFpen and other text editing software. When you OCR your document, the transformation occurs directly on the page as a text layer image-- it would not create another document. There is no extra output file. After the OCR progress bar finishes, you can edit the content of your document on the page in front of you.
Note: OCR will not produce an exact rendering of the text. You will need to proofread and edit the results. Some scanned documents perform better than others. See our OCR tips.

OCR isn't working very well.

For tips on how to get the best OCR results see our OCR tips.

The OCR option is grayed out. How do I manually activate OCR?

Simultaneously hold down the Command+Option keys while choosing Edit > OCR Document. If you let go of Command+Option while in the Edit menu, the OCR option will switch from “OCR Document” to “OCR Page.”

Which OCR engine does PDFpen use?

On Intel-based Macs, PDFpen uses the OmniPage OCR engine, version 15.5, from Nuance Communications, Inc. For more info on OmniPage, please choose Help > License Agreement from the menu or visit and note that not all features of the SDK are licensed for use in PDFpen.

On PowerPC-based Macs, PDFpen uses the Tesseract Open Source OCR Engine. For more info on Tesseract, please choose Help > License Agreement from the menu or visit

Working with Images & Annotations

I want to sign my document. How can I do that?

You can sign your document by importing a scanned image of your signature onto the document. Images in JPEG, TIFFs and PNG formats work best. You can find more information on working with signatures here. If you do not have a scanned image available, you can also sign the document using the freehand Scribble Tool.

How can I “white-out” marks on poor/unclean scans or handwritten marks on my document?

If an image is embedded on your document like a watermark (unselectable), you can “white-out” the images by using drawing annotations e.g. scribble tool/textbox/ rectangle tool. For example, creating a rectangle using the Rectangle shape tool with white background fill should cover up the marks.

How can I create or eliminate borders around my textboxes?

You can create or eliminate borders around the textboxes. To create borders, increase the Stroke width > 1.00 in Object Properties. Conversely, if you want to eliminate borders, change Stroke to "None" in Object Properties; or, click on the square color swatch to change the border color to "white".

Document-specific Issues

What should I do when one of my PDFs is crashing PDFpen?

The original document may be off spec, or you may have uncovered a bug. Please try opening the original in PDFpen then select File > Print > PDF > Save as PDF... Open the newly saved document and perform your edits. If that works, please consider sending us the original document so that we can analyze why and hopefully make PDFpen handle that more gracefully in a future release. You can also send us your crash log to examine.

When I “select text” on my document: text disappears, text partially selectable, text changes to strange symbols etc. Why?

The document may be off spec or you may want to check your system for font errors. To check your system for font errors, launch Font Book in your Applications folder. Select the first item in the Fonts (middle) column, then choose Edit > Select All from the menu followed by File > Validate Fonts. If there are problems, you'll need to remove the problem fonts then quit and re-launch PDFpen again. Otherwise, feel free to email us with a copy of your document with details of what you are trying to do and the problems you are having editing so we can examine and reproduce your issue from our end.

I can’t select anything on this document. The tools are grayed out.

Is your document a scanned document or a bitmap image of text the size of a page? If so, please OCR your document.

I OCRed the document, but I still can’t select anything. Why?

The issue may be that you are working with vector graphics (images embedded onto the document like a watermark). In these cases, text cannot be selected. To edit your document, use the Text tool and create a text imprint box with solid background fill and type over the existing text.

Creating Forms & PDFpenPro

I just created a form with PDFpenPro but my recipients using PDF readers cannot save their forms. Why?

PDF readers only have read and write capabilities, and typically cannot save forms. Only PDF editors can save forms. This is how it works across the board. If you are using PDFpenPro v.5x, you can create a "Submit" button which allows users and recipients to work beyond the limitations of PDF Readers. Most Readers support submitting forms in HTML, FDF, XFDF, and PDF formats. You can find more information on PDF applications and submitting forms via Help in PDFpen or online.

How can I adjust tab order?

Choose Arrange > Show Tab order to adjust tab order on your form.

Permissions & Security

Can you limit user interaction on a PDF e.g. Read and Write only?

As of version 6, you can set document permissions. This is a PDFpenPro only feature. (See more on PDFpenPro). 


Does PDFpen support Bates numbering?

Yes, to do this choose Script > Number Pages Using Bates Numbering… If you are familiar with AppleScript, you can hold down the Option key and change the script in the Script Editor.

How can I apply a Header or Footer?

To create a Header or Footer, choose the graphic you want to use. Drag the graphic onto the first page and position it. Then, choose "Imprint all Pages as First" from the Script menu. The Header or Footer should apply throughout the document. If you do not have a graphic, you can create a textbox with the Text tool. Type your text in the box. Then, go to the Script menu > Imprint all Pages as First.

More questions?

Please send us a detailed email and our fast and friendly support team will respond.

Lost your serial number?

Online serial number lookup is available.


People are talking

"You are the best! What wonderful support. Thank you so much for all 
the "how to" emails and the video support. You make this program so
 easy to learn. I write a newsletter and was sent a form to insert in a PDF format. I wanted to add to the bottom "Created by..." and you people made it a snap with your support."

-Rose Marie T., Redondo Beach, CA

"Thanks very much for the prompt response to my question. I've heard on podcasts how responsive Smile is, and I've now experienced it firsthand."

-Martin from Maryland

System Requirements

PDFpen and PDFpenPro 7.x are compatible with Mac OS X 10.10 (Yosemite).

PDFpen 6.x and PDFpenPro 6.x are compatible with Mac OS X 10.7, 10.8, and 10.9 (Lion, Mountain Lion, and Mavericks).

PDFpen 5.x and PDFpenPro 5.x are compatible with Mac OS X 10.6, 10.7, 10.8, and 10.9 (Snow Leopard, Lion, Mountain Lion, and Mavericks). Version 5.8 requires 64-bit Intel Core 2 Duo Mac.

For Intel Core Duo and Solo Macs, please download PDFpen 5.7.2 or PDFpenPro 5.7.2.

For 10.4 and 10.5, please download PDFpen 4.7.2 or PDFpenPro 4.7.2.


Take Control of PDFpen

Take Control CoverFrom Take Control: The ultimate road map to becoming a PDFpen power user!
177 pp., $10

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Need Tips?

Do you miss receiving our tips emails? You can find our Email Tips Archive here.

Available for Download on the App Store

System Requirements:

PDFpen 7 and PDFpenPro 7 require a Mac running OS X 10.10 or later. For previous versions see our downloads page.