How to automatically attach a PDF to Gmail (or any web-based email)

Here’s another question we see quite frequently.  Win2PDF has a feature to “Send file” that can be enabled on the file save window (see below).

Send PDF option in Win2PDF
Send PDF from Win2PDF file save window

When this option is checked, Win2PDF will create the PDF file and automatically attach it to a new email message using the computer’s default MAPI email client (which is typically Microsoft Outlook or Windows Live Mail).

But what do you do if you want to attach the PDF to a web-based e-mail client like Gmail or Outlook Web Access?  Since these programs don’t install as a full-fledged email client, how can you use these programs with Win2PDF?

There may be other ways to do this, but we found a software program called Affixa that has a handy way of solving this issue.  Many applications have the built-in capability to send emails, including Win2PDF, but most rely on an external email client.  Affixa  effectively resides in the background and acts as a connector to these web-based email services.  When you use the “Send file” feature in Win2PDF, for example, it will automatically create a draft web email message with the PDF attached.  Voilà!

Affixa Software

Affixa is free for personal use and only about $3 per license for business use.  And it works for any application that has a similar ‘Send to email’ capability, like Microsoft Word.  And it can be configured to work with multiple accounts (like Gmail, Outlook Web Access, Yahoo mail, etc.)

[Note:  we have no affiliation with Affixa – we just found their solution to be quite useful when used with our Win2PDF software].

For more information, please refer to this and other how to articles at our Win2PDF online user guide.

PDF/A – the PDF file for Archiving

Since we added PDF/A support in our most recent Win2PDF 7 release, we’ve had some questions about this new type of PDF file.  First, the basics.

What is PDF/A?

It’s basically a subset of the PDF file format used to archive data for long-term storage (the A stands for PDF/Archive).  It is an ISO standard (ISO 19005-1:2005) that does not need to depend on external programs or information to be displayed, all information is entirely self contained.  It does not permit the inclusion of any executable scripts, audio, video and/or encryption.  In contrast, a regular PDF file may substitute fonts (because not all fonts are saved in the original file), and may have these other types of data “linked” within the PDF file, but not “contained” within the PDF file.

For a longer description, please check out the Wikipedia entry on PDF/A.

Why is it increasingly being used in government (and courts in particular)?

  1. It’s an ISO standard file format.  Regardless of what application creates the PDF/A file, all PDF/A files will conform to the same rules.  Which is good for…
  2. Archiving.  Since these files are self contained buckets of information, the file will be able to be viewed in the future and look exactly as it did when it was created. If the PDF file linked to external information, there is no guarantee that information would be accessible in the future.
  3. It’s more secure and readily accessible.  Again, since it doesn’t allow encryption  it keeps the document accessible, and since it doesn’t allow external links to data sources, it prevents security exploits.  And finally…
  4. It’s mandated in many situations.  The Administrative Office of the US Courts identified the potential risk of not being able to reliably access archived digital files in the future in 2010.  Since then, many district Courts  now mandate the PDF/A standard for court documents.  It is also mandated by law in several European countries.

There’s other interesting information on the Legal Case for PDF/A from the PDF Association’s web site (

How do I make a PDF/A file?

With Win2PDF 7,  just select “PDF for Archiving (PDF/A)” as the Win2PDF file save type.  [Update:  Win2PDF will create a file that complies with the PDF/A-1b standard)].  It will still have a .pdf file extension, and it is just as easy to create a PDF/A file as it is to create a normal PDF file.

Win2PDF Save As PDF/A
Win2PDF file save window - Save as PDF/A

How do I know Win2PDF has created a PDF/A file?

First, make sure you have the latest version of Adobe Reader installed.  Then, open the PDF file and you’ll see a notice in Adobe Reader that states:  “The file you have opened complies with the PDF/A standard and has been opened read-only to prevent modification.”

PDF/A file in Adobe Reader
PDF/A file in Adobe Reader

Signed, Sealed, Delivered – Digital Signatures vs. Electronic Signatures

We frequently get questions about our product (Win2PDF) and its support of digital signatures.  While we have investigated adding this as a feature, there are many variations in implementation and some general misunderstandings of what “digital signatures” really are that makes it difficult to provide a universal solution to this problem.

Generally, when people speak of ‘signing a document’ they mean to apply some form of electronic signature to the PDF, and this can be done either simply (typically called an electronic signature), or in a way that is more advanced (typically called a digital signature).  A brief explanation of both:

  • An electronic signature is a general method of signing an electronic document, and it typically works by associating a marker (such as a .JPG representation of a person’s hand-written signature) to a PDF file. An electronic signature is easy to implement, but also offers fewer protections and can be easier to forge.
  • digital signature is a more sophisticated implementation of electronic signatures that associates an encrypted “fingerprint” on a PDF file. This “fingerprint” is unique to both the document and the signer and ensures the authenticity of the signer. If the PDF is changed after it is signed, it invalidates the signature.  Generally, it is a more secure method of protecting the integrity of a signed PDF file.

If you’re interested, more details can be found at this FAQ about digital signatures.

There are several different approaches to signing PDF files, and different organizations may require different levels of sophistication in their files.  A legal document sent by a lawyer, for example, may have a more stringent requirement for authentication than, say, a document that just needs an ‘sign-off’ by a manager for a particular internal process.

So, which version will you need?  That will require some more investigation on the type of solution that best fits your business needs.  One interesting recent development is that the latest version of Adobe Reader has announced some native support for “electronic signatures”.  While this isn’t an advanced digital signature solution it may suffice for many users.  And because the basic signing capability is included with Adobe Reader the implementation is easy.

Adobe acquired Echosign (a company specializing in signature technology) in July of 2011, and earlier this month they announced that the native Echosign functionality was included in the latest Adobe Reader application.  This integration will allow users to electronically sign any document in Adobe Reader (with a new “Sign” button) and then send the document out for others to sign through the Echosign web site.  Here’s a screen shot of the new Adobe Reader interface.

Adobe digital signature screen shot
Adobe Digital Signature

There are some free capabilities for a single user, but to effectively use this electronic signature capability within an organization requires a subscription to Echosign.

This is an interesting development for many users, but it still may not be the right solution for all companies.  Other companies offering digital signature solutions include IdentrustAppligent, Arx, and DocuSign.

Back to the discussion of incorporating the digital signature feature into Win2PDF?  Well, because of the variety of solutions available, and the different requirements for different organizations, we’ve found it best to provide a method to integrate with other solutions instead of trying to create a solution that will fit every user’s needs.  We do this by providing a mechanism to a launch an external application after creating the PDF file with Win2PDF.

Actually, if you are interested in this Win2PDF mechanism, send an e-mail to [email protected] and ask for more details.  We have a Win2PDF Admin Utility that can make this a little easier, but we don’t have it fully documented…  yet.

Signing off…