28 December 2015

How to Select Email Encryption Software? 4 Practical Questions to Answer Before Making a Choice.

Every day, we field phone calls, live chats and (unencrypted) email messages from people who are in search of information about email encryption.  The caller will usually begin their Q&A with a very general statement such as, "I need to encrypt emails. Tell me how to do it."

Because Encryptomatic LLC has been helping people encrypt sensitive emails for more than a decade, this is where I usually pause the conversation to get more information.  By the time I get to speak to the caller, they have already been overwhelmed with arcane terms, even more arcane encryption technologies, government regulations that threaten terrible consequences, prices that range from hundreds of thousands of dollars to free open source software, and they are confused.

Before I frustrate them any further, I ask them four questions that will help me determine whether or not any of our products are a fit.

1. Which email client, if any, do you or your organization work with?

Start with your email client and work backwards.  If you represent a company with 1,000 desktops, and everyone is a seasoned Microsoft Outlook user, then you really want to find a solution that works well with Outlook. Likewise, if you use Thunderbird, or Gmail, that's where you should begin your search.

2. What regulations bind you?

Understanding the requirements of your industry is crucial.  Don't take shortcuts. It will serve you well to make a knowledge investment here.  Convince your boss to send you to that industry security conference so that you can obtain this expertise for your organization. Beware of any sales people who tell you that they are already "compliant," and that you can just trust their self-certified software.  While you can certainly take their advice (or my advice for that matter), what your organization needs is an in-house expert who has some exposure to the industry regs that bind you. Also be aware of compliance and archiving requirements for your industry.

3. Who will be receiving your encrypted messages?

Don't forget that sending encrypted emails is only half of what is required.  You can send secure emails all day long, but it won't help if the recipient cannot receive your messages.  Understand who is the intended recpient, and how much work are they willing to do to open your messages.  Do they share your motivation to encrypt email messages?  It is different to ask someone who is tech saavy to install encryption software versus someone who is a casual customer. Make sure that your important intiative to protect email communications doesn't fail at the point of reception.

4. Who are you willing to deal with?

Selecting email encryption software for your organization is a big commitment in training, implementation and processes. It means partnering with your supplier to protect crucial communications.  Don't choose the wrong company to work with. Encryption software will need regular updates. You will have questions and need answers, so make sure they answer the phone and respond to emails.

Open source software is great for the right companies,  especially those with a developer on staff who understands encryption and can fix bugs along the way. If that's not your company, then working with a software publisher that issues updates and can respond to your customization requests will be important.

Which Email Encryption Solution is Best?

If there was a single answer to that questions, your job would be easy.  You could just go into the market and find the best price and voila! Problem solved.

As you no doubt have discovered, there are many different approaches to email encryption. Lets break a few of them out.

Pretty Good Privacy, or PGP has been around since the 1990's and is still generally considered to be both the most secure method of email encryption, as well as the most difficulty. In this case, high security equals high difficulty.  PGP is supported by both large corporation entities such as Symantec as well as a core of dedicated open source encryption enthusiasts with a passion for privacy.   Each person has a public key that they share with the world, and a private that they keep safe and secret.  Anyone can encrypt an email for you using your public key, then you use your private key to unlock that message. The math is complicated, but it works very well.  Just remember: share you public key, and protect your private key.

Encryptomatic Open PGP add-in for Outlook, shown in Outlook 2016 toolbar.
OpenPGP Add-in for MS Outlook

Encryptomatic LLC has contributed to OpenPGP with an add-in designed specifically for Microsoft Outlook users.  We wanted to make it accessible, so Encryptomatic OpenPGP for Outlook is free for personal use, journalists, activists and non-profit organizations, and affordable for everyone else. You can learn more and try it free.

Symmetric Key Solutions
There are lots of email encryption solutions that rely on the sender and receiver knowing the same key.  These are generally quite easy to use, but less secure and the key (or password) must be shared privately between the sender and receiver, and this sharing creates a vulnerability.

Symmetric key email encryption has its place. It's easy for recipients.  Encryptomatic LLC has designed a couple of symmetric key email encryption add-ins for Outlook.

MessageLock is useful when both recipients have Outlook and MessageLock. The process of sending and receiving secure messages can be made seamless, automatic and invisible.

Screen image of MessageLock add-in for Outlook.
MessageLock email encryption for Outlook

For cross platform compatibility and ease of use, our PDF Postman solution is hard to beat. PDF Postman encrypted emails and files and places them within an encrypted PDF envelope, which means that any recipient who knows the password and has a device with a PDF reader can open the message.

Image showing PDF Postman message in Gmail inbox.
PDF Postman for Outlook

Email Encryption as a Service
Many companies have discovered that they need something between end-to-end OpenPGP and simple password encryption. That is where a mediated solution might be the best fit.  Encryptomatic LLC operates Lockbin.com, which implements encrypted messaging as a service that enables sending and receiving to anyone.  The recipient does not need special software. A simple and non-invasive signup process for a free Lockbin account is all that is asked of the recipient. Management of public and private keys happens behind the scenes, even while the Lockbin acocunt holder maintains full control over their public/private key pair.

While there are many other service providers in this space, Lockbin differentiates itself through its longevity and through a product set that includes online access via Lockbin.com, an Android app on Google Play, a Java app and an convenient add-in for Microsoft Outlook.

The downside to using email encryption as a service is that it is never trustless. The service provider could, if required by law, capture the credentials and supply them to the demanding authority.

In conclusion...
We hope this has been useful. Feel free to contact Encrptomatic's support and sales people. We will be happy to discuss your requirements, and recommend the best product for your needs as we understand them, even if it is not our own product.  Life is too short for unhappy customers, and so if you are not a good fit for our products, we will tell you so.

If you found this article helpful, please tell us below or feel free to share.

15 December 2015

Becoming an Email-to-PDF Conversion Jedi

When Stars Wars launched in 1977, relatively few people had ever heard of email, let alone received one. Even though other forms of messaging have largely overtaken email in our personal lives, business and customer communications often are sent by email because of it's open characteristics. The same openness that has allowed spam to become a huge problem for email administrators is also what makes it useful for communicating with customers and others who want to do business with our organizations.

At Encryptomatic LLC, we are focused on helping our customers manage their e-mail content. One of the important tasks that help people perform is converting email into different formats. In particular, PDF portable document format.  PDF is everywhere. It's used for storing, organizing and sharing email across platforms.

Our customers frequently find our products after spending days trying to cobble together an email-to-pdf conversion solution. While installing a PDF print driver sounds like a reasonable way to go, and is often cited as the first method that our customers try,  the problems of this method quickly become aparent.

PDF print drivers just can't handle complex email formatting, and they don't offer the functionality that quickly becomes an obvious need:
  • They don't provide custom file naming, forcing you to manually name the files
  • They can't handle email file attachments automatically
  • They can't export email in bulk
  • Bulk exported email can't be organized in subfolders
  • and so on...
Encryptomatic LLC offers products that push the traditional limitations on email conversion, addressing all of the aforementioned problems.  Ten years of listening to our customers and dealing with their issues have helped us to develop an uncommon set of products that help you get your email conversion work done accurately and quickly.

Email messages that can not be accurately read, printed or converted by competitor's products will probably render just fine in our software. If they don't, let us know and we will code a fix.  Over the years our developers have discovered and coded solutions into our products for hundreds of unique and uncommon format exceptions that exist in the wild.

Yes, there are published email specifications that if respected to by all developers would make life much easier for software developers.  The reality,  however is that there are many email clients and applications that produce poorly formatted email content.  Our email rendering engine, MVCOM is probably the most accurate and expansive product of its type ever developed.  MVCOM drives the rendering of email content in PstViewer Pro, and MsgViewer Lite, two of our email viewing products.

For Microsoft Windows Office Outlook users, MessageExport  vastly expands and simplifies converting Outlook email to PDF and many other formats.  It lets you automate routine email export tasks, and perform PDF conversion with uncommon simplicity and utility.

Screen image of MessageExport toolbar in Outlook 2016.
MessageExport add-in for Outlook.

We hope you'll take our products for a test drive. They are well worth the price. It will not take you very long to recover your investment in our products in time savings and productivity.  The average moderately-heavy MessageExport user recovers their investment in about one week.

Thanks for stopping by, and feel free to post any questions for us here. We love to hear from you.

03 December 2015

MessageExport add-in for Outlook, version 4.0 released.

Screen image of MessageExport addin, in Outlook 2016.
Export Outlook emails with MessageExport add-in.

MessageExport was updated today. Version 4.0 is available through the software upgrade service, or at the product home page, https://www.encryptomatic.com/messageexport/

Version 4.0 brings tested support for Outlook 2016, an updated help system and fixes for customer contributed issues.
MessageExport add-in for Microsoft ‪#‎Outlook‬ is the premier tool for exporting, converting and copying Outlook ‪#‎email‬ messages to ‪#‎PDF‬ and many other formats. Convert emails in bulk, individually, or automate the email export process.

12 November 2015

Encryptomatic OpenPGP Addon for Microsoft Outlook now in Open Beta.

We are excited to introduce you to Encryptomatic Open PGP, our latest professional addon for Microsoft Outlook. Encryptomatic OpenPGP is now in open beta! This add-on brings strong eliptic curve encryption (public key encryption) to Microsoft Outlook 2016/2013/2010 for users of Microsoft Windows 10/8/7. And, it's free for personal use!

If you are someone who is required either by law or conscience to protect your email communications, or just a spy wanna-be, we think you will apppreciate the thought that has been given to Encryptomatic Open PGP.

As you might be aware, most people do not encrypt emails because it's difficult. In particular, sharing and importing public keys has proven to be a problem, as well as the availability of inexpensive and professionally supported software.

Our team paid a lot of attention to simplicity in sharing private keys.  Encryptomatic OpenPGP will automatically import public keys that others send you, and it's easy to share to your key with just a couple of clicks.

Like all of our products released over the past decade, there is no spyware, malware, adware, or anything or kind of privacy intruding software embedded within Encryptomatic OpenPGP.

Join us in this open Beta and tell us below how we can make it better. We want to hear from you.

01 September 2015

What is the Best Email Encryption Software For Microsoft Outlook? Four Add-ons Reviewed. (Part 2)

This is the second article in a two part series that examines the four email encryption add-ons developed for Microsoft Outlook by Encryptomatic LLC. I will assume you have absorbed the basic idea between symmetric and assymetric encryption schemes in part one.

Why does Encryptomatic LLC offer four different add-ons for encrypting Outlook email?  Why not just one? Each add-on has a sweet spot based mainly around processes.  It's no use sending a highly secure message to someone who will never be able to read it. Likelywise, if there is very little protection, then the message is probably best left unsent.

All of add-ons, if used responsibly, can provide a high degree of privacy for the message, especially against non-state actors. If you want to protect your message from people inside your company, your ISP, or Google, then any of our addons will suffice.  If you are trying to avoid NSA eavesdropping, then the best answer for you is OpenPGP.

Encryptomatic OpenPGP


Our new OpenPGP add-on for Microsoft Outlook will join our product lineup in late 2015. It is currently in beta. If you are interested in trying the beta, please email supportline at encryptomatic.com

We decided to create this product after listening to customers who were required to use OpenPGP to communicate with insurance companies.  They had no choice in the selection of the encryption method; they had to use OpenPGP, and they were struggling with the cost and complexity of installing it.

We also learned that some of the offerings available were simply not working very well in Outlook. They were difficult to use, and referenced outside applications for key management.  While Encryptomatic OpenPGP is still a work in progress, we believe that compared to other addons in the market, ours has the easiest setup and implementation process, a fair price (free for personal use) and a use process that is simple and unobtrusive.

OpenPGP email encryption add-on for MS Outlook.
Encryptomatic OpenPGP addon toolbar installed in Microsoft Outlook
Encryptomatic OpenPGP provide the ability to encrypt, sign and manage keys, and is interoperable with other PGP software.  We recommend Encryptomatic OpenPGP wherever PGP is used, and when security and privacy trumps convenience.  As OpenPGP integrations with Microsoft Outlook go, we think you'll find our software to be the most useable available. If not, please let us know and we'll make it better.

Price: Encryptomatic OpenPGP is free for personal use.  Contact support at encryptomatic.com for business pricing.


Lockbin is a service for secure communication build around convenience, and the ability to send a message to anyone. It is typically used by doctors, lawyers, accountants, transcriptionist,  and other smaller office professionals who need an effective and practical way to communicate with  patients, clients and customers who are not sophisticated enough to implement OpenPGP.

Although Lockbin has a free add-in for Microsoft Outlook, the secure messages can also be retrieved by signing in to Lockbin.com,  on an Android app, or through the Lockbin Java application.

Screen shot showing the icons of the Lockbin toolbar in Outlook 2013.  The icons are titled: Settings, Receive Messages, and Send Request
Lockbin email encryption toolbar in Microsoft Outlook.
Lockbin uses public/private key encryption, but has simplified the process.  All messages on the Lockbin servers are encrypted at all times. No private keys are accessible on the servers, even to staff.

Lockbin gives you the ability to easily send secure messages to anyone. When you want to send a message to someone who is unknown to Lockbin, it will send an invitation to the recipient inviting them to a free account.  The signup process is free, immediate, simple, advertising free and non-invasive. 

Lockbin works best when both parties have a Lockbin account, but you can optionally send a password protected symmetric key encryption message to the recipient.

There is no charge for the Lockbin add-on for Microsoft Outlook.  Lockbin basic accounts are free. Premium accounts start at $4.95 per month for a single user, with discounts for multiple users.
Download the Lockbin addon for Outlook.

PDF Postman

PDF Postman toolbar in Outlook 2013. Buttons read "PDF Encrypt Email," "PDF Encrypt Files," and "PDF Files."
PDF Postman encryption addon for Microsoft Outlook

PDF Postman is intended as a uni-directional communication process. That is, if you need to privately send a message and/or file to someone who cannot be bothered to sign up for anything or install special software, and a reply is not expected, then PDF Postman may be a good fit for you.

PDF Postman uses the common Portable Document Format, aka PDF files, to protect your messages.  AES-256 bit strong encryption is built into the PDF specification. Any spec compliant PDF reader such as Adobe Reader, can decrypt a PDF Postman message. This is useful because it means PDF Postman messages can be opened across any device platform: Windows, Linux, iOS, Android -- any device that has a compliant reader.

To open a PDF Postman encrypted PDF file, the recipient simply clicks on it. The encrypted PDF file is automatically loaded into the viewer, which recognizes that the file is encrypted and asks for a password.

PDF Exchange viewer prompting "Please enter valid user or owner passwrod for the document."
PDF viewer prompting for a password.
 When the correct password is entered, the PDF message can be viewed.

PDF Postman is $69.99 for a single license and one year of updates and support.
Download a free trial of PDF Postman


MessageLock toolbar. Text reads, Options, Help, Encrypt Message, Encrypt Attachments, Compress Files.
MessageLock toolbar in Microsoft Outlook

MessageLock is a simple and seamless end-to-end email encryption option for Microsoft Outlook. It is at its best when all users have Microsoft Outlook and MessageLock.

MessageLock can be sent to automatically encrypt messages to other MessageLock users. This is convenient and makes sending secure messages a essentially a background task that does not interrupt the sender or recipient.

MessageLock supports using different passwords for sending and receiving messages. Messages may be decrypted automatically when received and placed in the normal Outlook e-mail list.

If you will be regularly communicating with a small group of other Outlook users and end-to-end privacy is desired, then MessageLock may be right for you.

MessageLock also has an integration with Lockbin, so that you can send and receive messages through the Lockbin service. This makes MessageLock useful as both a end-to-end system, and as a "send to anyone" system.

MessageLock is $49.99 for a single license and one year of updates and support.
A free 15 day trial is available to download.

Which Email Encryption Add-on Is Best?

If you are still unclear which of the four Outlook email encryption add-ons we discussed is best for you,  just try them!  All are available on a 15 day free trial.

If you have any questions, post them in the comments below, or email us our Sales team at sales at encryptomatic.com. You can also call us, 1-651-851-4902.

We are always willing to listen to your situation and recommend the best product to fit your specific situation.

What is the Best Email Encryption Software For Microsoft Outlook? Four Add-ons Reviewed. (Part 1)

E-Mail encryption has quickly moved into the mainstream. Once the exclusive domain for spies, protecting our email communication will soon be as common as locking the doors and windows to our homes.  When email encryption is not mandated by law to protect certain kinds of data (Patient Health Information, for example), it is still a good idea.

Encryptomatic LLC has helped tens of thousands of companies find practical ways to encrypt email communications end-to-end. This article looks at four add-ons for Microsoft Outlook that our company developed and currently supports.  These add-ons are:

Why did we develop four add-ons, and not just one, especially when they are not compatible with each other?  We believe that the best e-mail encryption is the one that gets used. And while there are differences in overall defendability between the algorithms,  if the solution is so complicated, convoluted and impossible to implement, then it provides no protection in the end.

Each of our products as a "sweet spot" where it does certain things very well, mostly around process and convenience. In this article we will discuss each of our products, why it came to be, and what we see as the sweet spot for that product. By creating four differet products, our intent was not to confuse you, but to build a solution that would be a great fit for your business processes.  So that you will actually use it.

Symmetric versus Assymetric Key Encryption

Before we begin, let me say a few words about email encryption.  If you already understand this concept, then feel free to skip ahead to the next section.

The most difficult part of email encryption for the sender and receiver (outside of setting up the software) is exchanging keys. These keys are used to protect and open messages. An appropriate key is hopefully a very long and random sequence of numbers, letters and characters. Hopefully you would never use a key such as "Password123."  A key can also be computer generated, and split into a public part and a private part using complicated math.

OpenPGP is an assymetric scheme, which means each person particpating has a two keys: a public key and a private key. You are free to share the public key with anyone. You tweet your public key or even post it to Facebook. It is for the world to see. Your public key is used by others to encrypt messages destined for your inbox.  The amazing thing is that only your private key can open messages that have been encrypted with your public key.  It's important to keep your private key absolutely private.  But your public key can be given away to anyone.

In symmetric key encryption schemes are little more simple. The the same password that encrypts a message is used to decrypt the message.  It's sort of like those old movies when some knocks on a door and is asked "What's the password," before they can enter through.  A symmetric key must be kept secret by both the sender and the recipient.  It must also be agreed on between the sender and recipient.  Unless symmetric keys are agreed upon by two individuals in person, smmetric schemes are more susceptible to state actors who can monitor multiple sources of communication. Of course, you should never send the symmetric password in an email. But a state actor could possibly monitor you telephone or instant messaging or other mode of communication used to share the password.

Why use anything else?

If assymetric schemes like OpenPGP are clearly better, why would anyone use a symmetric password?   The trade off is often ease of use. If you are a sophisticated technologist and so are your friends and people you work with, then you should definitely use OpenPGP. No question about it.

But what if you want to send some important tax documents to your Dad, who is not very sophisticated? Ideally, you would invest the time to educate Dad (and maybe even Mom) and help them set everything up on there computer, show them how to generate a public/private key pair.

Depending on your situation, educating Dad and Mom may not be practical.  In this case, if the option is to just give up and say "To heck with it, I'll send it unencrypted," symmetric key (password) encryption is a much better option.  With a symmetric password communicated by phone, your Dad can receive the document and easily open it when it arrives by simply typing in the password.

In Part 2, we will take a look at the four Outlook email encryption add-ons  provided by Encryptomatic LLC.

Continue to PART 2

31 August 2015

We have updated the PDF Postman addon for Microsoft Outlook! Version 2.5, build 319 is the latest maintenance release. It's now available at https://www.encryptomatic.com/pdfpostman/download/

This update is recommended for all PDF Postman customers.

The following issues reported by users were resolved in this update:

- 0004881: [Fix] Replace notification image, due to misspelling
- 0004819: [Development] Message "The system cannot find the file specified" during the installation (protected 32-bit .msi)
- 0004694: [Fix] Crash when adding password entry to the remote database
- 0004792: [Fix] Synchronization for remote and local password storage databases

PDF Postman is an addin for Microsoft Outlook for end-to-end encrypted communications by email.. It's used to send encrypted PDF messages and files using the common PDF envelope. This method reduces the buden on recipients and makes it practical to protect important data.

#emailencryption #email #outlook

15 July 2015

OutDisk FTP add-in for Microsoft Outlook is Updated.

We have updated OutDisk FTP add-in for Microsoft Outlook. Version 4.62.15 of OutDisk FTP is available for download from the OutDisk product home page.

OutDisk is an add-in that integrates file upload capability directly into Microsoft Outlook.  With OutDisk, IT professionals can create an in-house file transfer service using their own servers, making it easy for non-technical users to send file attachments in Outlook e-mails.  To use OutDisk FTP, just attach files to an Outlook e-mail as normal, and send the email message. Files exceeding a pre-set size can be automatically uploaded to your company FTP server, and a link inserted into the e-mail. Recipient's can download the file through their web browser, bypassing strict email server file size limits.

This release of OutDisk adds some new features and resolves some bugs.
- 0001674: [Add] License release option 
- 0004253: [Fix] Zip file is created instead of self-extracting archive 
- 0002775: [Add] Improvements for registration system 
- 0004593: [Fix] Exception in add-in preferences

Learn more and download a free trial of OutDisk FTP!

24 June 2015

PstViewer Pro Update

We have released PstViewer Pro 7.5.460 maintenance release.

This release is optional, and focused on improving the experience for customers who use the command line switches.

PstViewer Pro is an email converter and viewer. Use PstViewer Pro to open email content contained in .pst, .ost, .msg and .eml files.  PstViewer Pro converts e-mail into PDF documents. 

Download the update.

22 June 2015

MessageExport 3.7 Email Export Add-in for Microsoft Outlook is Updated.

MessageExport version 3.7.0 is now available for download.  This is a maintenance update and is recommended for all users. It improves performance and resolves an issue that may occur during batch export operations of email file attachments.

Download MessageExport from the product home page. 

Convert Outlook e-mail as PDF with MessageExport toolbar.
MessageExport email export add-in for Microsoft Outlook.

What is MessageExport?
MessageExport is an add-on for Microsoft Office Outlook 2013/2010/2007 developed by Encryptomatic LLC. It integrates tightly with the Outlook menu system, adding new capabilities that facilitate the export and conversion of e-mail messages. 

With MessageExport, Outlook e-mail may be converted into PDF and other formats.