Email Security – Part 1: Certificate Signed Emails
1 Star2 Stars3 Stars4 Stars5 Stars (No Ratings Yet)

Email Security – Part 1: Certificate Signed Emails

How and why to install an email signing certificate

Long before Twitter or even SMS (Short Message Service), email was a dominant force in communication spanning from global business reach to the next cubicle over. It still is a highly utilized method of communication, but it brings many complications with it.

For example, the junk-mail game of the traditional stamp and drop method of the postal service was easily carried over into the digital space and renamed as spam. Some of this spam could be confusing to wade through. While some spam is as obvious as African royalty in a financial conundrum, some spam may be sourced as slight variances of trusted domain names. Does Amazon have a Customer Tracking and Assistance department and why are they asking for password verification through a poorly worded and logo-less email?

Conversely, how can one ensure that their legitimate outbound email communication is not flagged or mistaken as something insidious? In a 2015 study, Return Path reported that only 79% of (legitimate) commercial emails actually make it to the intended destination. 1 in 5 commercial emails gets filtered out or flagged one way or another. There are many ways in which this can happen and many points in an email’s lifecycle of WHERE filtering/flagging can happen.

We are going to kick off my venture into the world of commercial blogging with a series about email security. Not only will we be reviewing methods to identify bad emails coming in and how to protect oneself, but we will also be looking into methods to successfully delivering emails and establishing a trusted and reputable brand.

Will Anyone Vouch For This Person?!

Verification of identity can be seen all over the world:

Police officer? “Let me see your badge number so I can phone it in.”

Knock on the door? Let’s have a look through the peephole to see if it is someone recognizable. Don’t recognize them? “Who are you?… Show me your girl scout license number so I can phone it in.”

Technical support for your account? “Would you confirm your mother’s maiden shoe size?

Besides intuition, there are no basic human sense cues that can help verify the origins of an email so it is a little more of a challenge.  The display name, source email address and writing style would be the best indications as to whether the email is legitimate or was composed by a spoofer. One could also follow the cumbersome mail headers and follow the route the email took to see if it makes some sense. However, the email sender is able to make this scrutinization a little laxer.

Coupled with intuition, signing certificates via S/MIME (Secure/Multipurpose Internet Mail Extensions) assist in establishing trust between sender and receiver. The little red Outlook ribbon (green check in Gmail) on a signed email carries with it a hierarchy of root certificates from whichever issuing authority.

In a sense, a signing certificate tells the receiver, “I went out of my way to get a CA (certificate authority) to vouch for me. Also, I paid for it…..” For a recipient that one might be in frequent contact with, this can bring peace of mind at a glance.

Let’s Certify Some Emails

Now that we have gone over the generic overview of email certificates, let’s apply a certificate in practice. Despite the fact that it only accounts for a smallish percentage of total mail origination, this tutorial will go over the application of email certificates to Outlook 2016 on a Windows-based machine.


  • Windows 7+
  • Outlook 2016
  • Possession of a proper security certificate file (.crt)

Execution steps:

  • Open Outlook 2016
  • ‘File’->’Options’->’Trust Center’->’Trust Center Settings’
  • Trust Center window will appear
  • Select ‘Email Security’ in the left menu options

Installing an email signing certificate on Outlook

  • Select ‘Import/Export’ and the window will appear

Email Security

  • Browse to certificate and enter appropriate password (if applicable)
  • Select ‘OK’ and the certificate will import
  • Select ‘Publish to GAL’
    • NOTE: The Global Address List is a list that is tied to some domain management, such, as an LDAP, that will have the certificates available that should be ready for encryption. Otherwise, a sender would need to send a signed certificate to a recipient prior to sending an encrypted message so the recipient will get the certificate to decrypt.

Push to GAL

  • There will be notification that this has completed

Configure certificate for email client

    • Open Outlook 2016
    • Go to the trust center settings outlined in the previous section
    • There is an optional checkbox for ‘Add Digital Signature for Outgoing Messages’
    • This will sign every email generated for that particular email domain

Add Digital Signature

  • Select ‘Settings’
  • Under ‘Security Settings Name’, make sure the correct email domain is selected
  • In the ‘Certificates and Algorithms’ section, make sure the ‘Hash Algorithm’ is higher than ‘SHA1’ (selected by default). ‘SHA256’ is acceptable by most mail services/exchangers so that should be suffice.
  • Select ‘OK’

Security Setting

  • Select ‘OK’ to close the Trust Center.

In order to turn on/off certificate signing or encryption per email, pop the email out and click ‘Options’ up top and select ‘Signing’ or ‘Encrypt’ to enable/disable.

Are the signing certificates enough? Maybe not but that is where intuition comes into play. We’ll discuss that next time.

Happy scrutinizing!

Make sure to check out the rest of the Email Security series:

Check back every Monday for a new article.

  • Pretty component of content. I simply stumbled
    upon your web site and in accession capital to say that I
    acquire actually enjoyed account your blog posts. Anyway I’ll be subscribing for your feeds or
    even I achievement you access consistently quickly.

  • When someone writes an post he/she retains the idea of a user
    in his/her brain that how a user can be aware of it.
    Therefore that’s why this post is great. Thanks!

  • I’m amazed, I have to admit. Seldom do I come across a
    blog that’s equally educative and amusing, and let me tell you, you’ve hit the nail on the head.
    The issue is an issue that too few men and women are speaking intelligently about.
    I’m very happy that I came across this during my search for something regarding this.

  • Men’s gym bags comfortable all look the same- plain black or grey exterior, focused only on functionality, not
    style. Recent years, however, have seen a lean towards
    more colorful and expressive gym bags. Distinct do these bags show a little personality, but additionally they also make it easier to monitor of your things from
    a crowded gym.

    Walking with good posture is in order to make sure you don’t injure ones self.
    Walk as straight as you can and ensure that you do keep shoulders back.
    Bend your elbows at a 90 degree angle. Remember
    seeing people practice walking with a book on their head.

    that’s the idea! When your left feet are forward,
    your left arm should return and vice versa.
    With each step, allow your heel to get to the ground first
    then, roll uncooperative foot transfer.

    When seeking at tops, ab muscles slightly go for
    T-shirt, but a fashionable and an operating one, overly.
    Your best option is a T-shirt made of cotton, may also let your body to breathe while
    doing your exercises and which furthermore light.
    Make certain fabric when they are not avoid is polyester.

    Also, you should go for T-shirts which fit you.
    You need to be fashionable, you like to avoid mesh T-shirts.

    Wraps – I would recommend buying these at the health club if you
    can, they ought to be able to receive the right size for your family.
    My first mistake was buying them at the shop and I ended up getting wraps that were too small for anyone.
    Wraps will cost you about $10 a combine.

    Price always plays a crucial part picking a work out center
    or clothes gym. It could cost you up involving triple digits
    per four week period. Decide how much you will be making use of the gym 30 days and what features search for use to
    see if cost evens itself out. As gyms offer discounts or deals, ensure that to be
    upfront and ask. Oftentimes, military families have significant details.
    Some facilities, pertaining to instance the YMCA,
    offer discounts to pastors’ families and in addition those who use
    certain a insurance coverage or possess a limited gross income.

    Have strategy. If you just emerge at a gym and say, “Okay, I’m getting fit,” but all one does is
    wander around and fiddle by incorporating machines, ensure fail.
    Consult friends have got working out for a long-term time, do some Internet research and physician fellow bodybuilders.

    One of the best activities is use a trainer for a few sessions and let them know what your goals
    are. Look to see if contain an American Council on Exercise (ACE) or similar certification. A
    reliable trainer can instruct you how to put together a workout, track how well you’re progressing
    and even build supper plan.

    I come back to my point though; the most effective method to stay motivated in order
    to drag friends along to the gym. If you have an acquaintance who already goes to the health faithfully,
    fine! Piggy-back off of them! If not, you may have a friend who one other trying perform up the motivation to arrive at the
    gym more are inclined to. Perhaps by making a persistence for each other rather than simply yourselves you can finally
    make good on those promises to go to the gym and do exercises.

  • Wonderful experience. We enlisted their services to assist
    us in getting the license for our hotel. They helped in the total process
    and we have nothing but great reviews for their help.
    I would not hesitate to get their help again in future.
    They are a pleasure to work with! Not only are they extremely knowledgeable
    about their work, but they are also easy to work with, have a wonderful personality, provide excellent
    service, and treats each customer like family. They make every effort to provide a
    smooth license transfer process. They not only used their expertise to educate me
    and my client along the way, but made sure we maintained compliance each step of the way.
    I highly recommend them and Liquor License team.

    Thank you. You guys are great. Can’t wait for our 2nd location.
    Our experience with you was as smooth as we could ask for.
    You assisted us with every road block we encountered and answered all of our
    questions in a speedy manner. It was very easy to work
    with you and your team. We knew the process would be challenging but overall it was a pleasure working with you!

Leave a Reply

Your email address will not be published. We will only use your email address to respond to your comment and/or notify you of responses. Required fields are marked *

Captcha *