6 Ways to Beef Up Your Email Security

I have been setting up a Microsoft Exchange email server for a new project of mine that is related to my data privacy law practice. I hope to make an announcement sometime this week as to what the new project will look like. It’s all good stuff.

As I’m setting up my email server, I’m thinking about what steps I need to take to increase my own cybersecurity. It is obvious that I need to practice what I preach. So, here are some of the things that I’ve been implementing for my own business email:

Backups. Backups. Backups. Backups. Backups.

Everyone understands the concept of backing up your data. But backups are not a “set it and forget it” type of thing. What is being backed up? How? Where are the backups stored? How do you go about retrieving it? Do your backups work, are they secure themselves? There is a small section of hell where lost souls are punished by having their computers AND their backups destroyed in the same catastrophe (by a fire, obviously). Don’t be one of those souls.

I’ve been burned by not backing up very recent personal data. (See what I did there?) If you save anything at all on your computer’s hard drive, you are likely guilty of this. It is really frustrating. Especially when you know better. I put this at the top of the list, because if you haven’t recently backed up all of your data, then you are setting yourself up for heartbreak. Frequency is an issue, retrieval is an issue, and all of this stuff needs to be tested.

You can run a cloud drive like OneDrive, Dropbox, Google Drive, which have some security features built in. Make sure you understand what you are signing up for though. Free services are often free because your data will be mined. You might not care about that. As a lawyer, I have to care about that, because allowing Google to read my attorney-client communications can defeat the attorney-client privilege. So, there are pitfalls, and you need to know them. I don’t do any legal work on my free gmail. The paid-for Google Suite is more private, but I can’t say I’m very trusting of Google generally. So, I went more traditional with Microsoft.

You may want to also keep an external hard drive handy that is solely for the purpose of routine backups. I find these are the easiest to retrieve, but that is a two-way street. You need to make sure the backup drive itself is password protected and secure. Out of view is ideal. If anyone can just plug it in and access your files, all you are doing is creating more security holes. The thing with any of these methods is that its easy to forget your email data. Fortunately, Exchange backs up emails automatically and they should be accessible by anyone with admin privileges. Do yourself a favor though and attempt a retrieval now, BEFORE you actually have to.

Multi-factor identification

This should be at or near the top of your list (behind backups, if that is not already being done regularly). For the uninitiated, multi-factor identification (also known as two-step authentication) is a process you may have noticed on a lot of online applications that ask you to verify your login information by also putting in a code on your cell phone. Online banking was one of the early adopters. It can be done in a variety of ways. It may be a a text message, an app, or a follow up on subscription requests with a confirmation email that you have to click on. These are all examples of multi-factor identification.

Gmail and Microsoft Exchange both have a two-step authentication setting. When turned on, you will get a security code sent to your phone or a backup email. Both systems also have authenticator apps that can streamline this process a bit.

I was slow to adopt this at first, because of the times it might slow down your workflow. But actually, when I was forced to use it through various applications, I got used to it pretty quickly, and found it to be a good way to keep out the bad guys. If you are a law firm, or another repository of someone’s personal information, especially in email form, this is a really cheap and easy way to prevent a breach. Remember, the new law in New York is that even if data is only “accessed”, it can trigger a data breach event that must be reported to law enforcement and effected consumers. Even if the data is accessed inadvertently and non-maliciously, the law requires a five year documentation period. Two-step authentication can help prevent those very simple incidents.

Practice “Least Privilege”

Biggie Smalls might have said it best: : “Number three, never trust nobody.” If he were alive today, surely he would advocate for “Least Privilege” and “Zero Trust” security frameworks.

“Least Privilege” means that every user has the least privileges it can possibly get by with to perform its function. So, rather than giving your user name all admin privileges, you would have a user for your day-to-day work, and then a separate admin user only for performing administrative functions. Consider whether every employee should access to every file. In Microsoft Office Suite, you can set up multiple admins that are limited in the things that they can do (one would be an exchange admin, another would be able to change user passwords, etc.) The more you are able to separate these roles, the better.

“Least Privilege” is related to the framework for “Zero Trust” which is, I’m sure, going to be in the running for one of the most popular catch-phrases/buzzwords in 2020. The concepts are related, yet distinct. What they share is the idea that just because a user has gained access inside your network, doesn’t mean they should be given the keys to the company car (metaphorically).

As a lawyer, my office could have clients, adversaries, vendors, employees, and lost visitors looking for another office, on any given day. Unfortunately, any one of those people may intend harm on my system, or may just be an accident waiting to happen. You have to verify each step of the way. One example “zero trust” is to get rid of the idea that once you are connected to the network, that somehow entitles you to access the cloud. It doesn’t and it shouldn’t. Further, once inside the cloud, it doesn’t entitle you to access the entire system.

Develop Basic Security Literacy Within Your Organization

When the Nigerian Prince comes knocking, don’t let him in. Most of us understand that on a basic level. But in business, the scams are more sophisticated. Recently, I’ve received a few emails purportedly from one of my co-workers asking when I will be in the office. Another colleague received a similar email from me, asking for their help with an emergent issue. Those emails set off red flags because my colleagues and I were peers, and the language of the email was clearly designed to invoke fear of one’s supervisor. But, with a different target, or a different sender, I suspect they would have gotten a response from someone in my organization. Of course, the reply email isn’t actually the person you are expecting, it goes elsewhere, and who knows what kind of information they can gather. It is limitless.

So, you need to train the users in your organization on the basics of information security. My rule of thumb is that if someone is sending me something in an email and claiming it is an emergency, I follow up with a phone call. You don’t have to explain to the person why you are calling, you can just say that you want to make sure you get it right the first time. You may find that the person you thought was emailing you has no idea about the email.

Another way this is done by hackers is to take over one email account and use it to gain information from other people. So the email address itself could even be legitimate, but not actually sent from the person you expected. Imagine getting an email from your spouse that says something like “Hi Honey, I’m at the store and my debit card won’t work, can you send me your credit card number to try and use yours?” That’s a really simple scam and all it requires is access to your email. If the hacker doesn’t change the password, they might even be accessing it without anyone’s knowledge.

There is a lot of anti-phishing, anti-scamming educational materials out there online. So, I’m not going to reinvent the wheel here. Just look into it, and make sure your team is trained on this stuff.

Physical Security Is A Necessary Part of Information Security

You can have all of the bells and whistles in regards to password usage, training of employees, and backups, but if someone can just find your phone in the park and access your email without some sort of passcode, then you aren’t secure. Conversely, if you are sticking random USB drives into your computer, then all of those passcodes aren’t going to help you.

Movies and television would have you believe that hacking looks a lot like the Matrix, with some trendy electronic music blasting in the background, and an exciting GUI with colorful lines of code streaming across the screen. Hacking can be a version of that. Although leather pants are far less popular in the hacking community than the Wachowski brothers would have you believe. More often, it’s just a person on a phone, asking the right questions, being friendly to receptionists, and charming their way into our hearts (and data). Be wise to what social engineering looks like. Remember that getting your purse snatched can constitute a data breach under many state laws, if you are holding electronic devices that contain other people’s personal information.

Password Management

My view on password management starts to make more sense once you’ve thought about physical security. A lot of companies are still having employees change their password every few months. I don’t advocate for that. For the last 20 years or so, I’ve held the view that a person who does not know their own password may be as dangerous to the system as a person who has a very weak password. Password managers have softened that view a little, but let me explain the thinking.

If you are unable to reuse your passwords, and must change them every few months, the chances that an employee is going to write down their password and stick it to their monitor becomes much higher. In that instance, the organization went from very high security to a situation where the cleaning crew, all visitors, other co-workers, and all sort of potential invaders can plainly see your password. Now, this may be less of an issue for you if you are practicing two-step authentication. But, if your work computer is considered a “trusted” computer, you may still end up in a bad spot. I would rather that people have a password they can memorize and not have to write down, than have them use random digits and letters that have to be written out and left on their desk.

That said, reusing the same password repeatedly across systems is still considered poor practice, and remembering all of those passwords for all of those different accounts gets pretty challenging. For those reasons, you may want to consider using a password manager. Yes. They CAN be hacked too. But the data tends to be encrypted, and I still think the risk is lower than doing it as described above. I’ve seen good recommendations on 1password ($3 per month) and bitwarden (free for personal, $5 /month for business). I’m going with bitwarden, but there are a lot of good options out there.


As Biggie once said, “follow these rules and you’ll have maad bread to break up.” The last recommendation I can offer is to get a professional to look at your system if you are able. You don’t have to have an IT department to have a secure system. Most parts of the U.S. have plenty of IT firms that would be glad to come to your home or office and figure out what you can do to be more secure. These are just the starting points and steps that I’m taking. There is always more to do, and evolution is part of the security game.

Last, none of what I’ve said here ensures compliance with any data privacy laws. This is technical advice from my personal experience. So, don’t take it as legal advice for what you need to do in your state, and don’t take it as a definitive version of everything that an IT pro would suggest either.

Stay safe out there!

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