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There has certainly been no lack of punditry and controversy in the US regarding the hacking of John Podesta’s email account

There has certainly been no lack of punditry and controversy in the US regarding the hacking of John Podesta’s email account (along with the DNC email hack), with some claiming they were responsible for Mrs. Clinton’s loss in the election. I will leave the impact of these claims to those who write and talk about politics. I don’t discuss politics in a work setting, so will leave that aspect to them.

What I would like to address is the security infrastructure versus security posture that made this hack possible. For the uninitiated, Mr. Podesta received a targeted phishing email directing him to reset his password. This prompted him to contact IT support, who told him there was indeed a threat, and he should reset his password. Up to this point, it sounds like a day in the life of any enterprise. Reassured by IT support, he clicked on the link in the email to reset his password. The rest as they say is history.

Slide2At that point, it doesn’t matter what the security infrastructure of the organization was. Unless the organization is scanning outgoing connections for hazardous behavior (and even then, it would have had to be blacklisted, based on today’s user expectations), all security infrastructure was no hindrance to the attackers at all.

The IT support individual involved (his name is out there if you’re dying to know it, I will not besmirch him for the simplest – and potentially most clostly – of mistakes) has expressed regret for simply saying “Yes, this is a real threat, reset your password”, but it shows the difference in the world-view between leaders and IT. To security and support staff, “reset your password” implies “via the normal method you’ve always used”. While to the user, IT staff was implying “this is a legitimate request, please use it to reset your password”. The part that did not get communicated was “but not via the link in that email”.

It was a simple communication error. And though we will never know for certain the impact that it had, it is guaranteed that impact wasn’t good. It was at best neutral or more likely negative to the organization, it is just very difficult to gauge how negative.

The thing is, that one conversation and the resulting email – one email, one phone call, one click – bypassed whatever security infrastructure was in place. No matter how good, expensive, up-to-date, or all-encompassing it was.

In the case of Mr. Podesta, there was even another twist. This was his personal account, but as many of us do, there was a lot of work-related email on his personal account. This (gmail) account was outside of IT’s control, so any document they had telling users how to reset passwords was useless. Most organizations have these people in them, who really do work evenings at their home, and are productive doing so.

And if you are a company big enough to have IT support staff, it was your organization. You are every bit as vulnerable, and it could have happened to you. But it doesn’t have to be that way.

There are several things you can pursue to help avoid situations like this.

  • Teach employees to be cautious about links in email. Spear Phishing relies upon tricking a user, so give them the tools to avoid being tricked.
  • Give security communications training. There are multiple ways to go about this, but I’d recommend talking to Michael Santarcangelo over at Security Catalyst (https://securitycatalyst.com) he has a knack for teaching security folks communications.
  • Server side email filters will cut down on the number that get through, but shouldn’t be the only approach, simply because they will be unlikely to catch every phishing attempt.
  • Give Support and Security staff a script, or better yet, a web page on your self-help portal, that gives users explicit instructions to do things like reset passwords internally.
  • I’ve never recommended this before, but writing this blog has me thinking that it might be worthwhile for employers to get password managers for all employees. Something I’ll have to consider more deeply, but there you’re thinking with me. While Wikipedia lists tend to get out of date, as of this article’s writing, their list (https://en.wikipedia.org/wiki/List_of_password_managers) is a good starting point for looking over passwords. If, for some reason, a password manager is not an option, then at least convince your senior employees – the ones with the most strategic email and access to the most information – to use unique passwords at work.
  • Most most most important is to teach employees to be careful about what they say over email. I’ve been in subpoena situations for court cases, and sometimes what you find employees have said is cringe-worthy. In fact, the first time I realized what a subpoena of all email meant, I pondered how bad it would have been at my first development job… While rising through the ranks at a tax software company, I met and courted my wife. Things I said to woo her would have been hilariously embarrassing on the desk of an attorney hostile to the organization, even if they didn’t harm the company. Hacking is not required, those emails can be seen by people outside the company (M&A also being a scenario), so teach employees to conduct business, but leave the edgy/dark out. While retention policies are common, they’re not particularly effective, in my opinion, because there are copies of email all over the place – from backups to local PST files. Retention policies are better at keeping storage usage down, limiting access to damaging or dangerous information in email should be handled by training.

A political campaign is a short-term thing, and the window for potential damage was small. That is not true with your organization. Imagine someone having access to the email of a 10 or 20 year high-level employee, and having forever to use that in competitive situations against your organization. The potential for harm is large, and if there is bad enough stuff in there (I once wrote the CEO of an employer to tell him I had been commanded to fudge data, and that wasn’t the company I joined or he was running. While he fixed it, imagine that showing up competitively or in court – today I would call or wander over to his office to have that same conversation), it could cost not just business, but lawsuits to boot.

While doing all of this, remember to scale the approach so as to teach employees what is off limits, while reinforcing that email is a business tool and should be used for business goals. It is a powerful tool, but it can be a powerful tool in the hands of those who wish your organization ill also. It is important to keep the “powerful tool” part while reducing the risk.

Edit/Addendum: One of the companies I do business with has started inserting this line at the top of email coming from outside their network:

*** Exercise caution. This is an EXTERNAL email. DO NOT open attachments or click links from unknown senders or unexpected email. ***.

That line at the top of the phishing email may well have caused Mr. Podesta to stop and ask “Should I use the link in the email?”, thereby avoiding the entire unpleasantness. So add it to the list of things you can do to reduce risk.

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Sponsors of Cloud Expo @ThingsExpo will benefit from unmatched branding, profile building and lead generation opportunities through:

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With major technology companies and startups seriously embracing Cloud strategies, now is the perfect time to attend @CloudExpo@ThingsExpo, June 6-8, 2017, at the Javits Center in New York City, NY and October 31 - November 2, 2017, Santa Clara Convention Center, CA. Learn what is going on, contribute to the discussions, and ensure that your enterprise is on the right path to Digital Transformation.

Track 1. FinTech
Track 2. Enterprise Cloud | Digital Transformation
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Track 8. AI | ML | DL | Cognitive Computing

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More Stories By Don MacVittie

Don MacVittie is founder of Ingrained Technology, A technical advocacy and software development consultancy. He has experience in application development, architecture, infrastructure, technical writing,DevOps, and IT management. MacVittie holds a B.S. in Computer Science from Northern Michigan University, and an M.S. in Computer Science from Nova Southeastern University.

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