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Strategic activity mapping for software architects May 25, 2025 On the role of Distinguished Engineer and CTO Mindset Apr 27, 2025 The future is bright Mar 30, 2025 2024 Reflections Dec 31, 2024 My giant follows me wherever I go Sep 20, 2024 The day I became an architect Sep 11, 2024 Are developer jobs truly in decline? Jun 29, 2024 Leadership is About "We," Not "I" Jun 9, 2024 Form follows fiasco Mar 31, 2024 Software Engineering is here to stay Mar 3, 2024 Some thoughts on recent RTO announcements Jun 22, 2023 On Amazon Prime Video’s move to a monolith May 14, 2023 One size does not fit all: neither cloud nor on-prem Apr 10, 2023 Some thoughts on the latest LastPass fiasco Mar 5, 2023 Comparing AWS SQS, SNS, and Kinesis: A Technical Breakdown for Enterprise Developers Feb 11, 2023 Working from home works as well as any distributed team Nov 25, 2022 Why you should question the “database per service” pattern Oct 5, 2022 Stop Shakespearizing Sep 16, 2022 Why don’t they tell you that in the instructions? Aug 31, 2022 Monolithic repository vs a monolith Aug 23, 2022 Automation and coding tools for pet projects on the Apple hardware May 28, 2022 There is no such thing as one grand unified full-stack programming language May 27, 2022 Most terrifying professional artifact May 14, 2022 If you haven’t done it already, get yourself a Raspberry Pi and install Linux on it May 9, 2022 Good idea fairy strikes when you least expect it May 2, 2022 Kitchen table conversations Nov 7, 2021 Application developers like to think their app is the only one Apr 5, 2021 A year of COVID taught us all how to work remotely Feb 10, 2021 What programming language to use for a brand new project? Feb 18, 2020 The religion of JavaScript Nov 26, 2018 Teleportation can corrupt your data Sep 29, 2018 Let’s talk cloud neutrality Sep 17, 2018 What does a Chief Software Architect do? Jun 23, 2018 Nobody wants your app Aug 2, 2017 TypeScript starts where JavaScript leaves off Aug 2, 2017 Singletons in TypeScript Jul 16, 2017 Emails, politics, and common sense Jan 14, 2017 Online grocers have an additional burden to be reliable Jan 5, 2017 Collaborative work in the cloud: what I learned teaching my daughter how to code Dec 10, 2016 Apple’s recent announcements have been underwhelming Oct 29, 2016 What I learned from using Amazon Alexa for a month Sep 7, 2016 Why I switched to Android and Google Project Fi and why should you Aug 28, 2016 Amazon Alexa is eating the retailers alive Jun 22, 2016 In search for the mythical neutrality among top-tier public cloud providers Jun 18, 2016 In Support Of Gary Johnson Jun 13, 2016 Files and folders: apps vs documents May 26, 2016 What can we learn from the last week's salesforce.com outage ? May 15, 2016 Why it makes perfect sense for Dropbox to leave AWS May 7, 2016 JEE in the cloud era: building application servers Apr 22, 2016 Let's stop letting tools get in the way of results Apr 10, 2016 JavaScript as the language of the cloud Feb 20, 2016 LinkedIn needs a reset Feb 13, 2016 In memory of Ed Yourdon Jan 23, 2016 Our civilization has a single point of failure Dec 16, 2015 IT departments must transform in the face of the cloud revolution Nov 9, 2015 I Stand With Ahmed Sep 19, 2015 Setting Up Cross-Region Replication of AWS RDS for PostgreSQL Sep 12, 2015 Top Ten Differences Between ActiveMQ and Amazon SQS Sep 5, 2015 We Live in a Mobile Device Notification Hell Aug 22, 2015 What Every College Computer Science Freshman Should Know Aug 14, 2015 On Maintaining Personal Brand as a Software Engineer Aug 2, 2015 The Three Myths About JavaScript Simplicity Jul 10, 2015 Book Review: "Shop Class As Soulcraft" By Matthew B. Crawford Jul 5, 2015 Attracting STEM Graduates to Traditional Enterprise IT Jul 4, 2015 Your IT Department's Kodak Moment Jun 17, 2015 The longer the chain of responsibility the less likely there is anyone in the hierarchy who can actually accept it Jun 7, 2015 Big Data is not all about Hadoop May 30, 2015 Smart IT Departments Own Their Business API and Take Ownership of Data Governance May 13, 2015 The Clarkson School Class of 2015 Commencement speech May 5, 2015 My Brief Affair With Android Apr 25, 2015 Exploration of the Software Engineering as a Profession Apr 8, 2015 What can Evernote Teach Us About Enterprise App Architecture Apr 2, 2015 Microsoft and Apple Have Everything to Lose if Chromebooks Succeed Mar 31, 2015 Do not apply data science methods without understanding them Mar 25, 2015 On apprenticeship Feb 13, 2015 On Managing Stress, Multitasking and Other New Year's Resolutions Jan 1, 2015 Why I am Tempted to Replace Cassandra With DynamoDB Nov 13, 2014 Software Engineering and Domain Area Expertise Nov 7, 2014 Docker can fundamentally change how you think of server deployments Aug 26, 2014 Wall St. wakes up to underinvestment in OMS Aug 21, 2014 Software Engineers Are Not Doctors Aug 3, 2014 Thanking MIT Scratch Sep 14, 2013 Have computers become too complicated for teaching ? Jan 1, 2013 Thoughts on Wall Street Technology Aug 11, 2012 Scripting News: After X years programming Jun 5, 2012 Java, Linux and UNIX: How much things have progressed Dec 7, 2010

Emails, politics, and common sense

January 14, 2017

Like many Americans, I’ve been trying to explain and justify the 2016 election cycle. I am not an expert political scientist. I am a software engineer. The question I ask myself is “What role did computer technology play in this election ?” In particular, I want to focus on email.

Email is an insecure medium. Period.


I once attended an HR orientation session where we were told to write our emails in a way that wouldn’t embarrass the company if it showed up on the front page of the New York Times. The reason was that emails are inherently easy to leak. Even without someone hacking the email server (I will discuss this in a bit) it is incredibly easy to mistype an email address or add the wrong person or the wrong group to Cc or Bcc list.

We have all heard stories of someone broadcasting their private emails to entire departments or even entire companies. There are anecdotes of whistleblowers forwarding company emails to the newspapers. And of course, we’ve all heard of the DNC email leaks. Email is simply the wrong mechanism for private and secure communications.

Both the DNC and Hillary Clinton could learn a simple lesson that private sector companies teach their employees: write your emails as if you are writing for the New York Times. This way if the DNC CFO Brad Marshall feels the need to send an anti-Semitic email he will think twice.

DNC used an on-premise Microsoft Exchange


In order to understand what made the DNC email leaks possible and so seemingly trivial I went to Wikileaks and searched for a sample set of emails. In the raw source of the emails there is a clear indication the DNC email system used a custom configured Microsoft Exchange. There are signs that this is an internally setup private server.

I searched long and hard to find out who configured the on-premise Microsoft Exchange server for the DNC and why they did that. Did they properly configure it ? Did they rely on Microsoft alone to secure it ? Has DNC followed the advisories on Outlook and Exchange vulnerabilities ? Is DNC taking advantage of the Exchange compliance and security features ? Why is DNC not using Office365 or Google ?

All you need is a weak link


Any system designed to archive emails is bound to be vulnerable to a leak. A Microsoft Exchange server configured to archive emails is vulnerable to that one administrator user with a poorly chosen password or a phishing attack. Using a cloud provider isn’t going to solve all privacy and security questions. Google’s Vault that is part of the G Suite is subject to the same vulnerabilities.

Recent revelations about Yahoo password leaks, Dropbox hack, and the LinkedIn password leak just prove my point.

The implications for transparency and compliance


Knowing that email is an outdated and insecure form of communication, the politicians, public officials, and publicly traded company officers are likely to use end-to-end encrypted means of communication such as Edward Snowden approved Signal. This can weaken and rollback information retention, transparency and disclosure laws such as the [Freedom of Information Act](https://en.m.wikipedia.org/wiki/Freedom_of_Information_Act_(United_States) and Dodd-Frank Act. I worry that the institutions we trust with power will become even less transparent.

Storing sensitive emails on-premises doesn’t make it any more secure


The DNC emails were all leaked from an on-premise private Microsoft Exchange server. Personally identifiable data must meet PCI DSS and HIPAA requirements regardless of where it is stored. Sensitive data should be encrypted. As Edward Snowden and DNC email leaks demonstrated, sensitive data could be leaked from a walled garden environment. Moreover, the leaked documents revealed that NSA was equally harvesting the data from major U.S. companies private data centers and public cloud. Hillary Clinton’s private walled garden email server was not immune from government intrusion or hacking either.

All you need is common sense


You don’t need to abandon email or be in violation with information archival rules in order to feel secure about your communications. Following basic common sense with regards to your data is all that’s needed to avoid disastrous consequences for yourself and others:

  1. Don’t store anything you would not want to show up on the front page of a major newspaper in an un-encrypted form. This applies to your phone, your laptop, your company’s email server, or cloud. If somebody wants to look at your data, whether they are a government or a hacker, they will have to ask your permission first to unencrypt it.

  2. Use two-factor authentication. Stealing your password is not enough for a hacker to access your data because they will need a second mechanism to authenticate themselves.

  3. Do not use the same password for all of your accounts. Use a password manager, such as 1Password to generate and manage random and secure passwords.

  4. Apply common sense to your emails: do not click on links that look suspicious, verify the URLs before you fill out password forms, and take great care not to accidentally forward your emails to people you don’t trust. In other words, do not fall for phishing.






This article was originally published Dec 20, 2016 on my Cloud Power blog at Computerworld.