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On the role of Distinguished Engineer and CTO Mindset Apr 27, 2025 The future is bright Mar 30, 2025 On luck and gumption Oct 8, 2023 Some thoughts on recent RTO announcements Jun 22, 2023 One size does not fit all: neither cloud nor on-prem Apr 10, 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 Things to be Thankful for Nov 24, 2022 Why you should question the “database per service” pattern Oct 5, 2022 Stop Shakespearizing Sep 16, 2022 Using GNU Make with JavaScript and Node.js to build AWS Lambda functions Sep 4, 2022 Why don’t they tell you that in the instructions? Aug 31, 2022 Monolithic repository vs a monolith Aug 23, 2022 Keep your caching simple and inexpensive Jun 12, 2022 Java is no longer relevant May 29, 2022 There is no such thing as one grand unified full-stack programming language May 27, 2022 Peloton could monetize these ideas if they only listen May 15, 2022 Best practices for building a microservice architecture Apr 25, 2022 True identity verification should require a human Mar 16, 2020 The passwords are no longer a necessity. Let’s find a good alternative. Mar 2, 2020 What programming language to use for a brand new project? Feb 18, 2020 TDWI 2019: Architecting Modern Big Data API Ecosystems May 30, 2019 Configuring Peloton Apple Health integration Feb 16, 2019 All emails are free -- except they are not Feb 9, 2019 Using Markov Chain Generator to create Donald Trump's state of union speech Jan 20, 2019 The religion of JavaScript Nov 26, 2018 Teleportation can corrupt your data Sep 29, 2018 Let’s talk cloud neutrality Sep 17, 2018 A conservative version of Facebook? Aug 30, 2018 On Facebook and Twitter censorship Aug 20, 2018 Facebook is the new Microsoft Apr 14, 2018 Node.js is a perfect enterprise application platform Jul 30, 2017 Design patterns in TypeScript: Factory Jul 30, 2017 Design patterns in TypeScript: Chain of Responsibility Jul 22, 2017 Singletons in TypeScript Jul 16, 2017 Architecting API ecosystems: my interview with Anthony Brovchenko of R. Culturi Jun 5, 2017 TDWI 2017, Chicago, IL: Architecting Modern Big Data API Ecosystems May 30, 2017 I tried an Apple Watch for two days and I hated it Mar 30, 2017 Emails, politics, and common sense Jan 14, 2017 Online grocers have an additional burden to be reliable Jan 5, 2017 Here is to a great 2017! Dec 26, 2016 Apple’s recent announcements have been underwhelming Oct 29, 2016 I am addicted to Medium, and I am tempted to move my entire blog to it Sep 9, 2016 What I learned from using Amazon Alexa for a month Sep 7, 2016 Praising Bank of America's automated phone-based customer service Aug 23, 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 Why it makes perfect sense for Dropbox to leave AWS May 7, 2016 JEE in the cloud era: building application servers Apr 22, 2016 Managed IT is not the future of the cloud Apr 9, 2016 LinkedIn needs a reset Feb 13, 2016 In memory of Ed Yourdon Jan 23, 2016 OAuth 2.0: the protocol at the center of the universe Jan 1, 2016 IT departments must transform in the face of the cloud revolution Nov 9, 2015 Banking Technology is in Dire Need of Standartization and Openness Sep 28, 2015 Top Ten Differences Between ActiveMQ and Amazon SQS Sep 5, 2015 We Live in a Mobile Device Notification Hell Aug 22, 2015 On Maintaining Personal Brand as a Software Engineer Aug 2, 2015 Book Review: "Shop Class As Soulcraft" By Matthew B. Crawford Jul 5, 2015 Attracting STEM Graduates to Traditional Enterprise IT Jul 4, 2015 The longer the chain of responsibility the less likely there is anyone in the hierarchy who can actually accept it Jun 7, 2015 Guaranteeing Delivery of Messages with AWS SQS May 9, 2015 The Clarkson School Class of 2015 Commencement speech May 5, 2015 Apple is (or was) the Biggest User of Apache Cassandra Apr 23, 2015 Ordered Sets and Logs in Cassandra vs SQL Apr 8, 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 Where AWS Elastic BeanStalk Could be Better Mar 3, 2015 Configuring Master-Slave Replication With PostgreSQL Jan 31, 2015 Docker can fundamentally change how you think of server deployments Aug 26, 2014 Infrastructure in the cloud vs on-premise Aug 25, 2014 Things I wish Apache Cassandra was better at Feb 12, 2014 "Hello, World!" Using Apache Thrift Feb 24, 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.