You, (Windows) ME, And The Future Have a Lot In Common

The time was June of 2000.

Your Chevy Silverado got a new face lift. Your AOL logins got a little quicker, and, your desktop took a change. The internet was here, the future was clear, and with Windows 98 behind us, we knew exactly how the world was going to work – for the world was a friendly place and all would work out in the future, right?

Wrong.

Sandwiched somewhere between the rise of McDonalds and the explosive end of the dot com bubble lies the product of what happens when your bitcoin portfolio explodes too quickly and you have no exit strategy: Windows ME. Where were you in the summer of 2000? If you were me, you were stuck in a house all day, smashing away at a keyboard. No, I wasn’t stuck in some miserable desk job that will drive me to become a divorce statistic some 10 or so odd years from now – I was just a kid. The internet was the Wild West, and my horse was the sweet sound of that 56k dial up. I was unstoppable.

Trevor you have 5 minutes to get off that phone or you’re grounded. – Well, at least I thought I was. At the time, I knew close to nothing about PCs. I had no idea what Windows was, or what the internet was for that point. I just sat in front of that Systemax box, glaring into that 19 inch CRT monitor until my mom finished dinner. The world was just discovering what the internet was – and I was just discovering what my passion in life was going to be.

Ok, sweet, why are you writing this blog post? Windows 98? Windows ME? Easy cowboy, let me enjoy my nostalgia. There’s a purpose to why I’m writing this post – History repeats itself – And I’ll happily explain.

It’s 2017 and were in the mist of another dot com bubble. But not to fear- this time we have more at stake than just money. What’s at stake now is our identity. Now, I know what you are probably thinking No basis, just false claims like every other blog writer telling us how the markets are going to crash – Congratulations! You’re correct. But we have one thing in common with Windows ME, AOL, and 56k days – everyone’s rushing to the cloud the way we did into Windows ME, not realizing what we are getting into. Just like the old 2000’s playground of Wireshark, Netscape navigator and plaintext databases, the cloud is not a friendly place, and everyone wants to exploit it faster than Sean Spicer’s whois data. I have worked with many companies, both small and large, who anxiously ran to the cloud with open arms and handed the keys to their digital enterprise to Amazon or Microsoft. It’s an easy gig, right? Take all of your infrastructure, point it to AWS, and lie back on your lawn chair in Florida as Amazon takes care of all your worries.

Sorry, Brad – your 3pm Florida golf outing got interrupted by some script kiddies in Utah (Surprise! You left your RDP port open!) and now your customers are screaming on the phone as their SQL database is every bit of jacked up. But I have backups! Surely Amazon will help me there! Yup, the real world has moved on, and, in that 3 hour window that production SQL server now was written to over a million times. You can’t tell what data is new, old, or needs to be kept. You’re in hot water. This is worse than Panda antivirus on a hot ransomware filled day. Maybe I’m being a bit cynical, forgive me. However, stories like these are true and happen every day. I often tell my clients that the best network is the one that is the least connected. In this day and age we need to find our balance of connectivity and security – a challenge that is getting harder and harder to do each and every day.

So how do we secure our networks and adopt the cloud responsibly? This is an answer that I could write on for decades about. However, just like the early 2000’s where downloading every EXE you could find was a bad idea, so is jumping straight into the cloud. Sure, it’s easy to jump on Azure and spin a SQL server or a virtual network up in seconds, but taking your time and documenting each security measure as you go is vital to your network’s success. Here’s some easy steps you can take right now to increase your overall digital footprint:

• Take a week to review all your infrastructure. Talk with your network teams, figure out where everything is going and where data lies. Make sure you are using up to date encryption methods, everything from bitlocker drive encryption to password hashing.
• You do not need a degree in cyber security * to be smart about networking. Are you backing your enterprise to the cloud? Encrypt those backups. Do you have an open RDP port on a Windows box on AWS? Disable administrator, change ports, and use technologies like remote desktop gateways and lockout policies to prevent script kiddies.
• Do not expect, that, just because you wrote a fancy mobile app that someone won’t decompile it. Sorry to bust your bubble, Chad, but yes we can sniff out web sockets and unsecure traffic.

Opening up your network to the cloud is a give / take game. Yes, you have to worry very little about computing failures, but, your data is now in the hands of someone else. What could have been a private subnet spinning somewhere in a data closet is now accessible to the outside world. Remember: Computers do not understand you personally. Pass them enough data to authenticate with, and you are whoever you want to be. Just like with Windows ME, don’t jump in just because everyone says to – you might run into more problems than you expect. Take your time, review your data, and make an educated decision on where your company wants to be in the cloud.