Navigating Cloud Security Challenges with Real-Life Insights

Navigating Cloud Security Challenges with Real-Life Insights

Cloud tech has made our lives easier, helping us work together smoothly and efficiently.

But there’s a flip side to this tech wonderland: Cloud tools are an attractive, easy target for hackers, and we need to be extra vigilant.

In our Virtual Chief Information Security Officer (vCISO) practice (Do-Follow Link), we’ve seen how lax security can mess things up big time for businesses. And lately, all of the breaches have been in the cloud applications that our business clients rely on every day.

So, it’s high time organizations beefed up their cloud security to fend off evolving threats.

In this article, we’ll give you a few real-life examples we’ve come across and share some tips to help businesses stay one step ahead in the cloud security game.

Misaligned Settings: The Most Common Cloud Infrastructure Pitfall

When businesses migrate to the cloud, they often assume it’s super secure by default.

But the reality is way more complicated.

For instance, Microsoft 365 boasts a whopping 80 security settings, and Google Workspace has nearly 40.

Shockingly, when we work with businesses, we find that 50-75% of these settings are messed up.

And here’s the big surprise – every single one of these companies is already working with an IT firm.

These misconfigurations show that it’s time for a serious rethink of cloud security.

Take the time to really understand the cloud security settings.  If you’re not confident in your own abilities or your IT team’s abilities, call in an expert.

CEO’s Nightmare: A Lesson in Multi-Factor Authentication

This is a true story and highlights the importance of setting up multi-factor authentication properly.

Imagine the horror of your CEO’s email getting hacked.

It’s a nightmare scenario that can send shockwaves through any company, and it happened to one of our clients.

In this scary case, the CEO’s hacked email led to shady fake invoices being sent to innocent people from the CEO’s email address.


Crisis meetings, financial losses, and embarrassing phone calls followed, all because multi-factor authentication (MFA) was temporarily turned off for the CEO’s email.

A tiny slip-up with massive consequences.

This shows how easy it is for hackers to get hold of usernames and passwords.

MFA should be like Fort Knox – no casual suspensions allowed.

Just as importantly, always be sure you’re using phishing-resistant MFA. If your MFA code comes in a text message to your cell phone, you’re not using the right kind.

vCISO Recommendation: MFA needs to be enabled and enforced for ALL users, and there needs to be a process in place in the rare case MFA is temporarily disabled. Look into phishing-resistant MFA as well. Hackers are getting around MFA, so you need to use the strongest methods available.

Learning from Others’ Oops Moments: The Russian Hacker Wake-Up Call

The saying “learning the hard way” rings true in cybersecurity.

We had a client who woke up to the nightmare of Russian hackers breaking into their systems.

An audit revealed the critical error – MFA was set up, but it wasn’t set up correctly. Sometimes setting up MFA is unnecessarily complicated (looking at you, Microsoft) so you have to make sure you do it right. Unfortunately for our client, their IT team had two MFA rules canceling each other out.

This case reminds us that cloud systems can be sneaky in their complexity. You need to make sure they’re configured properly.

Assuming everything is secure can be a costly mistake.

So, businesses should ask themselves: Are their cloud settings really as safe as they think?

vCISO Recommendation: Check out the CIS Microsoft 365 (Resource Link) or CIS Google Workspace (Resource Link) configuration standards to learn more about securing your cloud email program.  Better yet, work with a qualified security expert to review your settings.

Good Documentation Makes the Lawyers Go Away

It’s common to think that breaches only happen to big companies.

This is simply not true – small and midsize companies experience breaches all the time, and the true story below highlights the importance of strong cloud security.

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One of our clients reached out about a possible breach. During discussions with their insurance company, the lawyers asked, “Did you disable legacy email protocols used by hackers?”

Because our client had detailed records and thorough audits showing these protocols had been disabled, this potential breach was a hiccup instead of a true disaster.

This shows being prepared and having solid evidence can make all the difference.

Pro tip: Not sure what legacy email protocols are? Basically, it means you only need a username and password to access – and unfortunately, usernames and passwords are incredibly easy to get. But it’s OK if you don’t understand what it actually means. What’s important is that your email system has these protocols disabled.  Google your email program + legacy email protocols to learn how to disable these settings. Focus on POP and IMAP.

CISO Recommendation: Be prepared to show documentation that proves you’ve taken the security settings seriously. Screenshots really work!

The Way Forward: Strengthening Cloud Security

The stories we’ve shared here aren’t just tales; they’re warnings.

They tell us how important it is to stay ahead of the game when it comes to cloud security.

It’s the responsibility of business leaders to protect their data, especially in a world where cyber threats are always evolving.

Be informed, stay alert, and be ready to tackle these challenges head-on.

We’ve provided important suggestions for any business owner:

  • Call in an expert like a Virtual CISO (Do-Follow Link) to make sure your cloud systems are secure
  • Make sure MFA is enabled and enforced for everyone
  • Use the strongest form of MFA available (sometimes called phishing-resistant)
  • Find and implement the CIS security standards for your email program
  • Turn off legacy email protocols

In Conclusion

To sum it up, the modern business world demands a solid approach to cloud security.

As you’ve seen from these real-life stories, the risks are real, and the consequences can be huge.

By digging into these insights, businesses can equip themselves to fortify their cloud infrastructure and defend against potential threats.

Stay safe out there!

Author Bio: Josh Ablett has 14 years of experience in cybersecurity, specializing in compliance and hacker prevention. He’s worked with various cybersecurity frameworks and led projects for Fortune 500 clients at companies like HP, Bottomline, and Dtex.

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Shankar is a tech blogger who occasionally enjoys penning historical fiction. With over a thousand articles written on tech, business, finance, marketing, mobile, social media, cloud storage, software, and general topics, he has been creating material for the past eight years.