10 Questions CISOs Should Be Asking About File Security

Every major breach leaves the same painful lesson in its wake: the attack often began with a single file. 

• A document that looked routine. 
• An attachment that seemed harmless.
• A download from a “reputable” source.
• A Teams message with an innocent PPT.

Yet despite this pattern, most security teams don’t stop to measure their exposure to file-borne risks until after an incident has already caused damage.

The reality is that files move everywhere in modern business. They flow through email, are shared across SaaS applications, uploaded to customer portals, exchanged with partners and contractors, and opened directly on endpoints. Each of these touchpoints represents an opportunity for hidden malware to slip through unnoticed and for sensitive data to spill outside intended boundaries.

So the question becomes: how safe are your files, really? To help you find out, we’ve put together a simple checklist. Just ten yes or no questions to see whether your current defenses can truly protect your organization from file-borne threats or if hidden risks are already waiting in your environment.

Note: Yes = 1 point, No/Unsure = 0 points

Section One: Email Attachments

Question 1: Do your email security tools sanitize attachments, or just block known bad senders?

Email is still the attacker’s favorite doorway. Employees receive invoices, contracts, and resumes every day, all of which can hide malicious code. Secure Email Gateways (SEGs) do well at filtering spam and obvious phishing, but they weren’t designed to sanitize attachments. That means hidden malware often slips through, looking harmless until the moment it’s opened.

Question 2: Can your employees quickly access a “safe” version of an attachment without IT intervention?

Even when suspicious files are flagged, the process for accessing a clean version is often slow. Quarantines and manual reviews frustrate employees, create backlogs, and sometimes push people to bypass security altogether just to keep working. If your teams can’t open a safe version instantly, the balance between security and productivity tips the wrong way.

💡 Mini-tip: Traditional SEGs stop spam, not embedded file threats. To truly close the gap, you need a way to deliver safe, fully functional files in real time.

Section Two: Web & Browser Risks

Question 3: Are files downloaded from websites automatically sanitized before reaching users?

Web browsing is part of every workday, from pulling down reports to grabbing product manuals. But files from the open web often carry hidden payloads. If those files aren’t automatically sanitized before employees use them, attackers have a direct path into your network. Relying on users to spot the difference between a safe and malicious download is a gamble most organizations lose.

Question 4: Can your browser isolation platform guarantee attachments are clean, not just rendered safely?

Browser isolation is an excellent way to protect users from drive-by downloads and malicious links. But isolation alone doesn’t ensure that the file itself is harmless; it only renders a safe version of the web session. If employees download the original file, any embedded threats may remain intact. Without file sanitization in place, you’re only solving half the problem.

💡 Mini-tip: Browser isolation protects the browsing experience, but only file sanitization ensures the download itself is clean.

Section Three: Cloud & SaaS Apps

Question 5: When employees share files via cloud storage or collaboration apps, are those files checked in real time?

From SharePoint to Slack, cloud and collaboration apps make file sharing effortless. But that convenience creates a security blind spot. If files aren’t sanitized in real time as they move across these platforms, a single infected upload can instantly spread to dozens of users. By the time security teams catch on, the damage may already be done.

Question 6: Is it easy for you to stop sensitive data exposure (PII, PHI, PCI) when files move across SaaS apps?

Cloud collaboration isn’t just about malware, it’s also about data privacy. Files often contain personally identifiable information (PII), healthcare data (PHI), or payment card details (PCI). Without controls in place, that sensitive data can slip across apps, partners, or external users unnoticed. Stopping malware is only half the job; protecting private data is just as critical.

💡 Mini-tip: Pairing Content Disarm & Reconstruction (CDR) with data masking closes both gaps, ensuring files are safe to use and compliant with privacy requirements, without slowing down collaboration.

Section Four: User Devices & Partner Portals

Question 7: Do files from USB drives, contractors, or external partners get sanitized before use?

Not every file enters through email or the cloud. USB drives, partner uploads, and contractor submissions are all common ways malicious content slips inside. These files often bypass the same scrutiny applied to email, leaving a hidden path for attackers. If you aren’t sanitizing files from every external source, you’re trusting outsiders with the keys to your network.

Question 8: Do protections exist for password-protected or zipped files?

Attackers know legacy security tools struggle with compressed or encrypted files. That’s why weaponized ZIPs and password-protected attachments are so prevalent in modern attacks. If your defenses can’t open, inspect, and sanitize these formats in real time, you’re leaving a wide-open gap for threats to hide in plain sight.

💡 Mini-tip: Legacy tools often skip encrypted file types, making them a favorite hiding spot for attackers. Advanced CDR, like Votiro, handles these complex types with ease.

Section Five: Compliance & Control

Question 9: Can you demonstrate file-level compliance for HIPAA, PCI, GDPR, or ISO requirements?

Regulators don’t just want to know your systems are protected. They want proof. HIPAA, PCI, GDPR, and ISO standards all carry file-level expectations around data privacy and security. If you can’t demonstrate that every file entering and leaving your environment is protected and compliant, you’re exposing the organization to fines, penalties, and reputational damage.

Question 10: Do your teams know the difference between perceived file safety and actual zero-day protection?

There’s a dangerous gap between what looks safe and what is safe. A file may pass through an antivirus or a gateway scan without raising alarms, but that doesn’t mean it’s free of hidden exploits. Zero-day threats are designed to slip past traditional checks. If your teams assume “no alert” equals “no risk,” they may work with compromised files without realizing it.

💡 Mini-tip: If you can’t prove compliance at the file level, auditors will find the gap and attackers will exploit it first.

Score Yourself & Reflect

Now that you’ve completed all 10 questions, it’s time to see where you stand. Give yourself 1 point for every “Yes” and 0 points for every “No” or “Unsure.”

• 7–10 points: You’re ahead of the curve. Your organization takes file safety seriously, but threats evolve quickly. Staying proactive is key.
• 4–6 points: You have notable gaps that leave sensitive data and critical systems at risk. It’s time to rethink how you secure files across channels.
• 0–3 points: You’re wide open to file-borne threats. Attackers count on this level of exposure, and for most organizations, it’s not a question of if but when.

This simple self-check shows the truth: file risk is everywhere, and traditional tools don’t catch it all. The question is, what will you do about it?

Why File Sanitization (CDR) Completes the Picture

Antivirus, secure email gateways, sandboxing, and even browser isolation all play a role in cybersecurity stacks, but none can guarantee that every file entering your environment is safe to use. That last gap is exactly where breaches happen.

Votiro’s automated file sanitization – aka our advanced content disarm and reconstruction – closes that gap. It delivers security without slowing business down by neutralizing hidden malware in real time while keeping files fully functional. No quarantines. No delays. No false positives. Just clean files, instantly.

Schedule a demo today to see how Votiro can help increase your file security score.