Technology
Top 7 tips for sending sensitive documents online
Gone are the days of mailing physical files or delivering them by hand to ensure the safe and secure delivery of sensitive files. While there is no guarantee or foolproof method of sharing files online, below are some of the best tips for how to share sensitive files as safely as possible.
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A man handing a folder to a co-worker (Kurt “CyberGuy” Knutsson)
Top 7 tips for safely sending sensitive files online
1) Restrict access to files
Red skull and bones next to protected file on a computer screen (Kurt “CyberGuy” Knutsson)
When transmitting sensitive files online, think of them as confidential documents that require stringent security protocols. Most file-sharing services offer robust access control settings, which are crucial for protecting your data. By default, shared links may allow anyone to access the file, posing a significant risk if the link is inadvertently shared with unauthorized individuals. To mitigate this, proactively adjust the settings to:
Limit access to specific individuals: Assign access rights exclusively to designated email addresses or registered users on the platform. This ensures that only verified individuals can view, edit or provide feedback on your files.
Use advanced permissions: Customize user permissions with granular control, determining who can download, edit or merely view the files. This prevents unauthorized alterations and distribution.
Enable link expiration: Set shared links to expire after a certain period or after the intended use, reducing the window of opportunity for unauthorized access.
Track file activity: Use the platform’s tracking features to monitor who accesses the files and when, providing an audit trail for security purposes.
By implementing these measures, you create a digital equivalent of a secure, locked filing cabinet, ensuring that your sensitive files remain confidential and only in the hands of those who are meant to see them.
HOW TO REMOVE YOUR PRIVATE DATA FROM THE INTERNET
2) Regularly update your software
If your system isn’t safe and protected, your files cannot stay safe and protected. By regularly updating your operating system’s software and the applications you use, you are less likely to be exposed to certain vulnerabilities. This practice is not just a recommendation; it’s a critical component of a robust cybersecurity strategy.
Software updates do more than introduce new features; they are often released to patch security holes and fix vulnerabilities that have been discovered since the last version. Cybercriminals constantly scan for systems with outdated software to exploit these weaknesses. By staying current with updates, you close these openings and make it significantly harder for attackers to gain unauthorized access to your system. Running outdated software is akin to leaving the door to your digital house unlocked. It invites a host of potential risks, including:
Malware infections: Outdated applications can become the perfect hosts for malicious software, which can spread across your network, corrupting files and stealing sensitive information.
Data breaches: Unpatched vulnerabilities can serve as entry points for data breaches, leading to the exposure of confidential data such as personal details, financial information and intellectual property.
3) Password-protect files
Username and password screen (Kurt “CyberGuy” Knutsson)
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When you can, password-protect any of the files you share online. It is an extra layer of protection that must be bypassed to access your file. Password protection requires anyone who has access to the recipient’s device to know the password to access your file, too. Consider using a password manager to generate and store complex passwords.
HOW YOUR PASSWORDS CAN BE STOLEN BY AI LISTENING TO YOUR KEYSTROKES
4) Opt for trusted file-sharing services
When it comes to transmitting sensitive data online, the integrity of your file-sharing service is paramount. Opting for established and trustworthy platforms can significantly mitigate the risk of unauthorized access or data breaches. Here are some of the most renowned and secure file-sharing services that have earned their reputation for reliability:
Microsoft OneDrive: Integrated seamlessly with Windows and Office 365, OneDrive provides a secure and efficient way to store and share files, with advanced features like Personal Vault for an extra layer of protection.
Dropbox: A pioneer in cloud storage, Dropbox has evolved to offer high-level security features, including two-factor authentication and file encryption, making it a solid choice for sensitive information.
Amazon Cloud Drive: With the backing of a tech giant, Amazon Cloud Drive delivers a secure and reliable platform for file storage and sharing, complete with comprehensive controls to manage access and permissions.
Google Drive: Renowned for its user-friendly interface, Google Drive offers robust sharing options and powerful collaboration tools, all while ensuring your data is protected with industry-leading security measures.
Each of these platforms offers unique features and security protocols. It’s essential to evaluate their offerings in relation to your specific needs. For instance, if collaboration is a key aspect of your workflow, Google Drive or Microsoft OneDrive might be more suitable due to their integration with productivity suites. On the other hand, if you’re looking for straightforward file storage with easy retrieval, Dropbox and Amazon Cloud Drive are excellent choices.
For a deeper dive into the capabilities and security features of these platforms, consider checking out “Best ways to save and restore documents,” which provides valuable insights into optimizing your file management practices while maintaining the highest security standards.
5) Install and use strong antivirus software
Before uploading or downloading any files you are sending or receiving, use your antivirus program to scan them for malware. There’s no point in securely sending or receiving corrupt files. If you don’t have one, you should, as it is also the best way to protect yourself from clicking malicious links that install malware that may access your private information. We recommend having strong antivirus protection installed on all your devices. This can also alert you of any phishing emails or ransomware scams. Get my picks for the best 2024 antivirus protection winners for your Windows, Mac, Android and iOS devices.
6) Encrypt your files
A person typing on a laptop with the words “Your personal files are encrypted” (Kurt “CyberGuy” Knutsson)
Even though emails seem almost instantaneous, the files you email can still be intercepted while traveling between you and your intended recipients. If cybercriminals intercept a file, but it is encrypted, then regardless of that breach, the file will be unreadable and useless to them. By encrypting your files, you create a formidable barrier that preserves the confidentiality and integrity of your data, ensuring that only the intended eyes can decipher the message within.
BEWARE OF ENCRYPTED PDFs AS LATEST TRICK TO DELIVER MALWARE TO YOU
7) Enable 2-factor authentication
In today’s digital world, protecting sensitive files during online transmission is crucial, and one of the most effective security measures available is two-factor authentication (2FA). This advanced security protocol requires two proofs of identity, significantly enhancing the protection of your digital assets. When you enable 2FA, you’ll first enter your username and password followed by a second form of identification, such as a code sent to your mobile device, a fingerprint or facial recognition.
The importance of 2FA cannot be overstated; it not only reduces the risk of password theft but also offers a variety of verification methods to suit your preferences, along with immediate security alerts for any unauthorized access attempts. To implement 2FA, always check the security settings of your platforms and enable it wherever possible.
For a more secure experience, consider using authenticator apps, which generate time-sensitive codes. It’s also wise to have backup codes or a secondary authentication device in case your primary 2FA method is unavailable. Incorporating 2FA into your security routine ensures that your sensitive files remain confidential and well-protected during online transactions.
Kurt’s key takeaways
While cloud and file-sharing services can make life a lot easier, it is important to protect what you are sharing, especially sensitive files. Because not all files can be password protected on every file-sharing platform or safe during online transit, the seven steps outlined above can keep your sensitive files safer when being shared online.
What additional measures do you think could enhance the security of file-sharing platforms currently available? Let us know by writing us at Cyberguy.com/Contact.
For more of my tech tips and security alerts, subscribe to my free CyberGuy Report Newsletter by heading to Cyberguy.com/Newsletter.
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Copyright 2024 CyberGuy.com. All rights reserved.
Meta might be the next company to make an always-on AI wearable. The company is working on prototype “super sensing” always-aware smart glasses that could continuously record audio and snap photos “every few seconds,” according to the Financial Times. The wearer could then ask Meta AI about the captured audio and images.
However, the images and audio might not be directly available to the user. Here’s how the FT describes one way the glasses could use the data:
In one proposed system, raw footage and audio would not be stored by Meta or made available to the user, several people said. Instead, the metadata from that audio and images would be extracted and uploaded to the server for Meta’s AI to query, which proponents argue would have fewer privacy implications.
But currently, Meta is planning for the LED recording indicator to remain off in “super sensing” mode, the FT reports. In a July 2025 whitepaper, the company said that it would reserve the LED indicator for “active capture” scenarios where the user is saving photos or videos, and leave it off during “AI Feature” use — such as scanning a menu — to avoid users becoming too used to the indicator. (If the indicator was on during the “super sensing” mode, it might also be harder to know when the glasses are actually recording video.)
Meta is also discussing if it would use the captured data for training its AI models. It may also bring the “super sensing” features to glasses it has already released, the FT says.
“While we don’t comment on internal prototypes, we’re committed to getting our glasses right because they need to be loved by both people wearing them and those around them,” Meta spokesperson Dave Arnold says in a statement to The Verge. Arnold also notes that “Our approach has been to develop new technologies that will help people throughout their day, with privacy built in from the ground up.”
Meta hasn’t been shy about some type of always-aware glasses being a possibility. CEO Mark Zuckerberg, in the company’s Q1 2026 earnings call, said that he was “really excited to see the glasses evolve from being able to answer questions to being able to be a personal agent that’s with you all day long, helping you remember things and achieve your goals.” In a March blog post about new Ray-Ban Meta glasses, the company wrote that “with ongoing software updates, Meta AI on glasses will transition from something you have to prompt with a question each time, to a more continuous, in-the-moment assistant that can help throughout the day.”
Even though they haven’t been officially announced yet, Samsung is giving you a chance to save some cash when you preorder what we’re expecting to be the brand’s updated Galaxy Z Fold phones. The next Galaxy Unpacked event will take place on July 22nd, 2026, and features the tagline “A new shape unfolds.” In addition to seeing updated versions of the existing Flip and Fold form factors, we anticipate the debut of a new, wider foldable phone. If you register your interest ahead of time and end up preordering one of the new phones shortly after they’re announced, Samsung will give you a $30 store credit at checkout.
There are some caveats to this offer. You have to use the credit when you preorder the phone. No saving it for later. Also, the credit can’t be applied to the cost of the phone either, so you’ll have to put it towards the cost of accessories or extra services. Samsung specifically calls out that select Galaxy rings, earbuds, watches, and tablets are eligible, or you can use it to help pay for Samsung Care Plus.
There are no downsides to registering your interest, so if you think you might be interested in buying one of the upcoming phones, it’s worth filling out the form. As long as you use the same email during checkout, the credit will be automatically applied.
Anthropic’s new AI model raises alarms over safety, cybersecurity concerns
Matt Shumer, co-founder and CEO of OthersideAI, details Anthropic’s new AI model, Mythos, on ‘The Sunday Briefing’. The model’s “emergent capabilities” to find software vulnerabilities autonomously raised alarms, prompting Anthropic to restrict public access. Shumer explains the proactive move of granting major companies and the US government early access to Mythos for cyber defense, anticipating future threats to critical infrastructure and national security.
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A security update rarely feels dramatic. You see the alert, promise yourself you will install it later and then go right back to whatever you were doing. This time, Apple is giving you a stronger reason to pay attention.
Apple released iOS 26.5.2, iPadOS 26.5.2 and macOS Tahoe 26.5.2 on June 29, 2026. The updates include security fixes for vulnerabilities tied to the kernel, WebKit and WebRTC. Apple says these fixes were first made available through the iOS 26.6, iPadOS 26.6 and macOS Tahoe 26.6 betas before being pushed out early to everyone.
That is the part that should make you pause. Apple usually rolls many security fixes into larger software updates. This time, the company moved faster.
AI IS NOW POWERING CYBERATTACKS, MICROSOFT WARNS
Apple pushed out security fixes early because AI can help hackers study software flaws faster. (Nikolas Kokovlis/NurPhoto via Getty Images)
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Why Apple released this AI security update early
Apple reportedly accelerated the updates because artificial intelligence can help speed the creation of malicious hacking tools. Once a fix appears in a beta, attackers may be able to study it, reverse-engineer the weakness and move faster than before.
Apple said there was no evidence that the newly patched vulnerabilities had been exploited. Still, the company wanted to shrink the time between when fixes were first visible and when they reached your devices.
That is a major shift. It suggests Apple sees AI as a force that changes the timing of security. A flaw that once gave defenders more breathing room may now become a race.
What Apple fixed in iOS 26.5.2
Apple’s iOS 26.5.2 and iPadOS 26.5.2 notes list fixes for iPhone 11 and later, along with several supported iPad models. The security content includes kernel vulnerabilities that could let an app crash the system, corrupt kernel memory or leak sensitive kernel state.
The update also fixes multiple WebKit issues. WebKit powers Safari and web content inside many apps. Some of these flaws involved malicious web content that could lead to crashes, memory corruption, data leaks or sandbox escapes.
Apple also fixed WebRTC issues that could be triggered by malicious web content and lead to Safari or process crashes.
For Mac, Apple lists macOS Tahoe 26.5.2 as the current release. If your Mac runs macOS Sonoma or macOS Sequoia, Apple also lists Safari 26.5.2 as a June 29, 2026, security release.
A woman uses a smartphone outside an Apple Store on June 20, 2026, in Shenzhen, Guangdong Province, China. (Cheng Xin/Getty Images)
Why AI hacking tools change the security race
AI can help legitimate researchers find bugs faster. That is good when the work leads to stronger software and responsible disclosure. However, the same general capability can also help bad actors move faster. A criminal does not need to understand every line of code if an AI tool can help summarize a patch, compare software changes or suggest where a weakness may be hiding.
That is why Apple’s move is important. It shows that big tech companies may need to release security fixes sooner and more often, even when those updates do not include flashy new features. The wider AI world adds pressure here. Frontier AI companies have released or tested systems with stronger coding and cybersecurity capabilities. Some models are available only through limited previews, approved access or extra safeguards because of their potential cyber use.
Similar efforts are also emerging outside the United States. Several international AI labs and security companies now promote models designed to find vulnerabilities, analyze code and assist cyber defense. The takeaway for you isn’t that AI is automatically bad. The real point is speed. Security teams, attackers and AI tools are now moving on a shorter clock.
How to update your iPhone or iPad
Before you update, plug in your device and connect to Wi-Fi. You may also want to back up your iPhone or iPad first.
Then do this: Open Settings > General > Software Update > Download and Install.
After the update finishes, go back to Settings > General > Software Update > Automatic Updates. Make sure automatic updates are turned on. Apple also lets your device automatically install system file updates that improve security without changing the full software version. If you do not see the update right away, check again later. Apple releases updates in stages, and your device also needs enough battery and storage.
How to update your Mac
On a Mac, start with a backup. Then click the Apple menu > System Settings > General > Software Update . Choose Update Now if macOS Tahoe 26.5.2 appears.
Next, check your background update settings. On macOS Tahoe 26 or later, go to Apple menu > System Settings > General > Software Update . Click the More Info button next to Automatic Updates and make sure Install system data files and security updates is turned on.
If your Mac runs Sonoma or Sequoia, look for Safari 26.5.2 in Software Update as well. That Safari update may be the protection your Mac needs if you are not on Tahoe.
BEWARE OF HACKERS SHOWING UP PRETENDING TO BE IT
What this Apple security update means to you
You may see more security updates that feel sudden or small. That can be annoying, especially when you are busy or your device needs to restart.
Still, these updates are becoming more important. Apple is reacting to a world where AI can help shorten the time between a public fix and a possible attack.
So, when your iPhone, iPad or Mac asks you to update, do not treat it like background noise. The update may be closing a door someone else is already trying to find.
Updating your iPhone, iPad and Mac helps close security holes before attackers get more time to exploit them. (Katharina Kausche/picture alliance via Getty Images)
How to stay safe after the Apple security update
Installing the Apple AI security update is the best first move. After that, tighten a few habits that make attacks harder.
1) Keep your apps updated
Your operating system is only part of the security picture. Outdated apps can still create risk, especially if they handle messages, web links, photos, files or account logins. Open the App Store and install available updates regularly.
2) Watch out for suspicious links
Be careful with links in texts, emails and social media messages. WebKit and browser flaws are a reminder that malicious web content can be part of an attack. When in doubt, open the official app or website yourself instead of tapping a link.
3) Use strong passwords and two-factor authentication
Use strong, unique passwords for every account and store them in a password manager. Then turn on two-factor authentication (2FA) wherever possible. If one password gets exposed, you do not want it opening the door to your email, bank or Apple account.
4) Use strong antivirus protection
Use strong antivirus protection on your Mac and other connected devices. It can help catch malicious files, phishing attempts and suspicious activity before they do damage. Get my picks for the best 2026 antivirus protection winners for your Windows, Mac, Android and iOS devices at CyberGuy.com.
5) Back up your data regularly
Back up your iPhone, iPad and Mac before problems hit. A recent backup can help you recover faster if an update fails, your device gets stolen or malware locks you out of important files. CyberGuy’s guide to backing up your devices walks you through ways to protect your files using cloud storage, an external drive or both.
6) Use a personal data removal service
Use a personal data removal service to reduce how much of your personal information is floating around online. Data brokers and people-search sites can expose your name, address, phone number and relatives. Scammers can use those details to make phishing messages feel more believable. Check out my top picks for data removal services and get a free scan to find out if your personal information is already out on the web by visiting CyberGuy.com.
Kurt’s key takeaways
Apple’s early security release shows how fast the cyber threat landscape is changing. The company says there is no evidence these newly patched flaws were exploited, but it still moved the fixes out before the wider 26.6 release. That tells me the old habit of waiting weeks to update is getting riskier. AI can help defenders, but it can also help criminals study weaknesses faster. My advice is direct: update your Apple devices now, turn on automatic security updates and stop putting off patches that protect the phone and computer you use every day.
Do you think AI will make your devices safer because companies can find flaws faster, or more vulnerable because hackers can move faster too? Let us know by writing to us at CyberGuy.com.
Automatic updates, strong passwords and a personal data removal service can make you a harder target after the update. (Silas Stein/picture alliance via Getty Images)
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Copyright 2026 CyberGuy.com. All rights reserved.
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