Every executive assistant plays a crucial role in managing sensitive information and ensuring the smooth operation of their executive’s digital life.

We could say they’re gatekeepers of information, entrusted with sensitive data, confidential communications, and the smooth operation of their executives’ digital lives. 

However this isn’t just about protecting your company’s data; it’s about protecting your productivity, reputation, and peace of mind.

A well-equipped cybersecurity toolkit empowers executive assistants to navigate the digital landscape safely and efficiently, minimizing risks and maximizing their effectiveness. 

Top Cybersecurity Apps and Tools for the Executive Assistant’s Toolkit

Executive assistants are entrusted with a unique blend of responsibilities: managing schedules, coordinating communication, and handling sensitive information. 

This access to confidential data makes cybersecurity a critical concern for EAs. 

Fortunately, a range of powerful tools and apps can help safeguard your information and streamline your workflow, allowing you to focus on your core tasks with confidence.

Password Management Apps & Tools to Protect Your Business Assets

Let’s face it, passwords are a pain. 

We all have dozens, if not hundreds, of them, and trying to remember them all is a recipe for disaster. 

Weak passwords, reused passwords, and scribbled-down passwords on sticky notes are all vulnerabilities that cybercriminals can exploit. 

In fact, 57% of users reported having a password written down on a sticky note, and a shocking 44% of users reported recycling passwords across personal and business-related accounts.

Password management tools offer a secure and efficient solution. 

These tools generate strong, unique passwords for each of your accounts, store them securely in an encrypted vault, and automatically fill them in when you need them. 

This not only enhances security but also saves you time and frustration, eliminating the need to remember or reset passwords constantly.

Here are a few top-rated password management tools:

Password ManagerBiggest Feature
BitwardenOpen-source and highly transparent. This appeals to users who prioritize security and want to be able to audit the code. It also offers a generous free plan.
LastPassWidely known and trusted, with a long history in the industry. This provides security and reliability for users who prefer a well-established solution.
1PasswordFocus on user experience and ease of use. This makes it a good choice for users new to password managers or who prefer a more intuitive interface.
DashlanePremium experience with advanced features. This appeals to users willing to pay for extra security and convenience.

Choosing the right password manager depends on your specific needs and preferences, but the key is to use something to protect your passwords and enhance your cybersecurity posture. 

Email Security Apps & Tools to Shield Your Inbox

Email is the lifeblood of modern business, but it’s also a prime target for cybercriminals. 

Phishing scams, malware attacks, and data breaches can all originate from a single malicious email, making inbox security a top priority for executive assistants. 

Fortunately, a range of powerful tools and apps can help you shield your inbox from these threats.

Advanced Threat Protection

Services like Mimecast offer comprehensive email security solutions that go beyond basic spam filters. 

They scan incoming and outgoing emails for malware, phishing attempts, and other malicious content, blocking threats before they reach your inbox. 

Mimecast also provides email archiving, backup, and recovery services, ensuring business continuity in case of a disruption. 

Security-Focused Email Clients

Some email clients, like Canary Mail, prioritize security with features such as end-to-end encryption, phishing protection, and read receipts. 

These clients offer a more secure alternative to traditional email platforms, especially for highly sensitive communications.

Anti-Phishing Extensions

Browser extensions like Netcraft and PhishDetector can help you identify phishing websites and emails, providing an extra layer of protection against these deceptive attacks. 

These extensions analyze website URLs, email headers, and other indicators to identify potential phishing attempts, alerting you to potential risks.

By combining these email security apps and tools, executive assistants can create a robust defense against email-borne threats, protecting their inboxes, their data, and their organizations. 

Device Security Apps & Tools to Safeguard Your Data In and Out of the Office

Executive assistants are increasingly mobile, working from laptops, smartphones, and tablets both in the office and on the go. 

This mobility, while offering flexibility and convenience, also expands the potential attack surface for cyber threats. Securing your devices is paramount to protecting sensitive data and maintaining productivity, wherever you’re working.

Endpoint Protection

Traditional antivirus software is no longer enough. 

Modern endpoint protection platforms, like CrowdStrike Falcon and Intercept X Advanced, offer comprehensive protection against malware, ransomware, and other sophisticated attacks. 

They use advanced technologies like artificial intelligence and machine learning to detect and respond to threats in real time. 

These tools go beyond simply scanning for known viruses; they actively monitor device behavior, identify anomalies, and block malicious activity before it can cause damage. 

Disk Encryption

Encrypting your device’s hard drive adds another layer of protection, ensuring that your data remains inaccessible even if your device is lost or stolen. Tools like VeraCrypt offer robust encryption capabilities, safeguarding your files and folders from unauthorized access. 

Let’s not forget that 73% of companies in North America use browsers that are out of date, leaving them vulnerable to attacks.

By implementing these device security measures, executive assistants can protect their data, maintain their productivity, and ensure the security of their organization’s information, regardless of where they’re working. 

LayerLogix can help you assess your device security needs and implement the right solutions to safeguard your business.

Essential Apps and Tools for Data Protection & Privacy

Data protection and privacy are paramount in today’s digital landscape, especially for executive assistants handling sensitive business information. 

Fortunately, a range of tools and apps can help you safeguard confidential data and maintain compliance with privacy regulations.

Data Loss Prevention (DLP) Software

DLP tools, like Forcepoint, monitor and control the movement of sensitive data within your organization, preventing accidental or intentional leaks. 

They can identify and block the sharing of confidential information via email, cloud storage, or other channels, ensuring your organization’s data remains protected. 

Encryption Tools

Encryption scrambles data into an unreadable format, making it useless to anyone who doesn’t have the decryption key. For example, tools like 7-Zip, a free and open-source file archiver, offer strong encryption capabilities for compressing and protecting files.

Secure File-Sharing Platforms

When sharing files with colleagues, clients, or partners, use secure file-sharing platforms that offer encryption and access controls. 

Consider tools like ShareFile or Tresorit, which provide secure file storage, sharing, and collaboration features.

On the other hand, avoid sending sensitive information via unencrypted email attachments, which are vulnerable to interception. 

Privacy-Focused Browsers and Extensions

Consider using privacy-focused browsers like Brave or Firefox with privacy-enhancing extensions like Privacy Badger or HTTPS Everywhere

These tools can block trackers, prevent websites from collecting your browsing data, and ensure you’re always using a secure HTTPS connection.

Data Privacy Management Software

Tools like OneTrust and BigID help organizations manage data privacy, comply with regulations like GDPR and CCPA, and build trust with customers. 

These platforms offer features such as data discovery, consent management, and data subject rights fulfillment.

Cybersecurity Best Practices for Executive Assistants

Executive assistants are on the front lines of business communication, often handling sensitive information and managing access to critical systems. 

This makes them prime targets for cybercriminals seeking to exploit vulnerabilities and gain unauthorized access to valuable data. 

While technology tools play a crucial role in cybersecurity, adopting best practices and cultivating a security-conscious mindset are equally important.

Here are some essential cybersecurity best practices for executive assistants and other C-suite professionals:

  1. Be Vigilant About Phishing: Phishing attacks are becoming increasingly sophisticated, often mimicking legitimate emails and websites to trick you into revealing sensitive information. Be wary of unsolicited emails, especially those requesting personal information, login credentials, or financial details. Verify the sender’s identity before clicking on links or opening attachments. If something feels “phishy,” trust your instincts and report it to your IT department. 
  2. Practice Strong Password Hygiene: Use strong, unique passwords for all your accounts, and avoid reusing passwords across multiple platforms. A password manager can help you generate and store strong passwords securely. Enable multi-factor authentication (MFA) whenever possible, adding an extra layer of security to your accounts.
  3. Secure Your Devices: Keep your laptops, smartphones, and tablets secure with strong passwords or biometric authentication. Install reputable antivirus software and keep your operating systems and applications updated with the latest security patches. Be cautious about connecting to public Wi-Fi networks, and use a VPN to encrypt your connection when working remotely or on public Wi-Fi.
  4. Handle Sensitive Data with Care: Be mindful of the data you handle and follow your organization’s data protection policies. Encrypt sensitive files before sharing them electronically, and use secure file-sharing platforms. Avoid sending confidential information via unencrypted email attachments. Dispose of sensitive documents securely, shredding them or using a secure disposal service.
  5. Back-Up Your Data Regularly: Regularly back up your critical data to a secure location, such as an external hard drive or a cloud-based backup service. This will help you recover your data in case of a ransomware attack, hardware failure, or accidental deletion.
  6. Stay Informed About Cybersecurity Threats: The threat landscape is constantly evolving, so staying informed about the latest threats and vulnerabilities is crucial. Read industry publications, attend cybersecurity webinars, and follow reputable security blogs to stay up-to-date.
  7. Report Suspicious Activity: If you notice any suspicious activity on your devices or network, such as unusual emails, unfamiliar software, or unexpected system behavior, report it to your IT department immediately. Early detection and response are crucial for mitigating the impact of cyberattacks.
  8. Think Before You Click: Be cautious about clicking on links or opening attachments from unknown sources. Hover over links to see the full URL before clicking, and be wary of shortened URLs or those that look suspicious. If you’re unsure about an email or attachment, contact the sender directly to verify its legitimacy.
  9. Use Secure Communication Channels: When discussing sensitive information, use secure communication channels, such as encrypted messaging apps or secure video conferencing platforms. Avoid discussing confidential matters over unsecured public Wi-Fi networks.
  10. Be Mindful of Social Engineering: Cybercriminals often use social engineering tactics to manipulate people into revealing sensitive information or granting access to systems. Be wary of unsolicited phone calls, emails, or social media messages requesting personal information or login credentials. Verify the identity of anyone requesting sensitive information before providing it.

By adopting these cybersecurity best practices, executive assistants can play a vital role in protecting their organizations from cyber threats. 

Remember, cybersecurity is everyone’s responsibility, and a proactive and vigilant approach is essential for staying safe in the digital age.

Cybercriminals are constantly devising new tactics to create and send dangerous email attachments, using them as a gateway to unleash malware, viruses, and other malicious software. 

To safeguard ourselves and our systems, it’s essential to understand why some email attachments are dangerous, which types pose a high risk, and how to spot them effectively. 

In this article, we will delve into the world of dangerous email attachments and equip you with the knowledge to protect yourself.


Why Are Some Email Attachments Dangerous and Which Are High Risk?

Email attachments pose a threat primarily because they can contain malicious files or code that can exploit vulnerabilities in our systems. 

Cybercriminals leverage social engineering techniques to trick recipients into opening these attachments, often disguising them as harmless or enticing files. 

Once opened, these attachments can unleash malware, viruses, ransomware, or other harmful software, leading to data breaches, system damage, or unauthorized access to sensitive information.

1) Executables

Among the high-risk email attachments, executables (.exe) are particularly dangerous. 

These files have the capability to run codes that can modify a computer system. 

Cybercriminals often disguise them with innocent-sounding names to deceive recipients into opening them. 

Executable files can be vehicles for ransomware, encrypting files and demanding payment for decryption, or they can serve as carriers for other malicious software.

Executables Dangerous Email Attachments
Source: Ascend Technologies


2) Scripts

Such as .js, .vbs, .php, or .asp files, are another high-risk attachment type. While not inherently malicious, cybercriminals utilize scripts to install malware on victims’ computers. 

By exploiting vulnerabilities in software or manipulating user interactions, malicious scripts can execute harmful commands or actions, compromising system integrity and privacy.


3) Documents

In various formats (.doc, .xls, .ppt, .pdf) also pose a significant risk. Cybercriminals inject malicious code into seemingly harmless documents, such as Microsoft Office files or PDFs, and prompt users to enable macros or click on phishing links. 

Enabling macros or interacting with these documents can lead to the activation of malware, unauthorized access, or theft of login credentials.

Document Dangerous Email Attachments
Source: Mailguard


4) Archive Files

Archive files, including .zip, .rar, or .7z, are commonly used by cybercriminals to conceal malware. These compressed files provide an effective means of delivering malicious executables, scripts, or infected documents. 

By enticing recipients with intriguing filenames or exploiting their curiosity, cybercriminals trick users into extracting the contents of the archive, inadvertently activating the hidden malware.


5) Disk Image Files

Disk image files, such as .iso, .img, or .dmg, are particularly risky, especially for macOS users. These files can contain executables, scripts, or documents that can compromise system security. 

Cybercriminals often bundle disk images with seemingly harmless files, using social engineering to entice users into executing the installer and unknowingly installing malware.

Disk Image File Dangerous Email Attachments


Tips to Spot Dangerous Email Attachments

  1. Be skeptical: Maintain a healthy level of skepticism when it comes to email attachments. Question the authenticity and relevance of the attachment before opening it. If something seems suspicious or out of the ordinary, it’s better to err on the side of caution.

  1. Verify the sender: Check the sender’s email address and ensure it matches the expected sender. Pay attention to any misspellings, unfamiliar addresses, or suspicious domains. If you have doubts about the sender’s identity, contact them through alternative means to verify the attachment’s legitimacy.

  1. Scan attachments: Utilize reputable antivirus software to scan email attachments before opening them. This can help detect and eliminate potential threats before they can harm your system.

  1. Avoid enabling macros: Exercise caution when enabling macros in documents, especially if they come from unknown or untrusted sources. Disable macros by default and only enable them if you trust the source and the content of the document.

  1. Keep software up to date: Regularly update your operating system and applications to ensure you have the latest security patches. This can help mitigate vulnerabilities that cybercriminals might exploit through malicious email attachments.

  1. Educate yourself: Stay informed about the latest email scams and malware trends. By educating yourself and staying updated on cybersecurity best practices, you can better recognize and avoid dangerous email attachments.


Additional FAQs

Can all email attachments be dangerous?

Not all email attachments are dangerous, but it’s essential to exercise caution and verify the authenticity of the attachment and the sender before opening it. 

Cybercriminals often use social engineering tactics to trick users into opening malicious attachments, so it’s crucial to be vigilant.


What should I do if I receive a suspicious email attachment?

If you receive a suspicious email attachment, it’s best to avoid opening it. 

Delete the email and attachment immediately. 

If the email appears to be from someone you know, contact them through another communication channel to verify the attachment’s legitimacy.


Are email attachments from trusted sources always safe?

While email attachments from trusted sources are generally safer, it’s still essential to exercise caution. 

Cybercriminals can compromise email accounts or use spoofing techniques to make an email appear legitimate. 

Always verify the sender and the content of the attachment before opening it.


Should I rely on antivirus software to detect dangerous email attachments?

Antivirus software is an essential layer of protection, but it’s not foolproof. 

Cybercriminals constantly develop new techniques to evade detection. 

Therefore, it’s crucial to adopt a multi-layered security approach, which includes being vigilant, staying informed, and following best practices for email safety.

To help mitigate the risks of cyber threats targeting unsuspecting users every day through email, many organizations rely on Secure Email Gateways (SEG), which are designed to block incoming threats and filter out unwanted or malicious messages. 

In this article, we’ll take a closer look at some of the leading SEG solutions on the market, including their key features and benefits, to help you choose the best one for your business.


What is a Secure Email Gateway (SEG) & How Does It Work? 

Secure email gateways (SEGs) are an essential tool for email security solutions, as they provide protection against email-borne threats. However, the effectiveness of SEGs has been limited in recent years. 

Many SEGs have failed to keep up with the ever-changing threat landscape, which has led to an increase in social engineering attacks. In addition, the design of SEGs makes them less suitable for protecting cloud-based email solutions.

One limitation of SEGs is that they rely heavily on a set of predefined rules and policies, which may not be enough to detect all types of email threats. 

Sophisticated phishing attacks that use new and creative techniques can often pass through these rules and policies, which makes it difficult for SEGs to protect against them.

Another limitation is that SEGs are less effective at protecting cloud-based email solutions such as Microsoft 365 and Google Workspace. This is because the design of SEGs is based on inspecting emails inline, which means that they need to sit in line on the path of emails from the public internet to the corporate email server. 

This design makes them less effective at protecting cloud-based email solutions, which often require an API-based approach.

To overcome these limitations, organizations need to implement more advanced email security solutions. One such solution is the cloud-native email security, which uses an API-based approach to protect cloud-based email solutions. 

Cloud-native email security solutions can analyze data from multiple sources, including email, identity, and web browsing behavior, to identify threats that traditional SEGs cannot.

Another solution is to use machine learning and artificial intelligence (AI) to improve the effectiveness of SEGs. Machine learning and AI can help identify new and emerging threats that SEGs might not have seen before, allowing organizations to quickly adapt and update their security measures.

Best Secure Email Gateways in 2023

In this article, we will explore the best secure email gateways for businesses, both small and large, for the year 2023.

  1. Cisco Secure Email – It is a cloud service that filters all incoming emails to protect users against attacks like phishing, business email compromise, malware attachments, and ransomware. It complies with government and industry regulations with robust data loss prevention and encryption capabilities.

    Cisco Secure Email monitors inbound emails continuously and offers maximum flexibility to be deployed on-premises, in the cloud, virtually, or in hybrid architectures.

  1. Microsoft Defender for Office 365 – It offers native protection for Office 365, including Microsoft Outlook, and is a cloud-based email filtering service. It protects against advanced threats like BEC, phishing, and zero-day malware attacks, and collaborates with real-time reports and automatic threat mitigation responses.

    Its anti-phishing protection is powered by machine learning and advanced algorithms that can detect attempts to impersonate users or domain spoofing. Administrators can run simulations of realistic attack scenarios to identify vulnerabilities.

  1. Avanan – It uses AI to protect against sophisticated attacks, making it an ideal solution for Office 365 and Google Workspace users. It integrates well into the environment and covers multiple layers, offering threat protection inside the email inbox and monitoring incoming, outgoing, and internal emails as they are in transit.

    It can detect zero-day phishing attacks, identify BEC by flagging logins made from unusual locations, and protect against malicious attachments and URLs.

  1. SpamTitan Email Security and Protection – It is easy to set up, deploy, manage, and use and offers antivirus protection on top of spam blocking. It has features like blacklisting, whitelisting, and advanced reporting for all inbound, outbound, and internal emails.


  1. Proofpoint Email Protection – Proofpoint Email Protection is an industry-leading email security solution that uses AI to defend against BEC attacks. It can classify various types of emails accurately and stop a wide variety of email fraud, including payment redirects and supplier invoicing fraud.

    Administrators can use log data to help with troubleshooting, and Proofpoint’s AI means it offers dynamic protection that continues to evolve and defend against new malware, threats, and other malicious technology.



  2. Mimecast – Mimecast is a cloud-based secure email gateway that is ideal for larger organizations. It offers features such as defense against malware, credential harvesting, impersonation attacks, and zero-day attacks.

    The tool uses machine learning technology to protect against BEC and targeted attacks from both outside and inside the organization.



  3. Forcepoint Email Security Solution – It has Optical Character Recognition (OCR) scanning to help spot sensitive data hidden in images like scanned documents or screen grabs.

    It also has encrypted file detection to recognize custom encrypted files intended to bypass identification screening and offers advanced analysis of macros embedded in MS Office files.

    Conditional security access curbs full access to sensitive email attachments on risky mobile devices, while allowing them to be still accessible on more secure devices.

Email is a ubiquitous communication tool used by individuals and businesses alike. Unfortunately, it’s also a prime target for cybercriminals, so it’s crucial to have the best email-scanning software in place to protect against these threats.

In this article, we’ll take a look at some of the top email scanners available in 2023. From Norton 360’s comprehensive suite of anti-virus tools to open-source solutions like MailScanner, there’s no shortage of options to choose from. 

Whether you’re a small business owner or a tech-savvy individual, you’re sure to find an email scanner that meets your needs.


What is Email Scanning & How Does It Work?

Email scanning is an automated process that checks every email message for viruses, malware, and spam. It also inspects links and attachments for possible malicious attacks and looks for signs of email spoofing commonly used in impersonation attacks. 

This technology is deployed both at the email perimeter and inside it, using the latest threat intelligence and corporate content control and DLP policies to block, quarantine, or flag emails that may contain any potential threats.

These solutions can use various techniques to identify malicious content, such as scanning for signatures of known malware variants and using AI and ML to detect novel threats or potential social engineering attacks.

But what are the exact malware and other threats that email scanners can detect?



List of Common Email Malware Threats

Email scanning solutions can help identify and block various types of email threats. These solutions include:

  1. Phishing: Social engineering attacks that trick users into taking actions that harm the organization. Email scanners can detect and block business email compromise (BEC) and other social engineering attacks.

  1. Malware: Including ransomware and info stealers, can be delivered through email. Email scanning solutions can inspect email attachments for potentially malicious content, including executables, ZIP archives, and documents. Scanners with Content Disarm and Reconstruction (CDR) functionality can dissect malicious documents, remove malicious content, and rebuild sanitized documents.

  1. Malicious URLs: Emails can also use malicious URLs to direct users to phishing pages. 

  1. Data Leakage: Email can be used to carry sensitive data out of the organization. Email scanning solutions may include data loss prevention (DLP) functionality that identifies and blocks emails carrying sensitive data to unauthorized recipients.



Best Email Scanners in 2023

Unfortunately, with the convenience of email comes the constant threat of cyber-attacks through malicious emails. That’s where email scanning software comes in.

Here are the top email scanners for 2023:

First on the list is Norton 360, the highly-rated anti-virus utility. Its Premium subscription offers a complete package of anti-spyware, antivirus, malware, and ransomware protection, including a separate email scanner that checks incoming attachments and hyperlinks for viruses, spyware, and malware.

Next is AVG Internet Security, which offers a freeware version and a premium version with a limited email scanner that can block suspicious email attachments, spam, and phishing emails. The software also includes various email configuration options and advanced features such as AI detection and behavior shields.

For those looking for an all-in-one solution, Mimecast provides email security, continuity, archiving, compliance, and backup and recovery, all in a cloud-based subscription service. Its email scanning system can scan all inbound, outbound, and internal emails for threats to the organization.

CheckPoint/Avanan also offers a comprehensive email security platform that can replace SEG and non-SEG for inbox security, with the recent acquisition of Avanan by Check Point making it a stronger WFH security contender. 

Barracuda Email Threat Scanner is another powerful email scanner, with an artificial intelligence platform that understands the sender’s intent to detect social engineering attacks.

SpamTitan is a double anti-virus email scanner with a 99.99% spam catch rate, while MailScanner is an open-source email security system designed for Linux-based email gateways, used by top government departments, corporations, and educational institutions worldwide.

With the constant threat of cyber attacks, it’s essential to have email scanning software that can keep you protected.

Choose the best email scanner for your needs and keep your emails safe and secure.

Email has become a crucial part of our communication in today’s digital world, so to send secure email becomes a top business priority. It is fast, convenient, and widely accessible. However, sending sensitive information via email can be risky if it is not protected properly. 

While Gmail and Outlook are popular email providers, many users are unaware of the options available to them for sending secure emails and attachments.

The truth is that not all emails are created equal in terms of security. 

If you’re sending casual emails with pictures of your latest vacation, you’re probably not too concerned about security. But if you’re a journalist, a business owner, or someone who frequently sends sensitive documents, it’s essential to know how to send secure or encrypted emails.

In this article, we will guide you through the process of sending secure emails and attached documents via Gmail and Outlook. Whether you’re a beginner or an experienced user, our step-by-step instructions will help you send your emails with confidence. Write down to send secure email as one of your pressing business goals of this year.


How to Send Emails & Documents Securely in Gmail 

Gmail is a popular email service that uses Transport Layer Security (TLS) as a standard for keeping emails secure during delivery. However, TLS doesn’t provide the added security of keeping emails safe after they’ve been delivered.

Fortunately, Gmail offers a solution for this problem with its Confidential Mode, available in both free and paid Gmail accounts. Here are the step-by-step instructions for using Gmail Confidential Mode in a free account:

  1. Log in to your Gmail account.
  1. Click on the Compose button to start a new email.
  1. Write your email as usual.
  1. In the lower ribbon, click on the “Confidential” button.
  1. A popup will appear where you can select the email’s expiration date from the Set Expiry dropdown menu. You can choose to have it expire in one week, one month, three months, or even five years.
  1. Choose whether you want the recipient to use an SMS passcode or receive the password via email.
  1. Click Save.
  1. Send your confidential email.

If you want to password-protect MS Office Suite files, such as Word, Excel, or PowerPoint, you can use the Encrypt with Password feature. This option can usually be found under the 

Prepare the document for distribution function, but the way to access it depends on the version of the software you are using. Keep in mind that even though MS Suite has encryption, the decryption key is reduced to a simple user-picked password, which makes the document more vulnerable to hacking.

As for sending secure email attachments and documents through Gmail, Google Docs is an option. However, Google Docs items cannot be password-protected as your account login is considered a security clearance. 

Therefore, sending a page link via email may not be the best idea. While there are third-party add-ons available to enable password protection for Google Docs, their reliability may vary.

How to Send Secure Email & Documentation in Outlook

Microsoft’s Outlook provides default encryption with TLS (Transport Layer Security), but it only works if the recipient’s service also supports it. Microsoft also has been caught working with US intelligence agencies, which raises privacy concerns.

If you want to send a more secure message in Outlook, you can enable enhanced encryption with Microsoft 365 Message Encryption (OME). However, this feature is only available with a premium account, such as Microsoft 365 Family or Microsoft 365 Personal, or an eligible enterprise account. 

Once you’ve enabled OME, you can send emails and documents attached through the Outlook.com web or desktop app. The recipient can open the email using a Microsoft account, or Outlook can send them a passcode to open it.

If you have the Outlook desktop app, you can also enable S/MIME (Secure/Multipurpose Internet Mail Extensions) encryption, but it requires an eligible paid Microsoft account and technical skills to set up. S/MIME allows you to encrypt emails with user-specific keys so that only the intended recipients can decrypt them. 

However, you cannot send a private message to anyone using a regular Outlook account or any other provider without S/MIME support. You also need to verify that they have S/MIME correctly set up before sending.

Sending documents securely through Outlook is also possible using password protection. 

  1. For Microsoft Office documents, you can select File → Info → Protect Document → Encrypt with Password and save the file with the password. 
  1. For PDF documents, you can select Tools → Protect and either restrict file editing with a password or encrypt the entire file with a certificate or password. 
  1. For presentations in Microsoft PowerPoint, you can select File → Info → Protect Presentation → Encrypt with Password and save the file with the password.

While digital document sharing is convenient, the safest way to send a document to someone is to hand it to them personally. 

However, this is rarely an option, so encrypting documents with passwords or using OME or S/MIME encryption in Outlook provides a more secure option for sending sensitive information.