7 Most Challenging Security Bottlenecks in Microsoft 365

7 Most Challenging Security Bottlenecks in Microsoft 365

As organizations embrace digital transformation, Microsoft 365 has emerged as a leading suite of productivity and collaboration tools. With its comprehensive range of services, including SharePoint, Exchange, Teams, and more, Microsoft 365 empowers businesses to enhance productivity and streamline workflows. However, as the digital landscape evolves, so do the security challenges associated with these powerful cloud-based tools.

Throughout this article, we will discuss practical insights, best practices, and effective strategies to address each security challenge head-on. By implementing the right security measures and adopting a comprehensive approach, organizations can fortify their Microsoft 365 environment and mitigate potential risks.

Let’s review challenges one by one.  

1.  Cracked Inboxes: Decoding the E-Mail Hacks

E-mail brings a typical yet significant vulnerability to M365 system security, as it remains one of the easiest targets for hackers. And then, insecure mailboxes followed by compromising e-mail user practices pose a substantial risk to the overall security of your M365 environment.

Weak and non-expiring passwords, as well as the absence of multi-factor authentication (MFA), contribute to the vulnerability of mailboxes. However, proactive measures can be taken to enhance the security of business-critical data by monitoring employee activities, particularly their email practices. This monitoring enables the identification of potentially risky behaviors, allowing for timely intervention.

How to Ensure Ultimate Email Protection?

Security measures such as blocking the automatic forwarding of emails to external addresses and limiting access to other users’ mailboxes can help to prevent the spread of malware and data leaks through email.

Moreover, remaining vigilant against abnormal email activity serves as a defense against targeted spam and social engineering tactics, which are prevalent in today’s cybersecurity landscape.

Microsoft 35 Mailbox Security

Regarding mailbox security, you need certain key principles related to user access rights. WME, for instance, finds out user accounts exhibiting unusual permissions, such as those with access to more than five other user mailboxes or accessing mailboxes outside their respective departments.

WME Mailbox Security Assessment & Remediation

A dependable security assessment & remediation effort should give attention to disabled accounts that retain mailbox access. The best part is, the WME security assessment specifically applies to individual user mailbox accounts, rather than Room, Shared, or Team mailboxes.

Any users found to possess advanced access rights to other users’ mailboxes undergo a thorough investigation to ascertain their compliance with acceptable business purposes.

That said, mailbox security is often at risk from spam and malicious malware. By leveraging WME’s M365-centric capabilities, instances of malware originating from within the organization via email can be effectively identified and perfectly tracked, providing granular insights into its possible spread.

2.  Unveiling Insider Threats: Breaches and User Misconduct

Security breaches originating from insiders, including within the IT department itself, are often overlooked but they definitely warrant more attention.

This observation is even more emphasized in one of the latest reports by Microsoft that mentions security breaches and challenges that M365 organizations have from insiders.

The 2023 Microsoft Report on M365 Security Status

The report found that insider threats are a major concern for M365 organizations, with 63% of organizations experiencing at least one insider threat event in the past year. The most common types of insider threats were data exfiltration (43%), account compromise (38%), and malicious insider activity (29%).

The report also found that M365 organizations are facing a number of challenges in protecting themselves from insider threats. The challenges include:

  • Lack of visibility into user activity: Organizations often lack the visibility they need to understand user activity and identify potential threats.
  • Lack of training for employees: Employees often do not receive the training they need to identify and report suspicious activity.
  • Lack of security controls: Organizations often do not have the right security controls in place to protect themselves from insider threats.

The report makes some recommendations for organizations to improve their protection from insider threats:

  • Increase visibility into user activity: Implement solutions to gain visibility into user activity, such as user behavior analytics (UBA) and data loss prevention (DLP) solutions.
  • Train employees on security best practices: Organizations should train employees on security best practices, such as how to identify and report suspicious activity.
  • Implement security controls: These controls can help you prevent and detect insider threats; they include multi-factor authentication (MFA) and access controls.

Insider Threats from within the Premises

Another astonishing observation has been that a significant majority of employees carry out their malicious actions within the office premises, right under the nose of their colleagues, rather than resorting to remote access from their homes.

These insider breaches are alarmingly common, as revealed by a report on security by Verizon, attributing 14% of breaches to insiders.

More the Types of Insiders, Subtler the Challenge

Insiders pose a greater threat compared to most external actors since they are already within the network and sometimes hold elevated privileges. Various types of insiders exist, each presenting distinct and diverse risks.

Example: Individuals who work in sensitive roles, such as human resources and upper management, typically have more extensive computer access.

Managers are the culprits often 

The severity of the problem escalates with the level of privilege. WME experts have noted that managers, including those in top-level positions, are increasingly implicated in such breaches.

These individuals often have access to sensitive data, including trade secrets, which may be of interest to competitors. Tragically, due to their privileged status within the company, they are also more likely to be exempt from adhering to security policies.

Solving the Insider Threat Problem

However, to effectively combat insider threats, a comprehensive security approach is necessary, coupled with addressing vulnerabilities specific to Microsoft 365. A crucial aspect involves gaining visibility into network activities and controlling risky behavior.

WME advises IT professionals to implement robust access controls tailored to actual needs, trust levels, and levels of responsibility. That said, we recommend establishing a process to review account activity when employees provide notice or are terminated, particularly those with access to sensitive data.

IT professionals bear the responsibility of safeguarding the organization’s IT infrastructure and protecting data, which includes defending against insider threats rather than solely focusing on external adversaries.

The WME Solution to Insider Threats

The solution lies in identifying both internal and external threats within the environment and bolstering defenses accordingly. WME can create a customized insider breach alert system that serves as an early warning mechanism for internal and external threats specific to the Microsoft 365 environment, enabling proactive identification and defense against security breaches before they occur.

Also, WME M365 security assessment reporting offers detailed insights, allowing further computerized data analysis at various levels such as department, business unit, and country. This granularity facilitates the precise identification of breach origins.

3.   The Challenge of Tracking and Blocking Malware Spread

WME tackles the persistent challenge of malware infiltration, particularly in the face of zero-day attacks that often bypass conventional anti-virus and anti-malware defenses.

The Malware Protection by WME

Our security teams address malware concerns by equipping organizations with robust auditing tools designed for cloud operations.

While a typical anti-virus software or Defender for M365 can merely indicate the presence of malware on a specific device, WME’s managed security ensures that we go beyond by meticulously recording every file accessed and every action performed by administrators and users following a security incident.

Comprehensive Scanning to Prevent Malware Spread

This comprehensive visibility that we gain allows for proactive prevention of malware propagation throughout the organization.

By monitoring and reporting on every touchpoint, WME enables deeper analysis and mitigates the prolonged impact of malware threats—an aspect that is not addressed by traditional anti-virus or Endpoint Protection Tools.

Accelerated Security Audits & Swift Forensic Analysis

Persistent threats targeting Microsoft 365, including, let’s say, KnockKnock or, for that matter, ShurL0ckr attacks, have remained active since June 2017 and continue to pose risks, alongside other malware exploits specific to Mcirosoft365.

WME has expertise with all these historically relevant malware. Detecting and tracing the audit trail for such attacks can be extremely challenging, and here we are bringing our legacy expertise to the table. We leverage specialized tools and our “secret security sauce” leading to robust auditing and analysis functionalities—ensuring a trustworthy and malware-secure environment.

4.  Caught in the Web: The Perils of Ransomware Exploitation


Here are a few recommendations by WME security professionals to prevent Ransomware Propagation:

Keep your software patches and anti-virus tools up to date

You can utilize WME’s Microsoft 365 Professional Security Services to verify the versions of software installed on workstations and mobile devices, ensuring that they have been updated. In other words, WME provides insights into how MDM (Mobile Device Management), MFA, and other policy applications are being used in organizations.

Create strong & unique passwords and regularly change them

WME security assessment gives a detailed report on passwords. It allows your team to identify accounts that lack password expiration settings, particularly service accounts. Bulk changes can be applied to these accounts using the delegated admin facilities provided by WME.

Enable Multi-Factor Authentication (MFA)

This is particularly important for remote logins.  WME Audits allow you to not only identify remote login attempts but also gain visibility into targeted accounts, MFA status, and failure reasons.

You can leverage this information to take immediate action and remediate the MFA status. If any devices are identified as infected, create a file access and file access extended report for the respective device owners.

Modernize Legacy Systems

Make sure their software is updated. WME offers the capability to validate workstations, ensuring that the software installed is the latest. That said, WME Azure AD Reports can be utilized to document third-party applications that have been granted access to and utilize Azure AD.

Limit granting administrative access

Granting global admin rights to too many individuals can significantly compromise network security. A WME-enabled environment restricts administrative rights to only what is necessary by providing functional least-privilege access and Role-Based Access Control (RBAC) functions. This creates a least-privilege access model that is more secure than traditional approaches.

In fact, WME auditing is beneficial for all Microsoft 365 workloads, providing visibility into all the Microsoft E5 security tools, even if only one E5 license is enabled.

That said, WME, while managing your security, stores an external, immutable log of every administrative action, ensuring transparency and accountability.

Enable auditing across all workloads

This is important to facilitate forensic analysis and gain detailed insights into the spread of ransomware. WME allows you to store logs in a separate, unalterable location, and you can define how long these logs will be retained.

By leveraging our services, you can ensure that your Microsoft 365 environment is configured correctly and meets regulatory guidelines, such as those outlined in the Texas DIR requirements. These measures significantly enhance your ability to prevent or withstand ransomware attacks.

5.  Challenges Arising from Former Employees


Only a few things can be as concerning as a former employee, especially when they have intentions to cause harm or take valuable competitive information as they depart.

Threat from Former-to-Be Employees

In fact, it is not uncommon for even current employees to plan their transition to a rival company, leveraging their knowledge of the market and potentially absconding with confidential data such as customer lists, contracts, and product plans.

These employees may engage in covert activities like forwarding emails to personal accounts and sharing files externally with themselves and new business partners. By tracking email forwards and external data sharing, organizations can detect data theft before it becomes a major problem.

How to Preempt the “Employee Threat”

When an employee gives notice of their departure, typically within a two-week timeframe, it should raise concerns within the IT department. This is the opportune moment to ensure that no confidential data is being shared externally and to monitor any suspicious activity.

On their departure, it becomes essential to initiate forensics procedures to verify they haven’t carried out any malicious or, for that matter, strange actions.

WME offers the capability to conduct an audit report that encompasses file access history, email forwarding to non-company accounts, and external sharing of data, such as OneDrive volumes, during the specified timeframe leading up to the employee’s exit from the organization. This thorough analysis allows for prompt action to be taken if any irregularities are detected.

Lack of Focus on Azure AD Security Measures

Azure serves as the host for Microsoft 365 and plays a critical role in identifying end users in the cloud. However, it also serves as a primary entry point for cybercriminals seeking unauthorized access to the network.

WME Azure & Security professionals have valuable insights to share here:

  • Plan for regular security enhancements.
  • Centralize identity management processes.
  • Manage connected tenants effectively.
  • Enforce multi-factor verification for users.
  • Utilize role-based access control.
  • Reduce exposure of privileged accounts.
  • Give paramount importance to identity as the primary security perimeter.
  • Enable single sign-on capabilities.
  • Activate Conditional Access to enhance security.
  • Implement strong password management protocols.

WME Azure Services to Complement M365 Security

WME’s Azure Activity Report provides comprehensive information, such as:

  • Application usage summaries,
  • Detailed audit logs,
  • Account provisioning error tracking,
  • User device and activity monitoring,
  • Group activity reports,
  • And password reset activity logs.

With Azure monitoring and reporting integrated into WME’s managed services, you can gain the ability to audit and report suspicious login activity, different device access methods, and data loss prevention (DLP) incidents, and ensure security and compliance.

Suspicious Sign-in activities in M365

Now, this is a critical task for IT administrators overseeing Microsoft Office 365 environments. WME’s customizable assessment reports empower your admins to efficiently monitor such activities, providing crucial information about the perpetrators, timing, and geographic locations (IP addresses) associated with suspicious sign-ins.

Let’s focus on this point comprehensively…

7.   Failure to Monitor doubtful Sign-in attempts in Microsoft Office 365

Understanding the frequency, origins, and targets of suspicious sign-in attempts is essential to implementing robust security measures. However, relying solely on the native M365 Admin Center provided makes this task nearly impossible.

Here is Why:

Numerous breaches originate from botnet-facilitated brute-force attacks, where cybercriminals systematically try various password combinations over segmented intervals until they gain unauthorized access.

Example: A notable example is the “KnockKnock” attack, as discussed above. It specifically targeted Microsoft Office 365 (Now Microsoft 365) system accounts.

To effectively identify such activities and proactively mitigate risks, WME offers Azure AD security monitoring and auditing reports. These reports empower IT teams to swiftly detect suspicious sign-in activities, enabling them to promptly block suspicious IP addresses and enforce security measures for targeted accounts.

Azure AD audits are Gold for Multi-location Organizations

These are the organizations having more than one site. A large business we engaged with reported a remarkable 340% improvement in response time for blocking remote hacker attempts.

The following types of suspicious sign-ins are effectively tracked by WME:

s from Infected Devices:

We identify account logins from infected devices that are part of a botnet. By correlating user sign-in IP addresses with those known to be associated with botnet servers, this report promptly identifies users infected with malware or other malicious infestations, enabling you to implement quick action. More importantly, these reports can be fully customized to meet specific requirements.

s from “Notorious” IP Addresses:

This report highlights sign-ins from IP addresses exhibiting suspicious activity. Sign-in activity that is considered suspicious may include a high number of failed sign-ins, which could indicate that someone is trying to access an account without the correct credentials. This may also be accompanied by sign-ins from different geographic locations, which could suggest that the account is being accessed by someone who is not authorized to do so.

s from Multiple Locations:

We identify sign-in activity that is considered suspicious if two successful sign-ins from the same account appear to originate from different geographic regions within a specific timeframe. This could indicate that someone is trying to access the account from a different location, which may be unauthorized. To provide additional insights to administrators, the report analyzes the time difference between the sign-ins, allowing your team to assess the plausibility of the user traveling between the identified regions.

Impossible Sign-Ins from Travelling Employees:

This is when a user signs in from two different locations at the same time or within a very short period of time. This can be caused by a legitimate user using a VPN or other remote access tool, but it can also be a sign of malicious activity. Essentially, it occurs when a single account successfully signs in from multiple geographic locations with overlapping time sequences, potentially indicating unauthorized access by a hacker.

Wrapping it Up:

To ensure the security of your Microsoft 365 environment, you really need to unveil the blind spot. These are hidden security dangers for your security team.

Your security executives should be aware of critical security considerations that they might not have previously considered. Initiating this conversation requires delicacy, as it involves informing them about potentially unsafe practices they have been operating with for an extended period, such as neglecting to thoroughly examine files following a malware incident.

So, to be sure of security measures, take advantage of WME’s Microsoft 365 Security Assessment, which is available at a very affordable price. One significant reason why you need to conduct a comprehensive Microsoft 365 Security Assessment is that Microsoft does not enable auditing by default. This is the recipe to stay one step ahead in safeguarding your Microsoft 365 infrastructure.



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