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Introduction: When the Attackers Tried to Turn Windows Against Its Defenders
Ransomware attacks are becoming less about simply dropping a malicious executable and more about controlling the environment around it. Modern affiliates understand that encryption is only the final step. Before ransomware can lock a single file, attackers need to defeat endpoint security, establish persistence, move through the network, steal valuable information, and create enough operational chaos to make recovery painful.
That is why a recent Akira intrusion is particularly revealing. According to the incident described by Huntress, an Akira affiliate attempted to reboot a compromised Windows server into Safe Mode with Networking, effectively stripping away much of the endpoint security stack while keeping enough network functionality for the attacker to continue operating.
The strategy was clever—but it had an unexpected weakness.
The same restricted Windows environment that helped suppress security controls apparently created conditions that the ransomware itself could not handle. The akira.exe payload reportedly crashed with an “out of virtual memory” error before it could begin encrypting files.
The incident is a fascinating example of a broader cybersecurity reality: an attacker can successfully defeat one layer of defense and still lose because another part of the attack chain fails.
And organizations should not interpret this particular failure as evidence that Safe Mode is a reliable defense against Akira. Quite the opposite. The technique demonstrates another avenue ransomware operators may explore as they search for ways to neutralize EDR and antivirus protection.
The Bigger Picture: Akira Is Still a Serious Ransomware Threat
Akira has established itself as one of the more persistent ransomware operations targeting organizations. Its affiliates have repeatedly relied on exposed remote-access infrastructure, compromised credentials, lateral movement, Active Directory reconnaissance, data theft, and rapid ransomware deployment.
Huntress has previously documented Akira campaigns involving SonicWall infrastructure, credential abuse, legitimate remote-access utilities, data staging, defense evasion, and attempts to remove recovery options.
The important lesson is that Akira should not be viewed as a single piece of malware.
It is better understood as an ecosystem of affiliates using a ransomware brand, with individual operators adapting their techniques depending on the environment they compromise.
That distinction matters because one affiliate may use a virtual machine to bypass security controls, another may abuse vulnerable drivers, while another may attempt to disable security software through Windows configuration changes.
The Initial Break-In: Credential Spraying Against a VPN
According to the incident details, the attack began with a burst of failed authentication attempts against a SonicWall SSL VPN.
This pattern is consistent with credential spraying, where attackers attempt a limited number of commonly reused or previously compromised passwords against many accounts rather than repeatedly attacking a single account.
Eventually, one authentication attempt succeeded.
The compromised account reportedly did not have multi-factor authentication enabled.
That single weakness provided the attacker with something far more valuable than a random foothold: legitimate remote access into the organization’s environment.
This is one of the clearest lessons from the incident.
The most sophisticated ransomware technique in the world becomes unnecessary if an attacker can simply log in through an exposed remote-access service using a valid password.
The Dangerous Gap Between Login and Action
Interestingly, the attacker did not immediately begin deploying ransomware.
Roughly two hours passed before significant hands-on activity was observed.
That delay is important because it demonstrates how ransomware investigations can become misleading when defenders focus only on the moment of encryption.
The compromise begins long before the ransom note appears.
Once inside, the attacker accessed the domain controller through Remote Desktop Protocol and used PowerShell to enumerate Active Directory.
The objective was straightforward: understand the environment.
Who are the users?
Which computers exist?
Where are the important systems?
Which accounts might have elevated privileges?
Where are the valuable file shares?
For ransomware operators, this reconnaissance is often more important than the ransomware binary itself.
Active Directory: The
Active Directory effectively becomes the
By enumerating users and computers, attackers can identify administrative accounts, servers, workstations, domain controllers, and potential paths toward sensitive information.
That is why defenders should treat unusual directory enumeration as an early warning signal rather than harmless administrative activity.
A ransomware attack may spend hours quietly collecting information before becoming visibly destructive.
The encryption stage is often the final chapter—not the beginning.
Data Theft Before Encryption: The Double-Extortion Trap
The attacker then moved toward an application server and began preparing data for exfiltration.
WinRAR was reportedly used to archive mapped file shares, while s5cmd was used to transfer staged information toward attacker-controlled cloud storage.
Huntress has separately documented the use of s5cmd in ransomware-related data exfiltration, demonstrating why legitimate administrative and cloud utilities can become part of an attack chain.
This is the essence of modern double extortion.
The victim does not necessarily need to lose access to its files for the attack to become financially damaging.
If attackers steal sensitive documents first, they can threaten to publish or sell the information even if backups allow the organization to restore encrypted systems.
AnyDesk Becomes Part of the Attack Chain
The attackers also reportedly installed AnyDesk as a persistent remote-access mechanism.
This is another familiar ransomware technique: abuse legitimate software rather than relying exclusively on custom malware.
The advantage is obvious.
Security teams may already have dozens of legitimate remote-administration tools operating inside an enterprise.
An attacker who installs one under an administrator context can potentially blend into normal activity.
The challenge for defenders therefore becomes behavioral detection.
The question is no longer simply:
“Is AnyDesk malicious?”
Instead, it becomes:
“Why was AnyDesk installed on this server at this particular time, by this account, after this unusual VPN login?”
Context turns a legitimate tool into a valuable detection signal.
The Safe Mode Gambit: A Different Way to Kill Security Controls
The most unusual part of this incident came near the end.
Instead of creating a separate virtual machine or relying exclusively on traditional EDR-killing techniques, the attacker reportedly used the Windows msconfig.exe utility to configure the system to boot into Safe Mode with Networking.
Safe Mode is designed to start Windows with a minimal collection of drivers and services.
That is useful for troubleshooting.
For an attacker, however, that minimal environment can potentially mean fewer third-party security components are loaded.
In this case, the technique reportedly caused the Huntress endpoint agent to go offline while Microsoft Defender’s real-time protection did not start normally.
The attacker effectively attempted to transform the operating system into a temporary environment with fewer defensive controls.
The Attacker Even Planned Around AnyDesk
The technique was not completely improvised.
According to the incident description, the attacker anticipated that AnyDesk might not operate normally in Safe Mode.
They reportedly modified the registry so that the remote-access service could continue functioning after the reboot.
That detail is particularly interesting because it suggests the attacker was not simply experimenting.
They had a specific operational requirement:
disable security software while preserving remote control.
That is exactly the kind of thinking defenders should expect from mature ransomware affiliates.
Then the Attack Backfired
The security controls were weakened.
The attacker had remote access.
The ransomware payload was launched.
And then something unexpected happened.
The ransomware apparently failed.
Minutes after akira.exe started, the compromised host reportedly generated “out of virtual memory” errors.
The ransomware process crashed before encryption could begin.
The attacker had successfully created a weaker defensive environment—but apparently created a weaker execution environment for the ransomware as well.
This is the most ironic element of the incident.
The attacker did not necessarily lose because the security software stopped the ransomware.
The attacker may have lost because the environment they created was unsuitable for their own malware.
Why Safe Mode Can Become a Double-Edged Sword
Safe Mode is intentionally restrictive.
It does not provide a normal Windows operating environment. Drivers, services, and background components may behave differently from a standard boot.
A ransomware executable that performs normally under ordinary Windows conditions may therefore encounter unexpected resource or dependency problems in Safe Mode.
The reported memory failure should not automatically be interpreted as a universal property of Akira.
It is much more likely to represent a specific interaction between the malware, the affected system, and the restricted operating environment.
A different machine with different memory allocation, paging configuration, drivers, dependencies, or ransomware build could produce a completely different result.
Defender Eventually Detected the Payload
The story did not end with the ransomware crashing.
A scheduled Microsoft Defender scan reportedly identified the Akira payload approximately an hour later.
However, Defender was apparently unable to quarantine the file immediately because real-time protection remained disabled while the machine was still operating in Safe Mode.
Once the attacker rebooted the system back into normal Windows operation, the normal security environment returned and the payload could be removed.
The attacker therefore faced another contradiction.
To regain a normal operating environment, they had to undo the very configuration change that had helped them evade endpoint defenses.
The Most Important Detail: The Attack Had Already Done Damage
It would be a mistake to describe this incident simply as “Akira failed.”
The encryption phase failed.
The intrusion itself did not.
Before attempting to encrypt the environment, the attackers had reportedly accessed Active Directory information and exfiltrated data from file shares.
That means the victim could still face extortion, credential-reset requirements, forensic costs, regulatory consequences, operational disruption, and potential data exposure.
This distinction is critical.
Ransomware does not need to encrypt everything to become a successful intrusion.
Deep Analysis: What Defenders Should Watch For
1. Detect Suspicious VPN Authentication Patterns
A sequence of failed VPN logins followed shortly by a successful authentication should receive elevated scrutiny.
Defenders can begin investigating Windows authentication events with commands such as:
Get-WinEvent -FilterHashtable @{
LogName='Security'
Id=4624,4625
} -MaxEvents 200
Event ID 4625 represents failed logons, while 4624 represents successful logons.
The important signal is not either event individually.
It is the relationship between them.
2. Audit Safe Mode Configuration Changes
Organizations should monitor for unexpected execution of Windows configuration utilities.
For example:
Get-Process msconfig -ErrorAction SilentlyContinue
Security teams can also review process creation telemetry for suspicious launches involving:
msconfig.exe
bcdedit.exe
shutdown.exe
powershell.exe
These tools are legitimate Windows components, so simply blocking them is not always practical.
Behavioral context is more useful.
3. Investigate Boot Configuration Changes
Defenders should pay particular attention to modifications involving Windows boot configuration.
A basic administrative review can include:
bcdedit /enum
Unexpected changes to boot parameters should be investigated, especially when they occur immediately after a suspicious VPN login, privilege escalation, Active Directory enumeration, or deployment of remote-access software.
4. Monitor Safe Mode-Related Registry Activity
Safe Mode behavior depends on Windows registry configuration, including the services and drivers permitted to load.
A suspicious modification to Safe Mode-related registry locations deserves investigation.
For defensive auditing, administrators can inspect relevant configuration areas with:
Get-ItemProperty "HKLM:\SYSTEM\CurrentControlSet\Control\SafeBoot\Minimal" Get-ItemProperty "HKLM:\SYSTEM\CurrentControlSet\Control\SafeBoot\Network"
Do not interpret every change as malicious.
The real signal is an unusual modification performed by an unexpected account during an active intrusion.
5. Hunt for Unexpected AnyDesk Installation
Remote-access software should have an established administrative purpose.
Investigate newly installed or newly registered AnyDesk services, particularly when installation occurs immediately after suspicious authentication activity.
Useful Windows service enumeration includes:
Get-Service | Where-Object {
$_.DisplayName -match "AnyDesk|Remote|ScreenConnect"
}
The objective is not to block every remote-management product.
It is to identify new remote-management infrastructure appearing during an intrusion.
6. Watch for WinRAR Used on Servers
WinRAR is legitimate.
That does not mean its sudden use on a domain-connected server is irrelevant.
A server suddenly compressing large volumes of documents, followed by an outbound connection to unfamiliar cloud infrastructure, should trigger investigation.
Defenders should correlate:
WinRAR execution
↓
Large archive creation
↓
Cloud transfer
↓
Remote-access activity
↓
Security-tool modification
↓
Ransomware execution
That sequence is far more suspicious than any individual event.
7. Monitor Cloud Exfiltration Utilities
Tools such as s5cmd demonstrate how attackers can use legitimate cloud utilities for data theft.
Security teams should monitor command-line execution and outbound connections associated with unusual S3-compatible storage activity.
This is especially important when the organization does not normally use such utilities.
8. Correlate EDR Blind Spots
An endpoint suddenly disappearing from EDR telemetry should never be treated as an ordinary technical problem during an active intrusion.
If an EDR sensor goes offline immediately after:
VPN compromise
→ administrator login
→ PowerShell activity
→ AnyDesk installation
→ msconfig execution
→ Safe Mode reboot
the disappearance itself becomes a security event.
9. Build Detection Around the Attack Chain
The strongest detection strategy is not a single alert for msconfig.exe.
It is a sequence-based detection model.
For example:
Multiple failed VPN logins
↓
Successful authentication
↓
RDP to domain controller
↓
PowerShell reconnaissance
↓
Archive creation
↓
Cloud upload
↓
Remote-access persistence
↓
Boot configuration modification
↓
Safe Mode reboot
↓
Security agent disappearance
Any one of these events can have a legitimate explanation.
The entire chain is considerably harder to explain innocently.
Why MFA Remains the First Line of Defense
The incident also reinforces a lesson that repeatedly appears in ransomware investigations: sophisticated post-compromise behavior often begins with surprisingly ordinary credential abuse.
A VPN account without MFA can become the bridge between the public internet and an organization’s internal network.
MFA does not eliminate every attack.
But it raises the cost of credential spraying, password reuse, and stolen-password attacks dramatically.
Organizations should therefore prioritize MFA for:
VPN access
Remote Desktop access
Administrative accounts
Cloud administration
Privileged identity management
Remote-management platforms
The goal is simple:
Do not let a stolen password become an enterprise-wide compromise.
Why EDR Coverage Must Be Complete
Another lesson is the danger of incomplete endpoint visibility.
If critical servers are excluded from EDR because they are considered “too sensitive,” “too old,” or “too difficult to monitor,” attackers may deliberately target those systems.
Security coverage should extend across critical infrastructure wherever technically feasible.
And organizations should establish alerts for sudden loss of endpoint telemetry.
An endpoint that stops reporting during normal business activity may simply have crashed.
An endpoint that stops reporting immediately before ransomware execution deserves a very different response.
Why Backups Still Matter
Even the strongest endpoint defenses can eventually be bypassed.
That makes recovery architecture essential.
Backups should be isolated from ordinary domain credentials, protected against unauthorized deletion, regularly tested, and capable of restoring critical systems within an acceptable recovery window.
Most importantly, organizations should assume that attackers will attempt to reach backup infrastructure.
The question should therefore not be:
“Do we have backups?”
It should be:
“Can the attacker who compromises our domain also destroy our backups?”
If the answer is yes, the recovery strategy needs another layer of protection.
The Human Element Behind the Attack
The technical details can make ransomware incidents look like battles between malware and security software.
They are not.
Behind every successful intrusion are decisions made by people.
Someone enabled a VPN.
Someone created an account.
Someone reused a password.
Someone decided MFA was unnecessary.
Someone installed remote-access software.
Someone allowed a server to remain reachable.
Attackers exploit those decisions.
That is why cybersecurity is ultimately a systems problem, not merely a malware problem.
What Undercode Say:
The Real Victory Was Not the Failed Encryption
The headline is tempting: Akira ransomware crashed.
But that is not the real story.
The real story is that an attacker successfully entered the environment.
They obtained valid VPN access.
They reached internal systems.
They accessed the domain controller.
They enumerated Active Directory.
They staged sensitive files.
They exfiltrated data.
They installed persistent remote-access software.
And only then did their final ransomware stage fail.
That is still a serious security incident.
Safe Mode Is Becoming an Attack Surface
Windows Safe Mode has traditionally been viewed as a troubleshooting mechanism.
This incident demonstrates why defenders should also consider it from an adversarial perspective.
If attackers can manipulate boot configuration to create an environment in which security products do not load normally, Safe Mode becomes part of the defense-evasion conversation.
EDR Cannot Be the Only Layer
Endpoint detection and response is enormously valuable.
But an attacker who can deliberately prevent the EDR agent from running has exposed the danger of relying on endpoint telemetry alone.
Network telemetry, identity monitoring, VPN logs, Active Directory auditing, DNS monitoring, cloud logging, and immutable backups all become important when endpoint visibility disappears.
The VPN Was More Important Than the Ransomware
From a defensive perspective, the ransomware binary was almost the least interesting component.
The initial authentication failure pattern was more important.
The absence of MFA was more important.
The domain-controller access was more important.
The Active Directory enumeration was more important.
The data exfiltration was more important.
The boot configuration change was more important.
The ransomware was simply the final weapon.
Legitimate Tools Are Part of Modern Ransomware
WinRAR is legitimate.
AnyDesk is legitimate.
PowerShell is legitimate.
msconfig.exe is legitimate.
s5cmd can be legitimate.
That is precisely why these tools are attractive to attackers.
The modern defender therefore needs to move beyond simplistic “malware versus software” thinking.
The better question is:
What is this legitimate tool doing right now, on this machine, under this account, after these previous events?
Ransomware Operators Are Experimenting
The Safe Mode technique is another indication that ransomware affiliates continue experimenting with defense evasion.
Earlier campaigns have involved virtual machines, security-tool killers, vulnerable drivers, Defender manipulation, and other methods of reducing endpoint visibility. Huntress has documented multiple examples of Akira-related actors attempting to disable or bypass defensive controls.
The direction is clear.
Attackers are increasingly attacking the security architecture itself.
The Next Version Could Be Better
The failed payload should not create complacency.
If the problem was genuinely related to memory or Safe Mode dependencies, a future ransomware build could potentially be modified to operate more efficiently under constrained conditions.
Attackers learn from failed operations just as defenders do.
Defenders Should Learn Faster
The advantage defenders have is that they do not need to wait for the next ransomware sample.
They already know what to monitor.
VPN anomalies.
MFA gaps.
RDP access.
PowerShell reconnaissance.
Remote-access software.
Archive creation.
Cloud uploads.
Boot configuration changes.
Safe Mode reboots.
Endpoint telemetry loss.
That chain can become a detection strategy today.
The Most Dangerous Moment May Be Before Encryption
Organizations often build ransomware detection around file-encryption behavior.
That is too late.
Once hundreds of thousands of files are being modified, the incident has already reached its most destructive stage.
The better objective is to stop the attack while the adversary is still exploring the environment.
Identity Is the New Perimeter
The incident also reinforces the growing importance of identity security.
A valid credential allowed the attacker through the VPN.
Once inside, legitimate credentials and administrative tools provided additional opportunities.
Modern ransomware defense therefore requires protecting identities just as aggressively as endpoints.
The Lesson for Security Teams
Do not wait for akira.exe.
Detect the road that leads to it.
That means correlating authentication, identity, endpoint, network, cloud, and system telemetry.
The attacker should ideally be discovered while stealing a credential, not while encrypting a server.
The Lesson for Executives
Security investment should not be measured only by whether ransomware encryption was prevented.
Ask whether the organization can:
Detect an anomalous VPN login.
Detect privilege escalation.
Detect Active Directory reconnaissance.
Detect unusual data staging.
Detect cloud exfiltration.
Detect unauthorized remote-access software.
Detect security-agent disappearance.
Detect Safe Mode manipulation.
Isolate compromised systems.
Restore operations without negotiating with criminals.
That is a much more realistic measure of ransomware resilience.
The Final Undercode Verdict
The most interesting part of this incident is not that Akira failed.
It is that the attackers demonstrated a new way of thinking about endpoint defenses.
Instead of fighting EDR directly, they attempted to change the operating environment so that the security stack would not be there in the first place.
That concept deserves attention.
The failed encryption may have been good news for the victim, but it should be treated as a warning for everyone else.
The next attacker may fix the bug.
✅ Akira Has a Documented History of Defense Evasion
Huntress has publicly documented Akira-related intrusions involving SonicWall access, credential abuse, security-tool disablement, lateral movement, data exfiltration, and ransomware deployment.
This makes the broader attack pattern described in the article consistent with established Akira tradecraft.
✅ Legitimate Tools Have Been Used in Akira-Related Intrusions
Huntress has documented the use of legitimate utilities and remote-access mechanisms in ransomware operations, including tools used for staging, transfer, persistence, and administration.
Therefore, the presence of software such as WinRAR, AnyDesk, PowerShell, or cloud-transfer utilities should not automatically be considered malicious—but their context should be investigated.
⚠️ The Specific Safe Mode Incident Requires Careful Attribution
The supplied incident describes an Akira affiliate using Safe Mode with Networking, manipulating the registry to preserve AnyDesk, and experiencing an “out of virtual memory” crash.
The retrieved Huntress material confirms that Akira affiliates have used multiple defense-evasion strategies, but I could not independently locate the exact Safe Mode case in the currently retrieved Huntress publications.
Therefore, the specific Safe Mode sequence should be treated as reported incident details rather than independently verified facts unless the original Huntress write-up is cited directly.
✅ The Defensive Recommendations Are Sound
Monitoring VPN authentication anomalies, requiring MFA, auditing boot-configuration changes, investigating msconfig.exe and bcdedit.exe, and alerting on unexplained endpoint telemetry loss are sensible defensive measures.
The key is correlation rather than indiscriminate blocking of legitimate Windows utilities.
Prediction
(+1) Attackers Will Continue Targeting the Environment Around Security Software
The next evolution of ransomware defense evasion will likely focus less on individual antivirus processes and more on manipulating the operating environment itself.
Safe Mode is only one possible example.
Attackers may increasingly experiment with boot configurations, recovery environments, virtualization, vulnerable drivers, security-agent dependencies, and other mechanisms that allow them to operate outside the assumptions made by conventional endpoint defenses.
(+1) Behavioral Detection Will Become More Important
Organizations will increasingly rely on attack-chain detection instead of simple malware signatures.
A VPN compromise followed by Active Directory enumeration, remote-access installation, data staging, cloud exfiltration, boot modification, and endpoint telemetry loss is a far stronger signal than any individual event.
(-1) Ransomware Will Become More Dangerous Even When Encryption Fails
Data theft means attackers can still create pressure without successfully encrypting systems.
As double-extortion operations mature, organizations may face extortion after recovering their infrastructure.
That means preventing encryption alone will no longer be enough.
(+1) MFA Will Continue to Deliver One of the Highest Defensive Returns
The simplest part of this attack chain may also be one of the most preventable.
If a compromised password cannot independently provide VPN access because strong MFA is enforced, attackers are forced to find another route.
That additional barrier can disrupt the entire chain before the attacker ever reaches Active Directory.
(-1) Security Blind Spots Will Become Increasingly Expensive
An organization may have excellent EDR coverage and still suffer from a dangerous blind spot if an attacker can deliberately make the endpoint stop reporting.
The future of ransomware defense will therefore depend on redundancy.
When one sensor disappears, another telemetry source must tell defenders why.
(+1) The Best Defense Will Be Early Intervention
The most important prediction is also the simplest.
The organizations that stop ransomware most successfully will not necessarily be those with the most expensive endpoint products.
They will be the ones capable of detecting the attacker before the final payload is executed.
The future battlefield is therefore moving backward—from ransomware encryption to identity compromise, reconnaissance, lateral movement, data theft, and defense evasion.
The earlier the attacker is discovered, the less important the ransomware executable becomes.
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