2026 Disk Cloning for Small Business

Disk Cloning: More Complex Than Ever

As I prepare for our upcoming in-depth review of WittyTool’s disk cloning software, which includes SID changing capabilities, I’ve been revisiting the core principles of cloning drives in corporate environments.

Once a straightforward solution for hardware upgrades, disk cloning in today’s enterprise landscapes presents unique challenges that differ significantly from those faced in home offices. Being well-prepared is now essential.

Farewell to WDS!

To complicate matters, Server/get-started/removed-deprecated-features-windows-Server?tabs=ws25″ data-type=”link” data-id=”https://learn.microsoft.com/en-us/windows-Server/get-started/removed-deprecated-features-windows-Server?tabs=ws25″ target=”_blank” rel=”noopener”>Microsoft has ceased development of Windows Deployment Services (WDS). While I found WDS invaluable for deploying new machines, SMBs are now pushed towards third-party solutions or higher investments in Intune + Autopilot. Even Windows 11 and Server 2025 are unsupported on WDS!

Emerging Security Challenges: EDR & DLP

One critical aspect to consider before diving into the full review is that disk cloning is no longer a covert operation within corporate environments. Previously, you could run a cloning tool under a local admin account with little to no oversight. Nowadays, almost every enterprise and many mid-sized businesses have implemented EDR (Endpoint Detection and Response) and DLP (Data Loss Prevention) systems that are highly sensitive to low-level disk activity.

Even if you are operating with a local admin account (not connected to the corporate Domain), these monitoring tools will flag events like Sysmon Event ID 9 (Raw Access Read). Security teams view block-level reading of drives as a serious threat to data integrity.

Attempting to clone a drive on a corporate network without whitelisting your chosen tool might prompt a call from the Security Operations Center (SOC) long before the progress bar reaches 30%. Prepare accordingly!

Navigating Identity: On-Prem vs Cloud

During my testing for the WittyTool review, I focused specifically on the challenges encountered when trying to boot a cloned disk on machines linked to identity providers like a Windows Domain or Azure Entra ID, particularly regarding encrypted drives. Whether dealing with a legacy on-premises domain or a contemporary cloud-only setup, a machine’s identity has become its most vulnerable aspect.

The classic trust relationship failure is a well-documented issue: Active Directory anticipates that every PC will regularly update its machine password every 30 days using the netlogon service (netlogon.dll). If your clone retains an outdated password, access will be denied.

With Windows 11 and Server 2025 evolving, the situation becomes increasingly complex, especially in Cloud-Only (Azure Entra ID joined) scenarios.

On-Prem Domain SID Challenges

Recent security updates, such as KB5065426 from September 2025, indicate that Windows 11 and Server 2025 now actively check for duplicate SIDs during Active Directory handshakes.

Azure Entra ID Domain Challenges

With Azure Entra ID cloud-only domains, complexities intensify because the identity is linked to the Trusted Platform Module (TPM) instead of merely the Server/identity/ad-ds/manage/understand-security-identifiers” target=”_blank” rel=”noopener”>SID. Cloning a drive to new hardware means that the hardware-bound device certificate remains tied to the old TPM. Although the OS may boot, authentication attempts with Entra ID will falter due to the hardware key mismatch. This results in not just trust errors but also MFA failures and issues with Windows Hello for Business.

Complexity Due to Encrypted Disks

With Windows 11 PCs now encrypted by default, most organisations employ tools such as BitLocker or third-party solutions like Sophos or Symantec for security. When cloning an encrypted disk, you have three options:

1. Decrypt the disk first, perform the clone, and then re-encrypt the disk on the new PC.
2. Utilise BitLocker’s “Suspend Protection” feature, which keeps data encrypted but allows the cloned disk to boot on new hardware by placing a “clear key” on the drive.
   • After the initial boot, simply select “Resume Protection” to bind it to the new TPM.
3. Conduct a SECTOR BY SECTOR clone, but be sure to have the BitLocker/SEE/Sophos encryption key ready for the first boot.
   • Keep in mind that SECTOR BY SECTOR cloning is considerably slower as it copies all data, including empty space, and requires the new disk to be equal to or larger than the original regardless of how full it is.

Challenges and Solutions in Disk Cloning

To assist in understanding and overcoming these challenges, I’ve compiled a table detailing common disk cloning blockers. Whether you’re utilising WittyTool, Macrium, or Acronis, the recovery reasoning for contemporary systems remains similar. Here are some critical issues to consider before licensing any cloning software.

In Conclusion: The Way Forward

In 2026, disk cloning is not merely about transferring data; it now involves managing certificates, TPM states, and security alerts. As I continue my in-depth exploration of WittyTool, the next article will specifically examine how it addresses SID changes without SysPrep and automates the re-joining process for both Entra ID and legacy Active Directory.

Stay tuned for an extensive breakdown where I will detail how WittyTool navigates these modern security challenges and whether it can circumvent the typical identity pitfalls.