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In place upgrade of Windows 2019 Standard server to windows 2025 standard server.

Tanvir Ahmed 0 Reputation points
2026-05-21T05:45:42.1766667+00:00

Hi

I am trying to do an in place upgrade of our Windows 2019 server to Windows 2025. I have bought the DVD from legitimate vendor, but my upgrade is erroring. I get this error
0xC1900101 - 0x30018 The installation failed in the FIRST_BOOT phase with an error during SYSPREP_SPECIALIZE operation

Help please

Windows for business | Windows Server | Devices and deployment | Set up upgrades and drivers

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  1. Debdyuti De 0 Reputation points
    2026-05-21T06:49:58.5833333+00:00

    The error 0xC1900101 - 0x30018 during FIRST_BOOT / SYSPREP_SPECIALIZE is almost always caused by a driver, service, security software, or low-level system component that breaks during the upgrade transition.

    For a Windows Server 2019 → Windows Server 2025 in-place upgrade, here’s the safest troubleshooting sequence.

    What the error means

    0xC1900101 = driver-related rollback error

    0x30018 = failure during the specialize phase of setup after reboot

    This usually points to:

    old NIC/storage/chipset drivers

    antivirus/EDR

    backup agents

    filter drivers

    virtualization tools

    outdated firmware

    unsupported server roles/features

    First: Verify Microsoft supports your upgrade path

    A direct in-place upgrade from:

    Windows Server 2019

    → Windows Server 2025

    is supported for Standard→Standard and Datacenter→Datacenter editions.

    But:

    language must match

    architecture must match (x64)

    Desktop Experience/Core compatibility matters

    See:

    Microsoft Windows Server upgrade paths

    Most common fixes (in order)

    1. Disconnect EVERYTHING nonessential

    Before retrying:

    unplug USB devices

    disconnect external storage

    remove dongles

    disable extra NICs

    disconnect SAN mappings if possible

    Leave only:

    boot disk

    keyboard/mouse

    primary NIC

    1. Remove antivirus / EDR completely

    This is the #1 cause.

    Temporarily uninstall:

    CrowdStrike

    SentinelOne

    Sophos

    Trend Micro

    Symantec/Broadcom

    backup agents

    DLP tools

    monitoring kernel agents

    Disable is often NOT enough — uninstall temporarily.

    1. Update drivers and firmware

    Especially:

    storage controller

    RAID controller

    NIC drivers

    chipset

    BIOS/iLO/iDRAC firmware

    Get them from your server vendor:

    Dell Support

    HPE Support

    Lenovo Support

    Old Intel/Broadcom NIC drivers are notorious for this exact error.

    1. Run Setup from local disk (NOT DVD)

    Copy the ISO contents locally first.

    Example:

    mkdir C:\Win2025

    Copy all files from the media there, then run:

    C:\Win2025\setup.exe

    Do NOT run from:

    mounted remote ISO

    network share

    USB/DVD directly

    1. Clean boot the server

    Run:

    msconfig

    Then:

    Hide Microsoft services

    Disable all non-Microsoft services

    Disable startup items

    Reboot and retry.

    1. Check free space

    You should realistically have:

    40–60 GB free minimum on C:

    Also clear:

    cleanmgr

    Or:

    DISM /Online /Cleanup-Image /StartComponentCleanup

    Important logs to inspect

    The exact failing driver/service is usually in these logs:

    C:$WINDOWS.~BT\Sources\Panther\setuperr.log

    C:$WINDOWS.~BT\Sources\Panther\setupact.log

    Also check:

    C:\Windows\Panther\

    Search for:

    MOSETUP

    Error

    Rollback

    SYSPREP

    specialize

    VERY useful command

    Run Microsoft compatibility scan first:

    setup.exe /compat scanonly

    From the Windows 2025 media.

    This often identifies blockers before reboot.

    Check for problematic drivers

    Run:

    pnputil /enum-drivers > C:\drivers.txt

    Look for:

    old NIC drivers

    old storage drivers

    filter drivers

    security software drivers

    Very old dates (2016–2018) are suspicious.

    If this is a VM

    If VMware:

    upgrade VM hardware compatibility

    update VMware Tools

    VMware Tools Documentation

    If Hyper-V:

    ensure integration services are current

    DISM + SFC repair beforehand

    Run:

    DISM /Online /Cleanup-Image /RestoreHealth

    sfc /scannow

    Then reboot before retrying.

    Domain Controller warning

    If this server is a Domain Controller:

    verify SYSVOL replication healthy

    verify AD replication healthy

    take full system state backup first

    Run:

    dcdiag /v

    repadmin /replsummary

    Best next step

    The fastest way to pinpoint the problem is:

    Run:

    setup.exe /compat scanonly

    Share:

    setuperr.log

    last 50–100 lines around the failure

    whether this is physical or VM

    server vendor/model

    antivirus/security tools installed

    That usually reveals the exact failing component.

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  2. Jason Nguyen Tran 17,760 Reputation points Independent Advisor
    2026-05-21T06:44:11.55+00:00

    Hello Tanvir Ahmed,

    From what I know, this particular error usually points to a driver or service conflict that prevents Windows Setup from completing the specialize phase. Common culprits include outdated storage or network drivers, third-party antivirus or endpoint protection software, or even firmware settings. Before retrying, I recommend updating all critical drivers (especially storage and NIC drivers) to the latest versions from the hardware vendor, and temporarily disabling or uninstalling any non-Microsoft antivirus or disk encryption tools.

    It’s also a good idea to check that the server has the latest cumulative updates for Windows Server 2019 installed before starting the upgrade. Running sfc /scannow and DISM /Online /Cleanup-Image /RestoreHealth can help ensure system files are healthy. If you’re using specialized hardware (RAID controllers, HBA cards), confirm that the drivers are Windows Server 2025-compatible.

    Another step is to disconnect any non-essential peripherals and ensure there’s enough free disk space for the upgrade process. Sometimes even USB devices can interfere with the first boot phase.

    I hope this explanation helps you move forward with your upgrade. If this answer is helpful, please don’t forget to hit “Accept Answer”.

    Jason.

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  3. AI answer

    2026-05-21T05:45:56.6333333+00:00

    Error 0xC1900101 - 0x30018 is a driver-related failure during the FIRST_BOOT phase (SYSPREP_SPECIALIZE). To address it when upgrading Windows Server 2019 Standard to Windows Server 2025 Standard from DVD, use these steps:

    1. Confirm the upgrade path is supported
      • Windows Server 2019 → Windows Server 2025 is a supported in-place upgrade path when using installation media on nonclustered systems.
      • See the supported paths table to ensure the source and target versions and editions match.
    2. Collect pre-upgrade diagnostics and ensure backup
      • Before retrying, collect system information and back up the server: 
             Get-ComputerInfo -Property WindowsBuildLabEx,WindowsEditionID | Out-File -FilePath .\computerinfo.txt
     systeminfo.exe | Out-File -FilePath systeminfo.txt
     ipconfig /all | Out-File -FilePath ipconfig.txt
      • Copy these files off the server and ensure a full backup of OS, apps, and data is available.
    3. Free disk space and check basic requirements
      • Ensure there is sufficient free space on the system drive for the upgrade. Low disk space can contribute to 0xC1900101 errors.
      • Verify hardware and storage meet Windows Server 2025 requirements.
    4. Update Windows and drivers on Windows Server 2019
      • Install all available Windows Updates on the existing 2019 server, including cumulative updates and any driver updates offered via Windows Update.
      • 0xC1900101 errors are commonly caused by outdated or incompatible drivers. Update storage, network, chipset, and other critical drivers from the hardware vendor if available.
    5. Remove or disconnect nonessential hardware
      • Temporarily disconnect or disable nonessential devices and drivers:
        • USB drives, external storage, docks, and other peripherals not required for the upgrade.
        • Third-party storage controllers or filter drivers where possible.
    6. Disable security/endpoint software
      • Temporarily disable third-party antivirus, anti-spyware, and host-based firewall products before starting Setup, as they can interfere with the SYSPREP_SPECIALIZE phase.
      • Re-enable them after a successful upgrade.
    7. Retry the in-place upgrade from installation media
      • Boot into the existing Windows Server 2019, mount or insert the Windows Server 2025 DVD, and run Setup from within the OS.
      • Choose the option to keep files, settings, and apps if available.
      • If the error recurs, proceed to log analysis.
    8. Analyze setup logs for the failing driver or component
      • After a failure, review Setup logs under C:\Windows\Panther as recommended:
        • Use the SetupDiag tool to analyze the logs and identify the specific driver or component causing the rollback.
      • Once identified, update, disable, or uninstall the problematic driver or software and retry the upgrade.
    9. Verify after successful upgrade
      • After the upgrade completes and the server restarts, verify the version and edition: 
             Get-ComputerInfo -Property WindowsProductName
      • Test applications and client connectivity.

    If repeated attempts fail even after driver cleanup and log-based remediation, consider a clean installation of Windows Server 2025 on new hardware or a new VM and migrate roles and data, as this avoids persistent driver or component issues that block in-place upgrades.

    References:

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