diff --git a/.ci/docker/scripts/install-choco-package.ps1 b/.ci/docker/scripts/install-choco-package.ps1
new file mode 100644
index 000000000..69484af79
--- /dev/null
+++ b/.ci/docker/scripts/install-choco-package.ps1
@@ -0,0 +1,107 @@
+param(
+    [string]$PackageName,
+
+    [string]$Version = "",
+
+    [string]$InstallArgs = "",
+
+    [ValidateRange(0, 20)]
+    [int]$RetryCount = 2,
+
+    [ValidateRange(1, 3600)]
+    [int]$RetryDelaySeconds = 30,
+
+    [ValidateRange(0, 100000)]
+    [int]$LogTailLines = 300,
+
+    [Alias('h')]
+    [switch]$Help,
+
+    [Parameter(ValueFromRemainingArguments = $true)]
+    [string[]]$ExtraArgs
+)
+
+function Show-Usage {
+    Write-Host "Usage:"
+    Write-Host "  powershell -NoProfile -ExecutionPolicy Bypass -File install-choco-package.ps1 -PackageName <name> [-Version <version>] [-InstallArgs <args>] [-RetryCount <n>] [-RetryDelaySeconds <sec>]"
+    Write-Host ""
+    Write-Host "Options:"
+    Write-Host "  -PackageName   Chocolatey package ID (required)."
+    Write-Host "  -Version       Optional package version passed as --version."
+    Write-Host "  -InstallArgs   Optional installer args passed as --installargs."
+    Write-Host "  -RetryCount    Number of retries after the first failed attempt (default: 2)."
+    Write-Host "  -RetryDelaySeconds   Wait time between retries in seconds (default: 30)."
+    Write-Host "  -LogTailLines  Number of log lines to show on final failure (default: 300, use 0 to disable)."
+    Write-Host "  -Help, --help  Show this help text."
+    Write-Host ""
+    Write-Host "Examples:"
+    Write-Host "  powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 -PackageName doxygen.install -Version 1.9.8"
+    Write-Host "  powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 -PackageName cmake.install -Version 3.22.3 -InstallArgs \"ADD_CMAKE_TO_PATH=System\""
+    Write-Host "  powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 -PackageName git"
+    Write-Host "  powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 -PackageName doxygen.install -Version 1.9.8 -RetryCount 3 -RetryDelaySeconds 30"
+    Write-Host "  powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 -PackageName doxygen.install -Version 1.9.8 -LogTailLines 1000"
+}
+
+if ($Help -or ($ExtraArgs -contains '--help')) {
+    Show-Usage
+    exit 0
+}
+
+if (-not $PackageName) {
+    Write-Host "Error: -PackageName is required."
+    Write-Host "Run with --help to see usage."
+    exit 2
+}
+
+$ErrorActionPreference = 'Stop'
+
+$chocoRoot = if ($env:ChocolateyInstall) { $env:ChocolateyInstall } else { 'C:\ProgramData\chocolatey' }
+$logPath = Join-Path $chocoRoot 'logs\chocolatey.log'
+$packageLibPath = Join-Path (Join-Path $chocoRoot 'lib') $PackageName
+$maxAttempts = $RetryCount + 1
+
+$chocoArgs = @('install', '-y', $PackageName)
+if ($Version) {
+    $chocoArgs += @('--version', $Version)
+}
+if ($InstallArgs) {
+    $chocoArgs += @('--installargs', $InstallArgs)
+}
+
+for ($attempt = 1; $attempt -le $maxAttempts; $attempt++) {
+    Write-Host "Installing Chocolatey package: $PackageName (attempt $attempt of $maxAttempts)"
+    & choco @chocoArgs
+    $exitCode = $LASTEXITCODE
+
+    if ($exitCode -eq 0) {
+        Write-Host "Successfully installed Chocolatey package: $PackageName"
+        exit 0
+    }
+
+    Write-Host "Chocolatey install failed for package '$PackageName' (exit code $exitCode)."
+
+    if ($attempt -lt $maxAttempts) {
+        Write-Host "Retrying in $RetryDelaySeconds seconds..."
+        Start-Sleep -Seconds $RetryDelaySeconds
+    }
+}
+
+if ($LogTailLines -gt 0) {
+    if (Test-Path $logPath) {
+        Write-Host "Showing last $LogTailLines lines from $logPath"
+        Get-Content $logPath -Tail $LogTailLines
+    }
+    else {
+        Write-Host "Chocolatey log not found at $logPath"
+    }
+}
+else {
+    Write-Host "Skipping Chocolatey log output because -LogTailLines is set to 0"
+}
+
+if (Test-Path $packageLibPath) {
+    Write-Host "Contents of $packageLibPath"
+    Get-ChildItem -Path $packageLibPath -Force
+}
+
+exit $exitCode
diff --git a/.ci/docker/scripts/install-vcpkg-triplet.ps1 b/.ci/docker/scripts/install-vcpkg-triplet.ps1
new file mode 100644
index 000000000..c0285587a
--- /dev/null
+++ b/.ci/docker/scripts/install-vcpkg-triplet.ps1
@@ -0,0 +1,176 @@
+param(
+    [Parameter(Mandatory = $true)]
+    [string]$ManifestDir,
+
+    [Parameter(Mandatory = $true)]
+    [string]$Triplet,
+
+    [string]$VcpkgRoot = 'C:\vcpkg'
+)
+
+Set-StrictMode -Version Latest
+$ErrorActionPreference = 'Stop'
+
+$vcpkgExe = Join-Path $VcpkgRoot 'vcpkg.exe'
+if (-not (Test-Path -LiteralPath $vcpkgExe)) {
+    Write-Error "vcpkg executable not found at: $vcpkgExe"
+    exit 2
+}
+
+if (-not (Test-Path -LiteralPath $ManifestDir)) {
+    Write-Error "Manifest directory not found: $ManifestDir"
+    exit 2
+}
+
+Write-Host "Running vcpkg install in: $ManifestDir"
+Write-Host "Triplet: $Triplet"
+
+Push-Location $ManifestDir
+try {
+    & $vcpkgExe install --triplet $Triplet --clean-after-build
+    $vcpkgExitCode = $LASTEXITCODE
+}
+finally {
+    Pop-Location
+}
+
+if ($vcpkgExitCode -eq 0) {
+    exit 0
+}
+
+Write-Host "##[error]vcpkg install failed with exit code: $vcpkgExitCode"
+
+$buildtreesRoot = Join-Path $VcpkgRoot 'buildtrees'
+if (-not (Test-Path -LiteralPath $buildtreesRoot)) {
+    Write-Host "No buildtrees directory found at $buildtreesRoot"
+    exit $vcpkgExitCode
+}
+
+function Write-LogIfExists {
+    param([string]$Path)
+    if (Test-Path -LiteralPath $Path) {
+        $logInfo = Get-Item -LiteralPath $Path
+        Write-Host "===== BEGIN LOG: $Path ($([int64]$logInfo.Length) bytes) ====="
+        Get-Content -LiteralPath $Path -Raw
+        Write-Host "===== END LOG: $Path ====="
+        return $true
+    }
+    return $false
+}
+
+function Write-LogFiles {
+    param(
+        [Parameter(Mandatory = $true)]
+        [string]$Directory,
+
+        [Parameter(Mandatory = $true)]
+        [string]$Triplet
+    )
+
+    if (-not (Test-Path -LiteralPath $Directory)) {
+        return
+    }
+
+    function Get-LogPriority {
+        param([System.IO.FileInfo]$File)
+
+        if ($File.Name -match '^config-') {
+            return 0
+        }
+        if ($File.Name -match '^stdout-') {
+            return 1
+        }
+        if ($File.Name -match '^stderr-') {
+            return 2
+        }
+        return 3
+    }
+
+    $priorityLogs = Get-ChildItem -LiteralPath $Directory -File -Filter "*${Triplet}*.log" -ErrorAction SilentlyContinue |
+        Sort-Object @{ Expression = { Get-LogPriority -File $_ } },
+                     @{ Expression = { $_.LastWriteTimeUtc }; Descending = $true },
+                     Name
+
+    if (-not $priorityLogs) {
+        $priorityLogs = Get-ChildItem -LiteralPath $Directory -File -Filter '*.log' -ErrorAction SilentlyContinue |
+            Sort-Object @{ Expression = { Get-LogPriority -File $_ } },
+                         @{ Expression = { $_.LastWriteTimeUtc }; Descending = $true },
+                         Name
+    }
+
+    if (-not $priorityLogs) {
+        Write-Host "No log files found in $Directory"
+        return
+    }
+
+    Write-Host "Dumping log files from $Directory"
+    foreach ($log in $priorityLogs) {
+        if ($log.Length -eq 0) {
+            Write-Host "===== SKIP EMPTY LOG: $($log.FullName) ====="
+            continue
+        }
+
+        Write-Host "===== BEGIN LOG: $($log.FullName) ($([int64]$log.Length) bytes) ====="
+        Get-Content -LiteralPath $log.FullName -Raw
+        Write-Host "===== END LOG: $($log.FullName) ====="
+    }
+}
+
+# Use the most recently modified log of any type to identify the failing port.
+# This catches failures that occur before configure (fetch/extract/patch stage)
+# where no config-*-out.log is ever created.
+$candidate = Get-ChildItem -LiteralPath $buildtreesRoot -Recurse -File -Filter '*.log' -ErrorAction SilentlyContinue |
+    Sort-Object LastWriteTimeUtc -Descending |
+    Select-Object -First 1
+
+# If the most recent log is not a config-*-out.log, also try to find the newest
+# config-*-out.log in the same port directory to seed the related-log dump,
+# since config logs contain the most actionable CMake failure details.
+if ($candidate) {
+    $portDirFromRecent = $candidate.DirectoryName
+    $configInSamePort = Get-ChildItem -LiteralPath $portDirFromRecent -File -Filter "config-$Triplet-*-out.log" -ErrorAction SilentlyContinue |
+        Sort-Object LastWriteTimeUtc -Descending |
+        Select-Object -First 1
+    if ($configInSamePort) {
+        $candidate = $configInSamePort
+    }
+}
+
+if (-not $candidate) {
+    Write-Host "No log files found under $buildtreesRoot"
+    exit $vcpkgExitCode
+}
+
+$portDir = $candidate.DirectoryName
+$portName = Split-Path -Leaf $portDir
+
+Write-Host "Most recent failing dependency candidate: $portName"
+Write-Host "Selected log seed: $($candidate.FullName)"
+
+$seedName = [System.IO.Path]::GetFileNameWithoutExtension($candidate.Name)
+if ($seedName.EndsWith('-out', [System.StringComparison]::OrdinalIgnoreCase)) {
+    $seedPrefix = $seedName.Substring(0, $seedName.Length - 4)
+    $relatedLogs = @(
+        (Join-Path $portDir ($seedPrefix + '-CMakeCache.txt.log')),
+        (Join-Path $portDir ($seedPrefix + '-CMakeConfigureLog.yaml.log')),
+        (Join-Path $portDir ($seedPrefix + '-out.log'))
+    )
+
+    foreach ($log in $relatedLogs) {
+        [void](Write-LogIfExists -Path $log)
+    }
+} else {
+    [void](Write-LogIfExists -Path $candidate.FullName)
+}
+
+Write-LogFiles -Directory $portDir -Triplet $Triplet
+
+Write-Host 'Recent buildtrees logs (top 20 by timestamp):'
+Get-ChildItem -LiteralPath $buildtreesRoot -Recurse -File -Filter '*.log' -ErrorAction SilentlyContinue |
+    Sort-Object LastWriteTimeUtc -Descending |
+    Select-Object -First 20 FullName, LastWriteTimeUtc |
+    Format-Table -AutoSize |
+    Out-String |
+    Write-Host
+
+exit $vcpkgExitCode
diff --git a/.ci/docker/scripts/install-vs-buildtools.ps1 b/.ci/docker/scripts/install-vs-buildtools.ps1
new file mode 100644
index 000000000..e178399be
--- /dev/null
+++ b/.ci/docker/scripts/install-vs-buildtools.ps1
@@ -0,0 +1,101 @@
+param(
+    [Parameter(Mandatory = $true)]
+    [string]$Url,
+
+    # Optional base temp directory for download and installer extraction.
+    # A random subfolder is always created under this base path and cleaned up unless -PreserveTemp is set.
+    [string]$TempDir = '',
+
+    # Preserve the generated temp working directory for debugging.
+    [switch]$PreserveTemp,
+
+    # All remaining arguments are passed directly to vs_buildtools.exe.
+    # Example: -InstallerArgs '--quiet','--wait','--norestart','--installPath','C:\VS','--add','Microsoft.VisualStudio.Workload.VCTools','--includeRecommended'
+    [string[]]$InstallerArgs = @('--quiet', '--wait', '--norestart', '--add', 'Microsoft.VisualStudio.Workload.VCTools', '--includeRecommended')
+)
+
+Set-StrictMode -Version Latest
+$ErrorActionPreference = 'Stop'
+
+# --- URL validation (mirrors check-url.ps1 logic) ---
+if ([string]::IsNullOrWhiteSpace($Url)) {
+    throw "VS_BUILD_TOOLS_URL is empty. Provide a valid download URL."
+}
+
+Write-Host "Validating VS Build Tools URL: $Url"
+$resp = Invoke-WebRequest -Uri $Url -UseBasicParsing -Method Head
+if ($resp.StatusCode -ne 200) {
+    throw "URL check failed: StatusCode=$($resp.StatusCode)"
+}
+$ct = $resp.Headers['Content-Type']
+if ($ct -and $ct -match 'text/html') {
+    throw "URL check failed: Content-Type=$ct (expected binary)"
+}
+$cl = [int64]($resp.Headers['Content-Length'] | Select-Object -First 1)
+if ($cl -and $cl -lt 1048576) {
+    throw "URL check failed: Content-Length=$cl (suspiciously small)"
+}
+Write-Host "URL validation passed (Content-Type: $ct, Content-Length: $cl bytes)."
+
+# --- Setup temp directory ---
+if (-not [string]::IsNullOrWhiteSpace($TempDir)) {
+    $temp = Join-Path $TempDir ([System.IO.Path]::GetRandomFileName())
+} else {
+    $temp = Join-Path $env:TEMP ([System.IO.Path]::GetRandomFileName())
+}
+Write-Host "Using temp directory: $temp"
+New-Item -ItemType Directory -Path $temp -Force | Out-Null
+$env:TEMP = $temp
+$env:TMP  = $temp
+
+# --- Download ---
+$exe = Join-Path $temp 'vs_buildtools.exe'
+Write-Host "Downloading VS Build Tools to $exe ..."
+Invoke-WebRequest $Url -OutFile $exe -UseBasicParsing
+Write-Host "Download complete: $exe"
+
+# --- Install ---
+Push-Location $temp
+try {
+    $fullCmd = ".\vs_buildtools.exe " + ($InstallerArgs -join ' ')
+    Write-Host "Install command: $fullCmd"
+    $p = Start-Process -FilePath '.\vs_buildtools.exe' -ArgumentList $InstallerArgs -Wait -PassThru
+    $code = $p.ExitCode
+    Write-Host "VS installer exit code: $code"
+
+    if ($code -ne 0 -and $code -ne 3010) {
+        # Dump installer logs to stdout before cleanup
+        Get-ChildItem -Path $env:TEMP -Recurse -File -Include 'dd_*', '*.log' -ErrorAction SilentlyContinue |
+            Sort-Object LastWriteTime -Descending |
+            Select-Object -First 20 -ExpandProperty FullName |
+            ForEach-Object { Write-Host ('==== ' + $_ + ' ===='); Get-Content $_ -Tail 250 }
+
+        $b1 = Join-Path $env:ProgramData 'Microsoft\VisualStudio\Packages\_bootstrapper'
+        if (Test-Path $b1) {
+            Get-ChildItem -Path $b1 -Recurse -File -Filter '*.log' -ErrorAction SilentlyContinue |
+                Sort-Object LastWriteTime -Descending |
+                Select-Object -First 20 -ExpandProperty FullName |
+                ForEach-Object { Write-Host ('==== ' + $_ + ' ===='); Get-Content $_ -Tail 250 }
+        }
+
+        throw "Installer failed with exit code: $code"
+    }
+}
+finally {
+    Pop-Location
+    if ($PreserveTemp) {
+        Write-Host "Preserving temp directory: $temp"
+    } else {
+        Remove-Item -LiteralPath $temp -Recurse -Force -ErrorAction SilentlyContinue
+    }
+    # Give Windows time to flush pending filesystem writes (e.g. msiexec deferred
+    # operations) before Docker captures the layer. Without this, hcsshim::ImportLayer
+    # can fail with ERROR_PATH_NOT_FOUND (0x3) due to a race condition between
+    # NTFS lazy-write completion and the layer snapshot.
+    # Runs unconditionally: even a failed install may have partial writes pending.
+    Write-Host "Waiting 10 seconds for filesystem writes to flush..."
+    Start-Sleep -Seconds 10
+    Write-Host "Filesystem flush wait complete."
+}
+
+Write-Host "VS Build Tools installed successfully."
diff --git a/.ci/docker/uhd-builder-vs2022-v143-x64.Dockerfile b/.ci/docker/uhd-builder-vs2022-v143-x64.Dockerfile
index fb48ad3fb..3f0de4440 100644
--- a/.ci/docker/uhd-builder-vs2022-v143-x64.Dockerfile
+++ b/.ci/docker/uhd-builder-vs2022-v143-x64.Dockerfile
@@ -21,6 +21,15 @@ ENV VCPKG_DISABLE_METRICS=1
 # Enable long file paths (>260 characters)
 RUN reg add HKLM\SYSTEM\CurrentControlSet\Control\FileSystem /v LongPathsEnabled /t REG_DWORD /d 1 /f
 
+# Install vs build tools
+COPY .ci/docker/scripts/install-vs-buildtools.ps1 C:/Temp/install-vs-buildtools.ps1
+RUN powershell -NoProfile -ExecutionPolicy Bypass -Command \
+    "& 'C:\Temp\install-vs-buildtools.ps1' \
+    -Url '%VS_BUILD_TOOLS_URL%' \
+    -InstallerArgs '--quiet','--wait','--norestart','--nocache', \
+        '--add','Microsoft.VisualStudio.Workload.VCTools', \
+        '--includeRecommended'"
+
 RUN setx chocolateyVersion 1.4.0 /m
 RUN @"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" \
     -NoProfile -InputFormat None -ExecutionPolicy Bypass \
@@ -28,23 +37,19 @@ RUN @"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" \
     iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))" && \
     SET "PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin" && \
     choco config set webRequestTimeoutSeconds 600
-RUN choco install -y doxygen.install --version=1.9.8
-RUN choco install -y cmake.install --installargs 'ADD_CMAKE_TO_PATH=System' --version=3.22.3
-RUN choco install -y git
-RUN choco install -y NSIS --version=3.06.1
-RUN choco install -y vim
-RUN choco install -y python3 --version=%PYTHON_VERSION%
-
-# Install vs build tools
-COPY .ci/docker/scripts/check-url.ps1 C:/Temp/check-url.ps1
-RUN powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\check-url.ps1 \
-    -Url "%VS_BUILD_TOOLS_URL%"
-RUN powershell -NoProfile -ExecutionPolicy Bypass -Command \
-    Invoke-WebRequest "%VS_BUILD_TOOLS_URL%" \
-    -OutFile "%TEMP%\vs_buildtools.exe" -UseBasicParsing
-RUN "%TEMP%\vs_buildtools.exe"  --quiet --wait --norestart --noUpdateInstaller \
-    --add Microsoft.VisualStudio.Workload.VCTools \
-    --includeRecommended
+COPY .ci/docker/scripts/install-choco-package.ps1 C:/Temp/install-choco-package.ps1
+RUN powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName doxygen.install -Version 1.9.8 && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName cmake.install -Version 3.22.3 -InstallArgs ADD_CMAKE_TO_PATH=System && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName git && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName NSIS -Version 3.06.1 && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName vim && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName python3 -Version %PYTHON_VERSION%
 
 # Optionally use cached index.
 RUN if defined PIP_INDEX_URL ( \
@@ -53,9 +58,9 @@ RUN if defined PIP_INDEX_URL ( \
     )
 
 COPY host/python/requirements.txt C:/Temp/requirements.txt
-RUN pip config list
-RUN python -m pip install --upgrade pip
-RUN pip install -r C:/Temp/requirements.txt
+RUN pip config list && \
+    python -m pip install --upgrade pip && \
+    python -m pip install -r C:/Temp/requirements.txt
 
 RUN setx VCPKG_INSTALL_DIR "c:\\vcpkg" /m
 RUN git clone https://github.com/microsoft/vcpkg %VCPKG_INSTALL_DIR% && \
@@ -64,8 +69,11 @@ RUN git clone https://github.com/microsoft/vcpkg %VCPKG_INSTALL_DIR% && \
 # Add custom UHD vcpkg triplet
 COPY host/cmake/vcpkg/* c:/vcpkg/triplets/
 
-RUN mkdir c:\\uhd-vcpkg
+RUN powershell -NoProfile -ExecutionPolicy Bypass -Command \
+    "New-Item -ItemType Directory -Path 'c:\uhd-vcpkg' -Force | Out-Null"
 COPY .ci/docker/vcpkg/${VCPKG_MANIFEST_FILE} c:/uhd-vcpkg/vcpkg.json
-RUN cd c:\\uhd-vcpkg && %VCPKG_INSTALL_DIR%\vcpkg.exe install \
-    --triplet uhd-x64-windows-static-md \
-    --clean-after-build
+COPY .ci/docker/scripts/install-vcpkg-triplet.ps1 C:/Temp/install-vcpkg-triplet.ps1
+RUN powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-vcpkg-triplet.ps1 \
+    -ManifestDir C:\uhd-vcpkg \
+    -Triplet %VCPKG_TARGET_TRIPLET% \
+    -VcpkgRoot %VCPKG_INSTALL_DIR%
diff --git a/.ci/docker/uhd-builder-vs2026-v145-x64.Dockerfile b/.ci/docker/uhd-builder-vs2026-v145-x64.Dockerfile
index 4eca9022a..4bed03485 100644
--- a/.ci/docker/uhd-builder-vs2026-v145-x64.Dockerfile
+++ b/.ci/docker/uhd-builder-vs2026-v145-x64.Dockerfile
@@ -21,6 +21,15 @@ ENV VCPKG_DISABLE_METRICS=1
 # Enable long file paths (>260 characters)
 RUN reg add HKLM\SYSTEM\CurrentControlSet\Control\FileSystem /v LongPathsEnabled /t REG_DWORD /d 1 /f
 
+# Install vs build tools
+COPY .ci/docker/scripts/install-vs-buildtools.ps1 C:/Temp/install-vs-buildtools.ps1
+RUN powershell -NoProfile -ExecutionPolicy Bypass -Command \
+    "& 'C:\Temp\install-vs-buildtools.ps1' \
+    -Url '%VS_BUILD_TOOLS_URL%' \
+    -InstallerArgs '--quiet','--wait','--norestart','--nocache', \
+        '--add','Microsoft.VisualStudio.Workload.VCTools', \
+        '--includeRecommended'"
+
 RUN setx chocolateyVersion 2.5.1 /m
 RUN @"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" \
     -NoProfile -InputFormat None -ExecutionPolicy Bypass \
@@ -28,23 +37,19 @@ RUN @"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" \
     iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))" && \
     SET "PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin" && \
     choco config set webRequestTimeoutSeconds 600
-RUN choco install -y doxygen.install --version=1.9.8
-RUN choco install -y cmake.install --installargs 'ADD_CMAKE_TO_PATH=System' --version=4.2.1
-RUN choco install -y git
-RUN choco install -y NSIS --version=3.11.0
-RUN choco install -y vim
-RUN choco install -y python3 --version=%PYTHON_VERSION%
-
-# Install vs build tools
-COPY .ci/docker/scripts/check-url.ps1 C:/Temp/check-url.ps1
-RUN powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\check-url.ps1 \
-    -Url "%VS_BUILD_TOOLS_URL%"
-RUN powershell -NoProfile -ExecutionPolicy Bypass -Command \
-    Invoke-WebRequest "%VS_BUILD_TOOLS_URL%" \
-    -OutFile "%TEMP%\vs_buildtools.exe" -UseBasicParsing
-RUN "%TEMP%\vs_buildtools.exe"  --quiet --wait --norestart --noUpdateInstaller \
-    --add Microsoft.VisualStudio.Workload.VCTools \
-    --includeRecommended
+COPY .ci/docker/scripts/install-choco-package.ps1 C:/Temp/install-choco-package.ps1
+RUN powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName doxygen.install -Version 1.9.8 && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName cmake.install -Version 4.2.1 -InstallArgs ADD_CMAKE_TO_PATH=System && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName git && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName NSIS -Version 3.11.0 && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName vim && \
+    powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-choco-package.ps1 \
+        -PackageName python3 -Version %PYTHON_VERSION%
 
 # Optionally use cached index.
 RUN if defined PIP_INDEX_URL ( \
@@ -53,9 +58,9 @@ RUN if defined PIP_INDEX_URL ( \
     )
 
 COPY host/python/requirements.txt C:/Temp/requirements.txt
-RUN pip config list
-RUN python -m pip install --upgrade pip
-RUN pip install -r C:/Temp/requirements.txt
+RUN pip config list && \
+    python -m pip install --upgrade pip && \
+    python -m pip install -r C:/Temp/requirements.txt
 
 RUN setx VCPKG_INSTALL_DIR "c:\\vcpkg" /m
 RUN git clone https://github.com/microsoft/vcpkg %VCPKG_INSTALL_DIR% && \
@@ -64,8 +69,11 @@ RUN git clone https://github.com/microsoft/vcpkg %VCPKG_INSTALL_DIR% && \
 # Add custom UHD vcpkg triplet
 COPY host/cmake/vcpkg/* c:/vcpkg/triplets/
 
-RUN mkdir c:\\uhd-vcpkg
+RUN powershell -NoProfile -ExecutionPolicy Bypass -Command \
+    "New-Item -ItemType Directory -Path 'c:\uhd-vcpkg' -Force | Out-Null"
 COPY .ci/docker/vcpkg/${VCPKG_MANIFEST_FILE} c:/uhd-vcpkg/vcpkg.json
-RUN cd c:\\uhd-vcpkg && %VCPKG_INSTALL_DIR%\vcpkg.exe install \
-    --triplet uhd-x64-windows-static-md \
-    --clean-after-build
+COPY .ci/docker/scripts/install-vcpkg-triplet.ps1 C:/Temp/install-vcpkg-triplet.ps1
+RUN powershell -NoProfile -ExecutionPolicy Bypass -File C:\Temp\install-vcpkg-triplet.ps1 \
+    -ManifestDir C:\uhd-vcpkg \
+    -Triplet %VCPKG_TARGET_TRIPLET% \
+    -VcpkgRoot %VCPKG_INSTALL_DIR%
diff --git a/.ci/uhd-build-docker-container.yml b/.ci/uhd-build-docker-container.yml
index 02a51d755..7d9243fe2 100644
--- a/.ci/uhd-build-docker-container.yml
+++ b/.ci/uhd-build-docker-container.yml
@@ -266,6 +266,7 @@ jobs:
     displayName: Verify expected VS Tools Installer URL
   - task: Docker@2
     displayName: Build Image
+    retryCountOnTaskFailure: 3
     inputs:
       command: 'build'
       Dockerfile: '$(Build.SourcesDirectory)/.ci/docker/$(DOCKER_CONFIG).Dockerfile'