diff --git a/.azdo/ci.yml b/.azdo/ci.yml
index 624b9b5129d..04c2c64640f 100644
--- a/.azdo/ci.yml
+++ b/.azdo/ci.yml
@@ -11,8 +11,36 @@ pr:
     - latestw_all
 
 stages:
+- stage: BuildDependencies
+  displayName: Build Dependencies
+  jobs:
+  - job: InstallDeps_x64
+    displayName: Install vcpkg Dependencies (x64)
+    pool:
+      name: PS-PowerShell-x64
+      demands:
+      - ImageOverride -equals PSMMS2022-OpenSSH-Secure
+    steps:
+    - template: ./templates/install-vcpkg-dependencies.yml
+      parameters:
+        triplet: x64-custom
+        artifactSuffix: x64
+
+  - job: InstallDeps_x86
+    displayName: Install vcpkg Dependencies (x86)
+    pool:
+      name: PS-PowerShell-x64
+      demands:
+      - ImageOverride -equals PSMMS2022-OpenSSH-Secure
+    steps:
+    - template: ./templates/install-vcpkg-dependencies.yml
+      parameters:
+        triplet: x86-custom
+        artifactSuffix: x86
+
 - stage: Build
   displayName: Build Win32-OpenSSH
+  dependsOn: BuildDependencies
   jobs:
   - job: BuildPkg_x64
     displayName: Build Package (x64)
@@ -26,6 +54,7 @@ stages:
         nativeHostArch: x64
         buildOutputDir: x64
         artifactSuffix: x64
+        dependenciesArtifactName: vcpkg-dependencies-x64
         includeConfig: true
 
   - job: BuildPkg_x86
@@ -40,6 +69,7 @@ stages:
         nativeHostArch: x86
         buildOutputDir: Win32
         artifactSuffix: x86
+        dependenciesArtifactName: vcpkg-dependencies-x86
 
 - stage: Test
   displayName: Test Win32-OpenSSH
diff --git a/.azdo/templates/build-win32-openssh-job.yml b/.azdo/templates/build-win32-openssh-job.yml
index 21c10db14f2..016a7dd21be 100644
--- a/.azdo/templates/build-win32-openssh-job.yml
+++ b/.azdo/templates/build-win32-openssh-job.yml
@@ -5,36 +5,27 @@ parameters:
   type: string
 - name: artifactSuffix
   type: string
+- name: dependenciesArtifactName
+  type: string
 - name: includeConfig
   type: boolean
   default: false
 
 steps:
 - pwsh: |
-    # Compare LibreSSL versions in vcpkg.json and add-resource-file.patch
-    $vcpkgObj = Get-Content "$(Build.SourcesDirectory)/contrib/win32/openssh/vcpkg.json" | ConvertFrom-Json
-    $libresslVersionJson = $vcpkgObj | Select-Object -ExpandProperty overrides | Where-Object { $_.name -eq 'libressl' } | Select-Object -ExpandProperty version
-
-    # resource file version needs to be trimmed (e.g. 4.0.0.0 to 4.0.0)
-    $patchContent = Get-Content "$(Build.SourcesDirectory)/contrib/win32/openssh/vcpkg_overlay_ports/libressl/add-version-file.patch"
-    $libresslVersionPatch = ($patchContent -join "`n" | Select-String -Pattern '"FileVersion",\s*"(\d+\.\d+\.\d+\.\d+)"' -AllMatches).Matches | ForEach-Object { $_.Groups[1].Value }
-    $libresslVersionPatchParts = $libresslVersionPatch -split '\.'
-    $libresslVersionPatchShort = ($libresslVersionPatchParts[0..2] -join '.')
-
-    if ($libresslVersionJson -ne $libresslVersionPatchShort) {
-      Write-Error "LibreSSL version mismatch: vcpkg.json has $libresslVersionJson, patch file has $libresslVersionPatch"
-      exit 1
-    } else {
-      Write-Verbose -Verbose "LibreSSL versions match: $libresslVersionJson"
-    }
-  displayName: 'Verify version info'
-
-- pwsh: |-
+    $ErrorActionPreference = 'Stop'
     git clone https://github.com/microsoft/vcpkg
     cd vcpkg
     & ./bootstrap-vcpkg.bat
     & ./vcpkg.exe integrate install
-  displayName: Install vcpkg
+  displayName: Install and bootstrap vcpkg
+  
+- task: DownloadPipelineArtifact@2
+  displayName: 'Download vcpkg dependencies (${{ parameters.dependenciesArtifactName }})'
+  inputs:
+    buildType: current
+    artifactName: ${{ parameters.dependenciesArtifactName }}
+    targetPath: '$(Build.SourcesDirectory)/contrib/win32/openssh/vcpkg_installed'
 
 - pwsh: |
     $nativeArch = '${{ parameters.nativeHostArch }}'
diff --git a/.azdo/templates/install-vcpkg-dependencies.yml b/.azdo/templates/install-vcpkg-dependencies.yml
new file mode 100644
index 00000000000..d9360b6e0e2
--- /dev/null
+++ b/.azdo/templates/install-vcpkg-dependencies.yml
@@ -0,0 +1,66 @@
+parameters:
+- name: triplet
+  type: string
+- name: artifactSuffix
+  type: string
+
+steps:
+- pwsh: |
+    # Compare LibreSSL versions in vcpkg.json and add-resource-file.patch
+    $vcpkgObj = Get-Content "$(Build.SourcesDirectory)/contrib/win32/openssh/vcpkg.json" | ConvertFrom-Json
+    $libresslVersionJson = $vcpkgObj | Select-Object -ExpandProperty overrides | Where-Object { $_.name -eq 'libressl' } | Select-Object -ExpandProperty version
+
+    # resource file version needs to be trimmed (e.g. 4.0.0.0 to 4.0.0)
+    $patchContent = Get-Content "$(Build.SourcesDirectory)/contrib/win32/openssh/vcpkg_overlay_ports/libressl/add-version-file.patch"
+    $libresslVersionPatch = ($patchContent -join "`n" | Select-String -Pattern '"FileVersion",\s*"(\d+\.\d+\.\d+\.\d+)"' -AllMatches).Matches | ForEach-Object { $_.Groups[1].Value }
+    $libresslVersionPatchParts = $libresslVersionPatch -split '\.'
+    $libresslVersionPatchShort = ($libresslVersionPatchParts[0..2] -join '.')
+
+    if ($libresslVersionJson -ne $libresslVersionPatchShort) {
+      Write-Error "LibreSSL version mismatch: vcpkg.json has $libresslVersionJson, patch file has $libresslVersionPatch"
+      exit 1
+    } else {
+      Write-Verbose -Verbose "LibreSSL versions match: $libresslVersionJson"
+    }
+  displayName: 'Verify version info'
+
+- pwsh: |
+    $ErrorActionPreference = 'Stop'
+    git clone https://github.com/microsoft/vcpkg
+    cd vcpkg
+    & ./bootstrap-vcpkg.bat
+    & ./vcpkg.exe integrate install
+  displayName: Install and bootstrap vcpkg
+
+- pwsh: |
+    $triplet = '${{ parameters.triplet }}'
+    Write-Verbose -Verbose "Installing vcpkg dependencies for triplet: $triplet"
+    
+    Push-Location "$(Build.SourcesDirectory)/contrib/win32/openssh"
+    try {
+      & "$(Build.SourcesDirectory)/vcpkg/vcpkg.exe" install --triplet $triplet --overlay-triplets=.\vcpkg_triplets --overlay-ports=.\vcpkg_overlay_ports
+      if ($LASTEXITCODE -ne 0) {
+        throw "vcpkg install failed with exit code $LASTEXITCODE"
+      }
+    } finally {
+      Pop-Location
+    }
+  displayName: Install vcpkg dependencies (${{ parameters.triplet }})
+
+- pwsh: |
+    $artifactSuffix = '${{ parameters.artifactSuffix }}'
+    $vcpkgInstalledPath = "$(Build.SourcesDirectory)/contrib/win32/openssh/vcpkg_installed"
+    
+    if (Test-Path -Path $vcpkgInstalledPath) {
+      Write-Verbose -Verbose "vcpkg_installed directory contents:"
+      Get-ChildItem -Path $vcpkgInstalledPath -Recurse -Depth 2 | Select-Object -First 50
+      
+      # Upload vcpkg dependencies artifact
+      Write-Verbose -Verbose -Message "Uploading vcpkg dependencies artifact"
+      $artifactName = "vcpkg-dependencies-$artifactSuffix"
+      Write-Host "##vso[artifact.upload containerfolder=$artifactName;artifactname=$artifactName;]$vcpkgInstalledPath"
+    } else {
+      Write-Error "vcpkg_installed directory not found at: $vcpkgInstalledPath"
+      exit 1
+    }
+  displayName: Upload vcpkg dependencies (${{ parameters.artifactSuffix }})