diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 614306b..e4f3718 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -79,11 +79,26 @@ jobs:
 
       - name: Install OpenSSL (Windows)
         if: startsWith(matrix.os, 'windows-')
-        run: |
-          choco install openssl.light -y --params "/InstallDir:C:\OpenSSL" || echo "OpenSSL may already be installed"
-          # Persist OPENSSL_ROOT for later CMake configure step
-          Write-Output "OPENSSL_ROOT=C:\OpenSSL" | Out-File -FilePath $env:GITHUB_ENV -Encoding utf8 -Append
         shell: pwsh
+        run: |
+          $ErrorActionPreference = 'Stop'
+          $installDir = 'C:\OpenSSL'
+          $max = 3
+          for ($i = 1; $i -le $max; $i++) {
+            try {
+              choco install openssl.light -y --params "/InstallDir:$installDir"
+              break
+            } catch {
+              if ($i -eq $max) { throw }
+              Write-Host "OpenSSL install failed (attempt $i/$max). Retrying in 20s..."
+              Start-Sleep -Seconds 20
+            }
+          }
+          if (Test-Path "$installDir\bin\openssl.exe") {
+            "OPENSSL_ROOT=$installDir" | Out-File -FilePath $env:GITHUB_ENV -Encoding utf8 -Append
+          } else {
+            Write-Host "OpenSSL not found at $installDir; not setting OPENSSL_ROOT."
+          }
 
       # Qt
       - name: Install Qt 6.10.2 + QtIFW
diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index 8076670..dd807c8 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -283,9 +283,16 @@ if(WIN32)
     install(DIRECTORY ${_qt_deploy_dir}/ DESTINATION bin COMPONENT Application)
     install(FILES ${CMAKE_BINARY_DIR}/LICENSE.txt DESTINATION doc COMPONENT Application)
     if(OPENSSL_ROOT)
-        install(FILES ${OPENSSL_ROOT}/bin/openssl.exe DESTINATION bin COMPONENT Application)
-        install(FILES ${OPENSSL_ROOT}/bin/libcrypto-3-x64.dll DESTINATION bin COMPONENT Application)
-        install(FILES ${OPENSSL_ROOT}/bin/libssl-3-x64.dll DESTINATION bin COMPONENT Application)
+        set(_openssl_exe "${OPENSSL_ROOT}/bin/openssl.exe")
+        set(_openssl_crypto "${OPENSSL_ROOT}/bin/libcrypto-3-x64.dll")
+        set(_openssl_ssl "${OPENSSL_ROOT}/bin/libssl-3-x64.dll")
+        if(EXISTS "${_openssl_exe}" AND EXISTS "${_openssl_crypto}" AND EXISTS "${_openssl_ssl}")
+            install(FILES "${_openssl_exe}" DESTINATION bin COMPONENT Application)
+            install(FILES "${_openssl_crypto}" DESTINATION bin COMPONENT Application)
+            install(FILES "${_openssl_ssl}" DESTINATION bin COMPONENT Application)
+        else()
+            message(WARNING "OPENSSL_ROOT is set to '${OPENSSL_ROOT}', but required OpenSSL runtime files were not found. Skipping bundling OpenSSL into the installer.")
+        endif()
     endif()
 elseif(APPLE)
     install(DIRECTORY ${CMAKE_BINARY_DIR}/${PROJECT_TARGET_NAME}/${PROJECT_SHORT_REL_NAME}.app DESTINATION . USE_SOURCE_PERMISSIONS COMPONENT Application)