diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index f1bc314d013a..56177c65eab5 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -128,6 +128,7 @@ ENV CMAKE_BUILD_TYPE=${build_type} `
   VCPKG_DEFAULT_TRIPLET=amd64-windows-static-md-${build_type} `
   VCPKG_FEATURE_FLAGS="manifests"
 COPY ci/vcpkg/vcpkg.json arrow/ci/vcpkg/
+
 # cannot use the S3 feature here because while aws-sdk-cpp=1.9.160 contains
 # ssl related fixes as well as we can patch the vcpkg portfile to support
 # arm machines it hits ARROW-15141 where we would need to fall back to 1.8.186
diff --git a/ci/vcpkg/vcpkg.patch b/ci/vcpkg/vcpkg.patch
index a4c8d5209785..5a7d7b279554 100644
--- a/ci/vcpkg/vcpkg.patch
+++ b/ci/vcpkg/vcpkg.patch
@@ -1,3 +1,14 @@
+diff --git a/scripts/toolchains/windows.cmake b/scripts/toolchains/windows.cmake
+index 3cc90cc..36af495 100644
+--- a/scripts/toolchains/windows.cmake
++++ b/scripts/toolchains/windows.cmake
+@@ -88,4 +88,4 @@ if(NOT _VCPKG_WINDOWS_TOOLCHAIN)
+     set(CMAKE_C_FLAGS_DEBUG "${VCPKG_CRT_LINK_FLAG_PREFIX}d /Z7 /Ob0 /Od /RTC1 ${VCPKG_C_FLAGS_DEBUG}" CACHE STRING "")
+-    set(CMAKE_CXX_FLAGS_RELEASE "${VCPKG_CRT_LINK_FLAG_PREFIX} /O2 /Oi /Gy /DNDEBUG /Z7 ${VCPKG_CXX_FLAGS_RELEASE}" CACHE STRING "")
+-    set(CMAKE_C_FLAGS_RELEASE "${VCPKG_CRT_LINK_FLAG_PREFIX} /O2 /Oi /Gy /DNDEBUG /Z7 ${VCPKG_C_FLAGS_RELEASE}" CACHE STRING "")
++    set(CMAKE_CXX_FLAGS_RELEASE "${VCPKG_CRT_LINK_FLAG_PREFIX} /O2 /Oi /Gy /DNDEBUG ${VCPKG_CXX_FLAGS_RELEASE}" CACHE STRING "")
++    set(CMAKE_C_FLAGS_RELEASE "${VCPKG_CRT_LINK_FLAG_PREFIX} /O2 /Oi /Gy /DNDEBUG ${VCPKG_C_FLAGS_RELEASE}" CACHE STRING "")
+ 
 diff --git a/scripts/cmake/vcpkg_execute_build_process.cmake b/scripts/cmake/vcpkg_execute_build_process.cmake
 index 60fd5b587a..c8dc021af8 100644
 --- a/scripts/cmake/vcpkg_execute_build_process.cmake
diff --git a/cpp/src/arrow/compute/kernels/scalar_cast_nested.cc b/cpp/src/arrow/compute/kernels/scalar_cast_nested.cc
index 3ab42d89b6ee..392fd9fbb705 100644
--- a/cpp/src/arrow/compute/kernels/scalar_cast_nested.cc
+++ b/cpp/src/arrow/compute/kernels/scalar_cast_nested.cc
@@ -346,11 +346,13 @@ struct CastStruct {
     for (int out_field_index = 0; out_field_index < out_field_count; ++out_field_index) {
       const auto& out_field = out_type.field(out_field_index);
 
-      // Take the first field with matching name, if any. Extract it from the map so it
-      // can't be reused.
-      auto maybe_in_field_index = in_fields.extract(out_field->name());
-      if (!maybe_in_field_index.empty()) {
-        fields_to_select[out_field_index] = maybe_in_field_index.mapped();
+      // Take the first field with matching name, if any. Erase it from the map so it
+      // can't be reused. Use lower_bound (which guarantees first-match) instead of
+      // find/extract (which do not guarantee first for duplicate keys).
+      auto it = in_fields.lower_bound(out_field->name());
+      if (it != in_fields.end() && it->first == out_field->name()) {
+        fields_to_select[out_field_index] = it->second;
+        in_fields.erase(it);
       } else if (out_field->nullable()) {
         fields_to_select[out_field_index] = kFillNullSentinel;
       } else {
diff --git a/dev/tasks/python-wheels/github.windows.yml b/dev/tasks/python-wheels/github.windows.yml
index 77e2a04e3a0a..96605614e321 100644
--- a/dev/tasks/python-wheels/github.windows.yml
+++ b/dev/tasks/python-wheels/github.windows.yml
@@ -57,6 +57,28 @@ jobs:
           esac
           echo "TEST_IMAGE_PREFIX=${test_image_prefix}" >> ${GITHUB_ENV}
 
+      - name: Configure Docker data-root
+        shell: powershell
+        run: |
+          # The D: drive on windows-2022 GH Actions runners has ~44GB free vs ~14GB on C:.
+          # Moving Docker's data-root to D: prevents hcsshim::ImportLayer failures when
+          # building large Windows container layers (e.g. the vcpkg install layer). GH-49676
+          Stop-Service docker
+          $daemonJson = "C:\ProgramData\Docker\config\daemon.json"
+          New-Item -ItemType Directory -Force -Path (Split-Path $daemonJson) | Out-Null
+          if (Test-Path $daemonJson) {
+            $json = Get-Content $daemonJson | ConvertFrom-Json
+            $json | Add-Member -Force -NotePropertyName "data-root" -NotePropertyValue "D:\docker"
+            $json | ConvertTo-Json -Depth 10 | Set-Content $daemonJson
+          } else {
+            Set-Content $daemonJson -Value '{"data-root":"D:\docker"}'
+          }
+          Start-Service docker
+          Write-Host "=== daemon.json ==="
+          Get-Content $daemonJson
+          Write-Host "=== docker info ==="
+          docker info
+
       - name: Build wheel
         shell: cmd
         run: |