diff --git a/libcxx/test/libcxx/experimental/memory/memory.resource.adaptor/memory.resource.adaptor.mem/db_deallocate.pass.cpp b/libcxx/test/libcxx/experimental/memory/memory.resource.adaptor/memory.resource.adaptor.mem/db_deallocate.pass.cpp
--- a/libcxx/test/libcxx/experimental/memory/memory.resource.adaptor/memory.resource.adaptor.mem/db_deallocate.pass.cpp
+++ b/libcxx/test/libcxx/experimental/memory/memory.resource.adaptor/memory.resource.adaptor.mem/db_deallocate.pass.cpp
@@ -14,6 +14,8 @@
 
 // T* polymorphic_allocator<T>::deallocate(T*, size_t size)
 
+// XFAIL: LIBCXX-WINDOWS-FIXME
+
 int AssertCount = 0;
 
 #define _LIBCPP_ASSERT(x, m) ((x) ? (void)0 : (void)::AssertCount++)
diff --git a/libcxx/utils/ci/buildkite-pipeline.yml b/libcxx/utils/ci/buildkite-pipeline.yml
--- a/libcxx/utils/ci/buildkite-pipeline.yml
+++ b/libcxx/utils/ci/buildkite-pipeline.yml
@@ -329,8 +329,19 @@
         - exit_status: -1  # Agent was lost
           limit: 2
 
-  - label: "Windows"
-    command: "bash libcxx/utils/ci/run-buildbot generic-win"
+  - label: "Windows (DLL)"
+    command: "bash libcxx/utils/ci/run-buildbot windows-dll"
+    artifact_paths:
+      - "**/test-results.xml"
+    agents:
+      queue: "windows"
+    retry:
+      automatic:
+        - exit_status: -1  # Agent was lost
+          limit: 2
+
+  - label: "Windows (Static)"
+    command: "bash libcxx/utils/ci/run-buildbot windows-static"
     artifact_paths:
       - "**/test-results.xml"
     agents:
diff --git a/libcxx/utils/ci/run-buildbot b/libcxx/utils/ci/run-buildbot
--- a/libcxx/utils/ci/run-buildbot
+++ b/libcxx/utils/ci/run-buildbot
@@ -75,19 +75,44 @@
     rm -rf "${BUILD_DIR}"
 }
 
-function generate-cmake() {
+function generate-cmake-base() {
     echo "--- Generating CMake"
-    cmake -S "${MONOREPO_ROOT}/llvm" \
+    cmake \
           -B "${BUILD_DIR}" \
           -GNinja -DCMAKE_MAKE_PROGRAM="${NINJA}" \
           -DCMAKE_BUILD_TYPE=RelWithDebInfo \
           -DCMAKE_INSTALL_PREFIX="${INSTALL_DIR}" \
-          -DLLVM_ENABLE_PROJECTS="libcxx;libunwind;libcxxabi" \
           -DLLVM_LIT_ARGS="-sv --show-unsupported --xunit-xml-output test-results.xml" \
+          "${@}"
+}
+
+function generate-cmake() {
+    generate-cmake-base \
+          -S "${MONOREPO_ROOT}/llvm" \
+          -DLLVM_ENABLE_PROJECTS="libcxx;libunwind;libcxxabi" \
           -DLIBCXX_CXX_ABI=libcxxabi \
           "${@}"
 }
 
+function generate-cmake-libcxx-win() {
+    # TODO: Clang-cl in MSVC configurations don't have access to compiler_rt
+    # builtins helpers for int128 division. See
+    # https://reviews.llvm.org/D91139#2429595 for a comment about longterm
+    # intent for handling the issue. In the meantime, define
+    # -D_LIBCPP_HAS_NO_INT128 (both when building the library itself and
+    # when building tests) to allow enabling filesystem for running tests,
+    # even if it uses a non-permanent ABI.
+
+    generate-cmake-base \
+          -S "${MONOREPO_ROOT}/libcxx" \
+          -DCMAKE_C_COMPILER=clang-cl \
+          -DCMAKE_CXX_COMPILER=clang-cl \
+          -DLIBCXX_ENABLE_FILESYSTEM=YES \
+          -DCMAKE_CXX_FLAGS="-D_LIBCPP_HAS_NO_INT128" \
+          -DLIBCXX_TEST_COMPILER_FLAGS="-D_LIBCPP_HAS_NO_INT128" \
+          "${@}"
+}
+
 function check-cxx-cxxabi() {
     echo "--- Installing libc++ and libc++abi to a fake location"
     ${NINJA} -vC "${BUILD_DIR}" install-cxx install-cxxabi
@@ -485,35 +510,21 @@
     generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv7Thumb-noexceptions.cmake"
     check-cxx-cxxabi
 ;;
-generic-win)
+windows-dll)
     clean
-    # TODO: Clang-cl in MSVC configurations don't have access to compiler_rt
-    # builtins helpers for int128 division. See
-    # https://reviews.llvm.org/D91139#2429595 for a comment about longterm
-    # intent for handling the issue. In the meantime, define
-    # -D_LIBCPP_HAS_NO_INT128 (both when building the library itself and
-    # when building tests) to allow enabling filesystem for running tests,
-    # even if it uses a non-permanent ABI.
-
     # TODO: Currently, building with the experimental library breaks running
     # tests (the test linking look for the c++experimental library with the
     # wrong name, and the statically linked c++experimental can't be linked
     # correctly when libc++ visibility attributes indicate dllimport linkage
     # anyway), thus just disable the experimental library. Remove this
     # setting when cmake and the test driver does the right thing automatically.
-
-    echo "--- Generating CMake"
-    cmake -S "${MONOREPO_ROOT}/libcxx" \
-          -B "${BUILD_DIR}" \
-          -GNinja -DCMAKE_MAKE_PROGRAM="${NINJA}" \
-          -DCMAKE_BUILD_TYPE=RelWithDebInfo \
-          -DCMAKE_C_COMPILER=clang-cl \
-          -DCMAKE_CXX_COMPILER=clang-cl \
-          -DLLVM_LIT_ARGS="-sv --show-unsupported --xunit-xml-output test-results.xml" \
-          -DLIBCXX_ENABLE_EXPERIMENTAL_LIBRARY=NO \
-          -DLIBCXX_ENABLE_FILESYSTEM=YES \
-          -DCMAKE_CXX_FLAGS="-D_LIBCPP_HAS_NO_INT128" \
-          -DLIBCXX_TEST_COMPILER_FLAGS="-D_LIBCPP_HAS_NO_INT128"
+    generate-cmake-libcxx-win -DLIBCXX_ENABLE_EXPERIMENTAL_LIBRARY=OFF
+    echo "+++ Running the libc++ tests"
+    ${NINJA} -vC "${BUILD_DIR}" check-cxx
+;;
+windows-static)
+    clean
+    generate-cmake-libcxx-win -DLIBCXX_ENABLE_SHARED=OFF
     echo "+++ Running the libc++ tests"
     ${NINJA} -vC "${BUILD_DIR}" check-cxx
 ;;