diff --git a/libcxx/utils/ci/run-buildbot b/libcxx/utils/ci/run-buildbot
index e664ac8173bcf4..23708e680893fa 100755
--- a/libcxx/utils/ci/run-buildbot
+++ b/libcxx/utils/ci/run-buildbot
@@ -193,78 +193,67 @@ check-generated-output)
 ;;
 generic-cxx03)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx03.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx03.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-cxx11)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx11.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx11.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-cxx14)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx14.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx14.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-cxx17)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx17.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx17.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-cxx20)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx20.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx20.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-cxx2b)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx2b.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx2b.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-assertions)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-assertions.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-assertions.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-debug-iterators)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-debug-iterators.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-debug-iterators.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-noexceptions)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-noexceptions.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-noexceptions.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-modules)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-modules.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-modules.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-static)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-static.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-static.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-static.cmake"
     check-runtimes
 ;;
 generic-merged)
@@ -279,7 +268,7 @@ generic-clang-13)
     export CC=clang-13
     export CXX=clang++-13
     clean
-    generate-cmake -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake
     check-runtimes
     check-abi-list
 ;;
@@ -287,7 +276,7 @@ generic-clang-14)
     export CC=clang-14
     export CXX=clang++-14
     clean
-    generate-cmake -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake
     check-runtimes
     check-abi-list
 ;;
@@ -295,8 +284,7 @@ generic-gcc)
     export CC=gcc-11
     export CXX=g++-11
     clean
-    generate-cmake -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in" \
-                   -DLIBCXX_ENABLE_WERROR=NO \
+    generate-cmake -DLIBCXX_ENABLE_WERROR=NO \
                    -DLIBCXXABI_ENABLE_WERROR=NO \
                    -DLIBUNWIND_ENABLE_WERROR=NO
     check-runtimes
@@ -306,7 +294,6 @@ generic-gcc-cxx11)
     export CXX=g++-11
     clean
     generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-cxx11.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in" \
                    -DLIBCXX_ENABLE_WERROR=NO \
                    -DLIBCXXABI_ENABLE_WERROR=NO \
                    -DLIBUNWIND_ENABLE_WERROR=NO
@@ -314,88 +301,74 @@ generic-gcc-cxx11)
 ;;
 generic-asan)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-asan.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-asan.cmake"
     check-runtimes
 ;;
 generic-msan)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-msan.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-msan.cmake"
     check-runtimes
 ;;
 generic-tsan)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-tsan.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-tsan.cmake"
     check-runtimes
 ;;
 generic-ubsan)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-ubsan.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-ubsan.cmake"
     check-runtimes
 ;;
 generic-with_llvm_unwinder)
     clean
-    generate-cmake -DLIBCXXABI_USE_LLVM_UNWINDER=ON \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -DLIBCXXABI_USE_LLVM_UNWINDER=ON
     check-runtimes
 ;;
 generic-no-threads)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-threads.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-threads.cmake"
     check-runtimes
 ;;
 generic-no-debug)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-debug.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-debug.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-no-filesystem)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-filesystem.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-filesystem.cmake"
     check-runtimes
 ;;
 generic-no-random_device)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-random_device.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-random_device.cmake"
     check-runtimes
 ;;
 generic-no-localization)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-localization.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-localization.cmake"
     check-runtimes
 ;;
 generic-no-unicode)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-unicode.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-unicode.cmake"
     check-runtimes
 ;;
 generic-no-wide-characters)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-wide-characters.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-wide-characters.cmake"
     check-runtimes
 ;;
 generic-no-experimental)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-experimental.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-no-experimental.cmake"
     check-runtimes
     check-abi-list
 ;;
 generic-abi-unstable)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-abi-unstable.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Generic-abi-unstable.cmake"
     check-runtimes
 ;;
 apple-system)
@@ -427,10 +400,13 @@ apple-system-backdeployment-*)
 
     DEPLOYMENT_TARGET="${BUILDER#apple-system-backdeployment-}"
 
-    # TODO: On Apple platforms, we never produce libc++abi.1.dylib, always libc++abi.dylib.
-    #       Fix that in the build so that the tests stop searching for @rpath/libc++abi.1.dylib.
+    # TODO: On Apple platforms, we never produce libc++abi.1.dylib or libunwind.1.dylib,
+    #       only libc++abi.dylib and libunwind.dylib. Fix that in the build so that the
+    #       tests stop searching for @rpath/libc++abi.1.dylib and @rpath/libunwind.1.dylib.
     cp "${OSX_ROOTS}/macOS/libc++abi/${DEPLOYMENT_TARGET}/libc++abi.dylib" \
        "${OSX_ROOTS}/macOS/libc++abi/${DEPLOYMENT_TARGET}/libc++abi.1.dylib"
+    cp "${OSX_ROOTS}/macOS/libunwind/${DEPLOYMENT_TARGET}/libunwind.dylib" \
+       "${OSX_ROOTS}/macOS/libunwind/${DEPLOYMENT_TARGET}/libunwind.1.dylib"
 
     arch="$(uname -m)"
     PARAMS="target_triple=${arch}-apple-macosx${DEPLOYMENT_TARGET}"
@@ -439,18 +415,19 @@ apple-system-backdeployment-*)
     PARAMS+=";unwind_runtime_root=${OSX_ROOTS}/macOS/libunwind/${DEPLOYMENT_TARGET}"
     PARAMS+=";use_system_cxx_lib=True"
 
-    # TODO: We should run the libunwind tests using the back-deployment dylibs too.
     generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Apple.cmake" \
                    -DLIBCXX_TEST_CONFIG="apple-libc++-backdeployment.cfg.in" \
                    -DLIBCXXABI_TEST_CONFIG="apple-libc++abi-backdeployment.cfg.in" \
+                   -DLIBUNWIND_TEST_CONFIG="apple-libunwind-backdeployment.cfg.in" \
                    -DLIBCXX_TEST_PARAMS="${PARAMS}" \
-                   -DLIBCXXABI_TEST_PARAMS="${PARAMS}"
+                   -DLIBCXXABI_TEST_PARAMS="${PARAMS}" \
+                   -DLIBUNWIND_TEST_PARAMS="${PARAMS}"
 
     check-runtimes
 ;;
 benchmarks)
     clean
-    generate-cmake -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake
     check-cxx-benchmarks
 ;;
 documentation)
@@ -475,8 +452,7 @@ bootstrapping-build)
           -DLLVM_RUNTIME_TARGETS="$(c++ --print-target-triple)" \
           -DLLVM_TARGETS_TO_BUILD="host" \
           -DRUNTIMES_BUILD_ALLOW_DARWIN=ON \
-          -DLLVM_ENABLE_ASSERTIONS=ON \
-          -DRUNTIMES_LIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+          -DLLVM_ENABLE_ASSERTIONS=ON
 
     echo "+++ Running the libc++ and libc++abi tests"
     ${NINJA} -C "${BUILD_DIR}" check-runtimes
@@ -506,42 +482,36 @@ legacy-project-build)
 ;;
 aarch64)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/AArch64.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/AArch64.cmake"
     check-runtimes
 ;;
 aarch64-noexceptions)
     clean
     generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/AArch64.cmake" \
                    -DLIBCXX_ENABLE_EXCEPTIONS=OFF \
-                   -DLIBCXXABI_ENABLE_EXCEPTIONS=OFF \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+                   -DLIBCXXABI_ENABLE_EXCEPTIONS=OFF
     check-runtimes
 ;;
 # Aka Armv8 32 bit
 armv8)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv8Arm.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv8Arm.cmake"
     check-runtimes
 ;;
 armv8-noexceptions)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv8Thumb-noexceptions.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv8Thumb-noexceptions.cmake"
     check-runtimes
 ;;
 # Armv7 32 bit. One building Arm only one Thumb only code.
 armv7)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv7Arm.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv7Arm.cmake"
     check-runtimes
 ;;
 armv7-noexceptions)
     clean
-    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv7Thumb-noexceptions.cmake" \
-                   -DLIBUNWIND_TEST_CONFIG="llvm-libunwind-shared.cfg.in"
+    generate-cmake -C "${MONOREPO_ROOT}/libcxx/cmake/caches/Armv7Thumb-noexceptions.cmake"
     check-runtimes
 ;;
 clang-cl-dll)
diff --git a/libunwind/test/configs/apple-libunwind-backdeployment.cfg.in b/libunwind/test/configs/apple-libunwind-backdeployment.cfg.in
new file mode 100644
index 00000000000000..d4777e2f6917a7
--- /dev/null
+++ b/libunwind/test/configs/apple-libunwind-backdeployment.cfg.in
@@ -0,0 +1,64 @@
+# Testing configuration for back-deployment against older Apple system libunwind.
+#
+# Under this configuration, we compile and link all the test suite against the latest libunwind,
+# however we run against the libunwind on a different platform. This emulates the workflow of
+# a developer building their application using recent tools but with the goal of deploying
+# on existing devices running an older OS (and hence an older dylib).
+
+import os, site
+site.addsitedir(os.path.join('@LIBUNWIND_LIBCXX_PATH@', 'utils'))
+import libcxx.test.params, libcxx.test.newconfig, libcxx.test.dsl
+
+lit_config.load_config(config, '@CMAKE_CURRENT_BINARY_DIR@/cmake-bridge.cfg')
+
+BACKDEPLOYMENT_PARAMETERS = [
+    libcxx.test.dsl.Parameter(name='cxx_runtime_root', type=str,
+        actions=lambda root: [libcxx.test.dsl.AddSubstitution('%{cxx-runtime-root}', root)],
+        help="""
+        The simulated root of the system (for libc++) when running tests.
+
+        This should be a directory hierarchy under which the libc++ dylib can be found.
+        The dylib in that hierarchy is the one that will be used at runtime when running
+        the tests.
+        """),
+    libcxx.test.dsl.Parameter(name='abi_runtime_root', type=str,
+        actions=lambda root: [libcxx.test.dsl.AddSubstitution('%{abi-runtime-root}', root)],
+        help="""
+        The simulated root of the system (for libc++abi) when running tests.
+
+        This should be a directory hierarchy under which the libc++abi dylib can be found.
+        The dylib in that hierarchy is the one that will be used at runtime when running
+        the tests.
+        """),
+    libcxx.test.dsl.Parameter(name='unwind_runtime_root', type=str,
+        actions=lambda root: [libcxx.test.dsl.AddSubstitution('%{unwind-runtime-root}', root)],
+        help="""
+        The simulated root of the system (for libunwind) when running tests.
+
+        This should be a directory hierarchy under which the libunwind dylib can be found.
+        The dylib in that hierarchy is the one that will be used at runtime when running
+        the tests.
+        """),
+]
+
+config.substitutions.append(('%{flags}',
+    '-isysroot {}'.format('@CMAKE_OSX_SYSROOT@') if '@CMAKE_OSX_SYSROOT@' else ''
+))
+config.substitutions.append(('%{compile_flags}',
+    '-nostdinc++ -I %{include}'
+))
+config.substitutions.append(('%{link_flags}',
+    '-nostdlib++ -L %{lib} -lc++ -lc++abi -lunwind'
+))
+config.substitutions.append(('%{exec}',
+    '%{executor} --execdir %T --env DYLD_LIBRARY_PATH="%{cxx-runtime-root}:%{abi-runtime-root}:%{unwind-runtime-root}" -- '
+))
+
+import os, site
+import libcxx.test.params, libcxx.test.newconfig, libcxx.test.newconfig
+libcxx.test.newconfig.configure(
+    libcxx.test.params.DEFAULT_PARAMETERS + BACKDEPLOYMENT_PARAMETERS,
+    libcxx.test.features.DEFAULT_FEATURES,
+    config,
+    lit_config
+)
diff --git a/libunwind/test/libunwind_01.pass.cpp b/libunwind/test/libunwind_01.pass.cpp
index 8b4825ac30dca8..bbfaffd153cc28 100644
--- a/libunwind/test/libunwind_01.pass.cpp
+++ b/libunwind/test/libunwind_01.pass.cpp
@@ -7,8 +7,8 @@
 //
 //===----------------------------------------------------------------------===//
 
-// TODO: Investigate these failures on x86_64 macOS back deployment
-// UNSUPPORTED: target=x86_64-apple-darwin{{.+}}
+// TODO: Investigate this failure on x86_64 macOS back deployment
+// XFAIL: use_system_cxx_lib && target=x86_64-apple-macosx{{10.9|10.10|10.11|10.12|10.13|10.14|10.15|11.0|12.0}}
 
 // TODO: Figure out why this fails with Memory Sanitizer.
 // XFAIL: msan
diff --git a/libunwind/test/signal_frame.pass.cpp b/libunwind/test/signal_frame.pass.cpp
index d9fb439cd1e7f4..b17804efa08c8e 100644
--- a/libunwind/test/signal_frame.pass.cpp
+++ b/libunwind/test/signal_frame.pass.cpp
@@ -9,8 +9,8 @@
 
 // Ensure that functions marked as signal frames are reported as such.
 
-// TODO: Investigate this failure on macOS
-// XFAIL: target={{.+}}-apple-darwin{{.+}}
+// TODO: Investigate this failure on Apple
+// XFAIL: target={{.+}}-apple-{{.+}}
 
 // TODO: Figure out why this fails with Memory Sanitizer.
 // XFAIL: msan