diff --git a/lldb/bindings/python/CMakeLists.txt b/lldb/bindings/python/CMakeLists.txt
index e48fcb35aba3b..42299064fd8f7 100644
--- a/lldb/bindings/python/CMakeLists.txt
+++ b/lldb/bindings/python/CMakeLists.txt
@@ -198,6 +198,24 @@ function(finish_swig_python swig_target lldb_python_bindings_dir lldb_python_tar
       COMMENT "Copying Python DLL to LLDB binaries directory.")
   endif()
 
+  # Since Python3.8 the Windows runtime loads dependent DLLs only from the directory of the binary
+  # itself (and not Path). Windows has no RPATHs, so we must copy all DLLs that we depend on into
+  # the Python package.
+  if (WIN32)
+    # TARGET_RUNTIME_DLLS is supported in CMake 3.21+
+    if ("${CMAKE_VERSION}" VERSION_LESS "3.21.0")
+      if (LLDB_INCLUDE_TESTS)
+        message(SEND_ERROR
+          "Your CMake version is ${CMAKE_VERSION}. In order to run LLDB tests "
+          "on Windows please upgrade to 3.21.0 at least (or disable tests with "
+          "LLDB_INCLUDE_TESTS=Off)")
+      endif()
+    else()
+      add_custom_command(TARGET ${swig_target} POST_BUILD
+        COMMAND ${CMAKE_COMMAND} -E copy -t ${lldb_python_target_dir} $<TARGET_RUNTIME_DLLS:liblldb>
+        COMMAND_EXPAND_LISTS)
+    endif()
+  endif()
 
 endfunction()
 
diff --git a/lldb/packages/Python/lldbsuite/test/dotest.py b/lldb/packages/Python/lldbsuite/test/dotest.py
index 1cd5fec461460..e3fe46dada18e 100644
--- a/lldb/packages/Python/lldbsuite/test/dotest.py
+++ b/lldb/packages/Python/lldbsuite/test/dotest.py
@@ -268,10 +268,6 @@ def parseOptionsAndInitTestdirs():
 
     if args.make:
         configuration.make_path = args.make
-    elif platform_system == "FreeBSD" or platform_system == "NetBSD":
-        configuration.make_path = "gmake"
-    else:
-        configuration.make_path = "make"
 
     if args.dsymutil:
         configuration.dsymutil = args.dsymutil
diff --git a/lldb/test/API/CMakeLists.txt b/lldb/test/API/CMakeLists.txt
index 2b77531a13f6c..30a9b776fc3c4 100644
--- a/lldb/test/API/CMakeLists.txt
+++ b/lldb/test/API/CMakeLists.txt
@@ -65,6 +65,20 @@ set(LLDB_DEFAULT_TEST_EXECUTABLE "${LLVM_RUNTIME_OUTPUT_INTDIR}/lldb${CMAKE_EXEC
 
 set(LLDB_DEFAULT_TEST_DSYMUTIL "${LLVM_TOOLS_BINARY_DIR}/dsymutil${CMAKE_EXECUTABLE_SUFFIX}")
 
+if(LLDB_TEST_MAKE)
+  set(LLDB_DEFAULT_TEST_MAKE ${LLDB_TEST_MAKE})
+else()
+  find_program(LLDB_DEFAULT_TEST_MAKE make gmake)
+  if(LLDB_DEFAULT_TEST_MAKE)
+    message(STATUS "Found make: ${LLDB_DEFAULT_TEST_MAKE}")
+  else()
+    message(STATUS "Not found: make")
+    message(WARNING
+          "Many LLDB API tests require 'make' tool. Please provide it in Path "
+          "or pass via LLDB_TEST_MAKE.")
+  endif()
+endif()
+
 if (TARGET clang)
   set(LLDB_DEFAULT_TEST_COMPILER "${LLVM_TOOLS_BINARY_DIR}/clang${CMAKE_EXECUTABLE_SUFFIX}")
 else()
@@ -74,6 +88,7 @@ endif()
 set(LLDB_TEST_EXECUTABLE "${LLDB_DEFAULT_TEST_EXECUTABLE}" CACHE PATH "lldb executable used for testing")
 set(LLDB_TEST_COMPILER "${LLDB_DEFAULT_TEST_COMPILER}" CACHE PATH "C Compiler to use for building LLDB test inferiors")
 set(LLDB_TEST_DSYMUTIL "${LLDB_DEFAULT_TEST_DSYMUTIL}" CACHE PATH "dsymutil used for generating dSYM bundles")
+set(LLDB_TEST_MAKE "${LLDB_DEFAULT_TEST_MAKE}" CACHE PATH "make tool used for building test executables")
 
 if ("${LLDB_TEST_COMPILER}" STREQUAL "")
   message(FATAL_ERROR "LLDB test compiler not specified. Tests will not run.")
diff --git a/lldb/test/API/commands/expression/top-level/Makefile b/lldb/test/API/commands/expression/top-level/Makefile
index e5e9e78d4ead2..51b27ddbb3c2f 100644
--- a/lldb/test/API/commands/expression/top-level/Makefile
+++ b/lldb/test/API/commands/expression/top-level/Makefile
@@ -5,6 +5,6 @@ all: dummy
 include Makefile.rules
 
 dummy: dummy.cpp
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		CXX_SOURCES=dummy.cpp EXE=dummy
 
diff --git a/lldb/test/API/commands/expression/weak_symbols/Makefile b/lldb/test/API/commands/expression/weak_symbols/Makefile
index 6fd8133312ade..1636e9b303263 100644
--- a/lldb/test/API/commands/expression/weak_symbols/Makefile
+++ b/lldb/test/API/commands/expression/weak_symbols/Makefile
@@ -9,12 +9,12 @@ a.out: libdylib.dylib
 include Makefile.rules
 
 libdylib.dylib: dylib.c
-	$(MAKE) -C $(BUILDDIR) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -C $(BUILDDIR) -f $(MAKEFILE_RULES) \
 		C_SOURCES= DYLIB_C_SOURCES=dylib.c DYLIB_NAME=dylib \
 		CFLAGS_EXTRAS=-DHAS_THEM LD_EXTRAS=-dynamiclib
 
 hidden/libdylib.dylib:
 	mkdir hidden
-	$(MAKE) -C $(BUILDDIR)/hidden -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -C $(BUILDDIR)/hidden -f $(MAKEFILE_RULES) \
 		C_SOURCES= DYLIB_C_SOURCES=dylib.c DYLIB_NAME=dylib \
 		LD_EXTRAS=-dynamiclib
diff --git a/lldb/test/API/commands/target/create-deps/Makefile b/lldb/test/API/commands/target/create-deps/Makefile
index 3e5b1049b5a19..866d550ee7d0a 100644
--- a/lldb/test/API/commands/target/create-deps/Makefile
+++ b/lldb/test/API/commands/target/create-deps/Makefile
@@ -6,5 +6,5 @@ a.out: libload_a
 include Makefile.rules
 
 libload_a:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=load_a DYLIB_CXX_SOURCES=a.cpp
diff --git a/lldb/test/API/functionalities/breakpoint/break_in_loaded_dylib/Makefile b/lldb/test/API/functionalities/breakpoint/break_in_loaded_dylib/Makefile
index 0f3fb37bdadf3..112210e7e2c60 100644
--- a/lldb/test/API/functionalities/breakpoint/break_in_loaded_dylib/Makefile
+++ b/lldb/test/API/functionalities/breakpoint/break_in_loaded_dylib/Makefile
@@ -2,7 +2,7 @@ CXX_SOURCES := main.cpp
 USE_LIBDL := 1
 
 lib_b:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=b.cpp DYLIB_NAME=lib_b
 all: lib_b
 
diff --git a/lldb/test/API/functionalities/completion/Makefile b/lldb/test/API/functionalities/completion/Makefile
index f46742243bd96..e457693f62ca4 100644
--- a/lldb/test/API/functionalities/completion/Makefile
+++ b/lldb/test/API/functionalities/completion/Makefile
@@ -4,7 +4,7 @@ USE_LIBDL := 1
 a.out: lib_shared
 
 lib_shared:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=shared.cpp DYLIB_NAME=shared
 
 include Makefile.rules
diff --git a/lldb/test/API/functionalities/dlopen_other_executable/Makefile b/lldb/test/API/functionalities/dlopen_other_executable/Makefile
index 113b9fd7d3f18..51fc01bdde75a 100644
--- a/lldb/test/API/functionalities/dlopen_other_executable/Makefile
+++ b/lldb/test/API/functionalities/dlopen_other_executable/Makefile
@@ -2,7 +2,7 @@ C_SOURCES := main.c
 USE_LIBDL := 1
 
 other:
-	$(MAKE) -f $(MAKEFILE_RULES) C_SOURCES=other.c EXE=other
+	"$(MAKE)" -f $(MAKEFILE_RULES) C_SOURCES=other.c EXE=other
 all: other
 
 include Makefile.rules
diff --git a/lldb/test/API/functionalities/exec/Makefile b/lldb/test/API/functionalities/exec/Makefile
index 8b9148ea8a355..65d4680077d26 100644
--- a/lldb/test/API/functionalities/exec/Makefile
+++ b/lldb/test/API/functionalities/exec/Makefile
@@ -5,5 +5,5 @@ all: secondprog
 include Makefile.rules
 
 secondprog: secondprog.cpp
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		CXX_SOURCES=secondprog.cpp EXE=secondprog
diff --git a/lldb/test/API/functionalities/jitloader_gdb/Makefile b/lldb/test/API/functionalities/jitloader_gdb/Makefile
index 357b1f83684fe..9998cc9cf833c 100644
--- a/lldb/test/API/functionalities/jitloader_gdb/Makefile
+++ b/lldb/test/API/functionalities/jitloader_gdb/Makefile
@@ -5,5 +5,5 @@ all: a.out simple
 include Makefile.rules
 
 simple:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		C_SOURCES=simple.c EXE=simple
diff --git a/lldb/test/API/functionalities/limit-debug-info/Makefile b/lldb/test/API/functionalities/limit-debug-info/Makefile
index 874b3a15e0fee..fa867a7aeb7c6 100644
--- a/lldb/test/API/functionalities/limit-debug-info/Makefile
+++ b/lldb/test/API/functionalities/limit-debug-info/Makefile
@@ -17,11 +17,11 @@ include Makefile.rules
 a.out: libone libtwo
 
 libone:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 	  DYLIB_ONLY=YES DYLIB_CXX_SOURCES=one.cpp DYLIB_NAME=one \
 	  CFLAGS_EXTRAS="$(ONE_CXXFLAGS)"
 
 libtwo: libone
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 	  DYLIB_ONLY=YES DYLIB_CXX_SOURCES=two.cpp DYLIB_NAME=two \
 	  CFLAGS_EXTRAS="$(TWO_CXXFLAGS)" LD_EXTRAS="-L. -lone"
diff --git a/lldb/test/API/functionalities/load_after_attach/Makefile b/lldb/test/API/functionalities/load_after_attach/Makefile
index 0f3fb37bdadf3..112210e7e2c60 100644
--- a/lldb/test/API/functionalities/load_after_attach/Makefile
+++ b/lldb/test/API/functionalities/load_after_attach/Makefile
@@ -2,7 +2,7 @@ CXX_SOURCES := main.cpp
 USE_LIBDL := 1
 
 lib_b:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=b.cpp DYLIB_NAME=lib_b
 all: lib_b
 
diff --git a/lldb/test/API/functionalities/load_lazy/Makefile b/lldb/test/API/functionalities/load_lazy/Makefile
index 81bc7dcb4d05f..8e1d06b1e39c3 100644
--- a/lldb/test/API/functionalities/load_lazy/Makefile
+++ b/lldb/test/API/functionalities/load_lazy/Makefile
@@ -17,13 +17,13 @@ else
 endif
 
 t1: t2_0
-	$(MAKE) VPATH=$(SRCDIR) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" VPATH=$(SRCDIR) -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_C_SOURCES=t1.c DYLIB_NAME=t1 LD_EXTRAS="-L. $(LINKFLAGS)"
 
 t2_0:
-	$(MAKE) VPATH=$(SRCDIR) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" VPATH=$(SRCDIR) -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_C_SOURCES=t2_0.c DYLIB_NAME=t2_0
 
 t2_1:
-	$(MAKE) VPATH=$(SRCDIR) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" VPATH=$(SRCDIR) -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_C_SOURCES=t2_1.c DYLIB_NAME=t2_1
diff --git a/lldb/test/API/functionalities/load_unload/Makefile b/lldb/test/API/functionalities/load_unload/Makefile
index e73ec73108764..dd7d16029427a 100644
--- a/lldb/test/API/functionalities/load_unload/Makefile
+++ b/lldb/test/API/functionalities/load_unload/Makefile
@@ -7,25 +7,25 @@ a.out: lib_b lib_a lib_c lib_d hidden_lib_d
 include Makefile.rules
 
 lib_a: lib_b
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=a.cpp DYLIB_NAME=loadunload_a \
 		LD_EXTRAS="-L. -lloadunload_b"
 
 lib_b:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=b.cpp DYLIB_NAME=loadunload_b
 
 lib_c:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=c.cpp DYLIB_NAME=loadunload_c
 
 lib_d:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=d.cpp DYLIB_NAME=loadunload_d
 ifeq ($(OS),Darwin)
 	install_name_tool -id @executable_path/libloadunload_d.dylib libloadunload_d.dylib
 endif
 
 hidden_lib_d: hidden
-	$(MAKE) VPATH=$(SRCDIR)/hidden -C hidden -f $(MAKEFILE_RULES) \
+	"$(MAKE)" VPATH=$(SRCDIR)/hidden -C hidden -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=d.cpp DYLIB_NAME=loadunload_d
diff --git a/lldb/test/API/functionalities/load_using_paths/Makefile b/lldb/test/API/functionalities/load_using_paths/Makefile
index 814a96013756a..f973a389d585f 100644
--- a/lldb/test/API/functionalities/load_using_paths/Makefile
+++ b/lldb/test/API/functionalities/load_using_paths/Makefile
@@ -6,6 +6,6 @@ all: hidden_lib a.out
 include Makefile.rules
 
 hidden_lib:
-	$(MAKE) VPATH=$(SRCDIR)/hidden -C hidden -f $(MAKEFILE_RULES) \
+	"$(MAKE)" VPATH=$(SRCDIR)/hidden -C hidden -f $(MAKEFILE_RULES) \
 	DYLIB_ONLY=YES DYLIB_CXX_SOURCES=d.cpp DYLIB_NAME=loadunload
 
diff --git a/lldb/test/API/functionalities/scripted_process/Makefile b/lldb/test/API/functionalities/scripted_process/Makefile
index ba739451fc7ef..d4f12fbb3c4ef 100644
--- a/lldb/test/API/functionalities/scripted_process/Makefile
+++ b/lldb/test/API/functionalities/scripted_process/Makefile
@@ -9,7 +9,7 @@ CXXFLAGS_EXTRAS := -target $(TRIPLE)
 all: libbaz.dylib a.out
 
 libbaz.dylib: baz.cpp
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=baz DYLIB_CXX_SOURCES=baz.cpp
 
 include Makefile.rules
diff --git a/lldb/test/API/functionalities/stop-on-sharedlibrary-load/Makefile b/lldb/test/API/functionalities/stop-on-sharedlibrary-load/Makefile
index 4abcab84eac29..e4b0e86c0c36c 100644
--- a/lldb/test/API/functionalities/stop-on-sharedlibrary-load/Makefile
+++ b/lldb/test/API/functionalities/stop-on-sharedlibrary-load/Makefile
@@ -6,11 +6,11 @@ a.out: lib_a lib_b
 include Makefile.rules
 
 lib_a:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=a.cpp DYLIB_NAME=load_a
 
 lib_b:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=b.cpp DYLIB_NAME=load_b
 
 
diff --git a/lldb/test/API/functionalities/tail_call_frames/cross_dso/Makefile b/lldb/test/API/functionalities/tail_call_frames/cross_dso/Makefile
index 42c010be9a03a..963ce2ac94d92 100644
--- a/lldb/test/API/functionalities/tail_call_frames/cross_dso/Makefile
+++ b/lldb/test/API/functionalities/tail_call_frames/cross_dso/Makefile
@@ -10,4 +10,4 @@ a.out: lib_One lib_Two
 lib_One: lib_Two
 
 lib_%:
-	$(MAKE) VPATH=$(SRCDIR)/$* -I $(SRCDIR) -f $(SRCDIR)/$*.mk DSYMUTIL=$(DSYMUTIL)
+	"$(MAKE)" VPATH=$(SRCDIR)/$* -I $(SRCDIR) -f $(SRCDIR)/$*.mk DSYMUTIL=$(DSYMUTIL)
diff --git a/lldb/test/API/functionalities/target-new-solib-notifications/Makefile b/lldb/test/API/functionalities/target-new-solib-notifications/Makefile
index 6c61d210eeb2f..e3b48697fd783 100644
--- a/lldb/test/API/functionalities/target-new-solib-notifications/Makefile
+++ b/lldb/test/API/functionalities/target-new-solib-notifications/Makefile
@@ -1,23 +1,23 @@
 CXX_SOURCES := main.cpp
-LD_EXTRAS := -L. -l_d -l_c -l_a -l_b
+LD_EXTRAS := -L. -l_d -l_c -l_a -l_b
 
 a.out: lib_b lib_a lib_c lib_d
 
 include Makefile.rules
 
 lib_a: lib_b
-	$(MAKE) -f $(MAKEFILE_RULES) \
-		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=a.cpp DYLIB_NAME=_a \
-		LD_EXTRAS="-L. -l_b"
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
+		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=a.cpp DYLIB_NAME=_a \
+		LD_EXTRAS="-L. -l_b"
 
 lib_b:
-	$(MAKE) -f $(MAKEFILE_RULES) \
-		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=b.cpp DYLIB_NAME=_b
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
+		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=b.cpp DYLIB_NAME=_b
 
 lib_c:
-	$(MAKE) -f $(MAKEFILE_RULES) \
-		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=c.cpp DYLIB_NAME=_c
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
+		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=c.cpp DYLIB_NAME=_c
 
 lib_d:
-	$(MAKE) -f $(MAKEFILE_RULES) \
-		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=d.cpp DYLIB_NAME=_d
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
+		DYLIB_ONLY=YES DYLIB_CXX_SOURCES=d.cpp DYLIB_NAME=_d
diff --git a/lldb/test/API/lang/c/conflicting-symbol/Makefile b/lldb/test/API/lang/c/conflicting-symbol/Makefile
index 81594a1265da2..1331c4e1ebfaf 100644
--- a/lldb/test/API/lang/c/conflicting-symbol/Makefile
+++ b/lldb/test/API/lang/c/conflicting-symbol/Makefile
@@ -7,4 +7,4 @@ include Makefile.rules
 a.out: lib_One lib_Two
 
 lib_%:
-	$(MAKE) VPATH=$(SRCDIR)/$* -I $(SRCDIR) -f $(SRCDIR)/$*.mk
+	"$(MAKE)" VPATH=$(SRCDIR)/$* -I $(SRCDIR) -f $(SRCDIR)/$*.mk
diff --git a/lldb/test/API/lang/cpp/class-template-non-type-parameter-pack/TestClassTemplateNonTypeParameterPack.py b/lldb/test/API/lang/cpp/class-template-non-type-parameter-pack/TestClassTemplateNonTypeParameterPack.py
index 9e484e0132c83..730537da2fccf 100644
--- a/lldb/test/API/lang/cpp/class-template-non-type-parameter-pack/TestClassTemplateNonTypeParameterPack.py
+++ b/lldb/test/API/lang/cpp/class-template-non-type-parameter-pack/TestClassTemplateNonTypeParameterPack.py
@@ -5,9 +5,6 @@
 
 
 class TestCaseClassTemplateNonTypeParameterPack(TestBase):
-    @expectedFailureAll(
-        oslist=["windows"], archs=["i[3-6]86", "x86_64"]
-    )  # Fails to read memory from target.
     @no_debug_info_test
     def test(self):
         self.build()
diff --git a/lldb/test/API/lang/cpp/class-template-type-parameter-pack/TestClassTemplateTypeParameterPack.py b/lldb/test/API/lang/cpp/class-template-type-parameter-pack/TestClassTemplateTypeParameterPack.py
index 102c00dc603df..1ed643e6dd85c 100644
--- a/lldb/test/API/lang/cpp/class-template-type-parameter-pack/TestClassTemplateTypeParameterPack.py
+++ b/lldb/test/API/lang/cpp/class-template-type-parameter-pack/TestClassTemplateTypeParameterPack.py
@@ -5,9 +5,6 @@
 
 
 class TestCaseClassTemplateTypeParameterPack(TestBase):
-    @expectedFailureAll(
-        oslist=["windows"], archs=["i[3-6]86", "x86_64"]
-    )  # Fails to read memory from target.
     @no_debug_info_test
     def test(self):
         self.build()
diff --git a/lldb/test/API/lang/cpp/incomplete-types/Makefile b/lldb/test/API/lang/cpp/incomplete-types/Makefile
index f42ac2e81cc76..0cf3f6a31caa2 100644
--- a/lldb/test/API/lang/cpp/incomplete-types/Makefile
+++ b/lldb/test/API/lang/cpp/incomplete-types/Makefile
@@ -16,7 +16,7 @@ main.o: CFLAGS_EXTRAS = -flimit-debug-info
 
 limit: a.o main.o
 	mkdir -p build_limit
-	$(MAKE) -C $(BUILDDIR)/build_limit -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -C $(BUILDDIR)/build_limit -f $(MAKEFILE_RULES) \
 		EXE=../limit CXX_SOURCES="length.cpp ../a.o ../main.o" \
 		CFLAGS_EXTRAS=-flimit-debug-info NO_LIMIT_DEBUG_INFO_FLAGS=""
 
diff --git a/lldb/test/API/lang/cpp/namespace_definitions/Makefile b/lldb/test/API/lang/cpp/namespace_definitions/Makefile
index fc9165f67f428..b17d70fc92871 100644
--- a/lldb/test/API/lang/cpp/namespace_definitions/Makefile
+++ b/lldb/test/API/lang/cpp/namespace_definitions/Makefile
@@ -6,10 +6,10 @@ a.out: liba libb
 include Makefile.rules
 
 liba:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=a DYLIB_CXX_SOURCES=a.cpp
 
 libb:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=b DYLIB_CXX_SOURCES=b.cpp
 
diff --git a/lldb/test/API/lang/objc/conflicting-definition/Makefile b/lldb/test/API/lang/objc/conflicting-definition/Makefile
index 00a0769a086f0..cba79c94d46ba 100644
--- a/lldb/test/API/lang/objc/conflicting-definition/Makefile
+++ b/lldb/test/API/lang/objc/conflicting-definition/Makefile
@@ -9,14 +9,14 @@ include Makefile.rules
 
 libTest.dylib:	Test/Test.m
 	mkdir -p Test
-	$(MAKE) MAKE_DSYM=YES -f $(MAKEFILE_RULES) \
+	"$(MAKE)" MAKE_DSYM=YES -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=Test DYLIB_OBJC_SOURCES=Test/Test.m \
 		LD_EXTRAS="-lobjc -framework Foundation" \
 		CFLAGS_EXTRAS=-I$(SRCDIR)
 
 libTestExt.dylib: TestExt/TestExt.m
 	mkdir -p TestExt
-	$(MAKE) MAKE_DSYM=YES -f $(MAKEFILE_RULES) \
+	"$(MAKE)" MAKE_DSYM=YES -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=TestExt DYLIB_OBJC_SOURCES=TestExt/TestExt.m \
 		LD_EXTRAS="-lobjc -framework Foundation -lTest -L." \
 		CFLAGS_EXTRAS=-I$(SRCDIR)
diff --git a/lldb/test/API/lang/objc/modules-hash-mismatch/Makefile b/lldb/test/API/lang/objc/modules-hash-mismatch/Makefile
index 59bf009f68677..57da670b69ab3 100644
--- a/lldb/test/API/lang/objc/modules-hash-mismatch/Makefile
+++ b/lldb/test/API/lang/objc/modules-hash-mismatch/Makefile
@@ -5,7 +5,7 @@ USE_PRIVATE_MODULE_CACHE = YES
 .PHONY: update-module
 
 all: $(EXE)
-	$(MAKE) -f $(SRCDIR)/Makefile update-module
+	"$(MAKE)" -f $(SRCDIR)/Makefile update-module
 
 include Makefile.rules
 
diff --git a/lldb/test/API/lang/swift/clashing_abi_name/Makefile b/lldb/test/API/lang/swift/clashing_abi_name/Makefile
index 2237cdac0c039..553b52a209b66 100644
--- a/lldb/test/API/lang/swift/clashing_abi_name/Makefile
+++ b/lldb/test/API/lang/swift/clashing_abi_name/Makefile
@@ -7,11 +7,11 @@ all: libLibrary.dylib a.out
 include Makefile.rules
 
 libLibrary.dylib: Library.swift
-	$(MAKE) MAKE_DSYM=YES CC=$(CC) SWIFTC=$(SWIFTC) \
+	"$(MAKE)" MAKE_DSYM=YES CC=$(CC) SWIFTC=$(SWIFTC) \
 		ARCH=$(ARCH) DSYMUTIL=$(DSYMUTIL) \
 		BASENAME=Library \
 		SWIFTFLAGS_EXTRAS="-I$(BUILDDIR) -enable-library-evolution -emit-library -emit-module -parse-as-library -module-abi-name a" \
 		VPATH=$(SRCDIR) -I $(SRCDIR) -f $(SRCDIR)/dylib.mk all
 
 clean::
-	$(MAKE) BASENAME=Library VPATH=$(SRCDIR) -I $(SRCDIR) -f $(SRCDIR)/dylib.mk clean
+	"$(MAKE)" BASENAME=Library VPATH=$(SRCDIR) -I $(SRCDIR) -f $(SRCDIR)/dylib.mk clean
diff --git a/lldb/test/API/lang/swift/expression/error_missing_type/Makefile b/lldb/test/API/lang/swift/expression/error_missing_type/Makefile
index 8272b2ffbc43a..1879c567ae9aa 100644
--- a/lldb/test/API/lang/swift/expression/error_missing_type/Makefile
+++ b/lldb/test/API/lang/swift/expression/error_missing_type/Makefile
@@ -4,7 +4,7 @@ LD_EXTRAS = -lLibrary -L$(BUILDDIR)
 all: libLibrary.dylib a.out
 
 lib%.dylib: %.swift
-	$(MAKE) MAKE_DSYM=NO DYLIB_ONLY=YES \
+	"$(MAKE)" MAKE_DSYM=NO DYLIB_ONLY=YES \
 		DYLIB_HIDE_SWIFTMODULE=YES \
 		DYLIB_NAME=$(shell basename $< .swift) \
 		DYLIB_SWIFT_SOURCES=$(shell basename $<) \
diff --git a/lldb/test/API/lang/swift/import_spi/Makefile b/lldb/test/API/lang/swift/import_spi/Makefile
index 7bb7fa25c1aeb..325be6e6885c6 100644
--- a/lldb/test/API/lang/swift/import_spi/Makefile
+++ b/lldb/test/API/lang/swift/import_spi/Makefile
@@ -8,7 +8,7 @@ all: A.swiftmodule $(EXE)
 include Makefile.rules
 
 A.swiftmodule: $(SRCDIR)/A.swift B.swiftmodule
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES \
 		DYLIB_NAME=A \
 		DYLIB_SWIFT_SOURCES=A.swift \
@@ -17,7 +17,7 @@ A.swiftmodule: $(SRCDIR)/A.swift B.swiftmodule
 		LD_EXTRAS="-L$(BUILDDIR) -lB"
 
 B.swiftmodule: $(SRCDIR)/B.swift
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES \
 		DYLIB_NAME=B \
 		DYLIB_SWIFT_SOURCES=B.swift \
diff --git a/lldb/test/API/lit.cfg.py b/lldb/test/API/lit.cfg.py
index ee1e91597440a..d825ad330ff4f 100644
--- a/lldb/test/API/lit.cfg.py
+++ b/lldb/test/API/lit.cfg.py
@@ -278,6 +278,9 @@ def delete_module_cache(path):
 if is_configured("dsymutil"):
     dotest_cmd += ["--dsymutil", config.dsymutil]
 
+if is_configured("make"):
+    dotest_cmd += ["--make", config.make]
+
 if is_configured("llvm_tools_dir"):
     dotest_cmd += ["--llvm-tools-dir", config.llvm_tools_dir]
 
diff --git a/lldb/test/API/lit.site.cfg.py.in b/lldb/test/API/lit.site.cfg.py.in
index 4184436c63ba7..420e0aa4751b1 100644
--- a/lldb/test/API/lit.site.cfg.py.in
+++ b/lldb/test/API/lit.site.cfg.py.in
@@ -33,6 +33,7 @@ config.test_arch = '@LLDB_TEST_ARCH@'
 config.test_compiler = lit_config.substitute('@LLDB_TEST_COMPILER@')
 config.test_swift_compiler = lit_config.substitute('@LLDB_SWIFTC@')
 config.dsymutil = lit_config.substitute('@LLDB_TEST_DSYMUTIL@')
+config.make = lit_config.substitute('@LLDB_TEST_MAKE@')
 config.has_libcxx = @LLDB_HAS_LIBCXX@
 config.libcxx_libs_dir = "@LIBCXX_LIBRARY_DIR@"
 config.libcxx_include_dir = "@LIBCXX_GENERATED_INCLUDE_DIR@"
diff --git a/lldb/test/API/macosx/delay-init-dependency/Makefile b/lldb/test/API/macosx/delay-init-dependency/Makefile
index 246ea0f34e1a1..7421c68b79baa 100644
--- a/lldb/test/API/macosx/delay-init-dependency/Makefile
+++ b/lldb/test/API/macosx/delay-init-dependency/Makefile
@@ -7,5 +7,5 @@ all: build-libfoo a.out
 include Makefile.rules
 
 build-libfoo: foo.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_C_SOURCES=foo.c DYLIB_NAME=foo DYLIB_ONLY=YES
diff --git a/lldb/test/API/macosx/expedited-thread-pcs/Makefile b/lldb/test/API/macosx/expedited-thread-pcs/Makefile
index 7799f06e77097..73a969831e673 100644
--- a/lldb/test/API/macosx/expedited-thread-pcs/Makefile
+++ b/lldb/test/API/macosx/expedited-thread-pcs/Makefile
@@ -6,6 +6,6 @@ all: build-libfoo a.out
 include Makefile.rules
 
 build-libfoo: foo.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_C_SOURCES=foo.c DYLIB_NAME=foo DYLIB_ONLY=YES
 
diff --git a/lldb/test/API/macosx/indirect_symbol/Makefile b/lldb/test/API/macosx/indirect_symbol/Makefile
index 9069302b39c4f..dee3e184fe19b 100644
--- a/lldb/test/API/macosx/indirect_symbol/Makefile
+++ b/lldb/test/API/macosx/indirect_symbol/Makefile
@@ -7,11 +7,11 @@ all: build-libindirect build-libreepxoprt a.out
 include Makefile.rules
 
 build-libindirect: indirect.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_C_SOURCES=indirect.c DYLIB_NAME=indirect DYLIB_ONLY=YES \
 		LD_EXTRAS="-Wl,-image_base,0x200000000"
 
 build-libreepxoprt: reexport.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_C_SOURCES=reexport.c DYLIB_NAME=reexport DYLIB_ONLY=YES \
 		LD_EXTRAS="-L. -lindirect -Wl,-alias_list,$(SRCDIR)/alias.list"
diff --git a/lldb/test/API/macosx/lc-note/kern-ver-str/Makefile b/lldb/test/API/macosx/lc-note/kern-ver-str/Makefile
index 05d9552a80209..01b4acfdcfd2a 100644
--- a/lldb/test/API/macosx/lc-note/kern-ver-str/Makefile
+++ b/lldb/test/API/macosx/lc-note/kern-ver-str/Makefile
@@ -5,7 +5,7 @@ C_SOURCES := main.c
 all: a.out create-empty-corefile
 
 create-empty-corefile:
-	$(MAKE) -f $(MAKEFILE_RULES) EXE=create-empty-corefile \
+	"$(MAKE)" -f $(MAKEFILE_RULES) EXE=create-empty-corefile \
 	    CXX=$(CC) CXX_SOURCES=create-empty-corefile.cpp
 
 include Makefile.rules
diff --git a/lldb/test/API/macosx/lc-note/multiple-binary-corefile/Makefile b/lldb/test/API/macosx/lc-note/multiple-binary-corefile/Makefile
index 8e561f17383fe..229235cda999f 100644
--- a/lldb/test/API/macosx/lc-note/multiple-binary-corefile/Makefile
+++ b/lldb/test/API/macosx/lc-note/multiple-binary-corefile/Makefile
@@ -10,11 +10,11 @@ create-empty-corefile:
 		CXX_SOURCES=create-multibin-corefile.cpp
 
 libone.dylib: one.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=one DYLIB_C_SOURCES=one.c
 
 libtwo.dylib: two.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=two DYLIB_C_SOURCES=two.c
 
 include Makefile.rules
diff --git a/lldb/test/API/macosx/macCatalystAppMacOSFramework/Makefile b/lldb/test/API/macosx/macCatalystAppMacOSFramework/Makefile
index bb8df1869ef98..4d2ba1661ea30 100644
--- a/lldb/test/API/macosx/macCatalystAppMacOSFramework/Makefile
+++ b/lldb/test/API/macosx/macCatalystAppMacOSFramework/Makefile
@@ -9,7 +9,7 @@ override CC=xcrun clang
 all: libfoo.dylib a.out
 
 libfoo.dylib: foo.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_NAME=foo DYLIB_C_SOURCES=foo.c
 
 include Makefile.rules
diff --git a/lldb/test/API/macosx/skinny-corefile/Makefile b/lldb/test/API/macosx/skinny-corefile/Makefile
index efe37f3d2b8b2..fce43a36c33ac 100644
--- a/lldb/test/API/macosx/skinny-corefile/Makefile
+++ b/lldb/test/API/macosx/skinny-corefile/Makefile
@@ -6,10 +6,10 @@ include Makefile.rules
 a.out: libto-be-removed libpresent
 
 libto-be-removed: libpresent
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 	  DYLIB_ONLY=YES DYLIB_C_SOURCES=to-be-removed.c DYLIB_NAME=to-be-removed \
 	  LD_EXTRAS="-L. -lpresent"
 
 libpresent:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 	  DYLIB_ONLY=YES DYLIB_C_SOURCES=present.c DYLIB_NAME=present 
diff --git a/lldb/test/API/tools/lldb-dap/breakpoint/Makefile b/lldb/test/API/tools/lldb-dap/breakpoint/Makefile
index 30a6400184933..7634f513e8523 100644
--- a/lldb/test/API/tools/lldb-dap/breakpoint/Makefile
+++ b/lldb/test/API/tools/lldb-dap/breakpoint/Makefile
@@ -15,5 +15,5 @@ main-copy.cpp: main.cpp
 
 # The following shared library will be used to test breakpoints under dynamic loading
 libother:  other-copy.c
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_ONLY=YES DYLIB_C_SOURCES=other-copy.c DYLIB_NAME=other 
diff --git a/lldb/test/API/tools/lldb-server/libraries-svr4/Makefile b/lldb/test/API/tools/lldb-server/libraries-svr4/Makefile
index 5b5c1dcef783a..f13b1ac15928a 100644
--- a/lldb/test/API/tools/lldb-server/libraries-svr4/Makefile
+++ b/lldb/test/API/tools/lldb-server/libraries-svr4/Makefile
@@ -9,11 +9,11 @@ a.out: svr4lib_a svr4lib_b_quote
 include Makefile.rules
 
 svr4lib_a:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_NAME=svr4lib_a DYLIB_CXX_SOURCES=svr4lib_a.cpp \
 		DYLIB_ONLY=YES
 
 svr4lib_b_quote:
-	$(MAKE) -f $(MAKEFILE_RULES) \
+	"$(MAKE)" -f $(MAKEFILE_RULES) \
 		DYLIB_NAME=svr4lib_b\\\" DYLIB_CXX_SOURCES=svr4lib_b_quote.cpp \
 		DYLIB_ONLY=YES
diff --git a/lldb/test/CMakeLists.txt b/lldb/test/CMakeLists.txt
index 25dc559ed926f..aef43dda67660 100644
--- a/lldb/test/CMakeLists.txt
+++ b/lldb/test/CMakeLists.txt
@@ -3,7 +3,7 @@
 # Lit requires a Python3 interpreter, let's be careful and fail early if it's
 # not present.
 if (NOT DEFINED Python3_EXECUTABLE)
-  message(FATAL_ERROR
+  message(SEND_ERROR
     "LLDB test suite requires a Python3 interpreter but none "
     "was found. Please install Python3 or disable tests with "
     "`LLDB_INCLUDE_TESTS=OFF`.")
@@ -12,7 +12,7 @@ endif()
 if(LLDB_ENFORCE_STRICT_TEST_REQUIREMENTS)
   message(STATUS "Enforcing strict test requirements for LLDB")
   # Lit uses psutil to do per-test timeouts.
-  set(useful_python_modules psutil)
+  set(useful_python_modules psutil packaging)
 
   if(NOT WIN32)
     # We no longer vendor pexpect and it is not used on Windows.
@@ -22,7 +22,7 @@ if(LLDB_ENFORCE_STRICT_TEST_REQUIREMENTS)
   foreach(module ${useful_python_modules})
     lldb_find_python_module(${module})
     if (NOT PY_${module}_FOUND)
-      message(FATAL_ERROR
+      message(SEND_ERROR
         "Python module '${module}' not found. Please install it via pip or via "
         "your operating system's package manager. Alternatively, disable "
         "strict testing requirements with "
@@ -66,10 +66,10 @@ if (LLDB_TEST_OBJC_GNUSTEP)
   find_package(GNUstepObjC)
   if (NOT GNUstepObjC_FOUND)
     if (LLDB_TEST_OBJC_GNUSTEP_DIR)
-      message(FATAL_ERROR "Failed to find GNUstep libobjc2 in ${LLDB_TEST_OBJC_GNUSTEP_DIR}. "
+      message(SEND_ERROR "Failed to find GNUstep libobjc2 in ${LLDB_TEST_OBJC_GNUSTEP_DIR}. "
                           "Please check LLDB_TEST_OBJC_GNUSTEP_DIR or turn off LLDB_TEST_OBJC_GNUSTEP.")
     else()
-      message(FATAL_ERROR "Failed to find GNUstep libobjc2. "
+      message(SEND_ERROR "Failed to find GNUstep libobjc2. "
                           "Please set LLDB_TEST_OBJC_GNUSTEP_DIR or turn off LLDB_TEST_OBJC_GNUSTEP.")
     endif()
   endif()
@@ -185,7 +185,7 @@ if(TARGET clang)
         set(LIBCXX_LIBRARY_DIR "${LLDB_TEST_LIBCXX_ROOT_DIR}/lib${LIBCXX_LIBDIR_SUFFIX}")
         set(LIBCXX_GENERATED_INCLUDE_DIR "${LLDB_TEST_LIBCXX_ROOT_DIR}/include/c++/v1")
       else()
-        message(FATAL_ERROR
+        message(SEND_ERROR
             "Couldn't find libcxx build in '${LLDB_TEST_LIBCXX_ROOT_DIR}'. To run the "
             "test-suite for a standalone LLDB build please build libcxx and point "
             "LLDB_TEST_LIBCXX_ROOT_DIR to it.")
@@ -194,7 +194,7 @@ if(TARGET clang)
       # We require libcxx for the test suite, so if we aren't building it,
       # provide a helpful error about how to resolve the situation.
       if(NOT LLDB_HAS_LIBCXX)
-        message(FATAL_ERROR
+        message(SEND_ERROR
           "LLDB test suite requires libc++, but it is currently disabled. "
           "Please add `libcxx` to `LLVM_ENABLE_RUNTIMES` or disable tests via "
           "`LLDB_INCLUDE_TESTS=OFF`.")
diff --git a/lldb/test/Shell/Commands/command-disassemble-mixed.c b/lldb/test/Shell/Commands/command-disassemble-mixed.c
index 1e530095c5c56..4af85c0a4c020 100644
--- a/lldb/test/Shell/Commands/command-disassemble-mixed.c
+++ b/lldb/test/Shell/Commands/command-disassemble-mixed.c
@@ -1,6 +1,6 @@
 // invalid mixed disassembly line
 
-// XFAIL: system-windows
+// XFAIL: target-windows
 
 // RUN: %clang_host -g %s -o %t
 // RUN: %lldb %t -o "dis -m -n main" -o "exit" | FileCheck %s
diff --git a/lldb/test/Shell/Commands/command-expr-diagnostics.test b/lldb/test/Shell/Commands/command-expr-diagnostics.test
index b242dba1980f0..3c827fb4516ec 100644
--- a/lldb/test/Shell/Commands/command-expr-diagnostics.test
+++ b/lldb/test/Shell/Commands/command-expr-diagnostics.test
@@ -1,3 +1,4 @@
+# XFAIL: target-windows
 # RUN: echo quit | %lldb -o "expression a+b" \
 # RUN:   | FileCheck %s --strict-whitespace --check-prefix=CHECK1
 #            (lldb) expression a+b
diff --git a/lldb/test/Shell/Commands/command-target-create-resolve-exe.test b/lldb/test/Shell/Commands/command-target-create-resolve-exe.test
index 0ebbaf25e652d..3a0c7bd91a73e 100644
--- a/lldb/test/Shell/Commands/command-target-create-resolve-exe.test
+++ b/lldb/test/Shell/Commands/command-target-create-resolve-exe.test
@@ -1,4 +1,4 @@
-# REQUIRES: system-windows
+# REQUIRES: target-windows
 
 ## This checks that when starting lldb (or using `target create`) with a
 ## program name which is on $PATH, or not specify the .exe suffix of a program
diff --git a/lldb/test/Shell/Expr/TestAnonNamespaceParamFunc.cpp b/lldb/test/Shell/Expr/TestAnonNamespaceParamFunc.cpp
index 3d7b193dc6aac..725b2d637637f 100644
--- a/lldb/test/Shell/Expr/TestAnonNamespaceParamFunc.cpp
+++ b/lldb/test/Shell/Expr/TestAnonNamespaceParamFunc.cpp
@@ -3,7 +3,7 @@
 // linkage. In this case, a function whose argument
 // is not legally usable outside this TU.
 
-// XFAIL: system-windows
+// XFAIL: target-windows
 
 // RUN: %build %s -o %t
 // RUN: %lldb %t -o run -o "expression func(a)" -o exit | FileCheck %s
diff --git a/lldb/test/Shell/Expr/TestIRMemoryMapWindows.test b/lldb/test/Shell/Expr/TestIRMemoryMapWindows.test
index ae29492c9ccc9..66f0bce304730 100644
--- a/lldb/test/Shell/Expr/TestIRMemoryMapWindows.test
+++ b/lldb/test/Shell/Expr/TestIRMemoryMapWindows.test
@@ -1,4 +1,4 @@
-# REQUIRES: system-windows
+# REQUIRES: target-windows
 
 # RUN: %clang_cl_host /Zi /GS- %p/Inputs/call-function.cpp /c /o %t.obj
 # RUN: %msvc_link /debug:full %t.obj /out:%t
diff --git a/lldb/test/Shell/Process/Windows/exception_access_violation.cpp b/lldb/test/Shell/Process/Windows/exception_access_violation.cpp
index 4835b498ee4df..93898a1991bc6 100644
--- a/lldb/test/Shell/Process/Windows/exception_access_violation.cpp
+++ b/lldb/test/Shell/Process/Windows/exception_access_violation.cpp
@@ -1,6 +1,6 @@
 // clang-format off
 
-// REQUIRES: system-windows
+// REQUIRES: target-windows
 // RUN: %build --compiler=clang-cl -o %t.exe -- %s
 // RUN: env LLDB_USE_NATIVE_PDB_READER=1 %lldb -f %t.exe -o "run" -- write | FileCheck --check-prefix=WRITE %s
 // RUN: env LLDB_USE_NATIVE_PDB_READER=1 %lldb -f %t.exe -o "run" -- read | FileCheck --check-prefix=READ %s
diff --git a/lldb/test/Shell/Process/Windows/process_load.cpp b/lldb/test/Shell/Process/Windows/process_load.cpp
index 43bf45865f9ba..de3b4afc77f87 100644
--- a/lldb/test/Shell/Process/Windows/process_load.cpp
+++ b/lldb/test/Shell/Process/Windows/process_load.cpp
@@ -1,6 +1,6 @@
 // clang-format off
 
-// REQUIRES: system-windows
+// REQUIRES: target-windows
 // RUN: %build --compiler=clang-cl -o %t.exe -- %s
 // RUN: env LLDB_USE_NATIVE_PDB_READER=1 %lldb -f %t.exe -o "b main" -o "process launch" -o "process load kernel32.dll" | FileCheck %s
 
diff --git a/lldb/test/Shell/SwiftREPL/lit.local.cfg b/lldb/test/Shell/SwiftREPL/lit.local.cfg
index 29d485ea63774..539418112b925 100644
--- a/lldb/test/Shell/SwiftREPL/lit.local.cfg
+++ b/lldb/test/Shell/SwiftREPL/lit.local.cfg
@@ -2,3 +2,14 @@ config.suffixes = ['.test']
 
 if 'lldb-repro' in config.available_features:
   config.unsupported = True
+
+def check_exists(path):
+  import os
+  if not os.path.isfile(path):
+    lit_config.warning(f"Runtime dependency not found: {path}")
+
+# Check runtime dependencies for SwiftREPL tests on Windows
+if sys.platform == "win32":
+  host_arch = config.host_triple.split("-")[0]
+  check_exists(f"{config.swift_libs_dir}/windows/{host_arch}/swiftrt.obj")
+  check_exists(f"{config.llvm_shlib_dir}/swiftCore.dll")
diff --git a/lldb/test/Shell/SymbolFile/DWARF/packed.cpp b/lldb/test/Shell/SymbolFile/DWARF/packed.cpp
index 56a4308ff7c5e..6a794a012a6e5 100644
--- a/lldb/test/Shell/SymbolFile/DWARF/packed.cpp
+++ b/lldb/test/Shell/SymbolFile/DWARF/packed.cpp
@@ -1,4 +1,4 @@
-// XFAIL: system-windows
+// XFAIL: target-windows
 // RUN: %clangxx_host -gdwarf -o %t %s
 // RUN: %lldb %t \
 // RUN:   -o "expr alignof(packed)" \
diff --git a/lldb/test/Shell/SymbolFile/NativePDB/local-variables.cpp b/lldb/test/Shell/SymbolFile/NativePDB/local-variables.cpp
index 9aa25adf6bcc7..df6ad8c306597 100644
--- a/lldb/test/Shell/SymbolFile/NativePDB/local-variables.cpp
+++ b/lldb/test/Shell/SymbolFile/NativePDB/local-variables.cpp
@@ -1,6 +1,6 @@
 // clang-format off
 
-// REQUIRES: system-windows
+// REQUIRES: target-windows
 // RUN: %build -o %t.exe -- %s
 // RUN: env LLDB_USE_NATIVE_PDB_READER=1 %lldb -f %t.exe -s \
 // RUN:     %p/Inputs/local-variables.lldbinit 2>&1 | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/NativePDB/stack_unwinding01.cpp b/lldb/test/Shell/SymbolFile/NativePDB/stack_unwinding01.cpp
index e96e3ed6a0107..d1b9c6dba3ca3 100644
--- a/lldb/test/Shell/SymbolFile/NativePDB/stack_unwinding01.cpp
+++ b/lldb/test/Shell/SymbolFile/NativePDB/stack_unwinding01.cpp
@@ -1,5 +1,5 @@
 // clang-format off
-// REQUIRES: lld, system-windows
+// REQUIRES: lld, target-windows
 
 // RUN: %build --compiler=clang-cl --nodefaultlib -o %t.exe -- %s
 // RUN: env LLDB_USE_NATIVE_PDB_READER=1 %lldb -f %t.exe -s \
diff --git a/lldb/test/Shell/SymbolFile/PDB/calling-conventions-arm.test b/lldb/test/Shell/SymbolFile/PDB/calling-conventions-arm.test
index 07dc89d460293..7dabf9157d47e 100644
--- a/lldb/test/Shell/SymbolFile/PDB/calling-conventions-arm.test
+++ b/lldb/test/Shell/SymbolFile/PDB/calling-conventions-arm.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, lld, (target-arm || target-aarch64) 
+REQUIRES: target-windows, lld, (target-arm || target-aarch64)
 RUN: %build --compiler=clang-cl --arch=32 --nodefaultlib --output=%t.exe %S/Inputs/CallingConventionsTest.cpp
 RUN: %build --compiler=clang-cl --arch=64 --nodefaultlib --output=%t.exe %S/Inputs/CallingConventionsTest.cpp
 RUN: lldb-test symbols -dump-ast %t.exe | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/class-layout.test b/lldb/test/Shell/SymbolFile/PDB/class-layout.test
index c99a180f4f632..efd52b8876ce0 100644
--- a/lldb/test/Shell/SymbolFile/PDB/class-layout.test
+++ b/lldb/test/Shell/SymbolFile/PDB/class-layout.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, msvc
+REQUIRES: target-windows, msvc
 RUN: %build --compiler=clang-cl --mode=compile --arch=32 --nodefaultlib --output=%T/ClassLayoutTest.cpp.obj %S/Inputs/ClassLayoutTest.cpp
 RUN: %build --compiler=msvc --mode=link --arch=32 --nodefaultlib --output=%T/ClassLayoutTest.cpp.exe %T/ClassLayoutTest.cpp.obj
 RUN: lldb-test symbols %T/ClassLayoutTest.cpp.exe | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/compilands.test b/lldb/test/Shell/SymbolFile/PDB/compilands.test
index ecee5eb50d399..1847d8d88b266 100644
--- a/lldb/test/Shell/SymbolFile/PDB/compilands.test
+++ b/lldb/test/Shell/SymbolFile/PDB/compilands.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, msvc
+REQUIRES: target-windows, msvc
 RUN: %build --compiler=clang-cl --mode=compile --arch=32 --nodefaultlib --output=%T/CompilandsTest.cpp.obj %S/Inputs/CompilandsTest.cpp
 RUN: %build --compiler=msvc --mode=link --arch=32 --nodefaultlib --output=%T/CompilandsTest.cpp.exe %T/CompilandsTest.cpp.obj
 RUN: env LLDB_USE_NATIVE_PDB_READER=1 lldb-test symbols %T/CompilandsTest.cpp.exe | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/expressions.test b/lldb/test/Shell/SymbolFile/PDB/expressions.test
index 89d7c94e7aa06..1932be74ca878 100644
--- a/lldb/test/Shell/SymbolFile/PDB/expressions.test
+++ b/lldb/test/Shell/SymbolFile/PDB/expressions.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, msvc
+REQUIRES: target-windows, msvc
 RUN: %build --compiler=msvc --nodefaultlib --output=%t.exe %S/Inputs/ExpressionsTest.cpp
 RUN: not %lldb -b -s %S/Inputs/ExpressionsTest0.script -s %S/Inputs/ExpressionsTest1.script -s %S/Inputs/ExpressionsTest2.script -- %t.exe 2>&1 | FileCheck %s
 
diff --git a/lldb/test/Shell/SymbolFile/PDB/func-symbols.test b/lldb/test/Shell/SymbolFile/PDB/func-symbols.test
index 5990952938e67..95e0dd5eb078e 100644
--- a/lldb/test/Shell/SymbolFile/PDB/func-symbols.test
+++ b/lldb/test/Shell/SymbolFile/PDB/func-symbols.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, lld
+REQUIRES: target-windows, lld
 RUN: %build --compiler=clang-cl --arch=32 --nodefaultlib --output=%T/FuncSymbolsTest.exe %S/Inputs/FuncSymbolsTestMain.cpp %S/Inputs/FuncSymbols.cpp
 RUN: lldb-test symbols %T/FuncSymbolsTest.exe | FileCheck --check-prefix=CHECK-ONE %s
 RUN: lldb-test symbols %T/FuncSymbolsTest.exe | FileCheck --check-prefix=CHECK-TWO %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/function-level-linking.test b/lldb/test/Shell/SymbolFile/PDB/function-level-linking.test
index ec0ef57440070..56343cdbd75bd 100644
--- a/lldb/test/Shell/SymbolFile/PDB/function-level-linking.test
+++ b/lldb/test/Shell/SymbolFile/PDB/function-level-linking.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, lld
+REQUIRES: target-windows, lld
 RUN: %clang_cl_host /c /Zi /Gy %S/Inputs/FunctionLevelLinkingTest.cpp /o %t.obj
 RUN: lld-link /debug:full /nodefaultlib /entry:main /order:@%S/Inputs/FunctionLevelLinkingTest.ord %t.obj /out:%t.exe
 RUN: env LLDB_USE_NATIVE_PDB_READER=1 lldb-test symbols -verify %t.exe
diff --git a/lldb/test/Shell/SymbolFile/PDB/pointers.test b/lldb/test/Shell/SymbolFile/PDB/pointers.test
index a3e6f557fed6f..355b5fa16839a 100644
--- a/lldb/test/Shell/SymbolFile/PDB/pointers.test
+++ b/lldb/test/Shell/SymbolFile/PDB/pointers.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, msvc
+REQUIRES: target-windows, msvc
 RUN: %build --compiler=clang-cl --mode=compile --arch=32 --nodefaultlib --output=%T/PointerTypeTest.cpp.obj %S/Inputs/PointerTypeTest.cpp
 RUN: %build --compiler=msvc --mode=link --arch=32 --nodefaultlib --output=%T/PointerTypeTest.cpp.exe %T/PointerTypeTest.cpp.obj
 RUN: lldb-test symbols %T/PointerTypeTest.cpp.exe | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/type-quals.test b/lldb/test/Shell/SymbolFile/PDB/type-quals.test
index cf65c79223b23..982bb70f3c6c5 100644
--- a/lldb/test/Shell/SymbolFile/PDB/type-quals.test
+++ b/lldb/test/Shell/SymbolFile/PDB/type-quals.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, msvc
+REQUIRES: target-windows, msvc
 RUN: %build --compiler=clang-cl --mode=compile --arch=32 --nodefaultlib --output=%T/TypeQualsTest.cpp.obj %S/Inputs/TypeQualsTest.cpp
 RUN: %build --compiler=msvc --mode=link --arch=32 --nodefaultlib --output=%T/TypeQualsTest.cpp.exe %T/TypeQualsTest.cpp.obj
 RUN: lldb-test symbols %T/TypeQualsTest.cpp.exe | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/udt-layout.test b/lldb/test/Shell/SymbolFile/PDB/udt-layout.test
index 84414cbf8440d..bc68539e25ec1 100644
--- a/lldb/test/Shell/SymbolFile/PDB/udt-layout.test
+++ b/lldb/test/Shell/SymbolFile/PDB/udt-layout.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, lld
+REQUIRES: target-windows, lld
 RUN: %build --compiler=clang-cl --output=%t.exe %S/Inputs/UdtLayoutTest.cpp
 RUN: %lldb -b -s %S/Inputs/UdtLayoutTest.script -- %t.exe | FileCheck %s
 
diff --git a/lldb/test/Shell/SymbolFile/PDB/variables-locations.test b/lldb/test/Shell/SymbolFile/PDB/variables-locations.test
index b5bfc6fe81af9..f8ba4f25ca96f 100644
--- a/lldb/test/Shell/SymbolFile/PDB/variables-locations.test
+++ b/lldb/test/Shell/SymbolFile/PDB/variables-locations.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, lld
+REQUIRES: target-windows, lld
 RUN: %build --compiler=clang-cl --output=%t.exe %S/Inputs/VariablesLocationsTest.cpp
 RUN: env LLDB_USE_NATIVE_PDB_READER=0 %lldb -b -s %S/Inputs/VariablesLocationsTest.script -- %t.exe | FileCheck %s
 RUN: env LLDB_USE_NATIVE_PDB_READER=1 %lldb -b -s %S/Inputs/VariablesLocationsTest.script -- %t.exe | FileCheck %s
diff --git a/lldb/test/Shell/SymbolFile/PDB/vbases.test b/lldb/test/Shell/SymbolFile/PDB/vbases.test
index 57239e07c87d6..b58e3edc3cc80 100644
--- a/lldb/test/Shell/SymbolFile/PDB/vbases.test
+++ b/lldb/test/Shell/SymbolFile/PDB/vbases.test
@@ -1,4 +1,4 @@
-REQUIRES: system-windows, lld
+REQUIRES: target-windows, lld
 RUN: %build --compiler=clang-cl --output=%t.exe %S/Inputs/VBases.cpp
 RUN: %lldb -b -s %S/Inputs/VBases.script -- %t.exe | FileCheck %s
 
diff --git a/lldb/test/Shell/Target/dependent-modules-nodupe-windows.test b/lldb/test/Shell/Target/dependent-modules-nodupe-windows.test
index 52e46cd0c9b21..78d7f7469b9f8 100644
--- a/lldb/test/Shell/Target/dependent-modules-nodupe-windows.test
+++ b/lldb/test/Shell/Target/dependent-modules-nodupe-windows.test
@@ -1,4 +1,4 @@
-# REQUIRES: system-windows
+# REQUIRES: target-windows
 
 # Checks that dependent modules preloaded by LLDB are not duplicated when the
 # process actually loads the DLL.
diff --git a/lldb/test/Shell/Unwind/windows-unaligned-x86_64.test b/lldb/test/Shell/Unwind/windows-unaligned-x86_64.test
index 94f1c011ebd2a..0356960424328 100644
--- a/lldb/test/Shell/Unwind/windows-unaligned-x86_64.test
+++ b/lldb/test/Shell/Unwind/windows-unaligned-x86_64.test
@@ -17,7 +17,7 @@ breakpoint set -n func
 # CHECK: Breakpoint 1: where = {{.*}}`{{(::)?}}func
 
 process launch
-# CHECK: stop reason = breakpoint 1.1
+# CHECK: stop reason = breakpoint 1
 
 thread backtrace
 # CHECK: frame #0: {{.*}}`{{(::)?}}func
diff --git a/lldb/test/Shell/helper/toolchain.py b/lldb/test/Shell/helper/toolchain.py
index d9702f21641b6..66f7d33e7de9e 100644
--- a/lldb/test/Shell/helper/toolchain.py
+++ b/lldb/test/Shell/helper/toolchain.py
@@ -149,7 +149,16 @@ def use_support_substitutions(config):
             sdk_path = lit.util.to_string(out)
             llvm_config.lit_config.note("using SDKROOT: %r" % sdk_path)
             host_flags += ["-isysroot", sdk_path]
-    elif sys.platform != "win32":
+    elif sys.platform == "win32":
+        # Required in SwiftREPL tests
+        sdk_path = os.environ.get("SDKROOT")
+        if sdk_path:
+            llvm_config.lit_config.note(f"using SDKROOT: {sdk_path}")
+            llvm_config.with_environment("SDKROOT", sdk_path)
+        else:
+            llvm_config.lit_config.warning(
+                "mandatory environment variable not found: SDKROOT")
+    else:
         host_flags += ["-pthread"]
 
     config.target_shared_library_suffix = (
diff --git a/lldb/test/Shell/lit.cfg.py b/lldb/test/Shell/lit.cfg.py
index 223612ba205b4..860a755dff100 100644
--- a/lldb/test/Shell/lit.cfg.py
+++ b/lldb/test/Shell/lit.cfg.py
@@ -87,6 +87,9 @@
 if re.match(r"^arm(hf.*-linux)|(.*-linux-gnuabihf)", config.target_triple):
     config.available_features.add("armhf-linux")
 
+if re.match(r".*-(windows|mingw32)", config.target_triple):
+    config.available_features.add("target-windows")
+
 if re.match(r".*-(windows-msvc)$", config.target_triple):
     config.available_features.add("windows-msvc")
 
diff --git a/lldb/test/Shell/lit.site.cfg.py.in b/lldb/test/Shell/lit.site.cfg.py.in
index 5e4e2676219f3..d0b8a6be6f9cd 100644
--- a/lldb/test/Shell/lit.site.cfg.py.in
+++ b/lldb/test/Shell/lit.site.cfg.py.in
@@ -17,6 +17,7 @@ config.cmake_sysroot = lit_config.substitute("@CMAKE_SYSROOT@")
 config.target_triple = "@LLVM_TARGET_TRIPLE@"
 config.python_executable = "@Python3_EXECUTABLE@"
 config.swiftc = "@LLDB_SWIFTC@"
+config.swift_libs_dir = '@LLDB_SWIFT_LIBS@'
 config.lldb_enable_swift = @LLDB_ENABLE_SWIFT_SUPPORT@
 config.have_zlib = @LLVM_ENABLE_ZLIB@
 config.objc_gnustep_dir = "@LLDB_TEST_OBJC_GNUSTEP_DIR@"