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/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@"