diff --git a/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp b/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp
index 4984445dcbab9..343d7477c66c7 100644
--- a/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp
+++ b/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp
@@ -1036,12 +1036,19 @@ void ObjectFilePECOFF::CreateSections(SectionList &unified_section_list) {
     m_sections_up->AddSection(header_sp);
     unified_section_list.AddSection(header_sp);
 
+    std::vector<llvm::StringRef> truncated_dwarf_sections;
     const uint32_t nsects = m_sect_headers.size();
     for (uint32_t idx = 0; idx < nsects; ++idx) {
       llvm::StringRef sect_name = GetSectionName(m_sect_headers[idx]);
       ConstString const_sect_name(sect_name);
       SectionType section_type = GetSectionType(sect_name, m_sect_headers[idx]);
 
+      // Detect unknown sections matching ^\.debug_[a-z]$
+      if (section_type == eSectionTypeOther && sect_name.size() == 8 &&
+          sect_name.starts_with(".debug_") && llvm::isLower(sect_name.back())) {
+        truncated_dwarf_sections.emplace_back(sect_name);
+      }
+
       SectionSP section_sp(new Section(
           module_sp,       // Module to which this section belongs
           this,            // Object file to which this section belongs
@@ -1071,6 +1078,16 @@ void ObjectFilePECOFF::CreateSections(SectionList &unified_section_list) {
       m_sections_up->AddSection(section_sp);
       unified_section_list.AddSection(section_sp);
     }
+
+    if (!truncated_dwarf_sections.empty()) {
+      module_sp->ReportWarning(
+          "contains {} truncated DWARF sections ({}).\n"
+          "Note: Executable images on Windows can't include the required names "
+          "when linking with the default link.exe. A third party linker like "
+          "lld-link is required (compile with -fuse-ld=lld-link on Clang).",
+          truncated_dwarf_sections.size(),
+          llvm::join(truncated_dwarf_sections, ", "));
+    }
   }
 }
 
diff --git a/lldb/test/Shell/ObjectFile/PECOFF/lit.local.cfg b/lldb/test/Shell/ObjectFile/PECOFF/lit.local.cfg
index 9ef350be1dee2..1ae00d07fc3e6 100644
--- a/lldb/test/Shell/ObjectFile/PECOFF/lit.local.cfg
+++ b/lldb/test/Shell/ObjectFile/PECOFF/lit.local.cfg
@@ -1 +1 @@
-config.suffixes = ['.yaml', '.test']
+config.suffixes = ['.yaml', '.test', '.c']
diff --git a/lldb/test/Shell/ObjectFile/PECOFF/truncated-dwarf.c b/lldb/test/Shell/ObjectFile/PECOFF/truncated-dwarf.c
new file mode 100644
index 0000000000000..92cb61050142a
--- /dev/null
+++ b/lldb/test/Shell/ObjectFile/PECOFF/truncated-dwarf.c
@@ -0,0 +1,7 @@
+// REQUIRES: target-windows
+// RUN: %build --compiler=clang-cl --force-dwarf-symbols --force-ms-link -o %t.exe -- %s
+// RUN: %lldb -f %t.exe 2>&1 | FileCheck %s
+
+int main(void) {}
+
+// CHECK: warning: {{.*}} contains 4 truncated DWARF sections (.debug_{{[a-z]}}, .debug_{{[a-z]}}, .debug_{{[a-z]}}, .debug_{{[a-z]}})
diff --git a/lldb/test/Shell/helper/build.py b/lldb/test/Shell/helper/build.py
index caaa14f90af1c..ecb02c1d7c87f 100755
--- a/lldb/test/Shell/helper/build.py
+++ b/lldb/test/Shell/helper/build.py
@@ -173,6 +173,22 @@
     help="Specify the C/C++ standard.",
 )
 
+if sys.platform == "win32":
+    parser.add_argument(
+        "--force-dwarf-symbols",
+        dest="force_dwarf_symbols",
+        action="store_true",
+        default=False,
+        help="When compiling with clang-cl on Windows, use DWARF instead of CodeView",
+    )
+    parser.add_argument(
+        "--force-ms-link",
+        dest="force_ms_link",
+        action="store_true",
+        default=False,
+        help="When compiling with clang-cl on Windows, always use link.exe",
+    )
+
 
 args = parser.parse_args(args=sys.argv[1:])
 
@@ -379,15 +395,20 @@ def __init__(self, toolchain_type, args):
                     )
 
         if self.mode == "link" or self.mode == "compile-and-link":
-            self.linker = (
-                self._find_linker("link")
-                if toolchain_type == "msvc"
-                else self._find_linker("lld-link", args.tools_dir)
-            )
+            if toolchain_type == "msvc" or args.force_ms_link:
+                search_paths = []
+                if toolchain_type != "msvc":
+                    search_paths.append(
+                        os.path.dirname(find_executable("cl", args.tools_dir))
+                    )
+                self.linker = self._find_linker("link", search_paths)
+            else:
+                self.linker = self._find_linker("lld-link", args.tools_dir)
             if not self.linker:
                 raise ValueError("Unable to find an appropriate linker.")
 
         self.compile_env, self.link_env = self._get_visual_studio_environment()
+        self.force_dwarf_symbols = args.force_dwarf_symbols
 
     def _find_linker(self, name, search_paths=[]):
         compiler_dir = os.path.dirname(self.compiler)
@@ -678,6 +699,8 @@ def _get_compilation_command(self, source, obj):
             args.append("/GR-")
         args.append("/Z7")
         if self.toolchain_type == "clang-cl":
+            if self.force_dwarf_symbols:
+                args.append("-gdwarf")
             args.append("-Xclang")
             args.append("-fkeep-static-consts")
             args.append("-fms-compatibility-version=19")