diff --git a/lldb/source/Plugins/ObjectFile/PDB/ObjectFilePDB.cpp b/lldb/source/Plugins/ObjectFile/PDB/ObjectFilePDB.cpp
--- a/lldb/source/Plugins/ObjectFile/PDB/ObjectFilePDB.cpp
+++ b/lldb/source/Plugins/ObjectFile/PDB/ObjectFilePDB.cpp
@@ -19,6 +19,7 @@
 #include "llvm/DebugInfo/PDB/Native/PDBFile.h"
 #include "llvm/DebugInfo/PDB/PDB.h"
 #include "llvm/Support/BinaryByteStream.h"
+#include "llvm/Support/Host.h"
 
 using namespace lldb;
 using namespace lldb_private;
@@ -128,24 +129,38 @@
   lldb_private::UUID &uuid = module_spec.GetUUID();
   uuid = GetPDBUUID(*info_stream);
 
+  static llvm::Triple::EnvironmentType default_env = [] {
+    auto def_target = llvm::Triple(
+        llvm::Triple::normalize(llvm::sys::getDefaultTargetTriple()));
+    if (def_target.getOS() == llvm::Triple::Win32 &&
+        def_target.getEnvironment() != llvm::Triple::UnknownEnvironment)
+      return def_target.getEnvironment();
+    return llvm::Triple::MSVC;
+  }();
+
   ArchSpec &module_arch = module_spec.GetArchitecture();
   switch (dbi_stream->getMachineType()) {
   case PDB_Machine::Amd64:
     module_arch.SetTriple("x86_64-pc-windows");
+    module_arch.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   case PDB_Machine::x86:
     module_arch.SetTriple("i386-pc-windows");
+    module_arch.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     module_arch.SetTriple("i686-pc-windows");
+    module_arch.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   case PDB_Machine::ArmNT:
     module_arch.SetTriple("armv7-pc-windows");
+    module_arch.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   case PDB_Machine::Arm64:
     module_arch.SetTriple("aarch64-pc-windows");
+    module_arch.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   default:
diff --git a/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp b/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp
--- a/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp
+++ b/lldb/source/Plugins/ObjectFile/PECOFF/ObjectFilePECOFF.cpp
@@ -32,6 +32,7 @@
 
 #include "llvm/Object/COFFImportFile.h"
 #include "llvm/Support/Error.h"
+#include "llvm/Support/Host.h"
 #include "llvm/Support/MemoryBuffer.h"
 
 #define IMAGE_DOS_SIGNATURE 0x5A4D    // MZ
@@ -155,23 +156,37 @@
   if (!uuid.IsValid())
     uuid = GetCoffUUID(*COFFObj);
 
+  static llvm::Triple::EnvironmentType default_env = [] {
+    auto def_target = llvm::Triple(
+        llvm::Triple::normalize(llvm::sys::getDefaultTargetTriple()));
+    if (def_target.getOS() == llvm::Triple::Win32 &&
+        def_target.getEnvironment() != llvm::Triple::UnknownEnvironment)
+      return def_target.getEnvironment();
+    return llvm::Triple::MSVC;
+  }();
+
   switch (COFFObj->getMachine()) {
   case MachineAmd64:
     spec.SetTriple("x86_64-pc-windows");
+    spec.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   case MachineX86:
     spec.SetTriple("i386-pc-windows");
+    spec.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     spec.SetTriple("i686-pc-windows");
+    spec.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   case MachineArmNt:
     spec.SetTriple("armv7-pc-windows");
+    spec.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   case MachineArm64:
     spec.SetTriple("aarch64-pc-windows");
+    spec.GetTriple().setEnvironment(default_env);
     specs.Append(module_spec);
     break;
   default:
diff --git a/lldb/test/Shell/ObjectFile/PDB/object.test b/lldb/test/Shell/ObjectFile/PDB/object.test
--- a/lldb/test/Shell/ObjectFile/PDB/object.test
+++ b/lldb/test/Shell/ObjectFile/PDB/object.test
@@ -1,3 +1,5 @@
+# XFAIL: windows-gnu
+
 # RUN: llvm-pdbutil yaml2pdb %s -pdb=%t.pdb
 # RUN: lldb-test object-file %t.pdb | FileCheck %s
 
diff --git a/lldb/test/Shell/ObjectFile/PECOFF/default-triple-windows-gnu.yaml b/lldb/test/Shell/ObjectFile/PECOFF/default-triple-windows-gnu.yaml
new file mode 100644
--- /dev/null
+++ b/lldb/test/Shell/ObjectFile/PECOFF/default-triple-windows-gnu.yaml
@@ -0,0 +1,41 @@
+# XFAIL: !windows-gnu
+
+# RUN: yaml2obj %s -o %t
+# RUN: lldb-test object-file %t | FileCheck %s
+
+# CHECK: Architecture: x86_64-pc-windows-gnu
+
+--- !COFF
+OptionalHeader:
+  AddressOfEntryPoint: 5152
+  ImageBase:       5368709120
+  SectionAlignment: 4096
+  FileAlignment:   512
+  MajorOperatingSystemVersion: 6
+  MinorOperatingSystemVersion: 0
+  MajorImageVersion: 0
+  MinorImageVersion: 0
+  MajorSubsystemVersion: 6
+  MinorSubsystemVersion: 0
+  Subsystem:       IMAGE_SUBSYSTEM_WINDOWS_CUI
+  DLLCharacteristics: [ IMAGE_DLL_CHARACTERISTICS_HIGH_ENTROPY_VA, IMAGE_DLL_CHARACTERISTICS_DYNAMIC_BASE, IMAGE_DLL_CHARACTERISTICS_NX_COMPAT, IMAGE_DLL_CHARACTERISTICS_TERMINAL_SERVER_AWARE ]
+  SizeOfStackReserve: 1048576
+  SizeOfStackCommit: 4096
+  SizeOfHeapReserve: 1048576
+  SizeOfHeapCommit: 4096
+header:
+  Machine:         IMAGE_FILE_MACHINE_AMD64
+  Characteristics: [ IMAGE_FILE_EXECUTABLE_IMAGE, IMAGE_FILE_LARGE_ADDRESS_AWARE ]
+sections:
+  - Name:            .text
+    Characteristics: [ IMAGE_SCN_CNT_CODE, IMAGE_SCN_MEM_EXECUTE, IMAGE_SCN_MEM_READ ]
+    VirtualAddress:  4096
+    VirtualSize:     64
+    SectionData:     DEADBEEFBAADF00D
+  - Name:            .data
+    Characteristics: [ IMAGE_SCN_CNT_INITIALIZED_DATA, IMAGE_SCN_MEM_READ ]
+    VirtualAddress:  8192
+    VirtualSize:     64
+    SectionData:     DEADBEEFBAADF00D
+symbols:         []
+...
diff --git a/lldb/test/Shell/ObjectFile/PECOFF/default-triple-windows-msvc.yaml b/lldb/test/Shell/ObjectFile/PECOFF/default-triple-windows-msvc.yaml
new file mode 100644
--- /dev/null
+++ b/lldb/test/Shell/ObjectFile/PECOFF/default-triple-windows-msvc.yaml
@@ -0,0 +1,41 @@
+# XFAIL: windows-gnu
+
+# RUN: yaml2obj %s -o %t
+# RUN: lldb-test object-file %t | FileCheck %s
+
+# CHECK: Architecture: x86_64-pc-windows-msvc
+
+--- !COFF
+OptionalHeader:
+  AddressOfEntryPoint: 5152
+  ImageBase:       5368709120
+  SectionAlignment: 4096
+  FileAlignment:   512
+  MajorOperatingSystemVersion: 6
+  MinorOperatingSystemVersion: 0
+  MajorImageVersion: 0
+  MinorImageVersion: 0
+  MajorSubsystemVersion: 6
+  MinorSubsystemVersion: 0
+  Subsystem:       IMAGE_SUBSYSTEM_WINDOWS_CUI
+  DLLCharacteristics: [ IMAGE_DLL_CHARACTERISTICS_HIGH_ENTROPY_VA, IMAGE_DLL_CHARACTERISTICS_DYNAMIC_BASE, IMAGE_DLL_CHARACTERISTICS_NX_COMPAT, IMAGE_DLL_CHARACTERISTICS_TERMINAL_SERVER_AWARE ]
+  SizeOfStackReserve: 1048576
+  SizeOfStackCommit: 4096
+  SizeOfHeapReserve: 1048576
+  SizeOfHeapCommit: 4096
+header:
+  Machine:         IMAGE_FILE_MACHINE_AMD64
+  Characteristics: [ IMAGE_FILE_EXECUTABLE_IMAGE, IMAGE_FILE_LARGE_ADDRESS_AWARE ]
+sections:
+  - Name:            .text
+    Characteristics: [ IMAGE_SCN_CNT_CODE, IMAGE_SCN_MEM_EXECUTE, IMAGE_SCN_MEM_READ ]
+    VirtualAddress:  4096
+    VirtualSize:     64
+    SectionData:     DEADBEEFBAADF00D
+  - Name:            .data
+    Characteristics: [ IMAGE_SCN_CNT_INITIALIZED_DATA, IMAGE_SCN_MEM_READ ]
+    VirtualAddress:  8192
+    VirtualSize:     64
+    SectionData:     DEADBEEFBAADF00D
+symbols:         []
+...
diff --git a/lldb/test/Shell/lit.cfg.py b/lldb/test/Shell/lit.cfg.py
--- a/lldb/test/Shell/lit.cfg.py
+++ b/lldb/test/Shell/lit.cfg.py
@@ -62,6 +62,12 @@
 if re.match(r'^arm(hf.*-linux)|(.*-linux-gnuabihf)', config.target_triple):
     config.available_features.add("armhf-linux")
 
+if re.match(r'.*-(windows-msvc)$', config.target_triple):
+    config.available_features.add("windows-msvc")
+
+if re.match(r'.*-(windows-gnu|mingw32)$', config.target_triple):
+    config.available_features.add("windows-gnu")
+
 def calculate_arch_features(arch_string):
     # This will add a feature such as x86, arm, mips, etc for each built
     # target