diff --git a/lldb/include/lldb/Host/windows/MainLoopWindows.h b/lldb/include/lldb/Host/windows/MainLoopWindows.h
index 3937a24645d95..53df815255c3d 100644
--- a/lldb/include/lldb/Host/windows/MainLoopWindows.h
+++ b/lldb/include/lldb/Host/windows/MainLoopWindows.h
@@ -31,17 +31,30 @@ class MainLoopWindows : public MainLoopBase {
 
   Status Run() override;
 
+  class IOEvent {
+  public:
+    IOEvent(IOObject::WaitableHandle event) : m_event(event) {}
+    virtual ~IOEvent() {}
+    virtual void WillPoll() {}
+    virtual void DidPoll() {}
+    virtual void Disarm() {}
+    IOObject::WaitableHandle GetHandle() { return m_event; }
+
+  protected:
+    IOObject::WaitableHandle m_event;
+  };
+  using IOEventUP = std::unique_ptr<IOEvent>;
+
 protected:
   void UnregisterReadObject(IOObject::WaitableHandle handle) override;
 
   void Interrupt() override;
 
 private:
-  void ProcessReadObject(IOObject::WaitableHandle handle);
   llvm::Expected<size_t> Poll();
 
   struct FdInfo {
-    void *event;
+    IOEventUP event;
     Callback callback;
   };
   llvm::DenseMap<IOObject::WaitableHandle, FdInfo> m_read_fds;
diff --git a/lldb/include/lldb/Utility/IOObject.h b/lldb/include/lldb/Utility/IOObject.h
index 8cf42992e7be5..de6532a637083 100644
--- a/lldb/include/lldb/Utility/IOObject.h
+++ b/lldb/include/lldb/Utility/IOObject.h
@@ -14,6 +14,7 @@
 #include <sys/types.h>
 
 #include "lldb/lldb-private.h"
+#include "lldb/lldb-types.h"
 
 namespace lldb_private {
 
@@ -24,9 +25,9 @@ class IOObject {
     eFDTypeSocket, // Socket requiring send/recv
   };
 
-  // TODO: On Windows this should be a HANDLE, and wait should use
-  // WaitForMultipleObjects
-  typedef int WaitableHandle;
+  // A handle for integrating with the host event loop model.
+  using WaitableHandle = lldb::file_t;
+
   static const WaitableHandle kInvalidHandleValue;
 
   IOObject(FDType type) : m_fd_type(type) {}
diff --git a/lldb/source/Host/common/File.cpp b/lldb/source/Host/common/File.cpp
index 9aa95ffda44cb..23b6dc9fe850d 100644
--- a/lldb/source/Host/common/File.cpp
+++ b/lldb/source/Host/common/File.cpp
@@ -274,7 +274,11 @@ int NativeFile::GetDescriptor() const {
 }
 
 IOObject::WaitableHandle NativeFile::GetWaitableHandle() {
+#ifdef _WIN32
+  return (HANDLE)_get_osfhandle(GetDescriptor());
+#else
   return GetDescriptor();
+#endif
 }
 
 FILE *NativeFile::GetStream() {
diff --git a/lldb/source/Host/common/JSONTransport.cpp b/lldb/source/Host/common/JSONTransport.cpp
index 1a0851d5c4365..bf269ffa45966 100644
--- a/lldb/source/Host/common/JSONTransport.cpp
+++ b/lldb/source/Host/common/JSONTransport.cpp
@@ -42,7 +42,7 @@ ReadFull(IOObject &descriptor, size_t length,
   if (timeout && timeout_supported) {
     SelectHelper sh;
     sh.SetTimeout(*timeout);
-    sh.FDSetRead(descriptor.GetWaitableHandle());
+    sh.FDSetRead((lldb::socket_t)descriptor.GetWaitableHandle());
     Status status = sh.Select();
     if (status.Fail()) {
       // Convert timeouts into a specific error.
diff --git a/lldb/source/Host/common/Socket.cpp b/lldb/source/Host/common/Socket.cpp
index 802ff9a1b5d1d..3511cde8bb36f 100644
--- a/lldb/source/Host/common/Socket.cpp
+++ b/lldb/source/Host/common/Socket.cpp
@@ -313,8 +313,7 @@ Socket::DecodeHostAndPort(llvm::StringRef host_and_port) {
 }
 
 IOObject::WaitableHandle Socket::GetWaitableHandle() {
-  // TODO: On Windows, use WSAEventSelect
-  return m_socket;
+  return (IOObject::WaitableHandle)m_socket;
 }
 
 Status Socket::Read(void *buf, size_t &num_bytes) {
diff --git a/lldb/source/Host/posix/ConnectionFileDescriptorPosix.cpp b/lldb/source/Host/posix/ConnectionFileDescriptorPosix.cpp
index 16e3f9910eefc..4fda978c092b3 100644
--- a/lldb/source/Host/posix/ConnectionFileDescriptorPosix.cpp
+++ b/lldb/source/Host/posix/ConnectionFileDescriptorPosix.cpp
@@ -276,7 +276,7 @@ size_t ConnectionFileDescriptor::Read(void *dst, size_t dst_len,
               "%p ConnectionFileDescriptor::Read()  fd = %" PRIu64
               ", dst = %p, dst_len = %" PRIu64 ") => %" PRIu64 ", error = %s",
               static_cast<void *>(this),
-              static_cast<uint64_t>(m_io_sp->GetWaitableHandle()),
+              static_cast<file_t>(m_io_sp->GetWaitableHandle()),
               static_cast<void *>(dst), static_cast<uint64_t>(dst_len),
               static_cast<uint64_t>(bytes_read), error.AsCString());
   }
@@ -380,7 +380,7 @@ size_t ConnectionFileDescriptor::Write(const void *src, size_t src_len,
               "%p ConnectionFileDescriptor::Write(fd = %" PRIu64
               ", src = %p, src_len = %" PRIu64 ") => %" PRIu64 " (error = %s)",
               static_cast<void *>(this),
-              static_cast<uint64_t>(m_io_sp->GetWaitableHandle()),
+              static_cast<file_t>(m_io_sp->GetWaitableHandle()),
               static_cast<const void *>(src), static_cast<uint64_t>(src_len),
               static_cast<uint64_t>(bytes_sent), error.AsCString());
   }
@@ -451,7 +451,8 @@ ConnectionFileDescriptor::BytesAvailable(const Timeout<std::micro> &timeout,
     if (timeout)
       select_helper.SetTimeout(*timeout);
 
-    select_helper.FDSetRead(handle);
+    // FIXME: Migrate to MainLoop.
+    select_helper.FDSetRead((lldb::socket_t)handle);
 #if defined(_WIN32)
     // select() won't accept pipes on Windows.  The entire Windows codepath
     // needs to be converted over to using WaitForMultipleObjects and event
@@ -493,7 +494,7 @@ ConnectionFileDescriptor::BytesAvailable(const Timeout<std::micro> &timeout,
           break; // Lets keep reading to until we timeout
         }
       } else {
-        if (select_helper.FDIsSetRead(handle))
+        if (select_helper.FDIsSetRead((lldb::socket_t)handle))
           return eConnectionStatusSuccess;
 
         if (select_helper.FDIsSetRead(pipe_fd)) {
diff --git a/lldb/source/Host/windows/MainLoopWindows.cpp b/lldb/source/Host/windows/MainLoopWindows.cpp
index f3ab2a710cd01..b4896dced0a48 100644
--- a/lldb/source/Host/windows/MainLoopWindows.cpp
+++ b/lldb/source/Host/windows/MainLoopWindows.cpp
@@ -8,8 +8,11 @@
 
 #include "lldb/Host/windows/MainLoopWindows.h"
 #include "lldb/Host/Config.h"
+#include "lldb/Host/Socket.h"
 #include "lldb/Utility/Status.h"
 #include "llvm/Config/llvm-config.h"
+#include "llvm/Support/Casting.h"
+#include "llvm/Support/WindowsError.h"
 #include <algorithm>
 #include <cassert>
 #include <cerrno>
@@ -31,6 +34,122 @@ static DWORD ToTimeout(std::optional<MainLoopWindows::TimePoint> point) {
   return ceil<milliseconds>(dur).count();
 }
 
+namespace {
+
+class PipeEvent : public MainLoopWindows::IOEvent {
+public:
+  explicit PipeEvent(HANDLE handle)
+      : IOEvent((IOObject::WaitableHandle)CreateEventW(
+            NULL, /*bManualReset=*/FALSE,
+            /*bInitialState=*/FALSE, NULL)),
+        m_handle(handle), m_ready(CreateEventW(NULL, /*bManualReset=*/FALSE,
+                                               /*bInitialState=*/FALSE, NULL)) {
+    assert(m_event && m_ready);
+  }
+
+  ~PipeEvent() override {
+    if (m_monitor_thread.joinable()) {
+      m_stopped = true;
+      SetEvent(m_ready);
+      // Keep trying to cancel ReadFile() until the thread exits.
+      do {
+        CancelIoEx((HANDLE)m_handle, /*lpOverlapped=*/NULL);
+      } while (WaitForSingleObject(m_monitor_thread.native_handle(), 1) ==
+               WAIT_TIMEOUT);
+      m_monitor_thread.join();
+    }
+    CloseHandle((HANDLE)m_event);
+    CloseHandle(m_ready);
+  }
+
+  void WillPoll() override {
+    if (!m_monitor_thread.joinable())
+      m_monitor_thread = std::thread(&PipeEvent::Monitor, this);
+  }
+
+  void Disarm() override { SetEvent(m_ready); }
+
+  /// Monitors the handle performing a zero byte read to determine when data is
+  /// avaiable.
+  void Monitor() {
+    do {
+      char buf[1];
+      DWORD bytes_read = 0;
+      OVERLAPPED ov = {0};
+      // Block on a 0-byte read; this will only resume when data is
+      // available in the pipe. The pipe must be PIPE_WAIT or this thread
+      // will spin.
+      BOOL success =
+          ReadFile(m_handle, buf, /*nNumberOfBytesToRead=*/0, &bytes_read, &ov);
+      DWORD bytes_available = 0;
+      DWORD err = GetLastError();
+      if (!success && err == ERROR_IO_PENDING) {
+        success = GetOverlappedResult(m_handle, &ov, &bytes_read,
+                                      /*bWait=*/TRUE);
+        err = GetLastError();
+      }
+      if (success) {
+        success =
+            PeekNamedPipe(m_handle, NULL, 0, NULL, &bytes_available, NULL);
+        err = GetLastError();
+      }
+      if (success) {
+        if (bytes_available == 0) {
+          // This can happen with a zero-byte write. Try again.
+          continue;
+        }
+      } else if (err == ERROR_NO_DATA) {
+        // The pipe is nonblocking. Try again.
+        Sleep(0);
+        continue;
+      } else if (err == ERROR_OPERATION_ABORTED) {
+        // Read may have been cancelled, try again.
+        continue;
+      }
+
+      SetEvent((HANDLE)m_event);
+
+      // Wait until the current read is consumed before doing the next read.
+      WaitForSingleObject(m_ready, INFINITE);
+    } while (!m_stopped);
+  }
+
+private:
+  HANDLE m_handle;
+  HANDLE m_ready;
+  std::thread m_monitor_thread;
+  std::atomic<bool> m_stopped = false;
+};
+
+class SocketEvent : public MainLoopWindows::IOEvent {
+public:
+  explicit SocketEvent(SOCKET socket)
+      : IOEvent((IOObject::WaitableHandle)WSACreateEvent()), m_socket(socket) {
+    assert(event != WSA_INVALID_EVENT);
+  }
+
+  ~SocketEvent() override { WSACloseEvent((HANDLE)m_event); }
+
+  void WillPoll() {
+    int result = WSAEventSelect(m_socket, (HANDLE)m_event,
+                                FD_READ | FD_ACCEPT | FD_CLOSE);
+    assert(result == 0);
+    UNUSED_IF_ASSERT_DISABLED(result);
+  }
+
+  void DidPoll() {
+    int result = WSAEventSelect(m_socket, WSA_INVALID_EVENT, 0);
+    assert(result == 0);
+    UNUSED_IF_ASSERT_DISABLED(result);
+  }
+
+  void Disarm() override { WSAResetEvent((HANDLE)m_event); }
+
+  SOCKET m_socket;
+};
+
+} // namespace
+
 MainLoopWindows::MainLoopWindows() {
   m_interrupt_event = WSACreateEvent();
   assert(m_interrupt_event != WSA_INVALID_EVENT);
@@ -44,14 +163,11 @@ MainLoopWindows::~MainLoopWindows() {
 }
 
 llvm::Expected<size_t> MainLoopWindows::Poll() {
-  std::vector<WSAEVENT> events;
+  std::vector<HANDLE> events;
   events.reserve(m_read_fds.size() + 1);
-  for (auto &[fd, info] : m_read_fds) {
-    int result = WSAEventSelect(fd, info.event, FD_READ | FD_ACCEPT | FD_CLOSE);
-    assert(result == 0);
-    UNUSED_IF_ASSERT_DISABLED(result);
-
-    events.push_back(info.event);
+  for (auto &[_, fd_info] : m_read_fds) {
+    fd_info.event->WillPoll();
+    events.push_back((HANDLE)fd_info.event->GetHandle());
   }
   events.push_back(m_interrupt_event);
 
@@ -59,11 +175,8 @@ llvm::Expected<size_t> MainLoopWindows::Poll() {
       WSAWaitForMultipleEvents(events.size(), events.data(), FALSE,
                                ToTimeout(GetNextWakeupTime()), FALSE);
 
-  for (auto &fd : m_read_fds) {
-    int result = WSAEventSelect(fd.first, WSA_INVALID_EVENT, 0);
-    assert(result == 0);
-    UNUSED_IF_ASSERT_DISABLED(result);
-  }
+  for (auto &[_, fd_info] : m_read_fds)
+    fd_info.event->DidPoll();
 
   if (result >= WSA_WAIT_EVENT_0 && result < WSA_WAIT_EVENT_0 + events.size())
     return result - WSA_WAIT_EVENT_0;
@@ -83,28 +196,25 @@ MainLoopWindows::RegisterReadObject(const IOObjectSP &object_sp,
     error = Status::FromErrorString("IO object is not valid.");
     return nullptr;
   }
-  if (object_sp->GetFdType() != IOObject::eFDTypeSocket) {
-    error = Status::FromErrorString(
-        "MainLoopWindows: non-socket types unsupported on Windows");
-    return nullptr;
-  }
 
-  WSAEVENT event = WSACreateEvent();
-  if (event == WSA_INVALID_EVENT) {
-    error =
-        Status::FromErrorStringWithFormat("Cannot create monitoring event.");
+  IOObject::WaitableHandle waitable_handle = object_sp->GetWaitableHandle();
+  assert(waitable_handle != IOObject::kInvalidHandleValue);
+
+  if (m_read_fds.find(waitable_handle) != m_read_fds.end()) {
+    error = Status::FromErrorStringWithFormat(
+        "File descriptor %d already monitored.", waitable_handle);
     return nullptr;
   }
 
-  const bool inserted =
-      m_read_fds
-          .try_emplace(object_sp->GetWaitableHandle(), FdInfo{event, callback})
-          .second;
-  if (!inserted) {
-    WSACloseEvent(event);
-    error = Status::FromErrorStringWithFormat(
-        "File descriptor %d already monitored.",
-        object_sp->GetWaitableHandle());
+  if (object_sp->GetFdType() == IOObject::eFDTypeSocket)
+    m_read_fds[waitable_handle] = {
+        std::make_unique<SocketEvent>((SOCKET)waitable_handle), callback};
+  else if (GetFileType(waitable_handle) == FILE_TYPE_PIPE)
+    m_read_fds[waitable_handle] = {
+        std::make_unique<PipeEvent>((HANDLE)waitable_handle), callback};
+  else {
+    error = Status::FromErrorStringWithFormat("Unsupported file type %d",
+                                              GetFileType(waitable_handle));
     return nullptr;
   }
 
@@ -114,18 +224,9 @@ MainLoopWindows::RegisterReadObject(const IOObjectSP &object_sp,
 void MainLoopWindows::UnregisterReadObject(IOObject::WaitableHandle handle) {
   auto it = m_read_fds.find(handle);
   assert(it != m_read_fds.end());
-  BOOL result = WSACloseEvent(it->second.event);
-  assert(result == TRUE);
-  UNUSED_IF_ASSERT_DISABLED(result);
   m_read_fds.erase(it);
 }
 
-void MainLoopWindows::ProcessReadObject(IOObject::WaitableHandle handle) {
-  auto it = m_read_fds.find(handle);
-  if (it != m_read_fds.end())
-    it->second.callback(*this); // Do the work
-}
-
 Status MainLoopWindows::Run() {
   m_terminate_request = false;
 
@@ -138,8 +239,8 @@ Status MainLoopWindows::Run() {
 
     if (*signaled_event < m_read_fds.size()) {
       auto &KV = *std::next(m_read_fds.begin(), *signaled_event);
-      WSAResetEvent(KV.second.event);
-      ProcessReadObject(KV.first);
+      KV.second.event->Disarm();
+      KV.second.callback(*this); // Do the work.
     } else {
       assert(*signaled_event == m_read_fds.size());
       WSAResetEvent(m_interrupt_event);
diff --git a/lldb/source/Utility/IOObject.cpp b/lldb/source/Utility/IOObject.cpp
index 964edce0ce10d..c0c07cc0b68e3 100644
--- a/lldb/source/Utility/IOObject.cpp
+++ b/lldb/source/Utility/IOObject.cpp
@@ -8,7 +8,16 @@
 
 #include "lldb/Utility/IOObject.h"
 
+#ifdef _WIN32
+#include "lldb/Host/windows/windows.h"
+#endif
+
 using namespace lldb_private;
 
+#ifdef _WIN32
+const IOObject::WaitableHandle IOObject::kInvalidHandleValue =
+    INVALID_HANDLE_VALUE;
+#else
 const IOObject::WaitableHandle IOObject::kInvalidHandleValue = -1;
+#endif
 IOObject::~IOObject() = default;
diff --git a/lldb/unittests/Host/FileTest.cpp b/lldb/unittests/Host/FileTest.cpp
index 35c87bb200fad..d973d19430596 100644
--- a/lldb/unittests/Host/FileTest.cpp
+++ b/lldb/unittests/Host/FileTest.cpp
@@ -14,6 +14,10 @@
 #include "llvm/Support/Program.h"
 #include "gtest/gtest.h"
 
+#ifdef _WIN32
+#include "lldb/Host/windows/windows.h"
+#endif
+
 using namespace lldb;
 using namespace lldb_private;
 
@@ -32,7 +36,11 @@ TEST(File, GetWaitableHandleFileno) {
   ASSERT_TRUE(stream);
 
   NativeFile file(stream, true);
-  EXPECT_EQ(file.GetWaitableHandle(), fd);
+#ifdef _WIN32
+  EXPECT_EQ(file.GetWaitableHandle(), (HANDLE)_get_osfhandle(fd));
+#else
+  EXPECT_EQ(file.GetWaitableHandle(), (file_t)fd);
+#endif
 }
 
 TEST(File, GetStreamFromDescriptor) {
@@ -53,5 +61,9 @@ TEST(File, GetStreamFromDescriptor) {
   ASSERT_TRUE(stream != NULL);
 
   EXPECT_EQ(file.GetDescriptor(), fd);
-  EXPECT_EQ(file.GetWaitableHandle(), fd);
+#ifdef _WIN32
+  EXPECT_EQ(file.GetWaitableHandle(), (HANDLE)_get_osfhandle(fd));
+#else
+  EXPECT_EQ(file.GetWaitableHandle(), (file_t)fd);
+#endif
 }
diff --git a/lldb/unittests/Host/MainLoopTest.cpp b/lldb/unittests/Host/MainLoopTest.cpp
index e18489978e90c..502028ae1a343 100644
--- a/lldb/unittests/Host/MainLoopTest.cpp
+++ b/lldb/unittests/Host/MainLoopTest.cpp
@@ -79,7 +79,69 @@ TEST_F(MainLoopTest, ReadObject) {
   ASSERT_EQ(1u, callback_count);
 }
 
-TEST_F(MainLoopTest, NoSpuriousReads) {
+TEST_F(MainLoopTest, ReadPipeObject) {
+  Pipe pipe;
+
+  ASSERT_TRUE(pipe.CreateNew().Success());
+
+  MainLoop loop;
+
+  char X = 'X';
+  size_t len = sizeof(X);
+  ASSERT_THAT_EXPECTED(pipe.Write(&X, len), llvm::HasValue(1));
+
+  Status error;
+  auto handle = loop.RegisterReadObject(
+      std::make_shared<NativeFile>(pipe.GetReadFileDescriptor(),
+                                   File::eOpenOptionReadOnly, false),
+      make_callback(), error);
+  ASSERT_TRUE(error.Success());
+  ASSERT_TRUE(handle);
+  ASSERT_TRUE(loop.Run().Success());
+  ASSERT_EQ(1u, callback_count);
+}
+
+TEST_F(MainLoopTest, NoSpuriousPipeReads) {
+  Pipe pipe;
+
+  ASSERT_TRUE(pipe.CreateNew().Success());
+
+  char X = 'X';
+  size_t len = sizeof(X);
+  ASSERT_THAT_EXPECTED(pipe.Write(&X, len), llvm::Succeeded());
+
+  lldb::IOObjectSP r = std::make_shared<NativeFile>(
+      pipe.GetReadFileDescriptor(), File::eOpenOptionReadOnly, false);
+
+  MainLoop loop;
+
+  Status error;
+  auto handle = loop.RegisterReadObject(
+      r,
+      [&](MainLoopBase &) {
+        if (callback_count == 0) {
+          // Read the byte back the first time we're called. After that, the
+          // pipe is empty, and we should not be called anymore.
+          char X;
+          size_t len = sizeof(X);
+          ASSERT_THAT_ERROR(r->Read(&X, len).ToError(), llvm::Succeeded());
+          EXPECT_EQ(len, sizeof(X));
+          EXPECT_EQ(X, 'X');
+        }
+        ++callback_count;
+      },
+      error);
+  ASSERT_THAT_ERROR(error.ToError(), llvm::Succeeded());
+  // Terminate the loop after one second.
+  loop.AddCallback([](MainLoopBase &loop) { loop.RequestTermination(); },
+                   std::chrono::seconds(1));
+  ASSERT_THAT_ERROR(loop.Run().ToError(), llvm::Succeeded());
+
+  // Make sure the callback was called only once.
+  ASSERT_EQ(1u, callback_count);
+}
+
+TEST_F(MainLoopTest, NoSpuriousSocketReads) {
   // Write one byte into the socket.
   char X = 'X';
   size_t len = sizeof(X);
@@ -99,6 +161,7 @@ TEST_F(MainLoopTest, NoSpuriousReads) {
           EXPECT_THAT_ERROR(socketpair[1]->Read(&X, len).ToError(),
                             llvm::Succeeded());
           EXPECT_EQ(len, sizeof(X));
+          EXPECT_EQ(X, 'X');
         }
         ++callback_count;
       },
@@ -164,9 +227,8 @@ TEST_F(MainLoopTest, PendingCallbackCalledOnlyOnce) {
       [&](MainLoopBase &loop) {
         // Add one pending callback on the first iteration.
         if (callback_count == 0) {
-          loop.AddPendingCallback([&](MainLoopBase &loop) {
-            callback_count++;
-          });
+          loop.AddPendingCallback(
+              [&](MainLoopBase &loop) { callback_count++; });
         }
         // Terminate the loop on second iteration.
         if (callback_count++ >= 1)
@@ -321,7 +383,7 @@ TEST_F(MainLoopTest, UnmonitoredSignal) {
   MainLoop loop;
   Status error;
   struct sigaction sa;
-  sa.sa_sigaction = [](int, siginfo_t *, void *) { };
+  sa.sa_sigaction = [](int, siginfo_t *, void *) {};
   sa.sa_flags = SA_SIGINFO; // important: no SA_RESTART
   sigemptyset(&sa.sa_mask);
   ASSERT_EQ(0, sigaction(SIGUSR2, &sa, nullptr));