diff --git a/lldb/include/lldb/Core/Communication.h b/lldb/include/lldb/Core/Communication.h
--- a/lldb/include/lldb/Core/Communication.h
+++ b/lldb/include/lldb/Core/Communication.h
@@ -209,6 +209,22 @@
   size_t Write(const void *src, size_t src_len, lldb::ConnectionStatus &status,
                Status *error_ptr);
 
+  /// Repeatedly attempt writing until either \a src_len bytes are written
+  /// or a permanent failure occurs.
+  ///
+  /// \param[in] src
+  ///     A source buffer that must be at least \a src_len bytes
+  ///     long.
+  ///
+  /// \param[in] src_len
+  ///     The number of bytes to attempt to write, and also the
+  ///     number of bytes are currently available in \a src.
+  ///
+  /// \return
+  ///     The number of bytes actually Written.
+  size_t WriteAll(const void *src, size_t src_len,
+                  lldb::ConnectionStatus &status, Status *error_ptr);
+
   /// Sets the connection that it to be used by this class.
   ///
   /// By making a communication class that uses different connections it
diff --git a/lldb/source/Core/Communication.cpp b/lldb/source/Core/Communication.cpp
--- a/lldb/source/Core/Communication.cpp
+++ b/lldb/source/Core/Communication.cpp
@@ -189,6 +189,16 @@
   return 0;
 }
 
+size_t Communication::WriteAll(const void *src, size_t src_len,
+                               ConnectionStatus &status, Status *error_ptr) {
+  size_t total_written = 0;
+  do
+    total_written += Write(static_cast<const char *>(src) + total_written,
+                           src_len - total_written, status, error_ptr);
+  while (status == eConnectionStatusSuccess && total_written < src_len);
+  return total_written;
+}
+
 bool Communication::StartReadThread(Status *error_ptr) {
   if (error_ptr)
     error_ptr->Clear();
diff --git a/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunication.cpp b/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunication.cpp
--- a/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunication.cpp
+++ b/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunication.cpp
@@ -101,7 +101,7 @@
   Log *log(ProcessGDBRemoteLog::GetLogIfAllCategoriesSet(GDBR_LOG_PACKETS));
   ConnectionStatus status = eConnectionStatusSuccess;
   char ch = '+';
-  const size_t bytes_written = Write(&ch, 1, status, nullptr);
+  const size_t bytes_written = WriteAll(&ch, 1, status, nullptr);
   LLDB_LOGF(log, "<%4" PRIu64 "> send packet: %c", (uint64_t)bytes_written, ch);
   m_history.AddPacket(ch, GDBRemotePacket::ePacketTypeSend, bytes_written);
   return bytes_written;
@@ -111,7 +111,7 @@
   Log *log(ProcessGDBRemoteLog::GetLogIfAllCategoriesSet(GDBR_LOG_PACKETS));
   ConnectionStatus status = eConnectionStatusSuccess;
   char ch = '-';
-  const size_t bytes_written = Write(&ch, 1, status, nullptr);
+  const size_t bytes_written = WriteAll(&ch, 1, status, nullptr);
   LLDB_LOGF(log, "<%4" PRIu64 "> send packet: %c", (uint64_t)bytes_written, ch);
   m_history.AddPacket(ch, GDBRemotePacket::ePacketTypeSend, bytes_written);
   return bytes_written;
@@ -137,7 +137,7 @@
     ConnectionStatus status = eConnectionStatusSuccess;
     const char *packet_data = packet.data();
     const size_t packet_length = packet.size();
-    size_t bytes_written = Write(packet_data, packet_length, status, nullptr);
+    size_t bytes_written = WriteAll(packet_data, packet_length, status, nullptr);
     if (log) {
       size_t binary_start_offset = 0;
       if (strncmp(packet_data, "$vFile:pwrite:", strlen("$vFile:pwrite:")) ==
diff --git a/lldb/unittests/Core/CommunicationTest.cpp b/lldb/unittests/Core/CommunicationTest.cpp
--- a/lldb/unittests/Core/CommunicationTest.cpp
+++ b/lldb/unittests/Core/CommunicationTest.cpp
@@ -7,11 +7,18 @@
 //===----------------------------------------------------------------------===//
 
 #include "lldb/Core/Communication.h"
+#include "lldb/Host/Config.h"
 #include "lldb/Host/ConnectionFileDescriptor.h"
 #include "lldb/Host/Pipe.h"
 #include "llvm/Testing/Support/Error.h"
 #include "gtest/gtest.h"
 
+#include <thread>
+
+#if LLDB_ENABLE_POSIX
+#include <fcntl.h>
+#endif
+
 using namespace lldb_private;
 
 #ifndef _WIN32
@@ -35,3 +42,48 @@
   ASSERT_TRUE(comm.StopReadThread());
 }
 #endif
+
+#if LLDB_ENABLE_POSIX
+TEST(CommunicationTest, WriteAll) {
+  Pipe pipe;
+  ASSERT_THAT_ERROR(pipe.CreateNew(/*child_process_inherit=*/false).ToError(),
+                    llvm::Succeeded());
+
+  // Make the write end non-blocking in order to easily reproduce a partial
+  // write.
+  int write_fd = pipe.ReleaseWriteFileDescriptor();
+  int flags = fcntl(write_fd, F_GETFL);
+  ASSERT_NE(flags, -1);
+  ASSERT_NE(fcntl(write_fd, F_SETFL, flags | O_NONBLOCK), -1);
+
+  ConnectionFileDescriptor read_conn{pipe.ReleaseReadFileDescriptor(),
+                                     /*owns_fd=*/true};
+  Communication write_comm("test");
+  write_comm.SetConnection(
+      std::make_unique<ConnectionFileDescriptor>(write_fd, /*owns_fd=*/true));
+
+  std::thread read_thread{[&read_conn]() {
+    // Read using a smaller buffer to increase chances of partial write.
+    char buf[128 * 1024];
+    lldb::ConnectionStatus conn_status;
+
+    do {
+      read_conn.Read(buf, sizeof(buf), std::chrono::seconds(1), conn_status,
+                     nullptr);
+    } while (conn_status != lldb::eConnectionStatusEndOfFile);
+  }};
+
+  // Write 1 MiB of data into the pipe.
+  lldb::ConnectionStatus conn_status;
+  Status error;
+  std::vector<char> data(1024 * 1024, 0x80);
+  EXPECT_EQ(write_comm.WriteAll(data.data(), data.size(), conn_status, &error),
+            data.size());
+  EXPECT_EQ(conn_status, lldb::eConnectionStatusSuccess);
+  EXPECT_FALSE(error.Fail());
+
+  // Close the write end in order to trigger EOF.
+  write_comm.Disconnect();
+  read_thread.join();
+}
+#endif