Index: include/lldb/Host/FileSpec.h
===================================================================
--- include/lldb/Host/FileSpec.h
+++ include/lldb/Host/FileSpec.h
@@ -78,6 +78,8 @@
     //------------------------------------------------------------------
     explicit FileSpec (const char *path, bool resolve_path, PathSyntax syntax = ePathSyntaxHostNative);
 
+    explicit FileSpec (const char *path, bool resolve_path, ArchSpec arch);
+
     //------------------------------------------------------------------
     /// Copy constructor
     ///
Index: source/Host/common/FileSpec.cpp
===================================================================
--- source/Host/common/FileSpec.cpp
+++ source/Host/common/FileSpec.cpp
@@ -27,6 +27,7 @@
 #include <pwd.h>
 #endif
 
+#include "lldb/Core/ArchSpec.h"
 #include "lldb/Core/DataBufferHeap.h"
 #include "lldb/Core/DataBufferMemoryMap.h"
 #include "lldb/Core/RegularExpression.h"
@@ -201,6 +202,11 @@
         SetFile(pathname, resolve_path, syntax);
 }
 
+FileSpec::FileSpec(const char *pathname, bool resolve_path, ArchSpec arch) :
+    FileSpec(pathname, resolve_path, arch.GetTriple().isOSWindows() ? ePathSyntaxWindows : ePathSyntaxPosix)
+{
+}
+
 //------------------------------------------------------------------
 // Copy constructor
 //------------------------------------------------------------------
@@ -605,7 +611,7 @@
 void
 FileSpec::Dump(Stream *s) const
 {
-    static ConstString g_slash_only ("/");
+    static ConstString g_slash_only("/");
     if (s)
     {
         m_directory.Dump(s);
@@ -810,10 +816,15 @@
 void
 FileSpec::GetPath(llvm::SmallVectorImpl<char> &path, bool denormalize) const
 {
+    static ConstString g_slash_only("/");
     if (m_directory)
-        path.append(m_directory.GetCString(), m_directory.GetCString() + m_directory.GetLength());
+        path.append(m_directory.GetStringRef().begin(), m_directory.GetStringRef().end());
     if (m_filename)
-        llvm::sys::path::append(path, m_filename.GetCString());
+    {
+        if (m_directory && m_directory != g_slash_only)
+            path.emplace_back('/');
+        path.append(m_filename.GetStringRef().begin(), m_filename.GetStringRef().end());
+    }
     Normalize(path, m_syntax);
     if (denormalize && !path.empty())
         DeNormalize(path, m_syntax);
Index: source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp
===================================================================
--- source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp
+++ source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp
@@ -1312,7 +1312,7 @@
     const char *arg = NULL;
     const Args &launch_args = launch_info.GetArguments();
     if (exe_file)
-        exe_path = exe_file.GetPath(false);
+        exe_path = exe_file.GetPath();
     else
     {
         arg = launch_args.GetArgumentAtIndex(0);
@@ -3744,8 +3744,8 @@
     packet.PutCString("qModuleInfo:");
     packet.PutCStringAsRawHex8(module_path.c_str());
     packet.PutCString(";");
-    const auto& tripple = arch_spec.GetTriple().getTriple();
-    packet.PutBytesAsRawHex8(tripple.c_str(), tripple.size());
+    const auto& triple = arch_spec.GetTriple().getTriple();
+    packet.PutBytesAsRawHex8(triple.c_str(), triple.size());
 
     StringExtractorGDBRemote response;
     if (SendPacketAndWaitForResponse (packet.GetData(), packet.GetSize(), response, false) != PacketResult::Success)
@@ -3795,7 +3795,7 @@
             extractor.GetStringRef ().swap (value);
             extractor.SetFilePos (0);
             extractor.GetHexByteString (value);
-            module_spec.GetFileSpec () = FileSpec (value.c_str(), false);
+            module_spec.GetFileSpec() = FileSpec(value.c_str(), false, arch_spec);
         }
     }
 
Index: source/Target/Target.cpp
===================================================================
--- source/Target/Target.cpp
+++ source/Target/Target.cpp
@@ -2366,8 +2366,9 @@
                                 if (is_main_executable) // TODO: add setting for always installing main executable???
                                 {
                                     // Always install the main executable
+                                    remote_file = FileSpec(module_sp->GetFileSpec().GetFilename().AsCString(),
+                                                           false, module_sp->GetArchitecture());
                                     remote_file.GetDirectory() = platform_sp->GetWorkingDirectory();
-                                    remote_file.GetFilename() = module_sp->GetFileSpec().GetFilename();
                                 }
                             }
                             if (remote_file)