diff --git a/lldb/cmake/caches/Apple-lldb-macOS.cmake b/lldb/cmake/caches/Apple-lldb-macOS.cmake
--- a/lldb/cmake/caches/Apple-lldb-macOS.cmake
+++ b/lldb/cmake/caches/Apple-lldb-macOS.cmake
@@ -13,6 +13,9 @@
 # CMAKE_INSTALL_PREFIX. In any case, DESTDIR will be an extra prefix.
 set(LLDB_FRAMEWORK_INSTALL_DIR /Applications/Xcode.app/Contents/SharedFrameworks CACHE STRING "")
 
+# DESTDIR will be an extra prefix
+set(LLDB_DEBUGINFO_INSTALL_PREFIX /debuginfo CACHE STRING "")
+
 # Release builds may change these:
 set(CMAKE_OSX_DEPLOYMENT_TARGET 10.11 CACHE STRING "")
 set(LLDB_USE_SYSTEM_DEBUGSERVER ON CACHE BOOL "")
diff --git a/lldb/cmake/modules/AddLLDB.cmake b/lldb/cmake/modules/AddLLDB.cmake
--- a/lldb/cmake/modules/AddLLDB.cmake
+++ b/lldb/cmake/modules/AddLLDB.cmake
@@ -3,7 +3,7 @@
   # MODULE;SHARED;STATIC library type and source files
   cmake_parse_arguments(PARAM
     "MODULE;SHARED;STATIC;OBJECT;PLUGIN"
-    "ENTITLEMENTS"
+    "INSTALL_PREFIX;ENTITLEMENTS"
     "EXTRA_CXXFLAGS;DEPENDS;LINK_LIBS;LINK_COMPONENTS"
     ${ARGN})
   llvm_process_sources(srcs ${PARAM_UNPARSED_ARGUMENTS})
@@ -58,38 +58,26 @@
       ${pass_ENTITLEMENTS}
       ${pass_NO_INSTALL_RPATH}
     )
+  endif()
 
-    if (NOT LLVM_INSTALL_TOOLCHAIN_ONLY OR ${name} STREQUAL "liblldb")
-      if (PARAM_SHARED)
-        if(${name} STREQUAL "liblldb" AND LLDB_BUILD_FRAMEWORK)
-          if(LLDB_FRAMEWORK_INSTALL_DIR)
-            set(install_dir ${LLDB_FRAMEWORK_INSTALL_DIR})
-          else()
-            set(install_dir ".")
-          endif()
-        else()
-          set(install_dir lib${LLVM_LIBDIR_SUFFIX})
-        endif()
-        install(TARGETS ${name}
-          COMPONENT ${name}
-          RUNTIME DESTINATION bin
-          LIBRARY DESTINATION ${install_dir}
-          ARCHIVE DESTINATION ${install_dir})
-      else()
-        install(TARGETS ${name}
-          COMPONENT ${name}
-          LIBRARY DESTINATION lib${LLVM_LIBDIR_SUFFIX}
-          ARCHIVE DESTINATION lib${LLVM_LIBDIR_SUFFIX})
-      endif()
-      if (NOT CMAKE_CONFIGURATION_TYPES)
-        add_llvm_install_targets(install-${name}
-                                 DEPENDS ${name}
-                                 COMPONENT ${name})
-      endif()
+  if(PARAM_SHARED)
+    set(install_dest lib${LLVM_LIBDIR_SUFFIX})
+    if(PARAM_INSTALL_PREFIX)
+      set(install_dest ${PARAM_INSTALL_PREFIX})
+    endif()
+    # RUNTIME is relevant for DLL platforms, FRAMEWORK for macOS
+    install(TARGETS ${name} COMPONENT ${name}
+      RUNTIME DESTINATION bin
+      LIBRARY DESTINATION ${install_dest}
+      ARCHIVE DESTINATION ${install_dest}
+      FRAMEWORK DESTINATION ${install_dest})
+    if (NOT CMAKE_CONFIGURATION_TYPES)
+      add_llvm_install_targets(install-${name}
+                              DEPENDS ${name}
+                              COMPONENT ${name})
     endif()
   endif()
 
-
   # Hack: only some LLDB libraries depend on the clang autogenerated headers,
   # but it is simple enough to make all of LLDB depend on some of those
   # headers without negatively impacting much of anything.
@@ -110,7 +98,7 @@
 function(add_lldb_executable name)
   cmake_parse_arguments(ARG
     "GENERATE_INSTALL"
-    "ENTITLEMENTS"
+    "INSTALL_PREFIX;ENTITLEMENTS"
     "LINK_LIBS;LINK_COMPONENTS"
     ${ARGN}
     )
@@ -134,16 +122,22 @@
   set_target_properties(${name} PROPERTIES FOLDER "lldb executables")
 
   if(ARG_GENERATE_INSTALL)
-    install(TARGETS ${name}
-            COMPONENT ${name}
-            RUNTIME DESTINATION bin)
+    set(install_dest bin)
+    if(ARG_INSTALL_PREFIX)
+      set(install_dest ${ARG_INSTALL_PREFIX})
+    endif()
+    install(TARGETS ${name} COMPONENT ${name}
+            RUNTIME DESTINATION ${install_dest})
     if (NOT CMAKE_CONFIGURATION_TYPES)
       add_llvm_install_targets(install-${name}
                                DEPENDS ${name}
                                COMPONENT ${name})
     endif()
+    if(APPLE AND ARG_INSTALL_PREFIX)
+      lldb_add_post_install_steps_darwin(${name} ${ARG_INSTALL_PREFIX})
+    endif()
   endif()
-endfunction(add_lldb_executable)
+endfunction()
 
 
 macro(add_lldb_tool_subdirectory name)
@@ -151,7 +145,19 @@
 endmacro()
 
 function(add_lldb_tool name)
-  add_lldb_executable(${name} GENERATE_INSTALL ${ARGN})
+  cmake_parse_arguments(ARG "ADD_TO_FRAMEWORK" "" "" ${ARGN})
+  if(LLDB_BUILD_FRAMEWORK AND ARG_ADD_TO_FRAMEWORK)
+    set(subdir LLDB.framework/Versions/${LLDB_FRAMEWORK_VERSION}/Resources)
+    add_lldb_executable(${name}
+      GENERATE_INSTALL
+      INSTALL_PREFIX ${LLDB_FRAMEWORK_INSTALL_DIR}/${subdir}
+      ${ARG_UNPARSED_ARGUMENTS}
+    )
+    lldb_add_to_buildtree_lldb_framework(${name} ${subdir})
+    return()
+  endif()
+
+  add_lldb_executable(${name} GENERATE_INSTALL ${ARG_UNPARSED_ARGUMENTS})
 endfunction()
 
 # Support appending linker flags to an existing target.
@@ -170,12 +176,7 @@
   set_target_properties(${target_name} PROPERTIES LINK_FLAGS ${new_link_flags})
 endfunction()
 
-# Unified handling for executable LLDB.framework resources. Given the name of an
-# executable target, this function adds a post-build step to copy it to the
-# framework bundle in the build-tree.
-function(lldb_add_to_framework name)
-  set(subdir "LLDB.framework/Versions/${LLDB_FRAMEWORK_VERSION}/Resources")
-
+function(lldb_add_to_buildtree_lldb_framework name subdir)
   # Destination for the copy in the build-tree. While the framework target may
   # not exist yet, it will exist when the generator expression gets expanded.
   set(copy_dest "$<TARGET_FILE_DIR:liblldb>/../../../${subdir}")
@@ -187,6 +188,61 @@
   )
 endfunction()
 
+function(lldb_add_post_install_steps_darwin name install_prefix)
+  if(NOT APPLE)
+    message(WARNING "Darwin-specific functionality; not currently available on non-Apple platforms.")
+    return()
+  endif()
+
+  get_target_property(output_name ${name} OUTPUT_NAME)
+  if(NOT output_name)
+    set(output_name ${name})
+  endif()
+
+  get_target_property(is_framework ${name} FRAMEWORK)
+  if(is_framework)
+    get_target_property(buildtree_dir ${name} LIBRARY_OUTPUT_DIRECTORY)
+    if(buildtree_dir)
+      set(bundle_subdir ${output_name}.framework/Versions/${LLDB_FRAMEWORK_VERSION}/)
+    else()
+      message(SEND_ERROR "Framework target ${name} missing property for output directory. Cannot generate post-install steps.")
+      return()
+    endif()
+  else()
+    get_target_property(target_type ${name} TYPE)
+    if(target_type STREQUAL "EXECUTABLE")
+      set(buildtree_dir ${LLVM_RUNTIME_OUTPUT_INTDIR})
+    else()
+      # Only ever install shared libraries.
+      set(output_name "lib${output_name}.dylib")
+      set(buildtree_dir ${LLVM_LIBRARY_OUTPUT_INTDIR})
+    endif()
+  endif()
+
+  # Generate dSYM in symroot
+  set(dsym_name ${output_name}.dSYM)
+  if(is_framework)
+    set(dsym_name ${output_name}.framework.dSYM)
+  endif()
+  if(LLDB_DEBUGINFO_INSTALL_PREFIX)
+    # This makes the path absolute, so we must respect DESTDIR.
+    set(dsym_name "\$ENV\{DESTDIR\}${LLDB_DEBUGINFO_INSTALL_PREFIX}/${dsym_name}")
+  endif()
+
+  set(buildtree_name ${buildtree_dir}/${bundle_subdir}${output_name})
+  install(CODE "message(STATUS \"Externalize debuginfo: ${dsym_name}\")" COMPONENT ${name})
+  install(CODE "execute_process(COMMAND xcrun dsymutil -o=${dsym_name} ${buildtree_name})"
+          COMPONENT ${name})
+
+  # Strip distribution binary with -ST (removing debug symbol table entries and
+  # Swift symbols). Avoid CMAKE_INSTALL_DO_STRIP and llvm_externalize_debuginfo()
+  # as they can't be configured sufficiently.
+  set(installtree_name "\$ENV\{DESTDIR\}${install_prefix}/${bundle_subdir}${output_name}")
+  install(CODE "message(STATUS \"Stripping: ${installtree_name}\")" COMPONENT ${name})
+  install(CODE "execute_process(COMMAND xcrun strip -ST ${installtree_name})"
+          COMPONENT ${name})
+endfunction()
+
 # CMake's set_target_properties() doesn't allow to pass lists for RPATH
 # properties directly (error: "called with incorrect number of arguments").
 # Instead of defining two list variables each time, use this helper function.
diff --git a/lldb/cmake/modules/LLDBConfig.cmake b/lldb/cmake/modules/LLDBConfig.cmake
--- a/lldb/cmake/modules/LLDBConfig.cmake
+++ b/lldb/cmake/modules/LLDBConfig.cmake
@@ -65,12 +65,9 @@
   set(LLDB_FRAMEWORK_BUILD_DIR bin CACHE STRING "Output directory for LLDB.framework")
   set(LLDB_FRAMEWORK_INSTALL_DIR Library/Frameworks CACHE STRING "Install directory for LLDB.framework")
 
-  # Set designated directory for all dSYMs. Essentially, this emits the
-  # framework's dSYM outside of the framework directory.
-  if(LLVM_EXTERNALIZE_DEBUGINFO)
-    set(LLVM_EXTERNALIZE_DEBUGINFO_OUTPUT_DIR ${CMAKE_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin CACHE STRING
-        "Directory to emit dSYM files stripped from executables and libraries (Darwin Only)")
-  endif()
+  # Essentially, emit the framework's dSYM outside of the framework directory.
+  set(LLDB_DEBUGINFO_INSTALL_PREFIX ${CMAKE_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin CACHE STRING
+      "Directory to emit dSYM files stripped from executables and libraries (Darwin Only)")
 endif()
 
 if (NOT CMAKE_SYSTEM_NAME MATCHES "Windows")
diff --git a/lldb/cmake/modules/LLDBFramework.cmake b/lldb/cmake/modules/LLDBFramework.cmake
--- a/lldb/cmake/modules/LLDBFramework.cmake
+++ b/lldb/cmake/modules/LLDBFramework.cmake
@@ -33,6 +33,8 @@
   LIBRARY_DIR ${framework_target_dir}
 )
 
+lldb_add_post_install_steps_darwin(liblldb ${LLDB_FRAMEWORK_INSTALL_DIR})
+
 # Affects the layout of the framework bundle (default is macOS layout).
 if(IOS)
   set_target_properties(liblldb PROPERTIES
diff --git a/lldb/source/API/CMakeLists.txt b/lldb/source/API/CMakeLists.txt
--- a/lldb/source/API/CMakeLists.txt
+++ b/lldb/source/API/CMakeLists.txt
@@ -9,8 +9,8 @@
   set(lldb_python_wrapper ${lldb_scripts_dir}/LLDBWrapPython.cpp)
 endif()
 
-if(LLDB_BUILD_FRAMEWORK AND LLVM_EXTERNALIZE_DEBUGINFO)
-  set(LLVM_EXTERNALIZE_DEBUGINFO_EXTENSION framework.dSYM)
+if(LLDB_BUILD_FRAMEWORK)
+  set(option_install_prefix INSTALL_PREFIX ${LLDB_FRAMEWORK_INSTALL_DIR})
 endif()
 
 add_lldb_library(liblldb SHARED
@@ -99,7 +99,9 @@
     ${LLDB_ALL_PLUGINS}
   LINK_COMPONENTS
     Support
-  )
+
+  ${option_install_prefix}
+)
 
 if (MSVC)
   set_source_files_properties(SBReproducer.cpp PROPERTIES COMPILE_FLAGS /bigobj)
diff --git a/lldb/tools/argdumper/CMakeLists.txt b/lldb/tools/argdumper/CMakeLists.txt
--- a/lldb/tools/argdumper/CMakeLists.txt
+++ b/lldb/tools/argdumper/CMakeLists.txt
@@ -1,10 +1,6 @@
-add_lldb_tool(lldb-argdumper
+add_lldb_tool(lldb-argdumper ADD_TO_FRAMEWORK
   argdumper.cpp
 
   LINK_LIBS
     lldbUtility
-  )
-
-if(LLDB_BUILD_FRAMEWORK)
-  lldb_add_to_framework(lldb-argdumper)
-endif()
+)
diff --git a/lldb/tools/darwin-debug/CMakeLists.txt b/lldb/tools/darwin-debug/CMakeLists.txt
--- a/lldb/tools/darwin-debug/CMakeLists.txt
+++ b/lldb/tools/darwin-debug/CMakeLists.txt
@@ -1,7 +1,3 @@
-add_lldb_tool(darwin-debug
+add_lldb_tool(darwin-debug ADD_TO_FRAMEWORK
   darwin-debug.cpp
-  )
-
-if(LLDB_BUILD_FRAMEWORK)
-  lldb_add_to_framework(darwin-debug)
-endif()
+)
diff --git a/lldb/tools/debugserver/source/CMakeLists.txt b/lldb/tools/debugserver/source/CMakeLists.txt
--- a/lldb/tools/debugserver/source/CMakeLists.txt
+++ b/lldb/tools/debugserver/source/CMakeLists.txt
@@ -272,22 +272,14 @@
                  COMPILE_DEFINITIONS HAVE_LIBCOMPRESSION)
   endif()
   set(LLVM_OPTIONAL_SOURCES ${lldbDebugserverCommonSources})
-  add_lldb_tool(debugserver
+  add_lldb_tool(debugserver ADD_TO_FRAMEWORK
     debugserver.cpp
-
-    LINK_LIBS
-      lldbDebugserverCommon
-
-    ENTITLEMENTS
-      ${entitlements}
-    )
+    LINK_LIBS lldbDebugserverCommon
+    ENTITLEMENTS ${entitlements}
+  )
 
   set_target_properties(debugserver PROPERTIES FOLDER "lldb libraries/debugserver")
 
-  if(LLDB_BUILD_FRAMEWORK)
-    lldb_add_to_framework(debugserver)
-  endif()
-
   if(IOS)
     set_property(TARGET lldbDebugserverCommon APPEND PROPERTY COMPILE_DEFINITIONS
       WITH_LOCKDOWN