diff --git a/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.cpp b/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.cpp
--- a/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.cpp
+++ b/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.cpp
@@ -1,12 +1,15 @@
 #include "llvm/ADT/ArrayRef.h"
 #include "llvm/ADT/DenseMap.h"
 #include "llvm/ADT/Optional.h"
+#include "llvm/ADT/PointerIntPair.h"
+#include "llvm/ADT/PointerUnion.h"
 #include "llvm/ADT/SmallString.h"
 #include "llvm/ADT/SmallVector.h"
 #include "llvm/ADT/Twine.h"
 #include "llvm/Support/Error.h"
 
 int Array[] = {1, 2, 3};
+auto IntPtr = reinterpret_cast<int *>(0xabc);
 
 llvm::ArrayRef<int> ArrayRef(Array);
 llvm::MutableArrayRef<int> MutableArrayRef(Array);
@@ -19,7 +22,7 @@
 llvm::SmallString<5> SmallString("foo");
 llvm::StringRef StringRef = "bar";
 llvm::Twine Twine = llvm::Twine(SmallString) + StringRef;
+llvm::PointerIntPair<int *, 1> PointerIntPair(IntPtr, 1);
+llvm::PointerUnion<float *, int *> PointerUnion(IntPtr);
 
-int main() {
-  return 0;
-}
+int main() { return 0; }
diff --git a/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.gdb b/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.gdb
--- a/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.gdb
+++ b/debuginfo-tests/llvm-prettyprinters/gdb/prettyprinters.gdb
@@ -39,3 +39,10 @@
 # CHECK: "\"foo\"\"bar\""
 p Twine
 
+# CHECK: llvm::PointerIntPair<int *> = {pointer = 0xabc, value = 1}
+p PointerIntPair
+
+# CHECK: llvm::PointerUnion containing int * = {pointer = 0xabc}
+p PointerUnion
+
+
diff --git a/llvm/include/llvm/ADT/PointerIntPair.h b/llvm/include/llvm/ADT/PointerIntPair.h
--- a/llvm/include/llvm/ADT/PointerIntPair.h
+++ b/llvm/include/llvm/ADT/PointerIntPair.h
@@ -147,7 +147,7 @@
                 "cannot use a pointer type that has all bits free");
   static_assert(IntBits <= PtrTraits::NumLowBitsAvailable,
                 "PointerIntPair with integer size too large for pointer");
-  enum : uintptr_t {
+  enum MaskAndShiftConstants : uintptr_t {
     /// PointerBitMask - The bits that come from the pointer.
     PointerBitMask =
         ~(uintptr_t)(((intptr_t)1 << PtrTraits::NumLowBitsAvailable) - 1),
diff --git a/llvm/utils/gdb-scripts/prettyprinters.py b/llvm/utils/gdb-scripts/prettyprinters.py
--- a/llvm/utils/gdb-scripts/prettyprinters.py
+++ b/llvm/utils/gdb-scripts/prettyprinters.py
@@ -2,6 +2,7 @@
 import sys
 
 import gdb.printing
+import gdb.types
 
 class Iterator:
   def __iter__(self):
@@ -315,6 +316,51 @@
   def to_string(self):
     return self.string_from_twine_object(self._val)
 
+def make_printer(string = None, children = None, hint = None):
+  """Create a printer from the parameters."""
+  class Printer : pass
+  printer = Printer()
+  if string:
+    setattr(printer, 'to_string', lambda: string)
+  if children:
+    setattr(printer, 'children', lambda: children)
+  if hint:
+    setattr(printer, 'display_hint', lambda: hint)
+  return printer
+
+def get_pointer_int_pair(val):
+  """Get iterable with zero or single tuple from llvm::PointerIntPair."""
+  info_name = val.type.template_argument(4).strip_typedefs().name
+  try:
+    enum_type = gdb.lookup_type(info_name + '::MaskAndShiftConstants')
+  except gdb.error:
+    return
+  enum_dict = gdb.types.make_enum_dict(enum_type)
+  ptr_mask = enum_dict[info_name + '::PointerBitMask']
+  int_shift = enum_dict[info_name + '::IntShift']
+  int_mask = enum_dict[info_name + '::IntMask']
+  pair_union = val['Value']
+  pointer = (pair_union & ptr_mask)
+  value = ((pair_union >> int_shift) & int_mask)
+  yield (pointer, value)
+
+def make_pointer_int_pair_printer(val):
+  """Factory for an llvm::PointerIntPair printer."""
+  for (pointer, value) in get_pointer_int_pair(val):
+    pointer_type = val.type.template_argument(0)
+    value_type = val.type.template_argument(2)
+    string = 'llvm::PointerIntPair<%s>' % pointer_type
+    children = [('pointer', pointer.cast(pointer_type)), 
+                ('value', value.cast(value_type))]
+    return make_printer(string, children)
+
+def make_pointer_union_printer(val):
+  """Factory for an llvm::PointerUnion printer."""
+  for (pointer, value) in get_pointer_int_pair(val['Val']):
+    pointer_type = val.type.template_argument(int(value))
+    string = 'llvm::PointerUnion containing %s' % pointer_type
+    return make_printer(string, [('pointer', pointer.cast(pointer_type))])
+
 pp = gdb.printing.RegexpCollectionPrettyPrinter("LLVMSupport")
 pp.add_printer('llvm::SmallString', '^llvm::SmallString<.*>$', SmallStringPrinter)
 pp.add_printer('llvm::StringRef', '^llvm::StringRef$', StringRefPrinter)
@@ -324,4 +370,6 @@
 pp.add_printer('llvm::Optional', '^llvm::Optional<.*>$', OptionalPrinter)
 pp.add_printer('llvm::DenseMap', '^llvm::DenseMap<.*>$', DenseMapPrinter)
 pp.add_printer('llvm::Twine', '^llvm::Twine$', TwinePrinter)
+pp.add_printer('llvm::PointerIntPair', '^llvm::PointerIntPair<.*>$', make_pointer_int_pair_printer)
+pp.add_printer('llvm::PointerUnion', '^llvm::PointerUnion<.*>$', make_pointer_union_printer)
 gdb.printing.register_pretty_printer(gdb.current_objfile(), pp)