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 = {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 +316,42 @@
   def to_string(self):
     return self.string_from_twine_object(self._val)
 
+class PointerIntPairPrinter:
+  """Print an llvm::PointerIntPair object."""
+
+  def __init__(self, val):
+    pointer_type = val.type.template_argument(0)
+    int_type = val.type.template_argument(2)
+    info_name = val.type.template_argument(4).name
+    enum_type = gdb.lookup_type(info_name + '::MaskAndShiftConstants')
+    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']
+    self.pointer = (pair_union & ptr_mask).cast(pointer_type)
+    self.value = ((pair_union >> int_shift) & int_mask).cast(int_type)
+
+  def children(self):
+    return [('pointer', self.pointer), ('value', self.value)]
+
+  def to_string(self):
+    return 'llvm::PointerIntPair'
+
+class PointerUnionPrinter:
+  """Print an llvm::PointerUnion object."""
+
+  def __init__(self, val):
+    pair_printer = PointerIntPairPrinter(val['Val'])
+    pointer_type = val.type.template_argument(int(pair_printer.value))
+    self.pointer = pair_printer.pointer.cast(pointer_type)
+
+  def children(self):
+    return [('pointer', self.pointer)]
+
+  def to_string(self):
+    return 'llvm::PointerUnion containing %s' % self.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 +361,6 @@
 pp.add_printer('llvm::Optional', '^llvm::Optional<.*>$', OptionalPrinter)
 pp.add_printer('llvm::DenseMap', '^llvm::DenseMap<.*>$', DenseMapPrinter)
 pp.add_printer('llvm::Twine', '^llvm::Twine$', TwinePrinter)
-gdb.printing.register_pretty_printer(gdb.current_objfile(), pp)
+pp.add_printer('llvm::PointerIntPair', '^llvm::PointerIntPair<.*>$', PointerIntPairPrinter)
+pp.add_printer('llvm::PointerUnion', '^llvm::PointerUnion<.*>$', PointerUnionPrinter)
+gdb.printing.register_pretty_printer(gdb.current_objfile(), pp, True)