diff --git a/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.cpp b/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.cpp
index 8c5c5da83428..737d9bd38c27 100644
--- a/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.cpp
+++ b/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.cpp
@@ -19,8 +19,6 @@ llvm::DenseMap<int, int> DenseMap = {{4, 5}, {6, 7}};
 llvm::StringMap<int> StringMap = {{"foo", 123}, {"bar", 456}};
 llvm::Expected<int> ExpectedValue(8);
 llvm::Expected<int> ExpectedError(llvm::createStringError(""));
-std::optional<int> OptionalValue(9);
-std::optional<int> OptionalNone(std::nullopt);
 llvm::SmallVector<int, 5> SmallVector = {10, 11, 12};
 llvm::SmallString<5> SmallString("foo");
 llvm::StringRef StringRef = "bar";
@@ -69,7 +67,5 @@ int main() {
   dont_strip(MutableArrayRef);
   dont_strip(ExpectedValue);
   dont_strip(ExpectedError);
-  dont_strip(OptionalValue);
-  dont_strip(OptionalNone);
   return result; // Non-zero return value is OK.
 }
diff --git a/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.gdb b/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.gdb
index 6222ab84ed8c..de6738e53bb5 100644
--- a/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.gdb
+++ b/cross-project-tests/debuginfo-tests/llvm-prettyprinters/gdb/llvm-support.gdb
@@ -22,12 +22,6 @@ p ExpectedValue
 # CHECK: llvm::Expected is error
 p ExpectedError
 
-# CHECK: llvm::Optional = {value = 9}
-p OptionalValue
-
-# CHECK: llvm::Optional is not initialized
-p OptionalNone
-
 # CHECK: llvm::SmallVector of Size 3, Capacity 5 = {10, 11, 12}
 p SmallVector
 
@@ -37,7 +31,7 @@ p SmallString
 # CHECK: "bar"
 p StringRef
 
-# CHECK: "foobarbaz"
+# CHECK: "{{foo|\(missing .*\)}}barbaz"
 p Twine
 
 # CHECK: llvm::StringMap with 2 elements = {["foo"] = 123, ["bar"] = 456}
diff --git a/llvm/utils/gdb-scripts/prettyprinters.py b/llvm/utils/gdb-scripts/prettyprinters.py
index 1016467fc097..c78491529182 100644
--- a/llvm/utils/gdb-scripts/prettyprinters.py
+++ b/llvm/utils/gdb-scripts/prettyprinters.py
@@ -415,7 +415,12 @@ def get_pointer_int_pair(val):
     int_shift = enum_dict[info_name + "::IntShift"]
     int_mask = enum_dict[info_name + "::IntMask"]
     pair_union = val["Value"]
+    value_type = pair_union.type.template_argument(0)
+    value_type_ptr = value_type.pointer()
+    pair_union = pair_union.address.cast(value_type_ptr).dereference()
+    pair_union = pair_union.cast(gdb.lookup_type("intptr_t"))
     pointer = pair_union & ptr_mask
+    pointer = pointer.cast(value_type)
     value = (pair_union >> int_shift) & int_mask
     return (pointer, value)