diff --git a/llvm/lib/TextAPI/InterfaceFile.cpp b/llvm/lib/TextAPI/InterfaceFile.cpp
index ce2feb65c9ec9..e2253723659e2 100644
--- a/llvm/lib/TextAPI/InterfaceFile.cpp
+++ b/llvm/lib/TextAPI/InterfaceFile.cpp
@@ -59,14 +59,11 @@ void InterfaceFile::addRPath(StringRef RPath, const Target &InputTarget) {
     return;
   using RPathEntryT = const std::pair<Target, std::string>;
   RPathEntryT Entry(InputTarget, RPath);
-  auto Iter =
-      lower_bound(RPaths, Entry,
-                  [](RPathEntryT &LHS, RPathEntryT &RHS) { return LHS < RHS; });
 
-  if ((Iter != RPaths.end()) && (*Iter == Entry))
+  if (is_contained(RPaths, Entry))
     return;
 
-  RPaths.emplace(Iter, Entry);
+  RPaths.emplace_back(Entry);
 }
 
 void InterfaceFile::addTarget(const Target &Target) {
diff --git a/llvm/lib/TextAPI/TextStubV5.cpp b/llvm/lib/TextAPI/TextStubV5.cpp
index b072c0b5d69d0..2e60b065f856c 100644
--- a/llvm/lib/TextAPI/TextStubV5.cpp
+++ b/llvm/lib/TextAPI/TextStubV5.cpp
@@ -83,6 +83,33 @@ using AttrToTargets = std::map<std::string, TargetList>;
 using TargetsToSymbols =
     SmallVector<std::pair<TargetList, std::vector<JSONSymbol>>>;
 
+/// Wrapper over a vector for handling textstub attributes, mapped to target
+/// triples, that require insertion order to be intact in the resulting \c
+/// InterfaceFile.
+class InOrderAttrToTargets {
+  using EntryT = std::pair<std::string, TargetList>;
+
+public:
+  void insert(EntryT &&Entry) {
+    auto &Element = get(Entry.first);
+    Element.second = Entry.second;
+  }
+
+  const EntryT *begin() { return Container.begin(); }
+  const EntryT *end() { return Container.end(); }
+
+private:
+  EntryT &get(std::string &Key) {
+    auto *It = find_if(Container,
+                       [&Key](EntryT &Input) { return Input.first == Key; });
+    if (It != Container.end())
+      return *It;
+    Container.push_back(EntryT(Key, {}));
+    return Container.back();
+  }
+  llvm::SmallVector<EntryT> Container;
+};
+
 enum TBDKey : size_t {
   TBDVersion = 0U,
   MainLibrary,
@@ -437,14 +464,14 @@ Expected<TargetsToSymbols> getSymbolSection(const Object *File, TBDKey Key,
   return std::move(Result);
 }
 
-Expected<AttrToTargets> getLibSection(const Object *File, TBDKey Key,
-                                      TBDKey SubKey,
-                                      const TargetList &Targets) {
+template <typename ReturnT = AttrToTargets>
+Expected<ReturnT> getLibSection(const Object *File, TBDKey Key, TBDKey SubKey,
+                                const TargetList &Targets) {
   auto *Section = File->getArray(Keys[Key]);
   if (!Section)
-    return AttrToTargets();
+    return ReturnT();
 
-  AttrToTargets Result;
+  ReturnT Result;
   TargetList MappedTargets;
   for (auto Val : *Section) {
     auto *Obj = Val.getAsObject();
@@ -460,7 +487,7 @@ Expected<AttrToTargets> getLibSection(const Object *File, TBDKey Key,
     }
     auto Err =
         collectFromArray(SubKey, Obj, [&Result, &MappedTargets](StringRef Key) {
-          Result[Key.str()] = MappedTargets;
+          Result.insert({Key.str(), MappedTargets});
         });
     if (Err)
       return std::move(Err);
@@ -629,10 +656,11 @@ Expected<IFPtr> parseToInterfaceFile(const Object *File) {
     return RLOrErr.takeError();
   AttrToTargets ReexportLibs = std::move(*RLOrErr);
 
-  auto RPathsOrErr = getLibSection(File, TBDKey::RPath, TBDKey::Paths, Targets);
+  auto RPathsOrErr = getLibSection<InOrderAttrToTargets>(
+      File, TBDKey::RPath, TBDKey::Paths, Targets);
   if (!RPathsOrErr)
     return RPathsOrErr.takeError();
-  AttrToTargets RPaths = std::move(*RPathsOrErr);
+  InOrderAttrToTargets RPaths = std::move(*RPathsOrErr);
 
   auto ExportsOrErr = getSymbolSection(File, TBDKey::Exports, Targets);
   if (!ExportsOrErr)
@@ -802,6 +830,8 @@ Array serializeAttrToTargets(AggregateT &Entries, TBDKey Key) {
   return Container;
 }
 
+/// When there is no significance in order, the common case, serialize all
+/// attributes in a stable order.
 template <typename ValueT = std::string,
           typename AggregateT = std::vector<std::pair<MachO::Target, ValueT>>>
 Array serializeField(TBDKey Key, const AggregateT &Values,
@@ -834,6 +864,21 @@ Array serializeField(TBDKey Key, const std::vector<InterfaceFileRef> &Values,
   return serializeAttrToTargets(FinalEntries, Key);
 }
 
+template <
+    typename AggregateT = std::vector<std::pair<MachO::Target, std::string>>>
+Array serializeFieldInInsertionOrder(TBDKey Key, const AggregateT &Values,
+                                     const TargetList &ActiveTargets) {
+  MapVector<StringRef, std::set<MachO::Target>> Entries;
+  for (const auto &[Target, Val] : Values)
+    Entries[Val].insert(Target);
+
+  TargetsToValuesMap FinalEntries;
+  for (const auto &[Val, Targets] : Entries)
+    FinalEntries[serializeTargets(Targets, ActiveTargets)].emplace_back(
+        Val.str());
+  return serializeAttrToTargets(FinalEntries, Key);
+}
+
 struct SymbolFields {
   struct SymbolTypes {
     std::vector<StringRef> Weaks;
@@ -963,7 +1008,8 @@ Expected<Object> serializeIF(const InterfaceFile *File) {
       TBDKey::ABI, File->getSwiftABIVersion(), 0u);
   insertNonEmptyValues(Library, TBDKey::SwiftABI, std::move(SwiftABI));
 
-  Array RPaths = serializeField(TBDKey::Paths, File->rpaths(), ActiveTargets);
+  Array RPaths = serializeFieldInInsertionOrder(TBDKey::Paths, File->rpaths(),
+                                                ActiveTargets);
   insertNonEmptyValues(Library, TBDKey::RPath, std::move(RPaths));
 
   Array Umbrellas = serializeField(TBDKey::Umbrella, File->umbrellas(),
diff --git a/llvm/test/tools/llvm-readtapi/compare-rpath-order.test b/llvm/test/tools/llvm-readtapi/compare-rpath-order.test
new file mode 100644
index 0000000000000..0514eb2cfbcd0
--- /dev/null
+++ b/llvm/test/tools/llvm-readtapi/compare-rpath-order.test
@@ -0,0 +1,14 @@
+; RUN: rm -rf %t
+; RUN: split-file %s %t  
+; RUN: not llvm-readtapi --compare %t/rpaths_diff_order.tbd  %t/rpaths.tbd 2>&1 | FileCheck %s 
+
+; CHECK: < {{.*}}rpaths_diff_order.tbd
+; CHECK: > {{.*}}rpaths.tbd
+
+; CHECK: 'Run Path Search Paths' differ by order
+
+//--- rpaths_diff_order.tbd
+{"main_library":{"exported_symbols":[{"text":{"global":["_foo"]}}],"rpaths": [{"paths": ["/usr/lib/swift", "@loader_path/../../../"]}], "flags":[{"attributes":["not_app_extension_safe"]}],"install_names":[{"name":"@rpath/libFake.dylib"}],"target_info":[{"min_deployment":"13","target":"x86_64-macos"},{"min_deployment":"13","target":"arm64-macos"}]},"tapi_tbd_version":5}
+
+//--- rpaths.tbd
+{"main_library":{"exported_symbols":[{"text":{"global":["_foo"]}}],"rpaths": [{"paths": [ "@loader_path/../../../", "/usr/lib/swift"]}], "flags":[{"attributes":["not_app_extension_safe"]}],"install_names":[{"name":"@rpath/libFake.dylib"}],"target_info":[{"min_deployment":"13","target":"x86_64-macos"},{"min_deployment":"13","target":"arm64-macos"}]},"tapi_tbd_version":5}
diff --git a/llvm/tools/llvm-readtapi/DiffEngine.cpp b/llvm/tools/llvm-readtapi/DiffEngine.cpp
index 8fc45f436109e..607be0b12c949 100644
--- a/llvm/tools/llvm-readtapi/DiffEngine.cpp
+++ b/llvm/tools/llvm-readtapi/DiffEngine.cpp
@@ -449,8 +449,10 @@ template <typename T> void sortTargetValues(std::vector<T> &TargValues) {
 
 template <typename T>
 void printVecVal(std::string Indent, const DiffOutput &Attr, raw_ostream &OS) {
-  if (Attr.Values.empty())
+  if (Attr.Values.empty()) {
+    OS << Indent << "'" << Attr.Name << "' differ by order\n";
     return;
+  }
 
   OS << Indent << Attr.Name << "\n";