diff --git a/clang-tools-extra/clangd/Hover.cpp b/clang-tools-extra/clangd/Hover.cpp
index 82323fe16c82b..06b949bc4a2b5 100644
--- a/clang-tools-extra/clangd/Hover.cpp
+++ b/clang-tools-extra/clangd/Hover.cpp
@@ -1194,7 +1194,7 @@ void maybeAddSymbolProviders(ParsedAST &AST, HoverInfo &HI,
 
   const SourceManager &SM = AST.getSourceManager();
   llvm::SmallVector<include_cleaner::Header> RankedProviders =
-      include_cleaner::headersForSymbol(Sym, SM, AST.getPragmaIncludes().get());
+      include_cleaner::headersForSymbol(Sym, SM, &AST.getPragmaIncludes());
   if (RankedProviders.empty())
     return;
 
@@ -1254,7 +1254,7 @@ void maybeAddUsedSymbols(ParsedAST &AST, HoverInfo &HI, const Inclusion &Inc) {
   llvm::DenseSet<include_cleaner::Symbol> UsedSymbols;
   include_cleaner::walkUsed(
       AST.getLocalTopLevelDecls(), collectMacroReferences(AST),
-      AST.getPragmaIncludes().get(), AST.getPreprocessor(),
+      &AST.getPragmaIncludes(), AST.getPreprocessor(),
       [&](const include_cleaner::SymbolReference &Ref,
           llvm::ArrayRef<include_cleaner::Header> Providers) {
         if (Ref.RT != include_cleaner::RefType::Explicit ||
diff --git a/clang-tools-extra/clangd/IncludeCleaner.cpp b/clang-tools-extra/clangd/IncludeCleaner.cpp
index 2f34c94934920..563a1f5d22f5b 100644
--- a/clang-tools-extra/clangd/IncludeCleaner.cpp
+++ b/clang-tools-extra/clangd/IncludeCleaner.cpp
@@ -311,7 +311,7 @@ getUnused(ParsedAST &AST,
     auto IncludeID = static_cast<IncludeStructure::HeaderID>(*MFI.HeaderID);
     if (ReferencedFiles.contains(IncludeID))
       continue;
-    if (!mayConsiderUnused(MFI, AST, AST.getPragmaIncludes().get())) {
+    if (!mayConsiderUnused(MFI, AST, &AST.getPragmaIncludes())) {
       dlog("{0} was not used, but is not eligible to be diagnosed as unused",
            MFI.Written);
       continue;
@@ -403,7 +403,7 @@ IncludeCleanerFindings computeIncludeCleanerFindings(ParsedAST &AST) {
                                               .getBuiltinDir();
   include_cleaner::walkUsed(
       AST.getLocalTopLevelDecls(), /*MacroRefs=*/Macros,
-      AST.getPragmaIncludes().get(), AST.getPreprocessor(),
+      &AST.getPragmaIncludes(), AST.getPreprocessor(),
       [&](const include_cleaner::SymbolReference &Ref,
           llvm::ArrayRef<include_cleaner::Header> Providers) {
         bool Satisfied = false;
diff --git a/clang-tools-extra/clangd/ParsedAST.cpp b/clang-tools-extra/clangd/ParsedAST.cpp
index d91ce7283ecee..14a91797f4d2e 100644
--- a/clang-tools-extra/clangd/ParsedAST.cpp
+++ b/clang-tools-extra/clangd/ParsedAST.cpp
@@ -653,6 +653,7 @@ ParsedAST::build(llvm::StringRef Filename, const ParseInputs &Inputs,
   }
 
   IncludeStructure Includes;
+  include_cleaner::PragmaIncludes PI;
   // If we are using a preamble, copy existing includes.
   if (Preamble) {
     Includes = Preamble->Includes;
@@ -660,11 +661,15 @@ ParsedAST::build(llvm::StringRef Filename, const ParseInputs &Inputs,
     // Replay the preamble includes so that clang-tidy checks can see them.
     ReplayPreamble::attach(Patch->preambleIncludes(), *Clang,
                            Patch->modifiedBounds());
+    PI = *Preamble->Pragmas;
   }
   // Important: collectIncludeStructure is registered *after* ReplayPreamble!
   // Otherwise we would collect the replayed includes again...
   // (We can't *just* use the replayed includes, they don't have Resolved path).
   Includes.collect(*Clang);
+  // Same for pragma-includes, we're already inheriting preamble includes, so we
+  // should only receive callbacks for non-preamble mainfile includes.
+  PI.record(*Clang);
   // Copy over the macros in the preamble region of the main file, and combine
   // with non-preamble macros below.
   MainFileMacros Macros;
@@ -735,7 +740,7 @@ ParsedAST::build(llvm::StringRef Filename, const ParseInputs &Inputs,
   ParsedAST Result(Filename, Inputs.Version, std::move(Preamble),
                    std::move(Clang), std::move(Action), std::move(Tokens),
                    std::move(Macros), std::move(Marks), std::move(ParsedDecls),
-                   std::move(Diags), std::move(Includes));
+                   std::move(Diags), std::move(Includes), std::move(PI));
   llvm::move(getIncludeCleanerDiags(Result, Inputs.Contents),
              std::back_inserter(Result.Diags));
   return std::move(Result);
@@ -828,23 +833,21 @@ ParsedAST::ParsedAST(PathRef TUPath, llvm::StringRef Version,
                      syntax::TokenBuffer Tokens, MainFileMacros Macros,
                      std::vector<PragmaMark> Marks,
                      std::vector<Decl *> LocalTopLevelDecls,
-                     std::vector<Diag> Diags, IncludeStructure Includes)
+                     std::vector<Diag> Diags, IncludeStructure Includes,
+                     include_cleaner::PragmaIncludes PI)
     : TUPath(TUPath), Version(Version), Preamble(std::move(Preamble)),
       Clang(std::move(Clang)), Action(std::move(Action)),
       Tokens(std::move(Tokens)), Macros(std::move(Macros)),
       Marks(std::move(Marks)), Diags(std::move(Diags)),
       LocalTopLevelDecls(std::move(LocalTopLevelDecls)),
-      Includes(std::move(Includes)) {
-  Resolver = std::make_unique<HeuristicResolver>(getASTContext());
+      Includes(std::move(Includes)), PI(std::move(PI)),
+      Resolver(std::make_unique<HeuristicResolver>(getASTContext())) {
   assert(this->Clang);
   assert(this->Action);
 }
 
-std::shared_ptr<const include_cleaner::PragmaIncludes>
-ParsedAST::getPragmaIncludes() const {
-  if (!Preamble)
-    return nullptr;
-  return Preamble->Pragmas;
+const include_cleaner::PragmaIncludes &ParsedAST::getPragmaIncludes() const {
+  return PI;
 }
 
 std::optional<llvm::StringRef> ParsedAST::preambleVersion() const {
diff --git a/clang-tools-extra/clangd/ParsedAST.h b/clang-tools-extra/clangd/ParsedAST.h
index c68fdba6bd26c..63e564bd68a78 100644
--- a/clang-tools-extra/clangd/ParsedAST.h
+++ b/clang-tools-extra/clangd/ParsedAST.h
@@ -103,10 +103,8 @@ class ParsedAST {
   /// Tokens recorded while parsing the main file.
   /// (!) does not have tokens from the preamble.
   const syntax::TokenBuffer &getTokens() const { return Tokens; }
-  /// Returns the PramaIncludes from the preamble.
-  /// Might be null if AST is built without a preamble.
-  std::shared_ptr<const include_cleaner::PragmaIncludes>
-  getPragmaIncludes() const;
+  /// Returns the PramaIncludes for preamble + main file includes.
+  const include_cleaner::PragmaIncludes &getPragmaIncludes() const;
 
   /// Returns the version of the ParseInputs this AST was built from.
   llvm::StringRef version() const { return Version; }
@@ -129,7 +127,7 @@ class ParsedAST {
             std::unique_ptr<FrontendAction> Action, syntax::TokenBuffer Tokens,
             MainFileMacros Macros, std::vector<PragmaMark> Marks,
             std::vector<Decl *> LocalTopLevelDecls, std::vector<Diag> Diags,
-            IncludeStructure Includes);
+            IncludeStructure Includes, include_cleaner::PragmaIncludes PI);
   Path TUPath;
   std::string Version;
   // In-memory preambles must outlive the AST, it is important that this member
@@ -159,6 +157,7 @@ class ParsedAST {
   // top-level decls from the preamble.
   std::vector<Decl *> LocalTopLevelDecls;
   IncludeStructure Includes;
+  include_cleaner::PragmaIncludes PI;
   std::unique_ptr<HeuristicResolver> Resolver;
 };
 
diff --git a/clang-tools-extra/clangd/XRefs.cpp b/clang-tools-extra/clangd/XRefs.cpp
index f55d2a5623956..5f41f788a6939 100644
--- a/clang-tools-extra/clangd/XRefs.cpp
+++ b/clang-tools-extra/clangd/XRefs.cpp
@@ -1339,7 +1339,7 @@ maybeFindIncludeReferences(ParsedAST &AST, Position Pos,
   auto Converted = convertIncludes(AST);
   include_cleaner::walkUsed(
       AST.getLocalTopLevelDecls(), collectMacroReferences(AST),
-      AST.getPragmaIncludes().get(), AST.getPreprocessor(),
+      &AST.getPragmaIncludes(), AST.getPreprocessor(),
       [&](const include_cleaner::SymbolReference &Ref,
           llvm::ArrayRef<include_cleaner::Header> Providers) {
         if (Ref.RT != include_cleaner::RefType::Explicit ||
diff --git a/clang-tools-extra/clangd/index/FileIndex.cpp b/clang-tools-extra/clangd/index/FileIndex.cpp
index 5052c661cfc5e..eb9562d2b6bf8 100644
--- a/clang-tools-extra/clangd/index/FileIndex.cpp
+++ b/clang-tools-extra/clangd/index/FileIndex.cpp
@@ -223,7 +223,7 @@ FileShardedIndex::getShard(llvm::StringRef Uri) const {
 SlabTuple indexMainDecls(ParsedAST &AST) {
   return indexSymbols(
       AST.getASTContext(), AST.getPreprocessor(), AST.getLocalTopLevelDecls(),
-      &AST.getMacros(), *AST.getPragmaIncludes(),
+      &AST.getMacros(), AST.getPragmaIncludes(),
       /*IsIndexMainAST=*/true, AST.version(), /*CollectMainFileRefs=*/true);
 }
 
diff --git a/clang-tools-extra/clangd/unittests/FileIndexTests.cpp b/clang-tools-extra/clangd/unittests/FileIndexTests.cpp
index cf30b388d234d..9f713564b2c01 100644
--- a/clang-tools-extra/clangd/unittests/FileIndexTests.cpp
+++ b/clang-tools-extra/clangd/unittests/FileIndexTests.cpp
@@ -176,7 +176,7 @@ void update(FileIndex &M, llvm::StringRef Basename, llvm::StringRef Code) {
   auto AST = File.build();
   M.updatePreamble(testPath(File.Filename), /*Version=*/"null",
                    AST.getASTContext(), AST.getPreprocessor(),
-                   *AST.getPragmaIncludes());
+                   AST.getPragmaIncludes());
 }
 
 TEST(FileIndexTest, CustomizedURIScheme) {
@@ -254,7 +254,7 @@ TEST(FileIndexTest, IWYUPragmaExport) {
   auto AST = File.build();
   M.updatePreamble(testPath(File.Filename), /*Version=*/"null",
                    AST.getASTContext(), AST.getPreprocessor(),
-                   *AST.getPragmaIncludes());
+                   AST.getPragmaIncludes());
 
   auto Symbols = runFuzzyFind(M, "");
   EXPECT_THAT(
@@ -446,7 +446,7 @@ TEST(FileIndexTest, Relations) {
   FileIndex Index;
   Index.updatePreamble(testPath(TU.Filename), /*Version=*/"null",
                        AST.getASTContext(), AST.getPreprocessor(),
-                       *AST.getPragmaIncludes());
+                       AST.getPragmaIncludes());
   SymbolID A = findSymbol(TU.headerSymbols(), "A").ID;
   uint32_t Results = 0;
   RelationsRequest Req;
@@ -567,7 +567,7 @@ TEST(FileIndexTest, StalePreambleSymbolsDeleted) {
   auto AST = File.build();
   M.updatePreamble(testPath(File.Filename), /*Version=*/"null",
                    AST.getASTContext(), AST.getPreprocessor(),
-                   *AST.getPragmaIncludes());
+                   AST.getPragmaIncludes());
   EXPECT_THAT(runFuzzyFind(M, ""), UnorderedElementsAre(qName("a")));
 
   File.Filename = "f2.cpp";
@@ -575,7 +575,7 @@ TEST(FileIndexTest, StalePreambleSymbolsDeleted) {
   AST = File.build();
   M.updatePreamble(testPath(File.Filename), /*Version=*/"null",
                    AST.getASTContext(), AST.getPreprocessor(),
-                   *AST.getPragmaIncludes());
+                   AST.getPragmaIncludes());
   EXPECT_THAT(runFuzzyFind(M, ""), UnorderedElementsAre(qName("b")));
 }
 
@@ -720,7 +720,7 @@ TEST(FileIndexTest, Profile) {
   auto AST = TestTU::withHeaderCode("int a;").build();
   FI.updateMain(FileName, AST);
   FI.updatePreamble(FileName, "v1", AST.getASTContext(), AST.getPreprocessor(),
-                    *AST.getPragmaIncludes());
+                    AST.getPragmaIncludes());
 
   llvm::BumpPtrAllocator Alloc;
   MemoryTree MT(&Alloc);
diff --git a/clang-tools-extra/clangd/unittests/IncludeCleanerTests.cpp b/clang-tools-extra/clangd/unittests/IncludeCleanerTests.cpp
index 5a6524dec2f09..7ed4a9103e1f2 100644
--- a/clang-tools-extra/clangd/unittests/IncludeCleanerTests.cpp
+++ b/clang-tools-extra/clangd/unittests/IncludeCleanerTests.cpp
@@ -316,8 +316,10 @@ TEST(IncludeCleaner, IWYUPragmas) {
     #include "public.h"
 
     void bar() { foo(); }
+    #include "keep_main_file.h" // IWYU pragma: keep
     )cpp";
   TU.AdditionalFiles["behind_keep.h"] = guard("");
+  TU.AdditionalFiles["keep_main_file.h"] = guard("");
   TU.AdditionalFiles["exported.h"] = guard("");
   TU.AdditionalFiles["public.h"] = guard("#include \"private.h\"");
   TU.AdditionalFiles["private.h"] = guard(R"cpp(
diff --git a/clang-tools-extra/clangd/unittests/TestTU.cpp b/clang-tools-extra/clangd/unittests/TestTU.cpp
index e65ae825b4167..1f02c04125b1e 100644
--- a/clang-tools-extra/clangd/unittests/TestTU.cpp
+++ b/clang-tools-extra/clangd/unittests/TestTU.cpp
@@ -164,7 +164,7 @@ SymbolSlab TestTU::headerSymbols() const {
   auto AST = build();
   return std::get<0>(indexHeaderSymbols(
       /*Version=*/"null", AST.getASTContext(), AST.getPreprocessor(),
-      *AST.getPragmaIncludes()));
+      AST.getPragmaIncludes()));
 }
 
 RefSlab TestTU::headerRefs() const {
@@ -177,7 +177,7 @@ std::unique_ptr<SymbolIndex> TestTU::index() const {
   auto Idx = std::make_unique<FileIndex>();
   Idx->updatePreamble(testPath(Filename), /*Version=*/"null",
                       AST.getASTContext(), AST.getPreprocessor(),
-                      *AST.getPragmaIncludes());
+                      AST.getPragmaIncludes());
   Idx->updateMain(testPath(Filename), AST);
   return std::move(Idx);
 }
diff --git a/clang-tools-extra/include-cleaner/include/clang-include-cleaner/Record.h b/clang-tools-extra/include-cleaner/include/clang-include-cleaner/Record.h
index 2e0b462ce16df..2dcb5ea2555c5 100644
--- a/clang-tools-extra/include-cleaner/include/clang-include-cleaner/Record.h
+++ b/clang-tools-extra/include-cleaner/include/clang-include-cleaner/Record.h
@@ -113,7 +113,8 @@ class PragmaIncludes {
   llvm::DenseSet<llvm::sys::fs::UniqueID> ShouldKeep;
 
   /// Owns the strings.
-  llvm::BumpPtrAllocator Arena;
+  /// Each record() pushes a new one, while keeping all the old strings alive.
+  std::vector<std::shared_ptr<const llvm::BumpPtrAllocator>> Arena;
 
   // FIXME: add support for clang use_instead pragma
 };
diff --git a/clang-tools-extra/include-cleaner/lib/Record.cpp b/clang-tools-extra/include-cleaner/lib/Record.cpp
index bd726cff12a97..c93c56adf650d 100644
--- a/clang-tools-extra/include-cleaner/lib/Record.cpp
+++ b/clang-tools-extra/include-cleaner/lib/Record.cpp
@@ -178,7 +178,8 @@ class PragmaIncludes::RecordPragma : public PPCallbacks, public CommentHandler {
       : RecordPragma(CI.getPreprocessor(), Out) {}
   RecordPragma(const Preprocessor &P, PragmaIncludes *Out)
       : SM(P.getSourceManager()), HeaderInfo(P.getHeaderSearchInfo()), Out(Out),
-        UniqueStrings(Arena) {}
+        Arena(std::make_shared<llvm::BumpPtrAllocator>()),
+        UniqueStrings(*Arena) {}
 
   void FileChanged(SourceLocation Loc, FileChangeReason Reason,
                    SrcMgr::CharacteristicKind FileType,
@@ -204,7 +205,7 @@ class PragmaIncludes::RecordPragma : public PPCallbacks, public CommentHandler {
           std::unique(It.getSecond().begin(), It.getSecond().end()),
           It.getSecond().end());
     }
-    Out->Arena = std::move(Arena);
+    Out->Arena.emplace_back(std::move(Arena));
   }
 
   void InclusionDirective(SourceLocation HashLoc, const Token &IncludeTok,
@@ -336,7 +337,7 @@ class PragmaIncludes::RecordPragma : public PPCallbacks, public CommentHandler {
   const SourceManager &SM;
   const HeaderSearch &HeaderInfo;
   PragmaIncludes *Out;
-  llvm::BumpPtrAllocator Arena;
+  std::shared_ptr<llvm::BumpPtrAllocator> Arena;
   /// Intern table for strings. Contents are on the arena.
   llvm::StringSaver UniqueStrings;
 
diff --git a/clang-tools-extra/include-cleaner/unittests/RecordTest.cpp b/clang-tools-extra/include-cleaner/unittests/RecordTest.cpp
index 0f2ded5f18345..d1f7590b22268 100644
--- a/clang-tools-extra/include-cleaner/unittests/RecordTest.cpp
+++ b/clang-tools-extra/include-cleaner/unittests/RecordTest.cpp
@@ -588,5 +588,30 @@ TEST_F(PragmaIncludeTest, OutlivesFMAndSM) {
   EXPECT_THAT(PI.getExporters(Private2FE.get(), FM),
               testing::ElementsAre(llvm::cantFail(FM.getFileRef("public.h"))));
 }
+
+TEST_F(PragmaIncludeTest, CanRecordManyTimes) {
+  Inputs.Code = R"cpp(
+    #include "public.h"
+  )cpp";
+  Inputs.ExtraFiles["public.h"] = R"cpp(
+    #include "private.h"
+  )cpp";
+  Inputs.ExtraFiles["private.h"] = R"cpp(
+    // IWYU pragma: private, include "public.h"
+  )cpp";
+
+  TestAST Processed = build();
+  auto &FM = Processed.fileManager();
+  auto PrivateFE = FM.getFile("private.h");
+  llvm::StringRef Public = PI.getPublic(PrivateFE.get());
+  EXPECT_EQ(Public, "\"public.h\"");
+
+  // This build populates same PI during build, but this time we don't have
+  // any IWYU pragmas. Make sure strings from previous recordings are still
+  // alive.
+  Inputs.Code = "";
+  build();
+  EXPECT_EQ(Public, "\"public.h\"");
+}
 } // namespace
 } // namespace clang::include_cleaner