diff --git a/lib/Serialization/Serialization.cpp b/lib/Serialization/Serialization.cpp
index 5ac366860ad17..e1b149205a6d6 100644
--- a/lib/Serialization/Serialization.cpp
+++ b/lib/Serialization/Serialization.cpp
@@ -1199,10 +1199,12 @@ void Serializer::writeHeader() {
 
         const auto &PathRemapper = Options.DebuggingOptionsPrefixMap;
         const auto &PathObfuscator = Options.PathObfuscator;
+        auto remapPath = [&PathRemapper, &PathObfuscator](StringRef Path) {
+          return PathObfuscator.obfuscate(PathRemapper.remapPath(Path));
+        };
+
         auto sdkPath = M->getASTContext().SearchPathOpts.getSDKPath();
-        SDKPath.emit(
-            ScratchRecord,
-            PathObfuscator.obfuscate(PathRemapper.remapPath(sdkPath)));
+        SDKPath.emit(ScratchRecord, remapPath(sdkPath));
         auto &Opts = Options.ExtraClangOptions;
         for (auto Arg = Opts.begin(), E = Opts.end(); Arg != E; ++Arg) {
           StringRef arg(*Arg);
@@ -1246,7 +1248,7 @@ void Serializer::writeHeader() {
             auto &opt = elem.get<PluginSearchOption::PluginPath>();
             PluginSearchOpt.emit(ScratchRecord,
                                  uint8_t(PluginSearchOptionKind::PluginPath),
-                                 opt.SearchPath);
+                                 remapPath(opt.SearchPath));
             continue;
           }
           case PluginSearchOption::Kind::ExternalPluginPath: {
@@ -1254,7 +1256,7 @@ void Serializer::writeHeader() {
             PluginSearchOpt.emit(
                 ScratchRecord,
                 uint8_t(PluginSearchOptionKind::ExternalPluginPath),
-                opt.SearchPath + "#" + opt.ServerPath);
+                remapPath(opt.SearchPath) + "#" + remapPath(opt.ServerPath));
             continue;
           }
           case PluginSearchOption::Kind::LoadPluginLibrary: {
@@ -1262,12 +1264,12 @@ void Serializer::writeHeader() {
             PluginSearchOpt.emit(
                 ScratchRecord,
                 uint8_t(PluginSearchOptionKind::LoadPluginLibrary),
-                opt.LibraryPath);
+                remapPath(opt.LibraryPath));
             continue;
           }
           case PluginSearchOption::Kind::LoadPluginExecutable: {
             auto &opt = elem.get<PluginSearchOption::LoadPluginExecutable>();
-            std::string optStr = opt.ExecutablePath + "#";
+            std::string optStr = remapPath(opt.ExecutablePath) + "#";
             llvm::interleave(
                 opt.ModuleNames, [&](auto &name) { optStr += name; },
                 [&]() { optStr += ","; });
@@ -1278,8 +1280,8 @@ void Serializer::writeHeader() {
           }
           case PluginSearchOption::Kind::ResolvedPluginConfig: {
             auto &opt = elem.get<PluginSearchOption::ResolvedPluginConfig>();
-            std::string optStr =
-                opt.LibraryPath + "#" + opt.ExecutablePath + "#";
+            std::string optStr = remapPath(opt.LibraryPath) + "#" +
+                                 remapPath(opt.ExecutablePath) + "#";
             llvm::interleave(
                 opt.ModuleNames, [&](auto &name) { optStr += name; },
                 [&]() { optStr += ","; });
diff --git a/test/Serialization/plugin_search_option_prefixing.swift b/test/Serialization/plugin_search_option_prefixing.swift
new file mode 100644
index 0000000000000..11df53ab13e2f
--- /dev/null
+++ b/test/Serialization/plugin_search_option_prefixing.swift
@@ -0,0 +1,63 @@
+// REQUIRES: swift_swift_parser
+
+/// Test loading dependencies that has macros.
+// RUN: %empty-directory(%t)
+// RUN: split-file %s %t
+
+/// Build macros.
+// RUN: %host-build-swift -swift-version 5 -emit-library -o %t/%target-library-name(MacroOne) -module-name=MacroOne %t/macro-1.swift
+// RUN: %host-build-swift -swift-version 5 -emit-library -o %t/%target-library-name(MacroTwo) -module-name=MacroTwo %t/macro-2.swift
+
+// RUN: %target-swift-frontend -emit-module %t/test.swift -module-name Test -o %t/Test.swiftmodule \
+// RUN:   -swift-version 5 -external-plugin-path %t#%swift-plugin-server -package-name Test \
+// RUN:   -plugin-path %swift-plugin-dir -prefix-serialized-debugging-options \
+// RUN:   -load-plugin-library %t/%target-library-name(MacroOne) \
+// RUN:   -debug-prefix-map %t=/externalsearchpath \
+// RUN:   -debug-prefix-map %swift-plugin-server=/externalserverpath \
+// RUN:   -debug-prefix-map %swift-plugin-dir=/plugindir
+// RUN: llvm-bcanalyzer -dump %t/Test.swiftmodule | %FileCheck %s
+
+// CHECK: <PLUGIN_SEARCH_OPTION abbrevid=8 op0=1/> blob data = '/externalsearchpath#/externalserverpath'
+// CHECK: <PLUGIN_SEARCH_OPTION abbrevid=8 op0=0/> blob data = '/plugindir'
+// CHECK: <PLUGIN_SEARCH_OPTION abbrevid=8 op0=2/> blob data = '/externalsearchpath/{{(lib)?}}MacroOne
+
+//--- macro-1.swift
+import SwiftSyntax
+@_spi(ExperimentalLanguageFeature) import SwiftSyntaxMacros
+
+public struct AssertMacro: ExpressionMacro {
+  public static func expansion(
+    of macro: some FreestandingMacroExpansionSyntax,
+    in context: some MacroExpansionContext
+  ) -> ExprSyntax {
+    guard let argument = macro.arguments.first?.expression else {
+      fatalError("boom")
+    }
+
+    return "assert(\(argument))"
+  }
+}
+
+//--- macro-2.swift
+import SwiftSyntax
+@_spi(ExperimentalLanguageFeature) import SwiftSyntaxMacros
+
+public struct StringifyMacro: ExpressionMacro {
+  public static func expansion(
+    of macro: some FreestandingMacroExpansionSyntax,
+    in context: some MacroExpansionContext
+  ) -> ExprSyntax {
+    guard let argument = macro.arguments.first?.expression else {
+      fatalError("boom")
+    }
+
+    return "(\(argument), \(StringLiteralExprSyntax(content: argument.description)))"
+  }
+}
+
+//--- test.swift
+import Swift
+@freestanding(expression) public macro assert(_: Bool) = #externalMacro(module: "MacroOne", type: "AssertMacro")
+@freestanding(expression) public macro assert_2(_: Bool) = #externalMacro(module: "MacroOne", type: "AssertMacro")
+@freestanding(expression) public macro stringify<T>(_ value: T) -> (T, String) = #externalMacro(module: "MacroTwo", type: "StringifyMacro")
+@freestanding(expression) public macro stringify_2<T>(_ value: T) -> (T, String) = #externalMacro(module: "MacroTwo", type: "StringifyMacro")