diff --git a/Sources/SwiftDriver/ExplicitModuleBuilds/ExplicitDependencyBuildPlanner.swift b/Sources/SwiftDriver/ExplicitModuleBuilds/ExplicitDependencyBuildPlanner.swift
index 5ab4f31b1..7c684cd6a 100644
--- a/Sources/SwiftDriver/ExplicitModuleBuilds/ExplicitDependencyBuildPlanner.swift
+++ b/Sources/SwiftDriver/ExplicitModuleBuilds/ExplicitDependencyBuildPlanner.swift
@@ -172,7 +172,7 @@ public typealias ExternalTargetModuleDetailsMap = [ModuleDependencyId: ExternalT
       jobs.append(Job(
         moduleName: moduleId.moduleName,
         kind: .emitModule,
-        tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+        tool: try toolchain.resolvedTool(.swiftCompiler),
         commandLine: commandLine,
         inputs: inputs,
         primaryInputs: [],
@@ -237,7 +237,7 @@ public typealias ExternalTargetModuleDetailsMap = [ModuleDependencyId: ExternalT
         jobs.append(Job(
           moduleName: moduleId.moduleName,
           kind: .generatePCM,
-          tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+          tool: try toolchain.resolvedTool(.swiftCompiler),
           commandLine: commandLine,
           inputs: inputs,
           primaryInputs: [],
diff --git a/Sources/SwiftDriver/ExplicitModuleBuilds/ModuleDependencyScanning.swift b/Sources/SwiftDriver/ExplicitModuleBuilds/ModuleDependencyScanning.swift
index 6952f4792..1fbf865e1 100644
--- a/Sources/SwiftDriver/ExplicitModuleBuilds/ModuleDependencyScanning.swift
+++ b/Sources/SwiftDriver/ExplicitModuleBuilds/ModuleDependencyScanning.swift
@@ -30,13 +30,12 @@ public extension Driver {
     // Construct the scanning job.
     return Job(moduleName: moduleOutputInfo.name,
                kind: .scanDependencies,
-               tool: VirtualPath.absolute(try toolchain.getToolPath(.swiftCompiler)),
+               tool: try toolchain.resolvedTool(.swiftCompiler),
                commandLine: commandLine,
                displayInputs: inputs,
                inputs: inputs,
                primaryInputs: [],
-               outputs: [TypedVirtualPath(file: .standardOutput, type: .jsonDependencies)],
-               supportsResponseFiles: false)
+               outputs: [TypedVirtualPath(file: .standardOutput, type: .jsonDependencies)])
   }
 
   /// Generate a full command-line invocation to be used for the dependency scanning action
@@ -263,13 +262,12 @@ public extension Driver {
     // Construct the scanning job.
     return Job(moduleName: moduleOutputInfo.name,
                kind: .scanDependencies,
-               tool: VirtualPath.absolute(try toolchain.getToolPath(.swiftCompiler)),
+               tool: try toolchain.resolvedTool(.swiftCompiler),
                commandLine: commandLine,
                displayInputs: inputs,
                inputs: inputs,
                primaryInputs: [],
-               outputs: [TypedVirtualPath(file: .standardOutput, type: .jsonDependencies)],
-               supportsResponseFiles: false)
+               outputs: [TypedVirtualPath(file: .standardOutput, type: .jsonDependencies)])
   }
 
   /// Precompute the dependencies for a given collection of modules using swift frontend's batch scanning mode
@@ -312,13 +310,12 @@ public extension Driver {
     // Construct the scanning job.
     return Job(moduleName: moduleOutputInfo.name,
                kind: .scanDependencies,
-               tool: VirtualPath.absolute(try toolchain.getToolPath(.swiftCompiler)),
+               tool: try toolchain.resolvedTool(.swiftCompiler),
                commandLine: commandLine,
                displayInputs: inputs,
                inputs: inputs,
                primaryInputs: [],
-               outputs: outputs,
-               supportsResponseFiles: false)
+               outputs: outputs)
   }
 
   /// Serialize a collection of modules into an input format expected by the batch module dependency scanner.
diff --git a/Sources/SwiftDriver/Jobs/APIDigesterJobs.swift b/Sources/SwiftDriver/Jobs/APIDigesterJobs.swift
index dacd0ad5f..84d8299e2 100644
--- a/Sources/SwiftDriver/Jobs/APIDigesterJobs.swift
+++ b/Sources/SwiftDriver/Jobs/APIDigesterJobs.swift
@@ -56,12 +56,11 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: mode.baselineGenerationJobKind,
-      tool: .absolute(try toolchain.getToolPath(.swiftAPIDigester)),
+      tool: try toolchain.resolvedTool(.swiftAPIDigester),
       commandLine: commandLine,
       inputs: [.init(file: modulePath, type: .swiftModule)],
       primaryInputs: [],
-      outputs: [.init(file: outputPath, type: mode.baselineFileType)],
-      supportsResponseFiles: true
+      outputs: [.init(file: outputPath, type: mode.baselineFileType)]
     )
   }
 
@@ -100,12 +99,11 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .compareABIBaseline,
-      tool: .absolute(try toolchain.getToolPath(.swiftAPIDigester)),
+      tool: try toolchain.resolvedTool(.swiftAPIDigester),
       commandLine: commandLine,
       inputs: inputs,
       primaryInputs: [],
-      outputs: [diag],
-      supportsResponseFiles: true
+      outputs: [diag]
     )
   }
 
@@ -141,12 +139,11 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: mode.baselineComparisonJobKind,
-      tool: .absolute(try toolchain.getToolPath(.swiftAPIDigester)),
+      tool: try toolchain.resolvedTool(.swiftAPIDigester),
       commandLine: commandLine,
       inputs: inputs,
       primaryInputs: [],
-      outputs: [.init(file: serializedDiagnosticsPath ?? VirtualPath.Handle.standardOutput, type: .diagnostics)],
-      supportsResponseFiles: true
+      outputs: [.init(file: serializedDiagnosticsPath ?? VirtualPath.Handle.standardOutput, type: .diagnostics)]
     )
   }
 
diff --git a/Sources/SwiftDriver/Jobs/AutolinkExtractJob.swift b/Sources/SwiftDriver/Jobs/AutolinkExtractJob.swift
index 6bfce40e8..f1553eb28 100644
--- a/Sources/SwiftDriver/Jobs/AutolinkExtractJob.swift
+++ b/Sources/SwiftDriver/Jobs/AutolinkExtractJob.swift
@@ -43,12 +43,11 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .autolinkExtract,
-      tool: .absolute(try toolchain.getToolPath(.swiftAutolinkExtract)),
+      tool: try toolchain.resolvedTool(.swiftAutolinkExtract),
       commandLine: commandLine,
       inputs: inputs,
       primaryInputs: [],
-      outputs: [.init(file: output.intern(), type: .autolink)],
-      supportsResponseFiles: true
+      outputs: [.init(file: output.intern(), type: .autolink)]
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/BackendJob.swift b/Sources/SwiftDriver/Jobs/BackendJob.swift
index b5c5bd7c2..dc6fa0718 100644
--- a/Sources/SwiftDriver/Jobs/BackendJob.swift
+++ b/Sources/SwiftDriver/Jobs/BackendJob.swift
@@ -70,13 +70,12 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .backend,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: inputs,
       inputs: inputs,
       primaryInputs: [],
-      outputs: outputs,
-      supportsResponseFiles: true
+      outputs: outputs
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/CompileJob.swift b/Sources/SwiftDriver/Jobs/CompileJob.swift
index 8f5461c29..9aeb94e9f 100644
--- a/Sources/SwiftDriver/Jobs/CompileJob.swift
+++ b/Sources/SwiftDriver/Jobs/CompileJob.swift
@@ -383,14 +383,13 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .compile,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: displayInputs,
       inputs: inputs,
       primaryInputs: primaryInputs,
       outputs: outputs,
-      inputOutputMap: inputOutputMap,
-      supportsResponseFiles: true
+      inputOutputMap: inputOutputMap
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/DarwinToolchain+LinkerSupport.swift b/Sources/SwiftDriver/Jobs/DarwinToolchain+LinkerSupport.swift
index a70e91afd..0ed583ffa 100644
--- a/Sources/SwiftDriver/Jobs/DarwinToolchain+LinkerSupport.swift
+++ b/Sources/SwiftDriver/Jobs/DarwinToolchain+LinkerSupport.swift
@@ -206,7 +206,7 @@ extension DarwinToolchain {
     lto: LTOKind?,
     sanitizers: Set<Sanitizer>,
     targetInfo: FrontendTargetInfo
-  ) throws -> AbsolutePath {
+  ) throws -> ResolvedTool {
     // Set up for linking.
     let linkerTool: Tool
     switch linkerOutputType {
@@ -251,7 +251,7 @@ extension DarwinToolchain {
     commandLine.appendFlag("-o")
     commandLine.appendPath(outputFile)
 
-    return try getToolPath(linkerTool)
+    return try resolvedTool(linkerTool)
   }
 
   private func addLinkInputs(shouldUseInputFileList: Bool,
diff --git a/Sources/SwiftDriver/Jobs/EmitModuleJob.swift b/Sources/SwiftDriver/Jobs/EmitModuleJob.swift
index f501ea178..bdfb14610 100644
--- a/Sources/SwiftDriver/Jobs/EmitModuleJob.swift
+++ b/Sources/SwiftDriver/Jobs/EmitModuleJob.swift
@@ -120,7 +120,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .emitModule,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       inputs: inputs,
       primaryInputs: [],
diff --git a/Sources/SwiftDriver/Jobs/EmitSupportedFeaturesJob.swift b/Sources/SwiftDriver/Jobs/EmitSupportedFeaturesJob.swift
index 37e0b555f..460695273 100644
--- a/Sources/SwiftDriver/Jobs/EmitSupportedFeaturesJob.swift
+++ b/Sources/SwiftDriver/Jobs/EmitSupportedFeaturesJob.swift
@@ -40,14 +40,13 @@ extension Toolchain {
     return Job(
       moduleName: "",
       kind: .emitSupportedFeatures,
-      tool: .absolute(try getToolPath(.swiftCompiler)),
+      tool: try resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: [],
       inputs: inputs,
       primaryInputs: [],
       outputs: [.init(file: .standardOutput, type: .jsonCompilerFeatures)],
-      requiresInPlaceExecution: requiresInPlaceExecution,
-      supportsResponseFiles: false
+      requiresInPlaceExecution: requiresInPlaceExecution
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/GenerateDSYMJob.swift b/Sources/SwiftDriver/Jobs/GenerateDSYMJob.swift
index 525625ea6..c03348ee9 100644
--- a/Sources/SwiftDriver/Jobs/GenerateDSYMJob.swift
+++ b/Sources/SwiftDriver/Jobs/GenerateDSYMJob.swift
@@ -33,7 +33,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .generateDSYM,
-      tool: .absolute(try toolchain.getToolPath(.dsymutil)),
+      tool: try toolchain.resolvedTool(.dsymutil),
       commandLine: commandLine,
       displayInputs: [],
       inputs: inputs,
diff --git a/Sources/SwiftDriver/Jobs/GeneratePCHJob.swift b/Sources/SwiftDriver/Jobs/GeneratePCHJob.swift
index 299655652..5637c3760 100644
--- a/Sources/SwiftDriver/Jobs/GeneratePCHJob.swift
+++ b/Sources/SwiftDriver/Jobs/GeneratePCHJob.swift
@@ -64,13 +64,12 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .generatePCH,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: [],
       inputs: inputs,
       primaryInputs: [],
-      outputs: outputs,
-      supportsResponseFiles: true
+      outputs: outputs
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/GeneratePCMJob.swift b/Sources/SwiftDriver/Jobs/GeneratePCMJob.swift
index 305c107e2..7a75a22af 100644
--- a/Sources/SwiftDriver/Jobs/GeneratePCMJob.swift
+++ b/Sources/SwiftDriver/Jobs/GeneratePCMJob.swift
@@ -55,7 +55,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .generatePCM,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: [],
       inputs: inputs,
@@ -84,7 +84,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .dumpPCM,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: [],
       inputs: inputs,
diff --git a/Sources/SwiftDriver/Jobs/GenericUnixToolchain+LinkerSupport.swift b/Sources/SwiftDriver/Jobs/GenericUnixToolchain+LinkerSupport.swift
index 2da0f108c..ff2799a82 100644
--- a/Sources/SwiftDriver/Jobs/GenericUnixToolchain+LinkerSupport.swift
+++ b/Sources/SwiftDriver/Jobs/GenericUnixToolchain+LinkerSupport.swift
@@ -58,7 +58,7 @@ extension GenericUnixToolchain {
     lto: LTOKind?,
     sanitizers: Set<Sanitizer>,
     targetInfo: FrontendTargetInfo
-  ) throws -> AbsolutePath {
+  ) throws -> ResolvedTool {
     let targetTriple = targetInfo.target.triple
     switch linkerOutputType {
     case .dynamicLibrary:
@@ -103,9 +103,9 @@ extension GenericUnixToolchain {
       // Windows rather than msvcprt).  When C++ interop is enabled, we will need to
       // surface this via a driver flag.  For now, opt for the simpler approach of
       // just using `clang` and avoid a dependency on the C++ runtime.
-      var clangPath = try parsedOptions.hasArgument(.enableExperimentalCxxInterop)
-                          ? getToolPath(.clangxx)
-                          : getToolPath(.clang)
+      let clangTool: Tool =
+        parsedOptions.hasArgument(.enableExperimentalCxxInterop) ? .clangxx : .clang
+      var clangPath = try getToolPath(clangTool)
       if let toolsDirPath = parsedOptions.getLastArgument(.toolsDirectory) {
         // FIXME: What if this isn't an absolute path?
         let toolsDir = try AbsolutePath(validating: toolsDirPath.asSingle)
@@ -296,7 +296,7 @@ extension GenericUnixToolchain {
       // This should be the last option, for convenience in checking output.
       commandLine.appendFlag(.o)
       commandLine.appendPath(outputFile)
-      return clangPath
+      return try resolvedTool(clangTool, pathOverride: clangPath)
     case .staticLibrary:
       // We're using 'ar' as a linker
       commandLine.appendFlag("crs")
@@ -308,9 +308,9 @@ extension GenericUnixToolchain {
                          }.map { .path($0.file) })
       if targetTriple.environment == .android {
         // Always use the LTO archiver llvm-ar for Android
-        return try getToolPath(.staticLinker(.llvmFull))
+        return try resolvedTool(.staticLinker(.llvmFull))
       } else {
-        return try getToolPath(.staticLinker(lto))
+        return try resolvedTool(.staticLinker(lto))
       }
     }
 
diff --git a/Sources/SwiftDriver/Jobs/InterpretJob.swift b/Sources/SwiftDriver/Jobs/InterpretJob.swift
index aae66aca4..ba91f91cf 100644
--- a/Sources/SwiftDriver/Jobs/InterpretJob.swift
+++ b/Sources/SwiftDriver/Jobs/InterpretJob.swift
@@ -44,14 +44,13 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .interpret,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       inputs: inputs,
       primaryInputs: [],
       outputs: [],
       extraEnvironment: extraEnvironment,
-      requiresInPlaceExecution: true,
-      supportsResponseFiles: true
+      requiresInPlaceExecution: true
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/Job.swift b/Sources/SwiftDriver/Jobs/Job.swift
index 8263849ce..6eee77987 100644
--- a/Sources/SwiftDriver/Jobs/Job.swift
+++ b/Sources/SwiftDriver/Jobs/Job.swift
@@ -106,7 +106,7 @@ public struct Job: Codable, Equatable, Hashable {
   public init(
     moduleName: String,
     kind: Kind,
-    tool: VirtualPath,
+    tool: ResolvedTool,
     commandLine: [ArgTemplate],
     displayInputs: [TypedVirtualPath]? = nil,
     inputs: [TypedVirtualPath],
@@ -114,12 +114,11 @@ public struct Job: Codable, Equatable, Hashable {
     outputs: [TypedVirtualPath],
     inputOutputMap: [TypedVirtualPath : [TypedVirtualPath]] = [:],
     extraEnvironment: [String: String] = [:],
-    requiresInPlaceExecution: Bool = false,
-    supportsResponseFiles: Bool = false
+    requiresInPlaceExecution: Bool = false
   ) {
     self.moduleName = moduleName
     self.kind = kind
-    self.tool = tool
+    self.tool = .absolute(tool.path)
     self.commandLine = commandLine
     self.displayInputs = displayInputs ?? []
     self.inputs = inputs
@@ -128,7 +127,7 @@ public struct Job: Codable, Equatable, Hashable {
     self.compileInputOutputMap = inputOutputMap
     self.extraEnvironment = extraEnvironment
     self.requiresInPlaceExecution = requiresInPlaceExecution
-    self.supportsResponseFiles = supportsResponseFiles
+    self.supportsResponseFiles = tool.supportsResponseFiles
   }
 
   public var primarySwiftSourceFiles: [SwiftSourceFile] { primaryInputs.swiftSourceFiles }
diff --git a/Sources/SwiftDriver/Jobs/LinkJob.swift b/Sources/SwiftDriver/Jobs/LinkJob.swift
index 3ed9353ea..257c642c7 100644
--- a/Sources/SwiftDriver/Jobs/LinkJob.swift
+++ b/Sources/SwiftDriver/Jobs/LinkJob.swift
@@ -52,7 +52,7 @@ extension Driver {
     }
 
     // Defer to the toolchain for platform-specific linking
-    let toolPath = try toolchain.addPlatformSpecificLinkerArgs(
+    let linkTool = try toolchain.addPlatformSpecificLinkerArgs(
       to: &commandLine,
       parsedOptions: &parsedOptions,
       linkerOutputType: linkerOutputType!,
@@ -67,15 +67,12 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .link,
-      tool: .absolute(toolPath),
+      tool: linkTool,
       commandLine: commandLine,
       displayInputs: inputs,
       inputs: inputs,
       primaryInputs: [],
-      outputs: [.init(file: outputFile.intern(), type: .image)],
-      // FIXME: newer ld64 supports response files as well, though really,
-      // Darwin should use clang as the linker driver like the other targets
-      supportsResponseFiles: !frontendTargetInfo.target.triple.isDarwin
+      outputs: [.init(file: outputFile.intern(), type: .image)]
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/MergeModuleJob.swift b/Sources/SwiftDriver/Jobs/MergeModuleJob.swift
index 34788ccee..4f1cfc0ae 100644
--- a/Sources/SwiftDriver/Jobs/MergeModuleJob.swift
+++ b/Sources/SwiftDriver/Jobs/MergeModuleJob.swift
@@ -86,12 +86,11 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .mergeModule,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       inputs: inputs,
       primaryInputs: [],
-      outputs: outputs,
-      supportsResponseFiles: true
+      outputs: outputs
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/ModuleWrapJob.swift b/Sources/SwiftDriver/Jobs/ModuleWrapJob.swift
index 9f498b66d..4d3b6d342 100644
--- a/Sources/SwiftDriver/Jobs/ModuleWrapJob.swift
+++ b/Sources/SwiftDriver/Jobs/ModuleWrapJob.swift
@@ -29,12 +29,11 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .moduleWrap,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       inputs: [moduleInput],
       primaryInputs: [],
-      outputs: [.init(file: outputPath.intern(), type: .object)],
-      supportsResponseFiles: true
+      outputs: [.init(file: outputPath.intern(), type: .object)]
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/Planning.swift b/Sources/SwiftDriver/Jobs/Planning.swift
index 05d254842..d51bc20bf 100644
--- a/Sources/SwiftDriver/Jobs/Planning.swift
+++ b/Sources/SwiftDriver/Jobs/Planning.swift
@@ -672,7 +672,7 @@ extension Driver {
       return Job(
         moduleName: moduleOutputInfo.name,
         kind: .versionRequest,
-        tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+        tool: try toolchain.resolvedTool(.swiftCompiler),
         commandLine: [.flag("--version")],
         inputs: [],
         primaryInputs: [],
@@ -688,7 +688,7 @@ extension Driver {
       return Job(
         moduleName: moduleOutputInfo.name,
         kind: .help,
-        tool: .absolute(try toolchain.getToolPath(.swiftHelp)),
+        tool: try toolchain.resolvedTool(.swiftHelp),
         commandLine: commandLine,
         inputs: [],
         primaryInputs: [],
diff --git a/Sources/SwiftDriver/Jobs/PrebuiltModulesJob.swift b/Sources/SwiftDriver/Jobs/PrebuiltModulesJob.swift
index f05f38a2a..514400ca2 100644
--- a/Sources/SwiftDriver/Jobs/PrebuiltModulesJob.swift
+++ b/Sources/SwiftDriver/Jobs/PrebuiltModulesJob.swift
@@ -435,7 +435,7 @@ extension Driver {
     return Job(
       moduleName: moduleName,
       kind: .compareABIBaseline,
-      tool: .absolute(try toolchain.getToolPath(.swiftAPIDigester)),
+      tool: try toolchain.resolvedTool(.swiftAPIDigester),
       commandLine: commandLine,
       inputs: [currentABI, baselineABI],
       primaryInputs: [],
@@ -501,7 +501,7 @@ extension Driver {
     allJobs.append(Job(
       moduleName: moduleName,
       kind: .compile,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       inputs: allInputs,
       primaryInputs: [],
diff --git a/Sources/SwiftDriver/Jobs/PrintTargetInfoJob.swift b/Sources/SwiftDriver/Jobs/PrintTargetInfoJob.swift
index 8226ab9eb..a5ff3723b 100644
--- a/Sources/SwiftDriver/Jobs/PrintTargetInfoJob.swift
+++ b/Sources/SwiftDriver/Jobs/PrintTargetInfoJob.swift
@@ -163,14 +163,13 @@ extension Toolchain {
     return Job(
       moduleName: "",
       kind: .printTargetInfo,
-      tool: .absolute(try getToolPath(.swiftCompiler)),
+      tool: try resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: [],
       inputs: [],
       primaryInputs: [],
       outputs: [.init(file: .standardOutput, type: .jsonTargetInfo)],
-      requiresInPlaceExecution: requiresInPlaceExecution,
-      supportsResponseFiles: false
+      requiresInPlaceExecution: requiresInPlaceExecution
     )
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/ReplJob.swift b/Sources/SwiftDriver/Jobs/ReplJob.swift
index 74f4bbe00..94ef06700 100644
--- a/Sources/SwiftDriver/Jobs/ReplJob.swift
+++ b/Sources/SwiftDriver/Jobs/ReplJob.swift
@@ -30,7 +30,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .repl,
-      tool: .absolute(try toolchain.getToolPath(.lldb)),
+      tool: try toolchain.resolvedTool(.lldb),
       commandLine: lldbCommandLine,
       inputs: inputs,
       primaryInputs: [],
diff --git a/Sources/SwiftDriver/Jobs/SwiftHelpIntroJob.swift b/Sources/SwiftDriver/Jobs/SwiftHelpIntroJob.swift
index e04c15523..51c6f766c 100644
--- a/Sources/SwiftDriver/Jobs/SwiftHelpIntroJob.swift
+++ b/Sources/SwiftDriver/Jobs/SwiftHelpIntroJob.swift
@@ -17,7 +17,7 @@ extension Driver {
       Job(
         moduleName: moduleOutputInfo.name,
         kind: .help,
-        tool: .absolute(try toolchain.getToolPath(.swiftHelp)),
+        tool: try toolchain.resolvedTool(.swiftHelp),
         commandLine: [.flag("intro")],
         inputs: [],
         primaryInputs: [],
diff --git a/Sources/SwiftDriver/Jobs/VerifyDebugInfoJob.swift b/Sources/SwiftDriver/Jobs/VerifyDebugInfoJob.swift
index 86268cbb4..3b1c42a25 100644
--- a/Sources/SwiftDriver/Jobs/VerifyDebugInfoJob.swift
+++ b/Sources/SwiftDriver/Jobs/VerifyDebugInfoJob.swift
@@ -23,7 +23,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .verifyDebugInfo,
-      tool: .absolute(try toolchain.getToolPath(.dwarfdump)),
+      tool: try toolchain.resolvedTool(.dwarfdump),
       commandLine: commandLine,
       displayInputs: [],
       inputs: inputs,
diff --git a/Sources/SwiftDriver/Jobs/VerifyModuleInterfaceJob.swift b/Sources/SwiftDriver/Jobs/VerifyModuleInterfaceJob.swift
index fd7d8e951..11c88be09 100644
--- a/Sources/SwiftDriver/Jobs/VerifyModuleInterfaceJob.swift
+++ b/Sources/SwiftDriver/Jobs/VerifyModuleInterfaceJob.swift
@@ -33,7 +33,7 @@ extension Driver {
     return Job(
       moduleName: moduleOutputInfo.name,
       kind: .verifyModuleInterface,
-      tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+      tool: try toolchain.resolvedTool(.swiftCompiler),
       commandLine: commandLine,
       displayInputs: [interfaceInput],
       inputs: inputs,
diff --git a/Sources/SwiftDriver/Jobs/WebAssemblyToolchain+LinkerSupport.swift b/Sources/SwiftDriver/Jobs/WebAssemblyToolchain+LinkerSupport.swift
index 72f00e6be..012cb7745 100644
--- a/Sources/SwiftDriver/Jobs/WebAssemblyToolchain+LinkerSupport.swift
+++ b/Sources/SwiftDriver/Jobs/WebAssemblyToolchain+LinkerSupport.swift
@@ -23,7 +23,7 @@ extension WebAssemblyToolchain {
     lto: LTOKind?,
     sanitizers: Set<Sanitizer>,
     targetInfo: FrontendTargetInfo
-  ) throws -> AbsolutePath {
+  ) throws -> ResolvedTool {
     let targetTriple = targetInfo.target.triple
     switch linkerOutputType {
     case .dynamicLibrary:
@@ -151,14 +151,14 @@ extension WebAssemblyToolchain {
         // This should be the last option, for convenience in checking output.
       commandLine.appendFlag(.o)
       commandLine.appendPath(outputFile)
-      return clangPath
+      return try resolvedTool(.clang, pathOverride: clangPath)
     case .staticLibrary:
       // We're using 'ar' as a linker
       commandLine.appendFlag("crs")
       commandLine.appendPath(outputFile)
 
       commandLine.append(contentsOf: inputs.map { .path($0.file) })
-      return try getToolPath(.staticLinker(lto))
+      return try resolvedTool(.staticLinker(lto))
     }
   }
 }
diff --git a/Sources/SwiftDriver/Jobs/WindowsToolchain+LinkerSupport.swift b/Sources/SwiftDriver/Jobs/WindowsToolchain+LinkerSupport.swift
index 3851ae95b..2c7de9b84 100644
--- a/Sources/SwiftDriver/Jobs/WindowsToolchain+LinkerSupport.swift
+++ b/Sources/SwiftDriver/Jobs/WindowsToolchain+LinkerSupport.swift
@@ -36,7 +36,7 @@ extension WindowsToolchain {
                                             lto: LTOKind?,
                                             sanitizers: Set<Sanitizer>,
                                             targetInfo: FrontendTargetInfo)
-      throws -> AbsolutePath {
+    throws -> ResolvedTool {
     // Special case static linking as clang cannot drive the operation.
     if linkerOutputType == .staticLibrary {
       let librarian: String
@@ -57,12 +57,12 @@ extension WindowsToolchain {
       commandLine.append(contentsOf: inputs.lazy.filter { types.contains($0.type) }
                                                 .map { .path($0.file) })
 
-      return try lookup(executable: librarian)
+      return try resolvedTool(.staticLinker(lto), pathOverride: lookup(executable: librarian))
     }
 
-    var clang = try parsedOptions.hasArgument(.enableExperimentalCxxInterop)
-                    ? getToolPath(.clangxx)
-                    : getToolPath(.clang)
+    let clangTool: Tool =
+      parsedOptions.hasArgument(.enableExperimentalCxxInterop) ? .clangxx : .clang
+    var clang = try getToolPath(clangTool)
 
     let targetTriple = targetInfo.target.triple
     if !targetTriple.triple.isEmpty {
@@ -194,6 +194,6 @@ extension WindowsToolchain {
     addLinkedLibArgs(to: &commandLine, parsedOptions: &parsedOptions)
 
     // TODO(compnerd) handle static libraries
-    return clang
+    return try resolvedTool(clangTool, pathOverride: clang)
   }
 }
diff --git a/Sources/SwiftDriver/Toolchains/Toolchain.swift b/Sources/SwiftDriver/Toolchains/Toolchain.swift
index fe6205ad7..e01af7c51 100644
--- a/Sources/SwiftDriver/Toolchains/Toolchain.swift
+++ b/Sources/SwiftDriver/Toolchains/Toolchain.swift
@@ -26,6 +26,46 @@ public enum Tool: Hashable {
   case dwarfdump
   case swiftHelp
   case swiftAPIDigester
+
+  /// Returns a value indicating whether or not the tool supports passing arguments via response
+  /// files.
+  public func supportsResponseFiles(in toolchain: Toolchain) -> Bool {
+    switch self {
+    case .swiftCompiler, .clang, .clangxx, .swiftAutolinkExtract, .swiftAPIDigester:
+      return true
+
+    case .dsymutil, .lldb, .dwarfdump, .swiftHelp:
+      // NOTE: Consider *very carefully* whether a tool actually belongs here when adding a new
+      // entry. Incorrectly marking a tool as not supporting response files when it does may cause
+      // large builds to fail that would have otherwise succeeded.
+      return false
+
+    case .staticLinker, .dynamicLinker:
+      // FIXME: newer ld64 supports response files as well, though really,
+      // Darwin should use clang as the linker driver like the other targets
+      return !(toolchain is DarwinToolchain)
+    }
+  }
+}
+
+/// Encapsulates the path to a tool and the knowledge of whether or not it supports taking long
+/// command lines as response files.
+public struct ResolvedTool {
+  /// The absolute path to the tool's executable.
+  public var path: AbsolutePath
+
+  /// Indicates whether the tool can accept long command lines in a response file.
+  public var supportsResponseFiles: Bool
+
+  /// Creates a new resolved tool with the given path and response file nature.
+  ///
+  /// - Note: In most cases, you should **not** call this initializer directly. Instead, use the
+  /// `Toolchain.resolvedTool(_:pathOverride:)` method, which computes these values based on the
+  /// requested tool and toolchain.
+  @_spi(Testing) public init(path: AbsolutePath, supportsResponseFiles: Bool) {
+    self.path = path
+    self.supportsResponseFiles = supportsResponseFiles
+  }
 }
 
 /// Describes a toolchain, which includes information about compilers, linkers
@@ -88,7 +128,7 @@ public protocol Toolchain {
     lto: LTOKind?,
     sanitizers: Set<Sanitizer>,
     targetInfo: FrontendTargetInfo
-  ) throws -> AbsolutePath
+  ) throws -> ResolvedTool
 
   func runtimeLibraryName(
     for sanitizer: Sanitizer,
@@ -233,6 +273,23 @@ extension Toolchain {
     frontendTargetInfo: FrontendTargetInfo,
     driver: Driver
   ) throws {}
+
+  /// Resolves the path to the given tool and whether or not it supports response files so that it
+  /// can be passed to a job.
+  ///
+  /// - Parameters:
+  ///   - tool: The `Tool` to resolve. Whether or not the invocation supports response files is
+  ///     determined based on how this value responds to the `supportsResponseFiles(in:)` method.
+  ///   - pathOverride: If provided, this path will be used as the path to the tool's executable
+  ///     instead of the default path determined by the toolchain.
+  /// - Returns: A `ResolvedTool` value that provides the path and response file information about
+  ///   the tool when creating a `Job`.
+  public func resolvedTool(_ tool: Tool, pathOverride: AbsolutePath? = nil) throws -> ResolvedTool {
+    return ResolvedTool(
+      path: try pathOverride ?? getToolPath(tool),
+      supportsResponseFiles: tool.supportsResponseFiles(in: self)
+    )
+  }
 }
 
 @_spi(Testing) public enum ToolchainError: Swift.Error {
diff --git a/Tests/SwiftDriverTests/JobExecutorTests.swift b/Tests/SwiftDriverTests/JobExecutorTests.swift
index 283811a94..f66cdf052 100644
--- a/Tests/SwiftDriverTests/JobExecutorTests.swift
+++ b/Tests/SwiftDriverTests/JobExecutorTests.swift
@@ -130,7 +130,7 @@ final class JobExecutorTests: XCTestCase {
       let compileFoo = Job(
         moduleName: "main",
         kind: .compile,
-        tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+        tool: try toolchain.resolvedTool(.swiftCompiler),
         commandLine: [
           "-frontend",
           "-c",
@@ -152,7 +152,7 @@ final class JobExecutorTests: XCTestCase {
       let compileMain = Job(
         moduleName: "main",
         kind: .compile,
-        tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+        tool: try toolchain.resolvedTool(.swiftCompiler),
         commandLine: [
           "-frontend",
           "-c",
@@ -174,7 +174,7 @@ final class JobExecutorTests: XCTestCase {
       let link = Job(
         moduleName: "main",
         kind: .link,
-        tool: .absolute(try toolchain.getToolPath(.dynamicLinker)),
+        tool: try toolchain.resolvedTool(.dynamicLinker),
         commandLine: [
           .path(.temporary(RelativePath("foo.o"))),
           .path(.temporary(RelativePath("main.o"))),
@@ -224,7 +224,7 @@ final class JobExecutorTests: XCTestCase {
       let compile = Job(
         moduleName: "main",
         kind: .compile,
-        tool: .absolute(try toolchain.getToolPath(.swiftCompiler)),
+        tool: try toolchain.resolvedTool(.swiftCompiler),
         commandLine: [
           "-frontend",
           "-c",
@@ -246,7 +246,7 @@ final class JobExecutorTests: XCTestCase {
       let link = Job(
         moduleName: "main",
         kind: .link,
-        tool: .absolute(try toolchain.getToolPath(.dynamicLinker)),
+        tool: try toolchain.resolvedTool(.dynamicLinker),
         commandLine: [
           .path(.temporary(RelativePath("main.o"))),
           .path(.absolute(try toolchain.clangRT.get())),
@@ -294,7 +294,7 @@ final class JobExecutorTests: XCTestCase {
     let job = Job(
       moduleName: "main",
       kind: .compile,
-      tool: .absolute(AbsolutePath("/usr/bin/swift")),
+      tool: ResolvedTool(path: AbsolutePath("/usr/bin/swift"), supportsResponseFiles: false),
       commandLine: [.flag("something")],
       inputs: [],
       primaryInputs: [],
@@ -380,7 +380,9 @@ final class JobExecutorTests: XCTestCase {
                                            env: [:])
     let job = Job(moduleName: "Module",
                   kind: .compile,
-                  tool: .absolute(.init("/path/to/the tool")),
+                  tool: ResolvedTool(
+                    path: AbsolutePath("/path/to/the tool"),
+                    supportsResponseFiles: false),
                   commandLine: [.path(.absolute(.init("/with space"))),
                                 .path(.absolute(.init("/withoutspace")))],
                   inputs: [], primaryInputs: [], outputs: [])
diff --git a/Tests/SwiftDriverTests/ModuleDependencyGraphTests.swift b/Tests/SwiftDriverTests/ModuleDependencyGraphTests.swift
index 9e618bdda..998899c27 100644
--- a/Tests/SwiftDriverTests/ModuleDependencyGraphTests.swift
+++ b/Tests/SwiftDriverTests/ModuleDependencyGraphTests.swift
@@ -1451,7 +1451,7 @@ extension Job {
                                       type: .swift)
     try! self.init(moduleName: "nothing",
                    kind: .compile,
-                   tool: VirtualPath(path: ""),
+                   tool: ResolvedTool(path: AbsolutePath("/dummy"), supportsResponseFiles: false),
                    commandLine: [],
                    inputs:  [input],
                    primaryInputs: [input],
diff --git a/Tests/SwiftDriverTests/SwiftDriverTests.swift b/Tests/SwiftDriverTests/SwiftDriverTests.swift
index 7e038d525..33a19a206 100644
--- a/Tests/SwiftDriverTests/SwiftDriverTests.swift
+++ b/Tests/SwiftDriverTests/SwiftDriverTests.swift
@@ -1260,6 +1260,81 @@ final class SwiftDriverTests: XCTestCase {
     }
   }
 
+  func testSpecificJobsResponseFiles() throws {
+    // The jobs below often take large command lines (e.g., when passing a large number of Clang
+    // modules to Swift). Ensure that they don't regress in their ability to pass response files
+    // from the driver to the frontend.
+    let manyArgs = (1...20000).map { "-DTEST_\($0)" }
+
+    // Compile + separate emit module job
+    do {
+      let resolver = try ArgsResolver(fileSystem: localFileSystem)
+      var driver = try Driver(
+        args: ["swiftc", "-emit-module"] + manyArgs
+          + ["-module-name", "foo", "foo.swift", "bar.swift"])
+      let jobs = try driver.planBuild().removingAutolinkExtractJobs()
+      XCTAssertEqual(jobs.count, 3)
+      XCTAssertEqual(Set(jobs.map { $0.kind }), Set([.emitModule, .compile]))
+
+      let emitModuleJob = jobs.first(where: { $0.kind == .emitModule })!
+      let emitModuleResolvedArgs: [String] =
+        try resolver.resolveArgumentList(for: emitModuleJob, forceResponseFiles: false)
+      XCTAssertEqual(emitModuleResolvedArgs.count, 2)
+      XCTAssertEqual(emitModuleResolvedArgs[1].first, "@")
+
+      let compileJobs = jobs.filter { $0.kind == .compile }
+      for compileJob in compileJobs {
+        XCTAssertEqual(compileJobs.count, 2)
+        let compileResolvedArgs: [String] =
+          try resolver.resolveArgumentList(for: compileJob, forceResponseFiles: false)
+        XCTAssertEqual(compileResolvedArgs.count, 2)
+        XCTAssertEqual(compileResolvedArgs[1].first, "@")
+      }
+    }
+
+    // Compile + no separate emit module job
+    do {
+      let resolver = try ArgsResolver(fileSystem: localFileSystem)
+      var driver = try Driver(
+        args: ["swiftc", "-emit-module", "-no-emit-module-separately"] + manyArgs
+          + ["-module-name", "foo", "foo.swift", "bar.swift"])
+      let jobs = try driver.planBuild().removingAutolinkExtractJobs()
+      XCTAssertEqual(jobs.count, 3)
+      XCTAssertEqual(Set(jobs.map { $0.kind }), Set([.compile, .mergeModule]))
+
+      let mergeModuleJob = jobs.first(where: { $0.kind == .mergeModule })!
+      let mergeModuleResolvedArgs: [String] =
+        try resolver.resolveArgumentList(for: mergeModuleJob, forceResponseFiles: false)
+      XCTAssertEqual(mergeModuleResolvedArgs.count, 2)
+      XCTAssertEqual(mergeModuleResolvedArgs[1].first, "@")
+
+      let compileJobs = jobs.filter { $0.kind == .compile }
+      for compileJob in compileJobs {
+        XCTAssertEqual(compileJobs.count, 2)
+        let compileResolvedArgs: [String] =
+          try resolver.resolveArgumentList(for: compileJob, forceResponseFiles: false)
+        XCTAssertEqual(compileResolvedArgs.count, 2)
+        XCTAssertEqual(compileResolvedArgs[1].first, "@")
+      }
+    }
+
+    // Generate PCM (precompiled Clang module) job
+    do {
+      let resolver = try ArgsResolver(fileSystem: localFileSystem)
+      var driver = try Driver(
+        args: ["swiftc", "-emit-pcm"] + manyArgs + ["-module-name", "foo", "foo.modulemap"])
+      let jobs = try driver.planBuild().removingAutolinkExtractJobs()
+      XCTAssertEqual(jobs.count, 1)
+      XCTAssertEqual(jobs[0].kind, .generatePCM)
+
+      let generatePCMJob = jobs[0]
+      let generatePCMResolvedArgs: [String] =
+        try resolver.resolveArgumentList(for: generatePCMJob, forceResponseFiles: false)
+      XCTAssertEqual(generatePCMResolvedArgs.count, 2)
+      XCTAssertEqual(generatePCMResolvedArgs[1].first, "@")
+    }
+  }
+
   func testLinking() throws {
     var env = ProcessEnv.vars
     env["SWIFT_DRIVER_TESTS_ENABLE_EXEC_PATH_FALLBACK"] = "1"