diff --git a/lib/src/executable.dart b/lib/src/executable.dart
index 7a1e9e3b..651b7f1f 100644
--- a/lib/src/executable.dart
+++ b/lib/src/executable.dart
@@ -4,50 +4,42 @@ import 'dart:io';
 import 'package:analyzer/dart/analysis/utilities.dart';
 import 'package:args/command_runner.dart';
 import 'package:dart_dev/dart_dev.dart';
-import 'package:dart_dev/src/dart_dev_tool.dart';
-import 'package:dart_dev/src/utils/format_tool_builder.dart';
-import 'package:dart_dev/src/utils/parse_flag_from_args.dart';
 import 'package:io/ansi.dart';
 import 'package:io/io.dart' show ExitCode;
 import 'package:logging/logging.dart';
 import 'package:path/path.dart' as p;
 
-import '../utils.dart';
 import 'dart_dev_runner.dart';
 import 'tools/over_react_format_tool.dart';
 import 'utils/assert_dir_is_dart_package.dart';
+import 'utils/cached_pubspec.dart';
+import 'utils/dart_dev_paths.dart';
 import 'utils/dart_tool_cache.dart';
 import 'utils/ensure_process_exit.dart';
+import 'utils/format_tool_builder.dart';
 import 'utils/logging.dart';
+import 'utils/parse_flag_from_args.dart';
 
 typedef _ConfigGetter = Map<String, DevTool> Function();
 
-final _runScriptPath = p.join(cacheDirPath, 'run.dart');
+final paths = DartDevPaths();
 
-final _runScript = File(_runScriptPath);
-
-const _configPath = 'tool/dart_dev/config.dart';
-
-const _oldDevDartPath = 'tool/dev.dart';
-
-final _relativeDevDartPath = p.relative(
-  p.absolute(_configPath),
-  from: p.absolute(p.dirname(_runScriptPath)),
-);
+final _runScript = File(paths.runScript);
 
 Future<void> run(List<String> args) async {
   attachLoggerToStdio(args);
-  final configExists = File(_configPath).existsSync();
-  final oldDevDartExists = File(_oldDevDartPath).existsSync();
+
+  final configExists = File(paths.config).existsSync();
+  final oldDevDartExists = File(paths.legacyConfig).existsSync();
 
   if (!configExists) {
-    log.fine('No custom `tool/dart_dev/config.dart` file found; '
+    log.fine('No custom `${paths.config}` file found; '
         'using default config.');
   }
   if (oldDevDartExists) {
     log.warning(yellow.wrap(
-        'dart_dev v3 now expects configuration to be at `$_configPath`,\n'
-        'but `$_oldDevDartPath` still exists. View the guide to see how to upgrade:\n'
+        'dart_dev v3 now expects configuration to be at `${paths.config}`,\n'
+        'but `${paths.legacyConfig}` still exists. View the guide to see how to upgrade:\n'
         'https://github.com/Workiva/dart_dev/blob/master/doc/v3-upgrade-guide.md'));
   }
 
@@ -59,7 +51,7 @@ Future<void> run(List<String> args) async {
 
   generateRunScript();
   final process = await Process.start(
-      Platform.executable, [_runScriptPath, ...args],
+      Platform.executable, [paths.runScript, ...args],
       mode: ProcessStartMode.inheritStdio);
   ensureProcessExit(process);
   exitCode = await process.exitCode;
@@ -69,7 +61,7 @@ Future<void> handleFastFormat(List<String> args) async {
   assertDirIsDartPackage();
 
   DevTool formatTool;
-  final configFile = File(_configPath);
+  final configFile = File(paths.config);
   if (configFile.existsSync()) {
     final toolBuilder = FormatToolBuilder();
     parseString(content: configFile.readAsStringSync())
@@ -115,13 +107,13 @@ bool get shouldWriteRunScript =>
     _runScript.readAsStringSync() != buildDartDevRunScriptContents();
 
 String buildDartDevRunScriptContents() {
-  final hasCustomToolDevDart = File(_configPath).existsSync();
+  final hasCustomToolDevDart = File(paths.config).existsSync();
   return '''
 import 'dart:io';
 
 import 'package:dart_dev/src/core_config.dart';
 import 'package:dart_dev/src/executable.dart' as executable;
-${hasCustomToolDevDart ? "import '$_relativeDevDartPath' as custom_dev;" : ""}
+${hasCustomToolDevDart ? "import '${paths.configFromRunScriptForDart}' as custom_dev;" : ""}
 
 void main(List<String> args) async {
   await executable.runWithConfig(args,
@@ -146,8 +138,7 @@ Future<void> runWithConfig(
     config = configGetter();
   } catch (error) {
     stderr
-      ..writeln(
-          'Invalid "tool/dart_dev/config.dart" in ${p.absolute(p.current)}')
+      ..writeln('Invalid "${paths.config}" in ${p.absolute(p.current)}')
       ..writeln()
       ..writeln('It should provide a `Map<String, DevTool> config;` getter,'
           ' but it either does not exist or threw unexpectedly:')
diff --git a/lib/src/tools/analyze_tool.dart b/lib/src/tools/analyze_tool.dart
index 43188a86..57007a80 100644
--- a/lib/src/tools/analyze_tool.dart
+++ b/lib/src/tools/analyze_tool.dart
@@ -8,6 +8,7 @@ import 'package:logging/logging.dart';
 import '../dart_dev_tool.dart';
 import '../utils/arg_results_utils.dart';
 import '../utils/assert_no_positional_args_nor_args_after_separator.dart';
+import '../utils/executables.dart' as exe;
 import '../utils/logging.dart';
 import '../utils/process_declaration.dart';
 import '../utils/run_process_and_ensure_exit.dart';
@@ -161,7 +162,7 @@ ProcessDeclaration buildProcess(
       verbose: context.verbose);
   final entrypoints = buildEntrypoints(include: include, root: path);
   logCommand(args, entrypoints, verbose: context.verbose);
-  return ProcessDeclaration('dartanalyzer', [...args, ...entrypoints],
+  return ProcessDeclaration(exe.dartanalyzer, [...args, ...entrypoints],
       mode: ProcessStartMode.inheritStdio);
 }
 
diff --git a/lib/src/tools/format_tool.dart b/lib/src/tools/format_tool.dart
index 4f1d5375..048f8675 100644
--- a/lib/src/tools/format_tool.dart
+++ b/lib/src/tools/format_tool.dart
@@ -12,6 +12,7 @@ import '../../utils.dart';
 import '../dart_dev_tool.dart';
 import '../utils/arg_results_utils.dart';
 import '../utils/assert_no_positional_args_nor_args_after_separator.dart';
+import '../utils/executables.dart' as exe;
 import '../utils/logging.dart';
 import '../utils/organize_directives/organize_directives_in_paths.dart';
 import '../utils/package_is_immediate_dependency.dart';
@@ -537,10 +538,10 @@ FormatExecution buildExecution(
 ProcessDeclaration buildFormatProcess([Formatter formatter]) {
   switch (formatter) {
     case Formatter.dartStyle:
-      return ProcessDeclaration('pub', ['run', 'dart_style:format']);
+      return ProcessDeclaration(exe.pub, ['run', 'dart_style:format']);
     case Formatter.dartfmt:
     default:
-      return ProcessDeclaration('dartfmt', []);
+      return ProcessDeclaration(exe.dartfmt, []);
   }
 }
 
diff --git a/lib/src/tools/over_react_format_tool.dart b/lib/src/tools/over_react_format_tool.dart
index f9899d1b..2951a7b7 100644
--- a/lib/src/tools/over_react_format_tool.dart
+++ b/lib/src/tools/over_react_format_tool.dart
@@ -5,6 +5,7 @@ import 'package:dart_dev/dart_dev.dart';
 import 'package:dart_dev/utils.dart';
 
 import '../tools/format_tool.dart';
+import '../utils/executables.dart' as exe;
 
 class OverReactFormatTool extends DevTool {
   /// Wrap lines longer than this.
@@ -31,9 +32,9 @@ class OverReactFormatTool extends DevTool {
       'over_react_format',
       if (lineLength != null) '--line-length=$lineLength'
     ];
-    final process = ProcessDeclaration('pub', [...args, ...paths],
+    final process = ProcessDeclaration(exe.pub, [...args, ...paths],
         mode: ProcessStartMode.inheritStdio);
-    logCommand('pub', paths, args, verbose: context?.verbose);
+    logCommand(exe.pub, paths, args, verbose: context?.verbose);
     return runProcessAndEnsureExit(process);
   }
 }
diff --git a/lib/src/tools/test_tool.dart b/lib/src/tools/test_tool.dart
index f621eda8..45d06da8 100644
--- a/lib/src/tools/test_tool.dart
+++ b/lib/src/tools/test_tool.dart
@@ -9,6 +9,7 @@ import 'package:logging/logging.dart';
 
 import '../dart_dev_tool.dart';
 import '../utils/arg_results_utils.dart';
+import '../utils/executables.dart' as exe;
 import '../utils/logging.dart';
 import '../utils/package_is_immediate_dependency.dart';
 import '../utils/process_declaration.dart';
@@ -315,7 +316,7 @@ TestExecution buildExecution(
       verbose: context.verbose);
   logSubprocessHeader(_log, 'pub ${args.join(' ')}'.trim());
   return TestExecution.process(
-      ProcessDeclaration('pub', args, mode: ProcessStartMode.inheritStdio));
+      ProcessDeclaration(exe.pub, args, mode: ProcessStartMode.inheritStdio));
 }
 
 // NOTE: This currently depends on https://github.com/dart-lang/build/pull/2445
diff --git a/lib/src/tools/tuneup_check_tool.dart b/lib/src/tools/tuneup_check_tool.dart
index 2af9e304..fa5206d8 100644
--- a/lib/src/tools/tuneup_check_tool.dart
+++ b/lib/src/tools/tuneup_check_tool.dart
@@ -9,6 +9,7 @@ import 'package:logging/logging.dart';
 import '../dart_dev_tool.dart';
 import '../utils/arg_results_utils.dart';
 import '../utils/assert_no_positional_args_nor_args_after_separator.dart';
+import '../utils/executables.dart' as exe;
 import '../utils/logging.dart';
 import '../utils/package_is_immediate_dependency.dart';
 import '../utils/process_declaration.dart';
@@ -152,5 +153,5 @@ TuneupExecution buildExecution(
       verbose: context.verbose);
   logSubprocessHeader(_log, 'pub ${args.join(' ')}');
   return TuneupExecution.process(
-      ProcessDeclaration('pub', args, mode: ProcessStartMode.inheritStdio));
+      ProcessDeclaration(exe.pub, args, mode: ProcessStartMode.inheritStdio));
 }
diff --git a/lib/src/tools/webdev_serve_tool.dart b/lib/src/tools/webdev_serve_tool.dart
index 69f3ba4f..dfabc339 100644
--- a/lib/src/tools/webdev_serve_tool.dart
+++ b/lib/src/tools/webdev_serve_tool.dart
@@ -10,6 +10,7 @@ import 'package:pub_semver/pub_semver.dart';
 import '../dart_dev_tool.dart';
 import '../utils/arg_results_utils.dart';
 import '../utils/assert_no_positional_args_nor_args_after_separator.dart';
+import '../utils/executables.dart' as exe;
 import '../utils/global_package_is_active_and_compatible.dart';
 import '../utils/logging.dart';
 import '../utils/process_declaration.dart';
@@ -226,5 +227,5 @@ WebdevServeExecution buildExecution(
       verbose: context.verbose);
   logSubprocessHeader(_log, 'pub ${args.join(' ')}'.trim());
   return WebdevServeExecution.process(
-      ProcessDeclaration('pub', args, mode: ProcessStartMode.inheritStdio));
+      ProcessDeclaration(exe.pub, args, mode: ProcessStartMode.inheritStdio));
 }
diff --git a/lib/src/utils/dart_dev_paths.dart b/lib/src/utils/dart_dev_paths.dart
new file mode 100644
index 00000000..6d83a038
--- /dev/null
+++ b/lib/src/utils/dart_dev_paths.dart
@@ -0,0 +1,31 @@
+import 'package:path/path.dart' as p;
+
+/// A collection of paths to files and directories constructed to be compatible
+/// with a given [p.Context].
+class DartDevPaths {
+  final p.Context _context;
+
+  DartDevPaths({p.Context context}) : _context = context ?? p.context;
+
+  String cache([String subPath]) => _context.normalize(
+      _context.joinAll([..._cacheParts, if (subPath != null) subPath]));
+
+  String get _cacheForDart => p.url.joinAll(_cacheParts);
+
+  final List<String> _cacheParts = ['.dart_tool', 'dart_dev'];
+
+  String get config => _context.joinAll(_configParts);
+
+  String get configForDart => p.url.joinAll(_configParts);
+
+  final List<String> _configParts = ['tool', 'dart_dev', 'config.dart'];
+
+  String get configFromRunScriptForDart => p.url.relative(
+        p.url.absolute(configForDart),
+        from: p.url.absolute(_cacheForDart),
+      );
+
+  String get legacyConfig => _context.join('tool', 'dev.dart');
+
+  String get runScript => cache('run.dart');
+}
diff --git a/lib/src/utils/dart_tool_cache.dart b/lib/src/utils/dart_tool_cache.dart
index 00a6772b..21d05a00 100644
--- a/lib/src/utils/dart_tool_cache.dart
+++ b/lib/src/utils/dart_tool_cache.dart
@@ -1,15 +1,9 @@
 import 'dart:io';
 
-import 'package:path/path.dart' as p;
-
-const cacheDirPath = '.dart_tool/dart_dev';
+import 'package:dart_dev/src/utils/dart_dev_paths.dart';
 
 void createCacheDir({String subPath}) {
-  var path = cacheDirPath;
-  if (subPath != null) {
-    path = p.join(path, subPath);
-  }
-  final dir = Directory(path);
+  final dir = Directory(DartDevPaths().cache(subPath));
   if (!dir.existsSync()) {
     dir.createSync(recursive: true);
   }
diff --git a/lib/src/utils/executables.dart b/lib/src/utils/executables.dart
new file mode 100644
index 00000000..7a5bac6d
--- /dev/null
+++ b/lib/src/utils/executables.dart
@@ -0,0 +1,9 @@
+import 'dart:io';
+
+final dart = 'dart';
+
+final dartanalyzer = Platform.isWindows ? 'dartanalyzer.bat' : 'dartanalyzer';
+
+final dartfmt = Platform.isWindows ? 'dartfmt.bat' : 'dartfmt';
+
+final pub = Platform.isWindows ? 'pub.bat' : 'pub';
diff --git a/lib/src/utils/global_package_is_active_and_compatible.dart b/lib/src/utils/global_package_is_active_and_compatible.dart
index 600187ea..33cb4ff2 100644
--- a/lib/src/utils/global_package_is_active_and_compatible.dart
+++ b/lib/src/utils/global_package_is_active_and_compatible.dart
@@ -3,6 +3,8 @@ import 'dart:io';
 
 import 'package:pub_semver/pub_semver.dart';
 
+import 'executables.dart' as exe;
+
 /// Returns `true` if [packageName] is globally activated at a version
 /// allowed by [constraint]. Returns `false` otherwise.
 ///
@@ -16,9 +18,9 @@ import 'package:pub_semver/pub_semver.dart';
 bool globalPackageIsActiveAndCompatible(
     String packageName, VersionConstraint constraint,
     {Map<String, String> environment}) {
-  final executable = 'pub';
+  final executable = exe.pub;
   final args = ['global', 'list'];
-  final result = Process.runSync('pub', ['global', 'list'],
+  final result = Process.runSync(exe.pub, ['global', 'list'],
       environment: environment, stderrEncoding: utf8, stdoutEncoding: utf8);
   if (result.exitCode != 0) {
     throw ProcessException(
diff --git a/test/utils/dart_dev_paths_test.dart b/test/utils/dart_dev_paths_test.dart
new file mode 100644
index 00000000..c64f7c2b
--- /dev/null
+++ b/test/utils/dart_dev_paths_test.dart
@@ -0,0 +1,73 @@
+import 'package:dart_dev/src/utils/dart_dev_paths.dart';
+import 'package:path/path.dart' as p;
+import 'package:test/test.dart';
+
+void main() {
+  group('DartDevPaths', () {
+    group('posix', () {
+      DartDevPaths paths;
+
+      setUp(() {
+        paths = DartDevPaths(context: p.posix);
+      });
+
+      test('cache', () {
+        expect(paths.cache(), '.dart_tool/dart_dev');
+      });
+
+      test('cache with subpath', () {
+        expect(paths.cache('sub/path'), '.dart_tool/dart_dev/sub/path');
+      });
+
+      test('config', () {
+        expect(paths.config, 'tool/dart_dev/config.dart');
+      });
+
+      test('configFromRunScriptForDart', () {
+        expect(paths.configFromRunScriptForDart,
+            '../../tool/dart_dev/config.dart');
+      });
+
+      test('legacyConfig', () {
+        expect(paths.legacyConfig, 'tool/dev.dart');
+      });
+
+      test('runScript', () {
+        expect(paths.runScript, '.dart_tool/dart_dev/run.dart');
+      });
+    });
+
+    group('windows', () {
+      DartDevPaths paths;
+
+      setUp(() {
+        paths = DartDevPaths(context: p.windows);
+      });
+
+      test('cache', () {
+        expect(paths.cache(), r'.dart_tool\dart_dev');
+      });
+
+      test('cache with subpath', () {
+        expect(paths.cache('sub/path'), r'.dart_tool\dart_dev\sub\path');
+      });
+
+      test('config', () {
+        expect(paths.config, r'tool\dart_dev\config.dart');
+      });
+
+      test('configFromRunScriptForDart', () {
+        expect(paths.configFromRunScriptForDart,
+            r'../../tool/dart_dev/config.dart');
+      });
+
+      test('legacyConfig', () {
+        expect(paths.legacyConfig, r'tool\dev.dart');
+      });
+
+      test('runScript', () {
+        expect(paths.runScript, r'.dart_tool\dart_dev\run.dart');
+      });
+    });
+  });
+}