@@ -39,7 +39,7 @@ export class ProjectBuildCache {
    * null === we haven't tried to initialize yet
    * undefined === unable to initialize
    */
-  private static _tarUtility: TarExecutable | null | undefined = null;
+  private static _tarUtilityPromise: Promise<TarExecutable | undefined> | null = null;
 
   private readonly _project: RushConfigurationProject;
   private readonly _localBuildCacheProvider: FileSystemBuildCacheProvider;
@@ -57,12 +57,12 @@ export class ProjectBuildCache {
     this._cacheId = cacheId;
   }
 
-  private static _tryGetTarUtility(terminal: ITerminal): TarExecutable | undefined {
-    if (ProjectBuildCache._tarUtility === null) {
-      ProjectBuildCache._tarUtility = TarExecutable.tryInitialize(terminal);
+  private static _tryGetTarUtility(terminal: ITerminal): Promise<TarExecutable | undefined> {
+    if (ProjectBuildCache._tarUtilityPromise === null) {
+      ProjectBuildCache._tarUtilityPromise = TarExecutable.tryInitializeAsync(terminal);
     }
 
-    return ProjectBuildCache._tarUtility;
+    return ProjectBuildCache._tarUtilityPromise;
   }
 
   public static async tryGetProjectBuildCache(
@@ -180,7 +180,7 @@ export class ProjectBuildCache {
       )
     );
 
-    const tarUtility: TarExecutable | undefined = ProjectBuildCache._tryGetTarUtility(terminal);
+    const tarUtility: TarExecutable | undefined = await ProjectBuildCache._tryGetTarUtility(terminal);
     let restoreSuccess: boolean = false;
     if (tarUtility && localCacheEntryPath) {
       const logFilePath: string = this._getTarLogFilePath();
@@ -263,7 +263,7 @@ export class ProjectBuildCache {
 
     let localCacheEntryPath: string | undefined;
 
-    const tarUtility: TarExecutable | undefined = ProjectBuildCache._tryGetTarUtility(terminal);
+    const tarUtility: TarExecutable | undefined = await ProjectBuildCache._tryGetTarUtility(terminal);
     if (tarUtility) {
       const tempLocalCacheEntryPath: string = this._localBuildCacheProvider.getCacheEntryPath(cacheId);
       const logFilePath: string = this._getTarLogFilePath();
 
@@ -2,6 +2,7 @@
 // See LICENSE in the project root for license information.
 
 import * as path from 'path';
+import os from 'os';
 import { Executable, FileSystem, FileWriter, ITerminal } from '@rushstack/node-core-library';
 import { ChildProcess } from 'child_process';
 import events from 'events';
@@ -31,10 +32,10 @@ export class TarExecutable {
     this._tarExecutablePath = tarExecutablePath;
   }
 
-  public static tryInitialize(terminal: ITerminal): TarExecutable | undefined {
+  public static async tryInitializeAsync(terminal: ITerminal): Promise<TarExecutable | undefined> {
     terminal.writeVerboseLine('Trying to find "tar" binary');
     const tarExecutablePath: string | undefined =
-      EnvironmentConfiguration.tarBinaryPath || Executable.tryResolve('tar');
+      EnvironmentConfiguration.tarBinaryPath || (await TarExecutable._tryFindTarExecutablePathAsync());
     if (!tarExecutablePath) {
       terminal.writeVerboseLine('"tar" was not found on the PATH');
       return undefined;
@@ -163,4 +164,22 @@ export class TarExecutable {
 
     return tarExitCode;
   }
+
+  private static async _tryFindTarExecutablePathAsync(): Promise<string | undefined> {
+    if (os.platform() === 'win32') {
+      // If we're running on Windows, first try to use the OOB tar executable. If
+      // we're running in the Git Bash, the tar executable on the PATH doesn't handle
+      // Windows file paths correctly.
+      // eslint-disable-next-line dot-notation
+      const windowsFolderPath: string | undefined = process.env['WINDIR'];
+      if (windowsFolderPath) {
+        const defaultWindowsTarExecutablePath: string = `${windowsFolderPath}\\system32\\tar.exe`;
+        if (await FileSystem.existsAsync(defaultWindowsTarExecutablePath)) {
+          return defaultWindowsTarExecutablePath;
+        }
+      }
+    }
+
+    return Executable.tryResolve('tar');
+  }
 }