diff --git a/src/ClaudeDo.Data/Environment/ExecutableResolver.cs b/src/ClaudeDo.Data/Environment/ExecutableResolver.cs
new file mode 100644
index 00000000..a859dc14
--- /dev/null
+++ b/src/ClaudeDo.Data/Environment/ExecutableResolver.cs
@@ -0,0 +1,112 @@
+using SysEnvironment = System.Environment;
+
+namespace ClaudeDo.Data.Environment;
+
+public sealed record ResolvedExecutable(string Path, bool IsShim);
+
+public sealed record ShimStartInfo(string FileName, string Arguments);
+
+/// <summary>
+/// Resolves a command the way Windows' CreateProcess/PATH search does, but also finds
+/// non-.exe shims (.cmd/.bat/.ps1) that UseShellExecute=false alone would miss.
+/// </summary>
+public static class ExecutableResolver
+{
+    private const string DefaultPathExt = ".COM;.EXE;.BAT;.CMD";
+
+    // Known npm/claude install locations to try when PATH search comes up empty.
+    private static readonly string[] FallbackDirectoryTemplates =
+    {
+        "%APPDATA%\\npm",
+        "%LOCALAPPDATA%\\Programs\\claude",
+        "%USERPROFILE%\\.local\\bin",
+    };
+
+    public static ResolvedExecutable? Resolve(string command, string? pathOverride = null, string? pathExtOverride = null)
+    {
+        var pathExts = ParsePathExt(pathExtOverride);
+
+        if (LooksLikePath(command))
+        {
+            return ResolveAsPath(command, pathExts);
+        }
+
+        var directories = ParsePath(pathOverride);
+        foreach (var dir in directories)
+        {
+            var resolved = ResolveInDirectory(dir, command, pathExts);
+            if (resolved is not null) return resolved;
+        }
+
+        foreach (var template in FallbackDirectoryTemplates)
+        {
+            var dir = SysEnvironment.ExpandEnvironmentVariables(template);
+            var resolved = ResolveInDirectory(dir, command, pathExts);
+            if (resolved is not null) return resolved;
+        }
+
+        return null;
+    }
+
+    public static ShimStartInfo BuildShimStartInfo(string shimPath, IReadOnlyList<string> arguments)
+    {
+        var parts = new List<string> { "/c", Quote(shimPath) };
+        parts.AddRange(arguments.Select(Quote));
+        return new ShimStartInfo("cmd.exe", string.Join(' ', parts));
+    }
+
+    private static bool LooksLikePath(string command) =>
+        command.Contains(Path.DirectorySeparatorChar) || command.Contains(Path.AltDirectorySeparatorChar);
+
+    private static ResolvedExecutable? ResolveAsPath(string command, IReadOnlyList<string> pathExts)
+    {
+        if (File.Exists(command)) return new ResolvedExecutable(command, IsShimExtension(Path.GetExtension(command)));
+
+        if (Path.HasExtension(command)) return null;
+
+        foreach (var ext in pathExts)
+        {
+            var candidate = command + ext;
+            if (File.Exists(candidate)) return new ResolvedExecutable(candidate, IsShimExtension(ext));
+        }
+
+        return null;
+    }
+
+    private static ResolvedExecutable? ResolveInDirectory(string directory, string command, IReadOnlyList<string> pathExts)
+    {
+        if (!Directory.Exists(directory)) return null;
+
+        if (Path.HasExtension(command))
+        {
+            var candidate = Path.Combine(directory, command);
+            return File.Exists(candidate) ? new ResolvedExecutable(candidate, IsShimExtension(Path.GetExtension(candidate))) : null;
+        }
+
+        foreach (var ext in pathExts)
+        {
+            var candidate = Path.Combine(directory, command + ext);
+            if (File.Exists(candidate)) return new ResolvedExecutable(candidate, IsShimExtension(ext));
+        }
+
+        return null;
+    }
+
+    private static bool IsShimExtension(string extension) =>
+        !extension.Equals(".exe", StringComparison.OrdinalIgnoreCase)
+        && !extension.Equals(".com", StringComparison.OrdinalIgnoreCase);
+
+    private static IReadOnlyList<string> ParsePathExt(string? pathExtOverride)
+    {
+        var raw = pathExtOverride ?? SysEnvironment.GetEnvironmentVariable("PATHEXT") ?? DefaultPathExt;
+        return raw.Split(';', StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries);
+    }
+
+    private static IReadOnlyList<string> ParsePath(string? pathOverride)
+    {
+        var raw = pathOverride ?? SysEnvironment.GetEnvironmentVariable("PATH") ?? "";
+        return raw.Split(Path.PathSeparator, StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries);
+    }
+
+    private static string Quote(string value) => value.Contains(' ') ? $"\"{value}\"" : value;
+}
diff --git a/src/ClaudeDo.Data/Paths.cs b/src/ClaudeDo.Data/Paths.cs
index c55037fa..093caa4f 100644
--- a/src/ClaudeDo.Data/Paths.cs
+++ b/src/ClaudeDo.Data/Paths.cs
@@ -11,16 +11,16 @@ public static class Paths
         if (string.IsNullOrWhiteSpace(path))
             throw new ArgumentException("Path must not be empty.", nameof(path));
 
-        var expanded = Environment.ExpandEnvironmentVariables(path);
+        var expanded = System.Environment.ExpandEnvironmentVariables(path);
 
         if (expanded.StartsWith("~", StringComparison.Ordinal))
         {
-            var home = Environment.GetFolderPath(Environment.SpecialFolder.UserProfile);
+            var home = System.Environment.GetFolderPath(System.Environment.SpecialFolder.UserProfile);
             expanded = home + expanded[1..];
         }
 
         if (!Path.IsPathRooted(expanded))
-            expanded = Path.GetFullPath(expanded, baseDir ?? Environment.CurrentDirectory);
+            expanded = Path.GetFullPath(expanded, baseDir ?? System.Environment.CurrentDirectory);
 
         return Path.GetFullPath(expanded);
     }
diff --git a/src/ClaudeDo.Worker/Lifecycle/ClaudeCliPreflight.cs b/src/ClaudeDo.Worker/Lifecycle/ClaudeCliPreflight.cs
index 1839e19d..26ceeda2 100644
--- a/src/ClaudeDo.Worker/Lifecycle/ClaudeCliPreflight.cs
+++ b/src/ClaudeDo.Worker/Lifecycle/ClaudeCliPreflight.cs
@@ -1,4 +1,5 @@
 using System.Diagnostics;
+using ClaudeDo.Data.Environment;
 
 namespace ClaudeDo.Worker.Lifecycle;
 
@@ -8,17 +9,23 @@ public static class ClaudeCliPreflight
 
     public static async Task<Result> CheckAsync(string claudeBin, CancellationToken ct = default)
     {
+        var resolved = ExecutableResolver.Resolve(claudeBin);
+        if (resolved is null)
+            return new Result(false, "", $"'{claudeBin}' not found on PATH.", -1);
+
         try
         {
-            var psi = new ProcessStartInfo
-            {
-                FileName = claudeBin,
-                Arguments = "--version",
-                UseShellExecute = false,
-                RedirectStandardOutput = true,
-                RedirectStandardError = true,
-                CreateNoWindow = true,
-            };
+            var psi = resolved.IsShim
+                ? BuildShimPsi(resolved.Path)
+                : new ProcessStartInfo
+                {
+                    FileName = resolved.Path,
+                    Arguments = "--version",
+                    UseShellExecute = false,
+                    RedirectStandardOutput = true,
+                    RedirectStandardError = true,
+                    CreateNoWindow = true,
+                };
             using var proc = Process.Start(psi);
             if (proc is null) return new Result(false, "", "Process.Start returned null", -1);
 
@@ -35,4 +42,18 @@ public static class ClaudeCliPreflight
             return new Result(false, "", ex.Message, -1);
         }
     }
+
+    private static ProcessStartInfo BuildShimPsi(string shimPath)
+    {
+        var shim = ExecutableResolver.BuildShimStartInfo(shimPath, new[] { "--version" });
+        return new ProcessStartInfo
+        {
+            FileName = shim.FileName,
+            Arguments = shim.Arguments,
+            UseShellExecute = false,
+            RedirectStandardOutput = true,
+            RedirectStandardError = true,
+            CreateNoWindow = true,
+        };
+    }
 }
diff --git a/src/ClaudeDo.Worker/Runner/ClaudeProcess.cs b/src/ClaudeDo.Worker/Runner/ClaudeProcess.cs
index d94b10ac..0ecd94b5 100644
--- a/src/ClaudeDo.Worker/Runner/ClaudeProcess.cs
+++ b/src/ClaudeDo.Worker/Runner/ClaudeProcess.cs
@@ -1,5 +1,6 @@
 using System.Diagnostics;
 using System.Text;
+using ClaudeDo.Data.Environment;
 using ClaudeDo.Worker.Config;
 
 namespace ClaudeDo.Worker.Runner;
@@ -24,9 +25,11 @@ public sealed class ClaudeProcess : IClaudeProcess
         Func<string, Task> onStdoutLine,
         CancellationToken ct)
     {
+        var resolved = ExecutableResolver.Resolve(_cfg.ClaudeBin)
+            ?? throw new InvalidOperationException($"'{_cfg.ClaudeBin}' not found on PATH.");
+
         var psi = new ProcessStartInfo
         {
-            FileName = _cfg.ClaudeBin,
             WorkingDirectory = workingDirectory,
             RedirectStandardInput = true,
             RedirectStandardOutput = true,
@@ -36,6 +39,20 @@ public sealed class ClaudeProcess : IClaudeProcess
             StandardOutputEncoding = Encoding.UTF8,
             StandardErrorEncoding = Encoding.UTF8,
         };
+
+        // A shim (.cmd/.bat) can't be launched directly with UseShellExecute=false;
+        // route it through cmd.exe /c so the real interpreter starts the target.
+        if (resolved.IsShim)
+        {
+            psi.FileName = "cmd.exe";
+            psi.ArgumentList.Add("/c");
+            psi.ArgumentList.Add(resolved.Path);
+        }
+        else
+        {
+            psi.FileName = resolved.Path;
+        }
+
         foreach (var arg in arguments)
             psi.ArgumentList.Add(arg);
 
diff --git a/tests/ClaudeDo.Data.Tests/ExecutableResolverTests.cs b/tests/ClaudeDo.Data.Tests/ExecutableResolverTests.cs
new file mode 100644
index 00000000..2160379a
--- /dev/null
+++ b/tests/ClaudeDo.Data.Tests/ExecutableResolverTests.cs
@@ -0,0 +1,127 @@
+using ClaudeDo.Data.Environment;
+
+namespace ClaudeDo.Data.Tests;
+
+public sealed class ExecutableResolverTests : IDisposable
+{
+    private readonly string _root;
+
+    public ExecutableResolverTests()
+    {
+        _root = Path.Combine(Path.GetTempPath(), $"claudedo_exeresolve_{Guid.NewGuid():N}");
+        Directory.CreateDirectory(_root);
+    }
+
+    public void Dispose()
+    {
+        try { Directory.Delete(_root, recursive: true); } catch { }
+    }
+
+    private string MakeDir(string name)
+    {
+        var dir = Path.Combine(_root, name);
+        Directory.CreateDirectory(dir);
+        return dir;
+    }
+
+    private static void Touch(string path) => File.WriteAllText(path, "");
+
+    [Fact]
+    public void Command_with_directory_separator_is_treated_as_path()
+    {
+        var dir = MakeDir("bin1");
+        var exePath = Path.Combine(dir, "myclaude.exe");
+        Touch(exePath);
+
+        var result = ExecutableResolver.Resolve(exePath, pathOverride: "C:\\does\\not\\matter");
+
+        Assert.NotNull(result);
+        Assert.Equal(exePath, result!.Path);
+        Assert.False(result.IsShim);
+    }
+
+    [Fact]
+    public void Path_like_command_without_extension_resolves_via_pathext()
+    {
+        var dir = MakeDir("bin2");
+        var cmdPath = Path.Combine(dir, "myclaude.cmd");
+        Touch(cmdPath);
+        var commandWithoutExt = Path.Combine(dir, "myclaude");
+
+        var result = ExecutableResolver.Resolve(commandWithoutExt, pathExtOverride: ".com;.exe;.bat;.cmd");
+
+        Assert.NotNull(result);
+        Assert.Equal(cmdPath, result!.Path);
+        Assert.True(result.IsShim);
+    }
+
+    [Fact]
+    public void Cmd_file_in_path_is_found_when_no_exe_exists()
+    {
+        var dir = MakeDir("bin3");
+        Touch(Path.Combine(dir, "claude.cmd"));
+
+        var result = ExecutableResolver.Resolve("claude", pathOverride: dir, pathExtOverride: ".com;.exe;.bat;.cmd");
+
+        Assert.NotNull(result);
+        Assert.Equal(Path.Combine(dir, "claude.cmd"), result!.Path);
+        Assert.True(result.IsShim);
+    }
+
+    [Fact]
+    public void Exe_wins_against_cmd_in_same_directory()
+    {
+        var dir = MakeDir("bin4");
+        Touch(Path.Combine(dir, "claude.cmd"));
+        Touch(Path.Combine(dir, "claude.exe"));
+
+        var result = ExecutableResolver.Resolve("claude", pathOverride: dir, pathExtOverride: ".com;.exe;.bat;.cmd");
+
+        Assert.NotNull(result);
+        Assert.Equal(Path.Combine(dir, "claude.exe"), result!.Path);
+        Assert.False(result.IsShim);
+    }
+
+    [Fact]
+    public void Directory_order_in_path_is_respected()
+    {
+        var dir1 = MakeDir("bin5a");
+        var dir2 = MakeDir("bin5b");
+        Touch(Path.Combine(dir1, "claude.cmd"));
+        Touch(Path.Combine(dir2, "claude.exe"));
+
+        var pathOverride = $"{dir1}{Path.PathSeparator}{dir2}";
+        var result = ExecutableResolver.Resolve("claude", pathOverride: pathOverride, pathExtOverride: ".com;.exe;.bat;.cmd");
+
+        Assert.NotNull(result);
+        Assert.Equal(Path.Combine(dir1, "claude.cmd"), result!.Path);
+        Assert.True(result.IsShim);
+    }
+
+    [Fact]
+    public void Unresolvable_command_returns_null()
+    {
+        var dir = MakeDir("bin6");
+
+        var result = ExecutableResolver.Resolve(
+            "claudedo_totally_missing_cmd_9f3a1",
+            pathOverride: dir,
+            pathExtOverride: ".com;.exe;.bat;.cmd");
+
+        Assert.Null(result);
+    }
+
+    [Fact]
+    public void BuildShimStartInfo_uses_cmd_exe_and_quotes_paths_with_spaces()
+    {
+        const string shimPath = @"C:\Program Files\claude\claude.cmd";
+
+        var startInfo = ExecutableResolver.BuildShimStartInfo(shimPath, new[] { "--version", "arg2" });
+
+        Assert.Equal("cmd.exe", startInfo.FileName);
+        Assert.Contains("/c", startInfo.Arguments);
+        Assert.Contains($"\"{shimPath}\"", startInfo.Arguments);
+        Assert.Contains("--version", startInfo.Arguments);
+        Assert.Contains("arg2", startInfo.Arguments);
+    }
+}