diff --git a/pkg/env/env.go b/pkg/env/env.go
index fcad5836..7402426d 100644
--- a/pkg/env/env.go
+++ b/pkg/env/env.go
@@ -39,6 +39,9 @@ func AppendPath(env []string, binPath string) []string {
 		if ok {
 			newEnv = append(newEnv, fmt.Sprintf("PATH=%s%s%s",
 				binPath, string(os.PathListSeparator), v))
+		} else if v, ok := strings.CutPrefix(path, "Path="); ok {
+			newEnv = append(newEnv, fmt.Sprintf("Path=%s%s%s",
+				binPath, string(os.PathListSeparator), v))
 		}
 	}
 	return newEnv
@@ -53,10 +56,12 @@ func Lookup(env []string, bin string) string {
 			if !ok {
 				continue
 			}
+			log.Debugf("Looking for %s in %s", bin, suffix)
 			for _, path := range strings.Split(suffix, string(os.PathListSeparator)) {
 				testPath := filepath.Join(path, bin)
 
 				if stat, err := os.Stat(testPath); err == nil && !stat.IsDir() {
+					log.Debugf("Found %s for %s in %s", testPath, bin, suffix)
 					return testPath
 				}
 
@@ -66,6 +71,7 @@ func Lookup(env []string, bin string) string {
 					}
 
 					if stat, err := os.Stat(testPath + ext); err == nil && !stat.IsDir() {
+						log.Debugf("Found %s for %s in %s", testPath+ext, bin, suffix)
 						return testPath + ext
 					}
 				}
diff --git a/pkg/env/log.go b/pkg/env/log.go
new file mode 100644
index 00000000..e02c181e
--- /dev/null
+++ b/pkg/env/log.go
@@ -0,0 +1,5 @@
+package env
+
+import "github.com/gptscript-ai/gptscript/pkg/mvl"
+
+var log = mvl.Package()
diff --git a/pkg/repos/get.go b/pkg/repos/get.go
index 3f25349e..b0555395 100644
--- a/pkg/repos/get.go
+++ b/pkg/repos/get.go
@@ -111,6 +111,7 @@ func (m *Manager) GetContext(ctx context.Context, tool types.Tool, cmd, env []st
 
 	for _, runtime := range m.runtimes {
 		if runtime.Supports(cmd) {
+			log.Debugf("Runtime %s supports %v", runtime.ID(), cmd)
 			return m.setup(ctx, runtime, tool, env)
 		}
 	}
diff --git a/pkg/repos/log.go b/pkg/repos/log.go
new file mode 100644
index 00000000..e9559f3e
--- /dev/null
+++ b/pkg/repos/log.go
@@ -0,0 +1,5 @@
+package repos
+
+import "github.com/gptscript-ai/gptscript/pkg/mvl"
+
+var log = mvl.Package()
diff --git a/pkg/repos/runtimes/env.old/env.go b/pkg/repos/runtimes/env.old/env.go
deleted file mode 100644
index 8c5c0ae3..00000000
--- a/pkg/repos/runtimes/env.old/env.go
+++ /dev/null
@@ -1,42 +0,0 @@
-package env
-
-import (
-	"fmt"
-	"os"
-	"strings"
-)
-
-func execEquals(bin, check string) bool {
-	return bin == check ||
-		bin == check+".exe"
-}
-
-func Matches(cmd []string, bin string) bool {
-	switch len(cmd) {
-	case 0:
-		return false
-	case 1:
-		return execEquals(cmd[0], bin)
-	}
-	if cmd[0] == bin {
-		return true
-	}
-	if cmd[0] == "/usr/bin/env" || cmd[0] == "/bin/env" {
-		return execEquals(cmd[1], bin)
-	}
-	return false
-}
-
-func AppendPath(env []string, binPath string) []string {
-	var newEnv []string
-	for _, path := range env {
-		for _, prefix := range []string{"PATH=", "Path="} {
-			v, ok := strings.CutPrefix(path, prefix)
-			if ok {
-				newEnv = append(newEnv, fmt.Sprintf(prefix+"%s%s%s",
-					binPath, string(os.PathListSeparator), v))
-			}
-		}
-	}
-	return newEnv
-}
diff --git a/pkg/repos/runtimes/python/python.go b/pkg/repos/runtimes/python/python.go
index cb85e639..31840d53 100644
--- a/pkg/repos/runtimes/python/python.go
+++ b/pkg/repos/runtimes/python/python.go
@@ -7,6 +7,7 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
+	"io"
 	"io/fs"
 	"os"
 	"path/filepath"
@@ -21,7 +22,7 @@ import (
 //go:embed python.json
 var releasesData []byte
 
-const uvVersion = "uv==0.1.15"
+const uvVersion = "uv==0.1.24"
 
 type Release struct {
 	OS      string `json:"os,omitempty"`
@@ -52,13 +53,65 @@ func (r *Runtime) Supports(cmd []string) bool {
 	return runtimeEnv.Matches(cmd, "python") || runtimeEnv.Matches(cmd, "python3")
 }
 
+func pythonCmd(base string) string {
+	if runtime.GOOS == "windows" {
+		return filepath.Join(base, "python.exe")
+	}
+	return filepath.Join(base, "python3")
+}
+
+func pythonBin(base string) string {
+	binDir := filepath.Join(base, "python")
+	if runtime.GOOS != "windows" {
+		binDir = filepath.Join(binDir, "bin")
+	}
+	return binDir
+}
+
+func uvBin(binDir string) string {
+	if runtime.GOOS == "windows" {
+		return filepath.Join(binDir, "Scripts", "uv")
+	}
+	return filepath.Join(binDir, "uv")
+}
+
 func (r *Runtime) installVenv(ctx context.Context, binDir, venvPath string) error {
 	log.Infof("Creating virtualenv in %s", venvPath)
-	cmd := debugcmd.New(ctx, filepath.Join(binDir, "uv"), "venv", "-p",
-		filepath.Join(binDir, "python3"), venvPath)
+	cmd := debugcmd.New(ctx, uvBin(binDir), "venv", "-p", pythonCmd(binDir), venvPath)
 	return cmd.Run()
 }
 
+func copyFile(to, from string) error {
+	in, err := os.Open(from)
+	if err != nil {
+		return err
+	}
+	defer in.Close()
+
+	out, err := os.Create(to)
+	if err != nil {
+		_ = out.Close()
+		return err
+	}
+	defer out.Close()
+
+	if _, err := io.Copy(out, in); err != nil {
+		return fmt.Errorf("copying %s => %s", from, to)
+	}
+
+	return nil
+}
+
+func (r *Runtime) copyPythonForWindows(binDir string) error {
+	for _, targetBin := range []string{"python3.exe", "python" + r.ID() + ".exe"} {
+		err := copyFile(filepath.Join(binDir, targetBin), filepath.Join(binDir, "python.exe"))
+		if err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
 func (r *Runtime) Setup(ctx context.Context, dataRoot, toolSource string, env []string) ([]string, error) {
 	binPath, err := r.getRuntime(ctx, dataRoot)
 	if err != nil {
@@ -67,6 +120,9 @@ func (r *Runtime) Setup(ctx context.Context, dataRoot, toolSource string, env []
 
 	venvPath := filepath.Join(dataRoot, "venv", hash.ID(binPath, toolSource))
 	venvBinPath := filepath.Join(venvPath, "bin")
+	if runtime.GOOS == "windows" {
+		venvBinPath = filepath.Join(venvPath, "Scripts")
+	}
 
 	// Cleanup failed runs
 	if err := os.RemoveAll(venvPath); err != nil {
@@ -80,6 +136,12 @@ func (r *Runtime) Setup(ctx context.Context, dataRoot, toolSource string, env []
 	newEnv := runtimeEnv.AppendPath(env, venvBinPath)
 	newEnv = append(newEnv, "VIRTUAL_ENV="+venvPath)
 
+	if runtime.GOOS == "windows" {
+		if err := r.copyPythonForWindows(venvBinPath); err != nil {
+			return nil, err
+		}
+	}
+
 	if err := r.runPip(ctx, toolSource, binPath, append(env, newEnv...)); err != nil {
 		return nil, err
 	}
@@ -110,7 +172,7 @@ func (r *Runtime) runPip(ctx context.Context, toolSource, binDir string, env []s
 	for _, req := range []string{"requirements-gptscript.txt", "requirements.txt"} {
 		reqFile := filepath.Join(toolSource, req)
 		if s, err := os.Stat(reqFile); err == nil && !s.IsDir() {
-			cmd := debugcmd.New(ctx, filepath.Join(binDir, "uv"), "pip", "install", "-r", reqFile)
+			cmd := debugcmd.New(ctx, uvBin(binDir), "pip", "install", "-r", reqFile)
 			cmd.Env = env
 			return cmd.Run()
 		}
@@ -120,9 +182,7 @@ func (r *Runtime) runPip(ctx context.Context, toolSource, binDir string, env []s
 }
 
 func (r *Runtime) setupUV(ctx context.Context, tmp string) error {
-	cmd := debugcmd.New(ctx, filepath.Join(tmp, "python", "bin", "python3"),
-		filepath.Join(tmp, "python", "bin", "pip"),
-		"install", uvVersion)
+	cmd := debugcmd.New(ctx, pythonCmd(tmp), "-m", "pip", "install", uvVersion)
 	return cmd.Run()
 }
 
@@ -133,7 +193,7 @@ func (r *Runtime) getRuntime(ctx context.Context, cwd string) (string, error) {
 	}
 
 	target := filepath.Join(cwd, "python", hash.ID(url, sha, uvVersion))
-	binDir := filepath.Join(target, "python", "bin")
+	binDir := pythonBin(target)
 	if _, err := os.Stat(target); err == nil {
 		return binDir, nil
 	} else if !errors.Is(err, fs.ErrNotExist) {
@@ -152,7 +212,7 @@ func (r *Runtime) getRuntime(ctx context.Context, cwd string) (string, error) {
 		return "", err
 	}
 
-	if err := r.setupUV(ctx, tmp); err != nil {
+	if err := r.setupUV(ctx, pythonBin(tmp)); err != nil {
 		return "", err
 	}