diff --git a/go.mod b/go.mod
index d52446c12a..8032023fa3 100644
--- a/go.mod
+++ b/go.mod
@@ -78,6 +78,7 @@ require (
 	github.com/KyleBanks/depth v1.2.1 // indirect
 	github.com/Microsoft/go-winio v0.6.2 // indirect
 	github.com/ProtonMail/go-crypto v1.0.0 // indirect
+	github.com/UserExistsError/conpty v0.1.4 // indirect
 	github.com/akutz/memconn v0.1.0 // indirect
 	github.com/alexbrainman/sspi v0.0.0-20231016080023-1a75b4708caa // indirect
 	github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be // indirect
@@ -332,7 +333,7 @@ require (
 	github.com/stretchr/objx v0.5.2 // indirect
 	github.com/xanzy/go-gitlab v0.97.0
 	golang.org/x/net v0.28.0 // indirect
-	golang.org/x/sys v0.28.0
+	golang.org/x/sys v0.29.0
 	golang.org/x/text v0.21.0 // indirect
 	golang.org/x/time v0.5.0 // indirect
 	google.golang.org/genproto/googleapis/rpc v0.0.0-20240903143218-8af14fe29dc1 // indirect
diff --git a/go.sum b/go.sum
index 8dc494ab65..4426403582 100644
--- a/go.sum
+++ b/go.sum
@@ -626,6 +626,8 @@ github.com/Microsoft/go-winio v0.6.2/go.mod h1:yd8OoFMLzJbo9gZq8j5qaps8bJ9aShtEA
 github.com/OneOfOne/xxhash v1.2.2/go.mod h1:HSdplMjZKSmBqAxg5vPj2TmRDmfkzw+cTzAElWljhcU=
 github.com/ProtonMail/go-crypto v1.0.0 h1:LRuvITjQWX+WIfr930YHG2HNfjR1uOfyf5vE0kC2U78=
 github.com/ProtonMail/go-crypto v1.0.0/go.mod h1:EjAoLdwvbIOoOQr3ihjnSoLZRtE8azugULFRteWMNc0=
+github.com/UserExistsError/conpty v0.1.4 h1:+3FhJhiqhyEJa+K5qaK3/w6w+sN3Nh9O9VbJyBS02to=
+github.com/UserExistsError/conpty v0.1.4/go.mod h1:PDglKIkX3O/2xVk0MV9a6bCWxRmPVfxqZoTG/5sSd9I=
 github.com/ajstarks/deck v0.0.0-20200831202436-30c9fc6549a9/go.mod h1:JynElWSGnm/4RlzPXRlREEwqTHAN3T56Bv2ITsFT3gY=
 github.com/ajstarks/deck/generate v0.0.0-20210309230005-c3f852c02e19/go.mod h1:T13YZdzov6OU0A1+RfKZiZN9ca6VeKdBdyDV+BY97Tk=
 github.com/ajstarks/svgo v0.0.0-20180226025133-644b8db467af/go.mod h1:K08gAheRH3/J6wwsYMMT4xOr94bZjxIelGM0+d/wbFw=
@@ -1881,6 +1883,8 @@ golang.org/x/sys v0.16.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.21.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.28.0 h1:Fksou7UEQUWlKvIdsqzJmUmCX3cZuD2+P3XyyzwMhlA=
 golang.org/x/sys v0.28.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
+golang.org/x/sys v0.29.0 h1:TPYlXGxvx1MGTn2GiZDhnjPA9wZzZeGKHHmKhHYvgaU=
+golang.org/x/sys v0.29.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
 golang.org/x/term v0.0.0-20210927222741-03fcf44c2211/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
 golang.org/x/term v0.1.0/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
diff --git a/pkg/agent/agent.go b/pkg/agent/agent.go
index 038d0b1097..dfd33c3d17 100644
--- a/pkg/agent/agent.go
+++ b/pkg/agent/agent.go
@@ -10,7 +10,6 @@ import (
 	"net/url"
 	"os"
 	"os/exec"
-	"syscall"
 	"time"
 
 	"github.com/daytonaio/daytona/cmd/daytona/config"
@@ -18,6 +17,7 @@ import (
 	apiclient_util "github.com/daytonaio/daytona/internal/util/apiclient"
 	"github.com/daytonaio/daytona/internal/util/apiclient/conversion"
 	agent_config "github.com/daytonaio/daytona/pkg/agent/config"
+	"github.com/daytonaio/daytona/pkg/agent/toolbox/fs"
 	"github.com/daytonaio/daytona/pkg/apiclient"
 	"github.com/daytonaio/daytona/pkg/gitprovider"
 	"github.com/daytonaio/daytona/pkg/models"
@@ -113,7 +113,11 @@ func (a *Agent) startWorkspaceMode() error {
 				log.Info("Repository already exists. Skipping clone...")
 			} else {
 				if stat, err := os.Stat(a.Config.WorkspaceDir); err == nil {
-					ownerUid := stat.Sys().(*syscall.Stat_t).Uid
+					ownerUid, err := fs.GetFileUid(stat)
+					if err != nil {
+						log.Error(err)
+					}
+
 					if ownerUid != uint32(os.Getuid()) {
 						chownCmd := exec.Command("sudo", "chown", "-R", fmt.Sprintf("%s:%s", a.Workspace.User, a.Workspace.User), a.Config.WorkspaceDir)
 						err = chownCmd.Run()
diff --git a/pkg/agent/ssh/server.go b/pkg/agent/ssh/server.go
index 9d464ae4d1..0c459df50e 100644
--- a/pkg/agent/ssh/server.go
+++ b/pkg/agent/ssh/server.go
@@ -8,15 +8,12 @@ import (
 	"io"
 	"os"
 	"os/exec"
-	"syscall"
-	"unsafe"
+	"runtime"
 
-	"github.com/creack/pty"
 	"github.com/daytonaio/daytona/pkg/agent/ssh/config"
 	"github.com/daytonaio/daytona/pkg/common"
 	"github.com/gliderlabs/ssh"
 	"github.com/pkg/sftp"
-	"golang.org/x/sys/unix"
 
 	log "github.com/sirupsen/logrus"
 )
@@ -104,16 +101,22 @@ func (s *Server) handlePty(session ssh.Session, ptyReq ssh.Pty, winCh <-chan ssh
 	cmd.Env = append(cmd.Env, fmt.Sprintf("TERM=%s", ptyReq.Term))
 	cmd.Env = append(cmd.Env, os.Environ()...)
 	cmd.Env = append(cmd.Env, fmt.Sprintf("SHELL=%s", shell))
-	f, err := pty.Start(cmd)
-	if err != nil {
-		log.Errorf("Unable to start command: %v", err)
-		return
-	}
 
+	var f io.ReadWriteCloser
+	if runtime.GOOS == "windows" {
+		output := Start(shell)
+		if output != nil {
+			f = output
+		}
+	} else {
+		output := Start(cmd)
+		if output != nil {
+			f = output
+		}
+	}
 	go func() {
 		for win := range winCh {
-			syscall.Syscall(syscall.SYS_IOCTL, f.Fd(), uintptr(syscall.TIOCSWINSZ),
-				uintptr(unsafe.Pointer(&struct{ h, w, x, y uint16 }{uint16(win.Height), uint16(win.Width), 0, 0})))
+			SetPtySize(f, win)
 		}
 	}()
 	go func() {
@@ -128,7 +131,7 @@ func (s *Server) handleNonPty(session ssh.Session) {
 		args = append([]string{"-c"}, session.RawCommand())
 	}
 
-	cmd := exec.Command("/bin/sh", args...)
+	cmd := exec.Command("sh", args...)
 
 	cmd.Env = append(cmd.Env, os.Environ()...)
 
@@ -177,7 +180,7 @@ func (s *Server) handleNonPty(session ssh.Session) {
 	}()
 	go func() {
 		for sig := range sigs {
-			signal := s.osSignalFrom(sig)
+			signal := OsSignalFrom(sig)
 			err := cmd.Process.Signal(signal)
 			if err != nil {
 				log.Warnf("Unable to send signal to process: %v", err)
@@ -198,41 +201,6 @@ func (s *Server) handleNonPty(session ssh.Session) {
 	}
 }
 
-func (s *Server) osSignalFrom(sig ssh.Signal) os.Signal {
-	switch sig {
-	case ssh.SIGABRT:
-		return unix.SIGABRT
-	case ssh.SIGALRM:
-		return unix.SIGALRM
-	case ssh.SIGFPE:
-		return unix.SIGFPE
-	case ssh.SIGHUP:
-		return unix.SIGHUP
-	case ssh.SIGILL:
-		return unix.SIGILL
-	case ssh.SIGINT:
-		return unix.SIGINT
-	case ssh.SIGKILL:
-		return unix.SIGKILL
-	case ssh.SIGPIPE:
-		return unix.SIGPIPE
-	case ssh.SIGQUIT:
-		return unix.SIGQUIT
-	case ssh.SIGSEGV:
-		return unix.SIGSEGV
-	case ssh.SIGTERM:
-		return unix.SIGTERM
-	case ssh.SIGUSR1:
-		return unix.SIGUSR1
-	case ssh.SIGUSR2:
-		return unix.SIGUSR2
-
-	// Unhandled, use sane fallback.
-	default:
-		return unix.SIGKILL
-	}
-}
-
 func (s *Server) sftpHandler(session ssh.Session) {
 	debugStream := io.Discard
 	serverOptions := []sftp.ServerOption{
diff --git a/pkg/agent/ssh/server_unix.go b/pkg/agent/ssh/server_unix.go
new file mode 100644
index 0000000000..198cccfd4d
--- /dev/null
+++ b/pkg/agent/ssh/server_unix.go
@@ -0,0 +1,74 @@
+//go:build !windows
+
+// Copyright 2024 Daytona Platforms Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+package ssh
+
+import (
+	"os"
+	"os/exec"
+	"syscall"
+	"unsafe"
+
+	"github.com/creack/pty"
+	"github.com/gliderlabs/ssh"
+	log "github.com/sirupsen/logrus"
+	"golang.org/x/sys/unix"
+)
+
+func Start(cmd interface{}) *os.File {
+	if command, ok := cmd.(*exec.Cmd); ok {
+		f, err := pty.Start(command)
+		if err != nil {
+			log.Errorf("Unable to start PTY: %v", err)
+			return nil
+		}
+		return f
+	}
+	return nil
+}
+
+func SetPtySize(f interface{}, win ssh.Window) {
+	if file, ok := f.(*os.File); ok {
+		syscall.Syscall(syscall.SYS_IOCTL, file.Fd(), uintptr(syscall.TIOCSWINSZ),
+			uintptr(unsafe.Pointer(&struct{ h, w, x, y uint16 }{uint16(win.Height), uint16(win.Width), 0, 0})))
+	} else {
+		log.Errorf("Unable to resize PTY")
+	}
+}
+
+func OsSignalFrom(sig ssh.Signal) os.Signal {
+	switch sig {
+	case ssh.SIGABRT:
+		return unix.SIGABRT
+	case ssh.SIGALRM:
+		return unix.SIGALRM
+	case ssh.SIGFPE:
+		return unix.SIGFPE
+	case ssh.SIGHUP:
+		return unix.SIGHUP
+	case ssh.SIGILL:
+		return unix.SIGILL
+	case ssh.SIGINT:
+		return unix.SIGINT
+	case ssh.SIGKILL:
+		return unix.SIGKILL
+	case ssh.SIGPIPE:
+		return unix.SIGPIPE
+	case ssh.SIGQUIT:
+		return unix.SIGQUIT
+	case ssh.SIGSEGV:
+		return unix.SIGSEGV
+	case ssh.SIGTERM:
+		return unix.SIGTERM
+	case ssh.SIGUSR1:
+		return unix.SIGUSR1
+	case ssh.SIGUSR2:
+		return unix.SIGUSR2
+
+	// Unhandled, use sane fallback.
+	default:
+		return unix.SIGKILL
+	}
+}
diff --git a/pkg/agent/ssh/server_win.go b/pkg/agent/ssh/server_win.go
new file mode 100644
index 0000000000..747957878d
--- /dev/null
+++ b/pkg/agent/ssh/server_win.go
@@ -0,0 +1,54 @@
+//go:build windows
+
+// Copyright 2024 Daytona Platforms Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+package ssh
+
+import (
+	"os"
+	"syscall"
+
+	"github.com/UserExistsError/conpty"
+	"github.com/gliderlabs/ssh"
+	log "github.com/sirupsen/logrus"
+)
+
+var (
+	kernel32             = syscall.NewLazyDLL("kernel32.dll")
+	setConsoleWindowInfo = kernel32.NewProc("SetConsoleWindowInfo")
+)
+
+func Start(cmd interface{}) *conpty.ConPty {
+	if shell, ok := cmd.(string); ok {
+		f, err := conpty.Start(shell)
+		if err != nil {
+			log.Errorf("Unable to start ConPTY: %v", err)
+			return nil
+		}
+		return f
+	}
+
+	return nil
+}
+
+func SetPtySize(f interface{}, win ssh.Window) {
+	if cpty, ok := f.(*conpty.ConPty); ok {
+		cpty.Resize(win.Width, win.Height)
+	} else {
+		log.Errorf("Unable to resize ConPTY")
+	}
+}
+
+func OsSignalFrom(sig ssh.Signal) os.Signal {
+	switch sig {
+	case ssh.SIGINT:
+		return os.Interrupt
+	case ssh.SIGTERM:
+		return os.Kill
+	case ssh.SIGKILL:
+		return os.Kill
+	default:
+		return os.Kill
+	}
+}
diff --git a/pkg/agent/toolbox/fs/get_file_info.go b/pkg/agent/toolbox/fs/get_file_info.go
index aa6b96670b..4fbb23a674 100644
--- a/pkg/agent/toolbox/fs/get_file_info.go
+++ b/pkg/agent/toolbox/fs/get_file_info.go
@@ -5,10 +5,7 @@ package fs
 
 import (
 	"errors"
-	"fmt"
 	"os"
-	"strconv"
-	"syscall"
 
 	"github.com/gin-gonic/gin"
 )
@@ -32,22 +29,3 @@ func GetFileInfo(c *gin.Context) {
 
 	c.JSON(200, info)
 }
-
-func getFileInfo(path string) (FileInfo, error) {
-	info, err := os.Stat(path)
-	if err != nil {
-		return FileInfo{}, err
-	}
-
-	stat := info.Sys().(*syscall.Stat_t)
-	return FileInfo{
-		Name:        info.Name(),
-		Size:        info.Size(),
-		Mode:        info.Mode().String(),
-		ModTime:     info.ModTime().String(),
-		IsDir:       info.IsDir(),
-		Owner:       strconv.FormatUint(uint64(stat.Uid), 10),
-		Group:       strconv.FormatUint(uint64(stat.Gid), 10),
-		Permissions: fmt.Sprintf("%04o", info.Mode().Perm()),
-	}, nil
-}
diff --git a/pkg/agent/toolbox/fs/info_unix.go b/pkg/agent/toolbox/fs/info_unix.go
new file mode 100644
index 0000000000..7ba7d9a5e6
--- /dev/null
+++ b/pkg/agent/toolbox/fs/info_unix.go
@@ -0,0 +1,36 @@
+//go:build !windows
+
+// Copyright 2024 Daytona Platforms Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+package fs
+
+import (
+	"fmt"
+	"os"
+	"strconv"
+	"syscall"
+)
+
+func getFileInfo(path string) (*FileInfo, error) {
+	info, err := os.Stat(path)
+	if err != nil {
+		return &FileInfo{}, err
+	}
+
+	stat := info.Sys().(*syscall.Stat_t)
+	return &FileInfo{
+		Name:        info.Name(),
+		Size:        info.Size(),
+		Mode:        info.Mode().String(),
+		ModTime:     info.ModTime().String(),
+		IsDir:       info.IsDir(),
+		Owner:       strconv.FormatUint(uint64(stat.Uid), 10),
+		Group:       strconv.FormatUint(uint64(stat.Gid), 10),
+		Permissions: fmt.Sprintf("%04o", info.Mode().Perm()),
+	}, nil
+}
+
+func GetFileUid(stat os.FileInfo) (uint32, error) {
+	return stat.Sys().(*syscall.Stat_t).Uid, nil
+}
diff --git a/pkg/agent/toolbox/fs/info_win.go b/pkg/agent/toolbox/fs/info_win.go
new file mode 100644
index 0000000000..b8b3c89d1b
--- /dev/null
+++ b/pkg/agent/toolbox/fs/info_win.go
@@ -0,0 +1,65 @@
+//go:build windows
+
+// Copyright 2024 Daytona Platforms Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+package fs
+
+import (
+	"fmt"
+	"os"
+	"strconv"
+
+	"golang.org/x/sys/windows"
+)
+
+func getFileInfo(path string) (*FileInfo, error) {
+	info, err := os.Stat(path)
+	if err != nil {
+		return &FileInfo{}, err
+	}
+
+	ownerSid, groupSid, err := getFileGidUid(path)
+	if err != nil {
+		return &FileInfo{}, err
+	}
+
+	return &FileInfo{
+		Name:        info.Name(),
+		Size:        info.Size(),
+		Mode:        info.Mode().String(),
+		ModTime:     info.ModTime().String(),
+		IsDir:       info.IsDir(),
+		Owner:       ownerSid,
+		Group:       groupSid,
+		Permissions: fmt.Sprintf("%04o", info.Mode().Perm()),
+	}, nil
+}
+
+func getFileGidUid(path string) (string, string, error) {
+	sd, err := windows.GetNamedSecurityInfo(path, windows.SE_FILE_OBJECT, windows.OWNER_SECURITY_INFORMATION|windows.GROUP_SECURITY_INFORMATION)
+	if err != nil {
+		return "", "", err
+	}
+	owner, _, err := sd.Owner()
+	if err != nil {
+		return "", "", err
+	}
+	group, _, err := sd.Group()
+	if err != nil {
+		return "", "", err
+	}
+	return owner.String(), group.String(), nil
+}
+
+func GetFileUid(stat os.FileInfo) (uint32, error) {
+	uid, _, err := getFileGidUid(stat.Name())
+	if err != nil {
+		return 0, err
+	}
+	uidInt, err := strconv.ParseUint(uid, 10, 32)
+	if err != nil {
+		return 0, err
+	}
+	return uint32(uidInt), nil
+}
diff --git a/pkg/agent/toolbox/fs/list_files.go b/pkg/agent/toolbox/fs/list_files.go
index eea4078747..406852ec29 100644
--- a/pkg/agent/toolbox/fs/list_files.go
+++ b/pkg/agent/toolbox/fs/list_files.go
@@ -32,7 +32,7 @@ func ListFiles(c *gin.Context) {
 		if err != nil {
 			continue
 		}
-		fileInfos = append(fileInfos, info)
+		fileInfos = append(fileInfos, *info)
 	}
 
 	c.JSON(200, fileInfos)
diff --git a/pkg/cmd/agent/agent.go b/pkg/cmd/agent/agent.go
index 6682cc9cd5..748d9352e9 100644
--- a/pkg/cmd/agent/agent.go
+++ b/pkg/cmd/agent/agent.go
@@ -1,5 +1,3 @@
-//go:build !windows
-
 // Copyright 2024 Daytona Platforms Inc.
 // SPDX-License-Identifier: Apache-2.0
 
diff --git a/pkg/cmd/agent/agent_windows.go b/pkg/cmd/agent/agent_windows.go
deleted file mode 100644
index 6bdf0cc62d..0000000000
--- a/pkg/cmd/agent/agent_windows.go
+++ /dev/null
@@ -1,19 +0,0 @@
-//go:build windows
-
-// Copyright 2024 Daytona Platforms Inc.
-// SPDX-License-Identifier: Apache-2.0
-
-package agent
-
-import (
-	"github.com/spf13/cobra"
-)
-
-var AgentCmd = &cobra.Command{
-	Use:   "agent",
-	Short: "Start the agent process",
-	Args:  cobra.NoArgs,
-	Run: func(cmd *cobra.Command, args []string) {
-		panic("Not implemented")
-	},
-}