diff --git a/go.mod b/go.mod
index 5189264e50..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
diff --git a/go.sum b/go.sum
index b2e9c69727..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=
diff --git a/pkg/agent/ssh/server.go b/pkg/agent/ssh/server.go
index 4585e92d0b..f1ff3ef2a5 100644
--- a/pkg/agent/ssh/server.go
+++ b/pkg/agent/ssh/server.go
@@ -8,9 +8,8 @@ import (
 	"io"
 	"os"
 	"os/exec"
-	"strings"
+	"runtime"
 
-	"github.com/creack/pty"
 	"github.com/daytonaio/daytona/pkg/agent/ssh/config"
 	"github.com/daytonaio/daytona/pkg/common"
 	"github.com/gliderlabs/ssh"
@@ -102,12 +101,19 @@ 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 {
 			SetPtySize(f, win)
@@ -125,7 +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()...)
 
@@ -196,33 +202,6 @@ func (s *Server) handleNonPty(session ssh.Session) {
 }
 
 func (s *Server) getShell() string {
-	out, err := exec.Command("sh", "-c", "grep '^[^#]' /etc/shells").Output()
-	if err != nil {
-		return "sh"
-	}
-
-	if strings.Contains(string(out), "/usr/bin/zsh") {
-		return "/usr/bin/zsh"
-	}
-
-	if strings.Contains(string(out), "/bin/zsh") {
-		return "/bin/zsh"
-	}
-
-	if strings.Contains(string(out), "/usr/bin/bash") {
-		return "/usr/bin/bash"
-	}
-
-	if strings.Contains(string(out), "/bin/bash") {
-		return "/bin/bash"
-	}
-
-	shellEnv, shellSet := os.LookupEnv("SHELL")
-
-	if shellSet {
-		return shellEnv
-	}
-
 	return "sh"
 }
 
diff --git a/pkg/agent/ssh/server_unix.go b/pkg/agent/ssh/server_unix.go
index 6c15478bdb..198cccfd4d 100644
--- a/pkg/agent/ssh/server_unix.go
+++ b/pkg/agent/ssh/server_unix.go
@@ -7,16 +7,35 @@ 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 SetPtySize(f *os.File, win ssh.Window) {
-	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})))
+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 {
diff --git a/pkg/agent/ssh/server_win.go b/pkg/agent/ssh/server_win.go
index 6eb271eb9b..747957878d 100644
--- a/pkg/agent/ssh/server_win.go
+++ b/pkg/agent/ssh/server_win.go
@@ -8,9 +8,10 @@ package ssh
 import (
 	"os"
 	"syscall"
-	"unsafe"
 
+	"github.com/UserExistsError/conpty"
 	"github.com/gliderlabs/ssh"
+	log "github.com/sirupsen/logrus"
 )
 
 var (
@@ -18,15 +19,25 @@ var (
 	setConsoleWindowInfo = kernel32.NewProc("SetConsoleWindowInfo")
 )
 
-func SetPtySize(f *os.File, win ssh.Window) {
-	handle := f.Fd()
-	var rect struct {
-		Left, Top, Right, Bottom int16
+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
 	}
-	rect.Right = int16(win.Width - 1)
-	rect.Bottom = int16(win.Height - 1)
 
-	setConsoleWindowInfo.Call(uintptr(handle), uintptr(1), uintptr(unsafe.Pointer(&rect)))
+	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 {