diff --git a/cli/ssh.go b/cli/ssh.go
index 7f40959a59..a291b3764b 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -25,12 +25,8 @@ import (
 	"golang.org/x/xerrors"
 	"gvisor.dev/gvisor/pkg/tcpip/adapters/gonet"
 
-	"github.com/coder/retry"
-	"github.com/coder/serpent"
-
 	"cdr.dev/slog"
 	"cdr.dev/slog/sloggers/sloghuman"
-
 	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/coder/v2/cli/cliutil"
 	"github.com/coder/coder/v2/coderd/autobuild/notify"
@@ -38,6 +34,9 @@ import (
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 	"github.com/coder/coder/v2/cryptorand"
+	"github.com/coder/coder/v2/pty"
+	"github.com/coder/retry"
+	"github.com/coder/serpent"
 )
 
 var (
@@ -341,15 +340,22 @@ func (r *RootCmd) ssh() *serpent.Command {
 				}
 			}
 
-			stdoutFile, validOut := inv.Stdout.(*os.File)
 			stdinFile, validIn := inv.Stdin.(*os.File)
-			if validOut && validIn && isatty.IsTerminal(stdoutFile.Fd()) {
-				state, err := term.MakeRaw(int(stdinFile.Fd()))
+			stdoutFile, validOut := inv.Stdout.(*os.File)
+			if validIn && validOut && isatty.IsTerminal(stdinFile.Fd()) && isatty.IsTerminal(stdoutFile.Fd()) {
+				inState, err := pty.MakeInputRaw(stdinFile.Fd())
 				if err != nil {
 					return err
 				}
 				defer func() {
-					_ = term.Restore(int(stdinFile.Fd()), state)
+					_ = pty.RestoreTerminal(stdinFile.Fd(), inState)
+				}()
+				outState, err := pty.MakeOutputRaw(stdoutFile.Fd())
+				if err != nil {
+					return err
+				}
+				defer func() {
+					_ = pty.RestoreTerminal(stdoutFile.Fd(), outState)
 				}()
 
 				windowChange := listenWindowSize(ctx)
diff --git a/pty/terminal.go b/pty/terminal.go
new file mode 100644
index 0000000000..2c1a35c3ee
--- /dev/null
+++ b/pty/terminal.go
@@ -0,0 +1,31 @@
+package pty
+
+// TerminalState differs per-platform.
+type TerminalState struct {
+	state terminalState
+}
+
+// MakeInputRaw calls term.MakeRaw on non-Windows platforms. On Windows it sets
+// special terminal modes that enable VT100 emulation as well as setting the
+// same modes that term.MakeRaw sets.
+//
+//nolint:revive
+func MakeInputRaw(fd uintptr) (*TerminalState, error) {
+	return makeInputRaw(fd)
+}
+
+// MakeOutputRaw does nothing on non-Windows platforms. On Windows it sets
+// special terminal modes that enable VT100 emulation as well as setting the
+// same modes that term.MakeRaw sets.
+//
+//nolint:revive
+func MakeOutputRaw(fd uintptr) (*TerminalState, error) {
+	return makeOutputRaw(fd)
+}
+
+// RestoreTerminal restores the terminal back to its original state.
+//
+//nolint:revive
+func RestoreTerminal(fd uintptr, state *TerminalState) error {
+	return restoreTerminal(fd, state)
+}
diff --git a/pty/terminal_other.go b/pty/terminal_other.go
new file mode 100644
index 0000000000..9c04354715
--- /dev/null
+++ b/pty/terminal_other.go
@@ -0,0 +1,36 @@
+//go:build !windows
+// +build !windows
+
+package pty
+
+import "golang.org/x/term"
+
+type terminalState *term.State
+
+//nolint:revive
+func makeInputRaw(fd uintptr) (*TerminalState, error) {
+	s, err := term.MakeRaw(int(fd))
+	if err != nil {
+		return nil, err
+	}
+	return &TerminalState{
+		state: s,
+	}, nil
+}
+
+//nolint:revive
+func makeOutputRaw(_ uintptr) (*TerminalState, error) {
+	// Does nothing. makeInputRaw does enough for both input and output.
+	return &TerminalState{
+		state: nil,
+	}, nil
+}
+
+//nolint:revive
+func restoreTerminal(fd uintptr, state *TerminalState) error {
+	if state == nil || state.state == nil {
+		return nil
+	}
+
+	return term.Restore(int(fd), state.state)
+}
diff --git a/pty/terminal_windows.go b/pty/terminal_windows.go
new file mode 100644
index 0000000000..1d8f99d5b9
--- /dev/null
+++ b/pty/terminal_windows.go
@@ -0,0 +1,65 @@
+//go:build windows
+// +build windows
+
+package pty
+
+import "golang.org/x/sys/windows"
+
+type terminalState uint32
+
+// This is adapted from term.MakeRaw, but adds
+// ENABLE_VIRTUAL_TERMINAL_PROCESSING to the output mode and
+// ENABLE_VIRTUAL_TERMINAL_INPUT to the input mode.
+//
+// See: https://github.com/golang/term/blob/5b15d269ba1f54e8da86c8aa5574253aea0c2198/term_windows.go#L23
+//
+// Copyright 2019 The Go Authors. BSD-3-Clause license. See:
+// https://github.com/golang/term/blob/master/LICENSE
+func makeRaw(handle windows.Handle, input bool) (uint32, error) {
+	var prevState uint32
+	if err := windows.GetConsoleMode(handle, &prevState); err != nil {
+		return 0, err
+	}
+
+	var raw uint32
+	if input {
+		raw = prevState &^ (windows.ENABLE_ECHO_INPUT | windows.ENABLE_PROCESSED_INPUT | windows.ENABLE_LINE_INPUT | windows.ENABLE_PROCESSED_OUTPUT)
+		raw |= windows.ENABLE_VIRTUAL_TERMINAL_INPUT
+	} else {
+		raw = prevState | windows.ENABLE_VIRTUAL_TERMINAL_PROCESSING
+	}
+
+	if err := windows.SetConsoleMode(handle, raw); err != nil {
+		return 0, err
+	}
+	return prevState, nil
+}
+
+//nolint:revive
+func makeInputRaw(handle uintptr) (*TerminalState, error) {
+	prevState, err := makeRaw(windows.Handle(handle), true)
+	if err != nil {
+		return nil, err
+	}
+
+	return &TerminalState{
+		state: terminalState(prevState),
+	}, nil
+}
+
+//nolint:revive
+func makeOutputRaw(handle uintptr) (*TerminalState, error) {
+	prevState, err := makeRaw(windows.Handle(handle), false)
+	if err != nil {
+		return nil, err
+	}
+
+	return &TerminalState{
+		state: terminalState(prevState),
+	}, nil
+}
+
+//nolint:revive
+func restoreTerminal(handle uintptr, state *TerminalState) error {
+	return windows.SetConsoleMode(windows.Handle(handle), uint32(state.state))
+}