diff --git a/cli/cliui/prompt.go b/cli/cliui/prompt.go
index b432f75afeaaf..264ebf2939780 100644
--- a/cli/cliui/prompt.go
+++ b/cli/cliui/prompt.go
@@ -1,6 +1,7 @@
 package cliui
 
 import (
+	"bufio"
 	"bytes"
 	"encoding/json"
 	"fmt"
@@ -8,19 +9,21 @@ import (
 	"os"
 	"os/signal"
 	"strings"
+	"unicode"
 
-	"github.com/bgentry/speakeasy"
 	"github.com/mattn/go-isatty"
 	"golang.org/x/xerrors"
 
+	"github.com/coder/coder/v2/pty"
 	"github.com/coder/pretty"
 	"github.com/coder/serpent"
 )
 
 // PromptOptions supply a set of options to the prompt.
 type PromptOptions struct {
-	Text      string
-	Default   string
+	Text    string
+	Default string
+	// When true, the input will be masked with asterisks.
 	Secret    bool
 	IsConfirm bool
 	Validate  func(string) error
@@ -88,14 +91,13 @@ func Prompt(inv *serpent.Invocation, opts PromptOptions) (string, error) {
 		var line string
 		var err error
 
+		signal.Notify(interrupt, os.Interrupt)
+		defer signal.Stop(interrupt)
+
 		inFile, isInputFile := inv.Stdin.(*os.File)
 		if opts.Secret && isInputFile && isatty.IsTerminal(inFile.Fd()) {
-			// we don't install a signal handler here because speakeasy has its own
-			line, err = speakeasy.Ask("")
+			line, err = readSecretInput(inFile, inv.Stdout)
 		} else {
-			signal.Notify(interrupt, os.Interrupt)
-			defer signal.Stop(interrupt)
-
 			line, err = readUntil(inv.Stdin, '\n')
 
 			// Check if the first line beings with JSON object or array chars.
@@ -204,3 +206,58 @@ func readUntil(r io.Reader, delim byte) (string, error) {
 		}
 	}
 }
+
+// readSecretInput reads secret input from the terminal rune-by-rune,
+// masking each character with an asterisk.
+func readSecretInput(f *os.File, w io.Writer) (string, error) {
+	// Put terminal into raw mode (no echo, no line buffering).
+	oldState, err := pty.MakeInputRaw(f.Fd())
+	if err != nil {
+		return "", err
+	}
+	defer func() {
+		_ = pty.RestoreTerminal(f.Fd(), oldState)
+	}()
+
+	reader := bufio.NewReader(f)
+	var runes []rune
+
+	for {
+		r, _, err := reader.ReadRune()
+		if err != nil {
+			return "", err
+		}
+
+		switch {
+		case r == '\r' || r == '\n':
+			// Finish on Enter
+			if _, err := fmt.Fprint(w, "\r\n"); err != nil {
+				return "", err
+			}
+			return string(runes), nil
+
+		case r == 3:
+			// Ctrl+C
+			return "", ErrCanceled
+
+		case r == 127 || r == '\b':
+			// Backspace/Delete: remove last rune
+			if len(runes) > 0 {
+				// Erase the last '*' on the screen
+				if _, err := fmt.Fprint(w, "\b \b"); err != nil {
+					return "", err
+				}
+				runes = runes[:len(runes)-1]
+			}
+
+		default:
+			// Only mask printable, non-control runes
+			if !unicode.IsControl(r) {
+				runes = append(runes, r)
+				if _, err := fmt.Fprint(w, "*"); err != nil {
+					return "", err
+				}
+			}
+		}
+	}
+}
diff --git a/cli/cliui/prompt_test.go b/cli/cliui/prompt_test.go
index 5ac0d906caae8..8b5a3e98ea1f7 100644
--- a/cli/cliui/prompt_test.go
+++ b/cli/cliui/prompt_test.go
@@ -6,6 +6,7 @@ import (
 	"io"
 	"os"
 	"os/exec"
+	"runtime"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -13,7 +14,6 @@ import (
 	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/cli/cliui"
-	"github.com/coder/coder/v2/pty"
 	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
 	"github.com/coder/serpent"
@@ -181,6 +181,48 @@ func TestPrompt(t *testing.T) {
 		resp := testutil.TryReceive(ctx, t, doneChan)
 		require.Equal(t, "valid", resp)
 	})
+
+	t.Run("MaskedSecret", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
+		ptty := ptytest.New(t)
+		doneChan := make(chan string)
+		go func() {
+			resp, err := newPrompt(ctx, ptty, cliui.PromptOptions{
+				Text:   "Password:",
+				Secret: true,
+			}, nil)
+			assert.NoError(t, err)
+			doneChan <- resp
+		}()
+		ptty.ExpectMatch("Password: ")
+
+		ptty.WriteLine("test")
+
+		resp := testutil.TryReceive(ctx, t, doneChan)
+		require.Equal(t, "test", resp)
+	})
+
+	t.Run("UTF8Password", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
+		ptty := ptytest.New(t)
+		doneChan := make(chan string)
+		go func() {
+			resp, err := newPrompt(ctx, ptty, cliui.PromptOptions{
+				Text:   "Password:",
+				Secret: true,
+			}, nil)
+			assert.NoError(t, err)
+			doneChan <- resp
+		}()
+		ptty.ExpectMatch("Password: ")
+
+		ptty.WriteLine("和製漢字")
+
+		resp := testutil.TryReceive(ctx, t, doneChan)
+		require.Equal(t, "和製漢字", resp)
+	})
 }
 
 func newPrompt(ctx context.Context, ptty *ptytest.PTY, opts cliui.PromptOptions, invOpt func(inv *serpent.Invocation)) (string, error) {
@@ -209,13 +251,12 @@ func TestPasswordTerminalState(t *testing.T) {
 		passwordHelper()
 		return
 	}
+	if runtime.GOOS == "windows" {
+		t.Skip("Skipping on windows. PTY doesn't read ptty.Write correctly.")
+	}
 	t.Parallel()
 
 	ptty := ptytest.New(t)
-	ptyWithFlags, ok := ptty.PTY.(pty.WithFlags)
-	if !ok {
-		t.Skip("unable to check PTY local echo on this platform")
-	}
 
 	cmd := exec.Command(os.Args[0], "-test.run=TestPasswordTerminalState") //nolint:gosec
 	cmd.Env = append(os.Environ(), "TEST_SUBPROCESS=1")
@@ -229,21 +270,16 @@ func TestPasswordTerminalState(t *testing.T) {
 	defer process.Kill()
 
 	ptty.ExpectMatch("Password: ")
-
-	require.Eventually(t, func() bool {
-		echo, err := ptyWithFlags.EchoEnabled()
-		return err == nil && !echo
-	}, testutil.WaitShort, testutil.IntervalMedium, "echo is on while reading password")
+	ptty.Write('t')
+	ptty.Write('e')
+	ptty.Write('s')
+	ptty.Write('t')
+	ptty.ExpectMatch("****")
 
 	err = process.Signal(os.Interrupt)
 	require.NoError(t, err)
 	_, err = process.Wait()
 	require.NoError(t, err)
-
-	require.Eventually(t, func() bool {
-		echo, err := ptyWithFlags.EchoEnabled()
-		return err == nil && echo
-	}, testutil.WaitShort, testutil.IntervalMedium, "echo is off after reading password")
 }
 
 // nolint:unused
diff --git a/go.mod b/go.mod
index 11da4f20eb80d..ed1042b699334 100644
--- a/go.mod
+++ b/go.mod
@@ -83,7 +83,6 @@ require (
 	github.com/armon/circbuf v0.0.0-20190214190532-5111143e8da2
 	github.com/awalterschulze/gographviz v2.0.3+incompatible
 	github.com/aws/smithy-go v1.22.3
-	github.com/bgentry/speakeasy v0.2.0
 	github.com/bramvdbogaerde/go-scp v1.5.0
 	github.com/briandowns/spinner v1.23.0
 	github.com/cakturk/go-netstat v0.0.0-20200220111822-e5b49efee7a5
diff --git a/go.sum b/go.sum
index 4bb24abd6be6b..695812397c14d 100644
--- a/go.sum
+++ b/go.sum
@@ -815,8 +815,6 @@ github.com/bep/tmc v0.5.1/go.mod h1:tGYHN8fS85aJPhDLgXETVKp+PR382OvFi2+q2GkGsq0=
 github.com/bgentry/go-netrc v0.0.0-20140422174119-9fd32a8b3d3d h1:xDfNPAt8lFiC1UJrqV3uuy861HCTo708pDMbjHHdCas=
 github.com/bgentry/go-netrc v0.0.0-20140422174119-9fd32a8b3d3d/go.mod h1:6QX/PXZ00z/TKoufEY6K/a0k6AhaJrQKdFe6OfVXsa4=
 github.com/bgentry/speakeasy v0.1.0/go.mod h1:+zsyZBPWlz7T6j88CTgSN5bM796AkVf0kBD4zp0CCIs=
-github.com/bgentry/speakeasy v0.2.0 h1:tgObeVOf8WAvtuAX6DhJ4xks4CFNwPDZiqzGqIHE51E=
-github.com/bgentry/speakeasy v0.2.0/go.mod h1:+zsyZBPWlz7T6j88CTgSN5bM796AkVf0kBD4zp0CCIs=
 github.com/bmatcuk/doublestar/v4 v4.8.1 h1:54Bopc5c2cAvhLRAzqOGCYHYyhcDHsFF4wWIR5wKP38=
 github.com/bmatcuk/doublestar/v4 v4.8.1/go.mod h1:xBQ8jztBU6kakFMg+8WGxn0c6z1fTSPVIjEY1Wr7jzc=
 github.com/bool64/shared v0.1.5 h1:fp3eUhBsrSjNCQPcSdQqZxxh9bBwrYiZ+zOKFkM0/2E=