diff --git a/cli/organization_test.go b/cli/organization_test.go
index 8c4997f4ae..ab5751b513 100644
--- a/cli/organization_test.go
+++ b/cli/organization_test.go
@@ -17,7 +17,8 @@ import (
 	"github.com/coder/coder/v2/cli/clitest"
 	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/pty/ptytest"
+	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 	"github.com/coder/pretty"
 )
 
@@ -29,6 +30,7 @@ func TestCurrentOrganization(t *testing.T) {
 	// 2. The user is connecting to an older Coder instance.
 	t.Run("no-default", func(t *testing.T) {
 		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitMedium)
 
 		orgID := uuid.New()
 		srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
@@ -49,13 +51,13 @@ func TestCurrentOrganization(t *testing.T) {
 		client := codersdk.New(must(url.Parse(srv.URL)))
 		inv, root := clitest.New(t, "organizations", "show", "selected")
 		clitest.SetupConfig(t, client, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		errC := make(chan error)
 		go func() {
 			errC <- inv.Run()
 		}()
 		require.NoError(t, <-errC)
-		pty.ExpectMatch(orgID.String())
+		stdout.ExpectMatchContext(ctx, orgID.String())
 	})
 }
 
@@ -140,6 +142,8 @@ func TestOrganizationDelete(t *testing.T) {
 
 	t.Run("Prompted", func(t *testing.T) {
 		t.Parallel()
+		logger := testutil.Logger(t)
+		ctx := testutil.Context(t, testutil.WaitMedium)
 
 		orgID := uuid.New()
 		var deleteCalled atomic.Bool
@@ -167,15 +171,16 @@ func TestOrganizationDelete(t *testing.T) {
 		client := codersdk.New(must(url.Parse(server.URL)))
 		inv, root := clitest.New(t, "organizations", "delete", "my-org")
 		clitest.SetupConfig(t, client, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 
 		execDone := make(chan error)
 		go func() {
 			execDone <- inv.Run()
 		}()
 
-		pty.ExpectMatch(fmt.Sprintf("Delete organization %s?", pretty.Sprint(cliui.DefaultStyles.Code, "my-org")))
-		pty.WriteLine("yes")
+		stdout.ExpectMatchContext(ctx, fmt.Sprintf("Delete organization %s?", pretty.Sprint(cliui.DefaultStyles.Code, "my-org")))
+		stdin.WriteLine("yes")
 
 		require.NoError(t, <-execDone)
 		require.True(t, deleteCalled.Load(), "expected delete request")
diff --git a/cli/portforward_test.go b/cli/portforward_test.go
index 91c13efabe..d0cfeeb8fb 100644
--- a/cli/portforward_test.go
+++ b/cli/portforward_test.go
@@ -25,8 +25,8 @@ import (
 	"github.com/coder/coder/v2/coderd/database/dbfake"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 )
 
 func TestPortForward_None(t *testing.T) {
@@ -160,10 +160,7 @@ func TestPortForward(t *testing.T) {
 			// the "local" listener.
 			inv, root := clitest.New(t, "-v", "port-forward", workspace.Name, flag)
 			clitest.SetupConfig(t, member, root)
-			pty := ptytest.New(t)
-			inv.Stdin = pty.Input()
-			inv.Stdout = pty.Output()
-			inv.Stderr = pty.Output()
+			stdout := expecter.NewAttachedToInvocation(t, inv)
 
 			iNet := testutil.NewInProcNet()
 			inv.Net = iNet
@@ -175,7 +172,7 @@ func TestPortForward(t *testing.T) {
 				t.Logf("command complete; err=%s", err.Error())
 				errC <- err
 			}()
-			pty.ExpectMatchContext(ctx, "Ready!")
+			stdout.ExpectMatchContext(ctx, "Ready!")
 
 			// Open two connections simultaneously and test them out of
 			// sync.
@@ -216,10 +213,7 @@ func TestPortForward(t *testing.T) {
 			// the "local" listeners.
 			inv, root := clitest.New(t, "-v", "port-forward", workspace.Name, flag1, flag2)
 			clitest.SetupConfig(t, member, root)
-			pty := ptytest.New(t)
-			inv.Stdin = pty.Input()
-			inv.Stdout = pty.Output()
-			inv.Stderr = pty.Output()
+			stdout := expecter.NewAttachedToInvocation(t, inv)
 
 			iNet := testutil.NewInProcNet()
 			inv.Net = iNet
@@ -229,7 +223,7 @@ func TestPortForward(t *testing.T) {
 			go func() {
 				errC <- inv.WithContext(ctx).Run()
 			}()
-			pty.ExpectMatchContext(ctx, "Ready!")
+			stdout.ExpectMatchContext(ctx, "Ready!")
 
 			// Open a connection to both listener 1 and 2 simultaneously and
 			// then test them out of order.
@@ -277,8 +271,7 @@ func TestPortForward(t *testing.T) {
 		// the "local" listeners.
 		inv, root := clitest.New(t, append([]string{"-v", "port-forward", workspace.Name}, flags...)...)
 		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stderr = pty.Output()
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		iNet := testutil.NewInProcNet()
 		inv.Net = iNet
@@ -288,7 +281,7 @@ func TestPortForward(t *testing.T) {
 		go func() {
 			errC <- inv.WithContext(ctx).Run()
 		}()
-		pty.ExpectMatchContext(ctx, "Ready!")
+		stdout.ExpectMatchContext(ctx, "Ready!")
 
 		// Open connections to all items in the "dial" array.
 		var (
@@ -338,10 +331,7 @@ func TestPortForward(t *testing.T) {
 		// the "local" listener.
 		inv, root := clitest.New(t, "-v", "port-forward", workspace.Name, flag)
 		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t)
-		inv.Stdin = pty.Input()
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		iNet := testutil.NewInProcNet()
 		inv.Net = iNet
@@ -359,7 +349,7 @@ func TestPortForward(t *testing.T) {
 			t.Logf("command complete; err=%s", err.Error())
 			errC <- err
 		}()
-		pty.ExpectMatchContext(ctx, "Ready!")
+		stdout.ExpectMatchContext(ctx, "Ready!")
 
 		// Test IPv4 still works
 		dialCtx, dialCtxCancel := context.WithTimeout(ctx, testutil.WaitShort)
diff --git a/cli/rename_test.go b/cli/rename_test.go
index 31d14e5e08..e9aa8d480d 100644
--- a/cli/rename_test.go
+++ b/cli/rename_test.go
@@ -8,12 +8,13 @@ import (
 
 	"github.com/coder/coder/v2/cli/clitest"
 	"github.com/coder/coder/v2/coderd/coderdtest"
-	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 )
 
 func TestRename(t *testing.T) {
 	t.Parallel()
+	logger := testutil.Logger(t)
 
 	client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true, AllowWorkspaceRenames: true})
 	owner := coderdtest.CreateFirstUser(t, client)
@@ -30,13 +31,13 @@ func TestRename(t *testing.T) {
 	want := coderdtest.RandomUsername(t)
 	inv, root := clitest.New(t, "rename", workspace.Name, want, "--yes")
 	clitest.SetupConfig(t, member, root)
-	pty := ptytest.New(t)
-	pty.Attach(inv)
+	stdout := expecter.NewAttachedToInvocation(t, inv)
+	stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 	clitest.Start(t, inv)
 
-	pty.ExpectMatch("confirm rename:")
-	pty.WriteLine(workspace.Name)
-	pty.ExpectMatch("renamed to")
+	stdout.ExpectMatchContext(ctx, "confirm rename:")
+	stdin.WriteLine(workspace.Name)
+	stdout.ExpectMatchContext(ctx, "renamed to")
 
 	ws, err := client.Workspace(ctx, workspace.ID)
 	assert.NoError(t, err)
diff --git a/cli/restart_test.go b/cli/restart_test.go
index a8cd7ee5f3..3506d313a2 100644
--- a/cli/restart_test.go
+++ b/cli/restart_test.go
@@ -1,7 +1,6 @@
 package cli_test
 
 import (
-	"context"
 	"fmt"
 	"testing"
 
@@ -14,8 +13,8 @@ import (
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/provisioner/echo"
 	"github.com/coder/coder/v2/provisionersdk/proto"
-	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 )
 
 func TestRestart(t *testing.T) {
@@ -49,15 +48,15 @@ func TestRestart(t *testing.T) {
 		inv, root := clitest.New(t, "restart", workspace.Name, "--yes")
 		clitest.SetupConfig(t, member, root)
 
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		done := make(chan error, 1)
 		go func() {
 			done <- inv.WithContext(ctx).Run()
 		}()
-		pty.ExpectMatch("Stopping workspace")
-		pty.ExpectMatch("Starting workspace")
-		pty.ExpectMatch("workspace has been restarted")
+		stdout.ExpectMatchContext(ctx, "Stopping workspace")
+		stdout.ExpectMatchContext(ctx, "Starting workspace")
+		stdout.ExpectMatchContext(ctx, "workspace has been restarted")
 
 		err := <-done
 		require.NoError(t, err, "execute failed")
@@ -66,6 +65,7 @@ func TestRestart(t *testing.T) {
 	t.Run("PromptEphemeralParameters", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 		owner := coderdtest.CreateFirstUser(t, client)
 		member, memberUser := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
@@ -84,13 +84,15 @@ func TestRestart(t *testing.T) {
 		inv, root := clitest.New(t, "restart", workspace.Name, "--prompt-ephemeral-parameters")
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		go func() {
 			defer close(doneChan)
 			err := inv.Run()
 			assert.NoError(t, err)
 		}()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		matches := []string{
 			ephemeralParameterDescription, ephemeralParameterValue,
 			"Restart workspace?", "yes",
@@ -101,18 +103,15 @@ func TestRestart(t *testing.T) {
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
 			value := matches[i+1]
-			pty.ExpectMatch(match)
+			stdout.ExpectMatchContext(ctx, match)
 
 			if value != "" {
-				pty.WriteLine(value)
+				stdin.WriteLine(value)
 			}
 		}
 		<-doneChan
 
 		// Verify if build option is set
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
 		workspace, err := client.WorkspaceByOwnerAndName(ctx, memberUser.ID.String(), workspace.Name, codersdk.WorkspaceOptions{})
 		require.NoError(t, err)
 		actualParameters, err := client.WorkspaceBuildParameters(ctx, workspace.LatestBuild.ID)
@@ -126,6 +125,7 @@ func TestRestart(t *testing.T) {
 	t.Run("EphemeralParameterFlags", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 		owner := coderdtest.CreateFirstUser(t, client)
 		member, memberUser := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
@@ -143,13 +143,15 @@ func TestRestart(t *testing.T) {
 			"--ephemeral-parameter", fmt.Sprintf("%s=%s", ephemeralParameterName, ephemeralParameterValue))
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		go func() {
 			defer close(doneChan)
 			err := inv.Run()
 			assert.NoError(t, err)
 		}()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		matches := []string{
 			"Restart workspace?", "yes",
 			"Stopping workspace", "",
@@ -159,18 +161,15 @@ func TestRestart(t *testing.T) {
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
 			value := matches[i+1]
-			pty.ExpectMatch(match)
+			stdout.ExpectMatchContext(ctx, match)
 
 			if value != "" {
-				pty.WriteLine(value)
+				stdin.WriteLine(value)
 			}
 		}
 		<-doneChan
 
 		// Verify if build option is set
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
 		workspace, err := client.WorkspaceByOwnerAndName(ctx, memberUser.ID.String(), workspace.Name, codersdk.WorkspaceOptions{})
 		require.NoError(t, err)
 		actualParameters, err := client.WorkspaceBuildParameters(ctx, workspace.LatestBuild.ID)
@@ -184,6 +183,7 @@ func TestRestart(t *testing.T) {
 	t.Run("with deprecated build-options flag", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 		owner := coderdtest.CreateFirstUser(t, client)
 		member, memberUser := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
@@ -202,13 +202,15 @@ func TestRestart(t *testing.T) {
 		inv, root := clitest.New(t, "restart", workspace.Name, "--build-options")
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		go func() {
 			defer close(doneChan)
 			err := inv.Run()
 			assert.NoError(t, err)
 		}()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		matches := []string{
 			ephemeralParameterDescription, ephemeralParameterValue,
 			"Restart workspace?", "yes",
@@ -219,18 +221,15 @@ func TestRestart(t *testing.T) {
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
 			value := matches[i+1]
-			pty.ExpectMatch(match)
+			stdout.ExpectMatchContext(ctx, match)
 
 			if value != "" {
-				pty.WriteLine(value)
+				stdin.WriteLine(value)
 			}
 		}
 		<-doneChan
 
 		// Verify if build option is set
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
 		workspace, err := client.WorkspaceByOwnerAndName(ctx, memberUser.ID.String(), workspace.Name, codersdk.WorkspaceOptions{})
 		require.NoError(t, err)
 		actualParameters, err := client.WorkspaceBuildParameters(ctx, workspace.LatestBuild.ID)
@@ -244,6 +243,7 @@ func TestRestart(t *testing.T) {
 	t.Run("with deprecated build-option flag", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 		owner := coderdtest.CreateFirstUser(t, client)
 		member, memberUser := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
@@ -261,13 +261,15 @@ func TestRestart(t *testing.T) {
 			"--build-option", fmt.Sprintf("%s=%s", ephemeralParameterName, ephemeralParameterValue))
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		go func() {
 			defer close(doneChan)
 			err := inv.Run()
 			assert.NoError(t, err)
 		}()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		matches := []string{
 			"Restart workspace?", "yes",
 			"Stopping workspace", "",
@@ -277,18 +279,15 @@ func TestRestart(t *testing.T) {
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
 			value := matches[i+1]
-			pty.ExpectMatch(match)
+			stdout.ExpectMatchContext(ctx, match)
 
 			if value != "" {
-				pty.WriteLine(value)
+				stdin.WriteLine(value)
 			}
 		}
 		<-doneChan
 
 		// Verify if build option is set
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
 		workspace, err := client.WorkspaceByOwnerAndName(ctx, memberUser.ID.String(), workspace.Name, codersdk.WorkspaceOptions{})
 		require.NoError(t, err)
 		actualParameters, err := client.WorkspaceBuildParameters(ctx, workspace.LatestBuild.ID)
@@ -349,20 +348,18 @@ func TestRestartWithParameters(t *testing.T) {
 		inv, root := clitest.New(t, "restart", workspace.Name, "-y")
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		go func() {
 			defer close(doneChan)
 			err := inv.Run()
 			assert.NoError(t, err)
 		}()
+		ctx := testutil.Context(t, testutil.WaitShort)
 
-		pty.ExpectMatch("workspace has been restarted")
+		stdout.ExpectMatchContext(ctx, "workspace has been restarted")
 		<-doneChan
 
 		// Verify if immutable parameter is set
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
 		workspace, err := client.WorkspaceByOwnerAndName(ctx, workspace.OwnerName, workspace.Name, codersdk.WorkspaceOptions{})
 		require.NoError(t, err)
 		actualParameters, err := client.WorkspaceBuildParameters(ctx, workspace.LatestBuild.ID)
@@ -376,6 +373,7 @@ func TestRestartWithParameters(t *testing.T) {
 	t.Run("AlwaysPrompt", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		// Create the workspace
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 		owner := coderdtest.CreateFirstUser(t, client)
@@ -396,24 +394,23 @@ func TestRestartWithParameters(t *testing.T) {
 		inv, root := clitest.New(t, "restart", workspace.Name, "-y", "--always-prompt")
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		go func() {
 			defer close(doneChan)
 			err := inv.Run()
 			assert.NoError(t, err)
 		}()
+		ctx := testutil.Context(t, testutil.WaitShort)
 
 		// We should be prompted for the parameters again.
 		newValue := "xyz"
-		pty.ExpectMatch(mutableParameterName)
-		pty.WriteLine(newValue)
-		pty.ExpectMatch("workspace has been restarted")
+		stdout.ExpectMatchContext(ctx, mutableParameterName)
+		stdin.WriteLine(newValue)
+		stdout.ExpectMatchContext(ctx, "workspace has been restarted")
 		<-doneChan
 
 		// Verify that the updated values are persisted.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
 		workspace, err := client.WorkspaceByOwnerAndName(ctx, workspace.OwnerName, workspace.Name, codersdk.WorkspaceOptions{})
 		require.NoError(t, err)
 		actualParameters, err := client.WorkspaceBuildParameters(ctx, workspace.LatestBuild.ID)
diff --git a/cli/schedule_test.go b/cli/schedule_test.go
index ed9c5b1743..c9f61345a1 100644
--- a/cli/schedule_test.go
+++ b/cli/schedule_test.go
@@ -19,8 +19,8 @@ import (
 	"github.com/coder/coder/v2/coderd/schedule/cron"
 	"github.com/coder/coder/v2/coderd/util/tz"
 	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 )
 
 // setupTestSchedule creates 4 workspaces:
@@ -97,20 +97,21 @@ func TestScheduleShow(t *testing.T) {
 		inv, root := clitest.New(t, "schedule", "show")
 		//nolint:gocritic // Testing that owner user sees all
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: they should see their own workspaces.
 		// 1st workspace: a-owner-ws1 has both autostart and autostop enabled.
-		pty.ExpectMatch(ws[0].OwnerName + "/" + ws[0].Name)
-		pty.ExpectMatch(sched.Humanize())
-		pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
-		pty.ExpectMatch("8h")
-		pty.ExpectMatch(ws[0].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[0].OwnerName+"/"+ws[0].Name)
+		stdout.ExpectMatchContext(ctx, sched.Humanize())
+		stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, "8h")
+		stdout.ExpectMatchContext(ctx, ws[0].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 		// 2nd workspace: b-owner-ws2 has only autostart enabled.
-		pty.ExpectMatch(ws[1].OwnerName + "/" + ws[1].Name)
-		pty.ExpectMatch(sched.Humanize())
-		pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[1].OwnerName+"/"+ws[1].Name)
+		stdout.ExpectMatchContext(ctx, sched.Humanize())
+		stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
 	})
 
 	t.Run("OwnerAll", func(t *testing.T) {
@@ -118,26 +119,27 @@ func TestScheduleShow(t *testing.T) {
 		inv, root := clitest.New(t, "schedule", "show", "--all")
 		//nolint:gocritic // Testing that owner user sees all
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: they should see all workspaces
 		// 1st workspace: a-owner-ws1 has both autostart and autostop enabled.
-		pty.ExpectMatch(ws[0].OwnerName + "/" + ws[0].Name)
-		pty.ExpectMatch(sched.Humanize())
-		pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
-		pty.ExpectMatch("8h")
-		pty.ExpectMatch(ws[0].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[0].OwnerName+"/"+ws[0].Name)
+		stdout.ExpectMatchContext(ctx, sched.Humanize())
+		stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, "8h")
+		stdout.ExpectMatchContext(ctx, ws[0].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 		// 2nd workspace: b-owner-ws2 has only autostart enabled.
-		pty.ExpectMatch(ws[1].OwnerName + "/" + ws[1].Name)
-		pty.ExpectMatch(sched.Humanize())
-		pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[1].OwnerName+"/"+ws[1].Name)
+		stdout.ExpectMatchContext(ctx, sched.Humanize())
+		stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
 		// 3rd workspace: c-member-ws3 has only autostop enabled.
-		pty.ExpectMatch(ws[2].OwnerName + "/" + ws[2].Name)
-		pty.ExpectMatch("8h")
-		pty.ExpectMatch(ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[2].OwnerName+"/"+ws[2].Name)
+		stdout.ExpectMatchContext(ctx, "8h")
+		stdout.ExpectMatchContext(ctx, ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 		// 4th workspace: d-member-ws4 has neither autostart nor autostop enabled.
-		pty.ExpectMatch(ws[3].OwnerName + "/" + ws[3].Name)
+		stdout.ExpectMatchContext(ctx, ws[3].OwnerName+"/"+ws[3].Name)
 	})
 
 	t.Run("OwnerSearchByName", func(t *testing.T) {
@@ -145,14 +147,15 @@ func TestScheduleShow(t *testing.T) {
 		inv, root := clitest.New(t, "schedule", "show", "--search", "name:"+ws[1].Name)
 		//nolint:gocritic // Testing that owner user sees all
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: they should see workspaces matching that query
 		// 2nd workspace: b-owner-ws2 has only autostart enabled.
-		pty.ExpectMatch(ws[1].OwnerName + "/" + ws[1].Name)
-		pty.ExpectMatch(sched.Humanize())
-		pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[1].OwnerName+"/"+ws[1].Name)
+		stdout.ExpectMatchContext(ctx, sched.Humanize())
+		stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
 	})
 
 	t.Run("OwnerOneArg", func(t *testing.T) {
@@ -160,37 +163,39 @@ func TestScheduleShow(t *testing.T) {
 		inv, root := clitest.New(t, "schedule", "show", ws[2].OwnerName+"/"+ws[2].Name)
 		//nolint:gocritic // Testing that owner user sees all
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: they should see that workspace
 		// 3rd workspace: c-member-ws3 has only autostop enabled.
-		pty.ExpectMatch(ws[2].OwnerName + "/" + ws[2].Name)
-		pty.ExpectMatch("8h")
-		pty.ExpectMatch(ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[2].OwnerName+"/"+ws[2].Name)
+		stdout.ExpectMatchContext(ctx, "8h")
+		stdout.ExpectMatchContext(ctx, ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 	})
 
 	t.Run("MemberNoArgs", func(t *testing.T) {
 		// When: a member specifies no args
 		inv, root := clitest.New(t, "schedule", "show")
 		clitest.SetupConfig(t, memberClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: they should see their own workspaces
 		// 1st workspace: c-member-ws3 has only autostop enabled.
-		pty.ExpectMatch(ws[2].OwnerName + "/" + ws[2].Name)
-		pty.ExpectMatch("8h")
-		pty.ExpectMatch(ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[2].OwnerName+"/"+ws[2].Name)
+		stdout.ExpectMatchContext(ctx, "8h")
+		stdout.ExpectMatchContext(ctx, ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 		// 2nd workspace: d-member-ws4 has neither autostart nor autostop enabled.
-		pty.ExpectMatch(ws[3].OwnerName + "/" + ws[3].Name)
+		stdout.ExpectMatchContext(ctx, ws[3].OwnerName+"/"+ws[3].Name)
 	})
 
 	t.Run("MemberAll", func(t *testing.T) {
 		// When: a member lists all workspaces
 		inv, root := clitest.New(t, "schedule", "show", "--all")
 		clitest.SetupConfig(t, memberClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		ctx := testutil.Context(t, testutil.WaitShort)
 		errC := make(chan error)
 		go func() {
@@ -200,11 +205,11 @@ func TestScheduleShow(t *testing.T) {
 
 		// Then: they should only see their own
 		// 1st workspace: c-member-ws3 has only autostop enabled.
-		pty.ExpectMatch(ws[2].OwnerName + "/" + ws[2].Name)
-		pty.ExpectMatch("8h")
-		pty.ExpectMatch(ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[2].OwnerName+"/"+ws[2].Name)
+		stdout.ExpectMatchContext(ctx, "8h")
+		stdout.ExpectMatchContext(ctx, ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 		// 2nd workspace: d-member-ws4 has neither autostart nor autostop enabled.
-		pty.ExpectMatch(ws[3].OwnerName + "/" + ws[3].Name)
+		stdout.ExpectMatchContext(ctx, ws[3].OwnerName+"/"+ws[3].Name)
 	})
 
 	t.Run("JSON", func(t *testing.T) {
@@ -276,13 +281,14 @@ func TestScheduleModify(t *testing.T) {
 		)
 		//nolint:gocritic // this workspace is not owned by the same user
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: the updated schedule should be shown
-		pty.ExpectMatch(ws[3].OwnerName + "/" + ws[3].Name)
-		pty.ExpectMatch(sched.Humanize())
-		pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[3].OwnerName+"/"+ws[3].Name)
+		stdout.ExpectMatchContext(ctx, sched.Humanize())
+		stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
 	})
 
 	t.Run("SetStop", func(t *testing.T) {
@@ -292,13 +298,14 @@ func TestScheduleModify(t *testing.T) {
 		)
 		//nolint:gocritic // this workspace is not owned by the same user
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: the updated schedule should be shown
-		pty.ExpectMatch(ws[2].OwnerName + "/" + ws[2].Name)
-		pty.ExpectMatch("8h30m")
-		pty.ExpectMatch(ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
+		stdout.ExpectMatchContext(ctx, ws[2].OwnerName+"/"+ws[2].Name)
+		stdout.ExpectMatchContext(ctx, "8h30m")
+		stdout.ExpectMatchContext(ctx, ws[2].LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339))
 	})
 
 	t.Run("UnsetStart", func(t *testing.T) {
@@ -308,11 +315,12 @@ func TestScheduleModify(t *testing.T) {
 		)
 		//nolint:gocritic // this workspace is owned by owner
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: the updated schedule should be shown
-		pty.ExpectMatch(ws[1].OwnerName + "/" + ws[1].Name)
+		stdout.ExpectMatchContext(ctx, ws[1].OwnerName+"/"+ws[1].Name)
 	})
 
 	t.Run("UnsetStop", func(t *testing.T) {
@@ -322,11 +330,12 @@ func TestScheduleModify(t *testing.T) {
 		)
 		//nolint:gocritic // this workspace is owned by owner
 		clitest.SetupConfig(t, ownerClient, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: the updated schedule should be shown
-		pty.ExpectMatch(ws[0].OwnerName + "/" + ws[0].Name)
+		stdout.ExpectMatchContext(ctx, ws[0].OwnerName+"/"+ws[0].Name)
 	})
 }
 
@@ -359,7 +368,8 @@ func TestScheduleOverride(t *testing.T) {
 			)
 
 			clitest.SetupConfig(t, ownerClient, root)
-			pty := ptytest.New(t).Attach(inv)
+			stdout := expecter.NewAttachedToInvocation(t, inv)
+			ctx := testutil.Context(t, testutil.WaitShort)
 			require.NoError(t, inv.Run())
 
 			// Fetch the workspace to get the actual deadline set by the
@@ -376,11 +386,11 @@ func TestScheduleOverride(t *testing.T) {
 			expectedDeadline := updated.LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339)
 
 			// Then: the updated schedule should be shown
-			pty.ExpectMatch(ws[0].OwnerName + "/" + ws[0].Name)
-			pty.ExpectMatch(sched.Humanize())
-			pty.ExpectMatch(sched.Next(now).In(loc).Format(time.RFC3339))
-			pty.ExpectMatch("8h")
-			pty.ExpectMatch(expectedDeadline)
+			stdout.ExpectMatchContext(ctx, ws[0].OwnerName+"/"+ws[0].Name)
+			stdout.ExpectMatchContext(ctx, sched.Humanize())
+			stdout.ExpectMatchContext(ctx, sched.Next(now).In(loc).Format(time.RFC3339))
+			stdout.ExpectMatchContext(ctx, "8h")
+			stdout.ExpectMatchContext(ctx, expectedDeadline)
 		})
 	}
 }
@@ -422,13 +432,14 @@ func TestScheduleStart_TemplateAutostartRequirement(t *testing.T) {
 			"schedule", "start", workspace.Name, "9:30AM", "Mon-Fri",
 		)
 		clitest.SetupConfig(t, client, root)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		require.NoError(t, inv.Run())
 
 		// Then: warning should be shown
 		// In AGPL, this will show all days (enterprise feature defaults to all days allowed)
-		pty.ExpectMatch("Warning")
-		pty.ExpectMatch("may only autostart")
+		stdout.ExpectMatchContext(ctx, "Warning")
+		stdout.ExpectMatchContext(ctx, "may only autostart")
 	})
 
 	t.Run("NoWarningWhenManual", func(t *testing.T) {
diff --git a/cli/secret_test.go b/cli/secret_test.go
index 3cbb6b89b8..06224d45c6 100644
--- a/cli/secret_test.go
+++ b/cli/secret_test.go
@@ -14,8 +14,8 @@ import (
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 )
 
 func TestSecretCreate(t *testing.T) {
@@ -501,6 +501,7 @@ func TestSecretDelete(t *testing.T) {
 	t.Run("Success", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		client := coderdtest.New(t, nil)
 		_ = coderdtest.CreateFirstUser(t, client)
 
@@ -516,12 +517,13 @@ func TestSecretDelete(t *testing.T) {
 
 		ctx := testutil.Context(t, testutil.WaitMedium)
 		inv = inv.WithContext(ctx)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		waiter := clitest.StartWithWaiter(t, inv)
-		pty.ExpectMatchContext(ctx, "Delete secret")
-		pty.ExpectMatchContext(ctx, "service-token")
-		pty.WriteLine("yes")
-		pty.ExpectMatchContext(ctx, "Deleted secret")
+		stdout.ExpectMatchContext(ctx, "Delete secret")
+		stdout.ExpectMatchContext(ctx, "service-token")
+		stdin.WriteLine("yes")
+		stdout.ExpectMatchContext(ctx, "Deleted secret")
 
 		require.NoError(t, waiter.Wait())
 
@@ -566,6 +568,7 @@ func TestSecretDelete(t *testing.T) {
 	t.Run("NotFound", func(t *testing.T) {
 		t.Parallel()
 
+		logger := testutil.Logger(t)
 		client := coderdtest.New(t, nil)
 		_ = coderdtest.CreateFirstUser(t, client)
 
@@ -574,11 +577,12 @@ func TestSecretDelete(t *testing.T) {
 
 		ctx := testutil.Context(t, testutil.WaitMedium)
 		inv = inv.WithContext(ctx)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 		waiter := clitest.StartWithWaiter(t, inv)
-		pty.ExpectMatchContext(ctx, "Delete secret")
-		pty.ExpectMatchContext(ctx, "missing-secret")
-		pty.WriteLine("yes")
+		stdout.ExpectMatchContext(ctx, "Delete secret")
+		stdout.ExpectMatchContext(ctx, "missing-secret")
+		stdin.WriteLine("yes")
 
 		err := waiter.Wait()
 		require.ErrorContains(t, err, `delete secret "missing-secret"`)
diff --git a/cli/server_createadminuser_test.go b/cli/server_createadminuser_test.go
index c0883a2d27..d0eef5f72d 100644
--- a/cli/server_createadminuser_test.go
+++ b/cli/server_createadminuser_test.go
@@ -21,6 +21,7 @@ import (
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 )
 
 //nolint:paralleltest, tparallel
@@ -128,19 +129,17 @@ func TestServerCreateAdminUser(t *testing.T) {
 			"--email", email,
 			"--password", password,
 		)
-		pty := ptytest.New(t)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		clitest.Start(t, inv)
 
-		pty.ExpectMatchContext(ctx, "Creating user...")
-		pty.ExpectMatchContext(ctx, "Generating user SSH key...")
-		pty.ExpectMatchContext(ctx, fmt.Sprintf("Adding user to organization %q (%s) as admin...", org1Name, org1ID.String()))
-		pty.ExpectMatchContext(ctx, fmt.Sprintf("Adding user to organization %q (%s) as admin...", org2Name, org2ID.String()))
-		pty.ExpectMatchContext(ctx, "User created successfully.")
-		pty.ExpectMatchContext(ctx, username)
-		pty.ExpectMatchContext(ctx, email)
-		pty.ExpectMatchContext(ctx, "****")
+		stdout.ExpectMatchContext(ctx, "Creating user...")
+		stdout.ExpectMatchContext(ctx, "Generating user SSH key...")
+		stdout.ExpectMatchContext(ctx, fmt.Sprintf("Adding user to organization %q (%s) as admin...", org1Name, org1ID.String()))
+		stdout.ExpectMatchContext(ctx, fmt.Sprintf("Adding user to organization %q (%s) as admin...", org2Name, org2ID.String()))
+		stdout.ExpectMatchContext(ctx, "User created successfully.")
+		stdout.ExpectMatchContext(ctx, username)
+		stdout.ExpectMatchContext(ctx, email)
+		stdout.ExpectMatchContext(ctx, "****")
 
 		verifyUser(t, connectionURL, username, email, password)
 	})
@@ -184,6 +183,7 @@ func TestServerCreateAdminUser(t *testing.T) {
 			// Skip on non-Linux because it spawns a PostgreSQL instance.
 			t.SkipNow()
 		}
+		logger := testutil.Logger(t)
 		connectionURL, err := dbtestutil.Open(t)
 		require.NoError(t, err)
 
@@ -195,23 +195,24 @@ func TestServerCreateAdminUser(t *testing.T) {
 			"--postgres-url", connectionURL,
 			"--ssh-keygen-algorithm", "ed25519",
 		)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
+		stdin := testutil.NewWriterAttachedToInvocation(t, logger.Named("stdin"), inv)
 
 		clitest.Start(t, inv)
 
-		pty.ExpectMatchContext(ctx, "Username")
-		pty.WriteLine(username)
-		pty.ExpectMatchContext(ctx, "Email")
-		pty.WriteLine(email)
-		pty.ExpectMatchContext(ctx, "Password")
-		pty.WriteLine(password)
-		pty.ExpectMatchContext(ctx, "Confirm password")
-		pty.WriteLine(password)
+		stdout.ExpectMatchContext(ctx, "Username")
+		stdin.WriteLine(username)
+		stdout.ExpectMatchContext(ctx, "Email")
+		stdin.WriteLine(email)
+		stdout.ExpectMatchContext(ctx, "Password")
+		stdin.WriteLine(password)
+		stdout.ExpectMatchContext(ctx, "Confirm password")
+		stdin.WriteLine(password)
 
-		pty.ExpectMatchContext(ctx, "User created successfully.")
-		pty.ExpectMatchContext(ctx, username)
-		pty.ExpectMatchContext(ctx, email)
-		pty.ExpectMatchContext(ctx, "****")
+		stdout.ExpectMatchContext(ctx, "User created successfully.")
+		stdout.ExpectMatchContext(ctx, username)
+		stdout.ExpectMatchContext(ctx, email)
+		stdout.ExpectMatchContext(ctx, "****")
 
 		verifyUser(t, connectionURL, username, email, password)
 	})
diff --git a/cli/server_test.go b/cli/server_test.go
index 89e0ba7048..6776e84424 100644
--- a/cli/server_test.go
+++ b/cli/server_test.go
@@ -59,6 +59,7 @@ import (
 	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/tailnet/tailnettest"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/coder/v2/testutil/expecter"
 	"github.com/coder/serpent"
 )
 
@@ -229,7 +230,7 @@ func TestServer(t *testing.T) {
 			"--access-url", "http://example.com",
 			"--ephemeral",
 		)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		// Embedded postgres takes a while to fire up.
 		const superDuperLong = testutil.WaitSuperLong * 3
@@ -240,7 +241,7 @@ func TestServer(t *testing.T) {
 		}()
 		matchCh1 := make(chan string, 1)
 		go func() {
-			matchCh1 <- pty.ExpectMatchContext(ctx, "Using an ephemeral deployment directory")
+			matchCh1 <- stdout.ExpectMatchContext(ctx, "Using an ephemeral deployment directory")
 		}()
 		select {
 		case err := <-errCh:
@@ -248,7 +249,7 @@ func TestServer(t *testing.T) {
 		case <-matchCh1:
 			// OK!
 		}
-		rootDirLine := pty.ReadLine(ctx)
+		rootDirLine := stdout.ReadLine(ctx)
 		rootDir := strings.TrimPrefix(rootDirLine, "Using an ephemeral deployment directory")
 		rootDir = strings.TrimSpace(rootDir)
 		rootDir = strings.TrimPrefix(rootDir, "(")
@@ -259,7 +260,7 @@ func TestServer(t *testing.T) {
 		matchCh2 := make(chan string, 1)
 		go func() {
 			// The "View the Web UI" log is a decent indicator that the server was successfully started.
-			matchCh2 <- pty.ExpectMatchContext(ctx, "View the Web UI")
+			matchCh2 <- stdout.ExpectMatchContext(ctx, "View the Web UI")
 		}()
 		select {
 		case err := <-errCh:
@@ -276,24 +277,23 @@ func TestServer(t *testing.T) {
 	t.Run("BuiltinPostgresURL", func(t *testing.T) {
 		t.Parallel()
 		root, _ := clitest.New(t, "server", "postgres-builtin-url")
-		pty := ptytest.New(t)
-		root.Stdout = pty.Output()
+		stdout := expecter.NewAttachedToInvocation(t, root)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		err := root.Run()
 		require.NoError(t, err)
 
-		pty.ExpectMatch("psql")
+		stdout.ExpectMatchContext(ctx, "psql")
 	})
 	t.Run("BuiltinPostgresURLRaw", func(t *testing.T) {
 		t.Parallel()
 		ctx := testutil.Context(t, testutil.WaitLong)
 
 		root, _ := clitest.New(t, "server", "postgres-builtin-url", "--raw-url")
-		pty := ptytest.New(t)
-		root.Stdout = pty.Output()
+		stdout := expecter.NewAttachedToInvocation(t, root)
 		err := root.WithContext(ctx).Run()
 		require.NoError(t, err)
 
-		got := pty.ReadLine(ctx)
+		got := stdout.ReadLine(ctx)
 		if !strings.HasPrefix(got, "postgres://") {
 			t.Fatalf("expected postgres URL to start with \"postgres://\", got %q", got)
 		}
@@ -506,6 +506,7 @@ func TestServer(t *testing.T) {
 	// reachable.
 	t.Run("LocalAccessURL", func(t *testing.T) {
 		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
 		inv, cfg := clitest.New(t,
 			"server",
 			dbArg(t),
@@ -513,7 +514,7 @@ func TestServer(t *testing.T) {
 			"--access-url", "http://localhost:3000/",
 			"--cache-dir", t.TempDir(),
 		)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		// Since we end the test after seeing the log lines about the access url, we could cancel the test before
 		// our initial interactions with PostgreSQL are complete. So, ignore errors of that type for this test.
 		startIgnoringPostgresQueryCancel(t, inv)
@@ -521,9 +522,9 @@ func TestServer(t *testing.T) {
 		// Just wait for startup
 		_ = waitAccessURL(t, cfg)
 
-		pty.ExpectMatch("this may cause unexpected problems when creating workspaces")
-		pty.ExpectMatch("View the Web UI:")
-		pty.ExpectMatch("http://localhost:3000/")
+		stdout.ExpectMatchContext(ctx, "this may cause unexpected problems when creating workspaces")
+		stdout.ExpectMatchContext(ctx, "View the Web UI:")
+		stdout.ExpectMatchContext(ctx, "http://localhost:3000/")
 	})
 
 	// Validate that an https scheme is prepended to a remote access URL
@@ -531,6 +532,7 @@ func TestServer(t *testing.T) {
 	t.Run("RemoteAccessURL", func(t *testing.T) {
 		t.Parallel()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		inv, cfg := clitest.New(t,
 			"server",
 			dbArg(t),
@@ -538,7 +540,7 @@ func TestServer(t *testing.T) {
 			"--access-url", "https://foobarbaz.mydomain",
 			"--cache-dir", t.TempDir(),
 		)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		// Since we end the test after seeing the log lines about the access url, we could cancel the test before
 		// our initial interactions with PostgreSQL are complete. So, ignore errors of that type for this test.
@@ -547,13 +549,14 @@ func TestServer(t *testing.T) {
 		// Just wait for startup
 		_ = waitAccessURL(t, cfg)
 
-		pty.ExpectMatch("this may cause unexpected problems when creating workspaces")
-		pty.ExpectMatch("View the Web UI:")
-		pty.ExpectMatch("https://foobarbaz.mydomain")
+		stdout.ExpectMatchContext(ctx, "this may cause unexpected problems when creating workspaces")
+		stdout.ExpectMatchContext(ctx, "View the Web UI:")
+		stdout.ExpectMatchContext(ctx, "https://foobarbaz.mydomain")
 	})
 
 	t.Run("NoWarningWithRemoteAccessURL", func(t *testing.T) {
 		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
 		inv, cfg := clitest.New(t,
 			"server",
 			dbArg(t),
@@ -561,7 +564,7 @@ func TestServer(t *testing.T) {
 			"--access-url", "https://google.com",
 			"--cache-dir", t.TempDir(),
 		)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		// Since we end the test after seeing the log lines about the access url, we could cancel the test before
 		// our initial interactions with PostgreSQL are complete. So, ignore errors of that type for this test.
 		startIgnoringPostgresQueryCancel(t, inv)
@@ -569,8 +572,8 @@ func TestServer(t *testing.T) {
 		// Just wait for startup
 		_ = waitAccessURL(t, cfg)
 
-		pty.ExpectMatch("View the Web UI:")
-		pty.ExpectMatch("https://google.com")
+		stdout.ExpectMatchContext(ctx, "View the Web UI:")
+		stdout.ExpectMatchContext(ctx, "https://google.com")
 	})
 
 	t.Run("NoSchemeAccessURL", func(t *testing.T) {
@@ -735,8 +738,6 @@ func TestServer(t *testing.T) {
 			"--tls-key-file", key2Path,
 			"--cache-dir", t.TempDir(),
 		)
-		pty := ptytest.New(t)
-		root.Stdout = pty.Output()
 		clitest.Start(t, root.WithContext(ctx))
 
 		accessURL := waitAccessURL(t, cfg)
@@ -814,18 +815,18 @@ func TestServer(t *testing.T) {
 			"--tls-key-file", keyPath,
 			"--cache-dir", t.TempDir(),
 		)
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		clitest.Start(t, inv)
 
 		// We can't use waitAccessURL as it will only return the HTTP URL.
 		const httpLinePrefix = "Started HTTP listener at"
-		pty.ExpectMatch(httpLinePrefix)
-		httpLine := pty.ReadLine(ctx)
+		stdout.ExpectMatchContext(ctx, httpLinePrefix)
+		httpLine := stdout.ReadLine(ctx)
 		httpAddr := strings.TrimSpace(strings.TrimPrefix(httpLine, httpLinePrefix))
 		require.NotEmpty(t, httpAddr)
 		const tlsLinePrefix = "Started TLS/HTTPS listener at "
-		pty.ExpectMatch(tlsLinePrefix)
-		tlsLine := pty.ReadLine(ctx)
+		stdout.ExpectMatchContext(ctx, tlsLinePrefix)
+		tlsLine := stdout.ReadLine(ctx)
 		tlsAddr := strings.TrimSpace(strings.TrimPrefix(tlsLine, tlsLinePrefix))
 		require.NotEmpty(t, tlsAddr)
 
@@ -951,8 +952,7 @@ func TestServer(t *testing.T) {
 				}
 
 				inv, _ := clitest.New(t, flags...)
-				pty := ptytest.New(t)
-				pty.Attach(inv)
+				stdout := expecter.NewAttachedToInvocation(t, inv)
 
 				clitest.Start(t, inv)
 
@@ -963,15 +963,15 @@ func TestServer(t *testing.T) {
 				// We can't use waitAccessURL as it will only return the HTTP URL.
 				if c.httpListener {
 					const httpLinePrefix = "Started HTTP listener at"
-					pty.ExpectMatch(httpLinePrefix)
-					httpLine := pty.ReadLine(ctx)
+					stdout.ExpectMatchContext(ctx, httpLinePrefix)
+					httpLine := stdout.ReadLine(ctx)
 					httpAddr = strings.TrimSpace(strings.TrimPrefix(httpLine, httpLinePrefix))
 					require.NotEmpty(t, httpAddr)
 				}
 				if c.tlsListener {
 					const tlsLinePrefix = "Started TLS/HTTPS listener at"
-					pty.ExpectMatch(tlsLinePrefix)
-					tlsLine := pty.ReadLine(ctx)
+					stdout.ExpectMatchContext(ctx, tlsLinePrefix)
+					tlsLine := stdout.ReadLine(ctx)
 					tlsAddr = strings.TrimSpace(strings.TrimPrefix(tlsLine, tlsLinePrefix))
 					require.NotEmpty(t, tlsAddr)
 				}
@@ -1041,6 +1041,7 @@ func TestServer(t *testing.T) {
 	t.Run("CanListenUnspecifiedv4", func(t *testing.T) {
 		t.Parallel()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		inv, _ := clitest.New(t,
 			"server",
 			dbArg(t),
@@ -1048,18 +1049,19 @@ func TestServer(t *testing.T) {
 			"--access-url", "http://example.com",
 		)
 
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		// Since we end the test after seeing the log lines about the HTTP listener, we could cancel the test before
 		// our initial interactions with PostgreSQL are complete. So, ignore errors of that type for this test.
 		startIgnoringPostgresQueryCancel(t, inv)
 
-		pty.ExpectMatch("Started HTTP listener")
-		pty.ExpectMatch("http://0.0.0.0:")
+		stdout.ExpectMatchContext(ctx, "Started HTTP listener")
+		stdout.ExpectMatchContext(ctx, "http://0.0.0.0:")
 	})
 
 	t.Run("CanListenUnspecifiedv6", func(t *testing.T) {
 		t.Parallel()
 
+		ctx := testutil.Context(t, testutil.WaitShort)
 		inv, _ := clitest.New(t,
 			"server",
 			dbArg(t),
@@ -1067,13 +1069,13 @@ func TestServer(t *testing.T) {
 			"--access-url", "http://example.com",
 		)
 
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		// Since we end the test after seeing the log lines about the HTTP listener, we could cancel the test before
 		// our initial interactions with PostgreSQL are complete. So, ignore errors of that type for this test.
 		startIgnoringPostgresQueryCancel(t, inv)
 
-		pty.ExpectMatch("Started HTTP listener at")
-		pty.ExpectMatch("http://[::]:")
+		stdout.ExpectMatchContext(ctx, "Started HTTP listener at")
+		stdout.ExpectMatchContext(ctx, "http://[::]:")
 	})
 
 	t.Run("NoAddress", func(t *testing.T) {
@@ -1128,12 +1130,10 @@ func TestServer(t *testing.T) {
 				"--access-url", "http://example.com",
 				"--cache-dir", t.TempDir(),
 			)
-			pty := ptytest.New(t)
-			inv.Stdout = pty.Output()
-			inv.Stderr = pty.Output()
+			stdout := expecter.NewAttachedToInvocation(t, inv)
 			clitest.Start(t, inv.WithContext(ctx))
 
-			pty.ExpectMatch("is deprecated")
+			stdout.ExpectMatchContext(ctx, "is deprecated")
 
 			accessURL := waitAccessURL(t, cfg)
 			require.Equal(t, "http", accessURL.Scheme)
@@ -1158,12 +1158,10 @@ func TestServer(t *testing.T) {
 				"--tls-key-file", keyPath,
 				"--cache-dir", t.TempDir(),
 			)
-			pty := ptytest.New(t)
-			root.Stdout = pty.Output()
-			root.Stderr = pty.Output()
+			stdout := expecter.NewAttachedToInvocation(t, root)
 			clitest.Start(t, root.WithContext(ctx))
 
-			pty.ExpectMatch("is deprecated")
+			stdout.ExpectMatchContext(ctx, "is deprecated")
 
 			accessURL := waitAccessURL(t, cfg)
 			require.Equal(t, "https", accessURL.Scheme)
@@ -1259,15 +1257,13 @@ func TestServer(t *testing.T) {
 				"--cache-dir", t.TempDir(),
 			)
 
-			pty := ptytest.New(t)
-			inv.Stdout = pty.Output()
-			inv.Stderr = pty.Output()
+			stdout := expecter.NewAttachedToInvocation(t, inv)
 
 			clitest.Start(t, inv)
 
 			// Wait until we see the prometheus address in the logs.
 			addrMatchExpr := `http server listening\s+addr=(\S+)\s+name=prometheus`
-			lineMatch := pty.ExpectRegexMatchContext(ctx, addrMatchExpr)
+			lineMatch := stdout.ExpectRegexMatchContext(ctx, addrMatchExpr)
 			promAddr := regexp.MustCompile(addrMatchExpr).FindStringSubmatch(lineMatch)[1]
 
 			testutil.Eventually(ctx, t, func(ctx context.Context) bool {
@@ -1322,15 +1318,13 @@ func TestServer(t *testing.T) {
 				"--cache-dir", t.TempDir(),
 			)
 
-			pty := ptytest.New(t)
-			inv.Stdout = pty.Output()
-			inv.Stderr = pty.Output()
+			stdout := expecter.NewAttachedToInvocation(t, inv)
 
 			clitest.Start(t, inv)
 
 			// Wait until we see the prometheus address in the logs.
 			addrMatchExpr := `http server listening\s+addr=(\S+)\s+name=prometheus`
-			lineMatch := pty.ExpectRegexMatchContext(ctx, addrMatchExpr)
+			lineMatch := stdout.ExpectRegexMatchContext(ctx, addrMatchExpr)
 			promAddr := regexp.MustCompile(addrMatchExpr).FindStringSubmatch(lineMatch)[1]
 
 			testutil.Eventually(ctx, t, func(ctx context.Context) bool {
@@ -1751,7 +1745,6 @@ func TestServer(t *testing.T) {
 			inv, cfg := clitest.New(t,
 				args...,
 			)
-			ptytest.New(t).Attach(inv)
 			inv = inv.WithContext(ctx)
 			w := clitest.StartWithWaiter(t, inv)
 			gotURL := waitAccessURL(t, cfg)
@@ -2019,15 +2012,15 @@ func TestServer_Logging_NoParallel(t *testing.T) {
 			"--provisioner-types=echo",
 			"--log-stackdriver", fi,
 		)
-		// Attach pty so we get debug output from the command if this test
+		// Attach expecter so we get debug output from the command if this test
 		// fails.
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		startIgnoringPostgresQueryCancel(t, inv.WithContext(ctx))
 
 		// Wait for server to listen on HTTP, this is a good
 		// starting point for expecting logs.
-		_ = pty.ExpectMatchContext(ctx, "Started HTTP listener at")
+		_ = stdout.ExpectMatchContext(ctx, "Started HTTP listener at")
 
 		loggingWaitFile(t, fi, testutil.WaitSuperLong)
 	})
@@ -2056,15 +2049,15 @@ func TestServer_Logging_NoParallel(t *testing.T) {
 			"--log-json", fi2,
 			"--log-stackdriver", fi3,
 		)
-		// Attach pty so we get debug output from the command if this test
+		// Attach expecter so we get debug output from the command if this test
 		// fails.
-		pty := ptytest.New(t).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 
 		startIgnoringPostgresQueryCancel(t, inv)
 
 		// Wait for server to listen on HTTP, this is a good
 		// starting point for expecting logs.
-		_ = pty.ExpectMatchContext(ctx, "Started HTTP listener at")
+		_ = stdout.ExpectMatchContext(ctx, "Started HTTP listener at")
 
 		loggingWaitFile(t, fi1, testutil.WaitSuperLong)
 		loggingWaitFile(t, fi2, testutil.WaitSuperLong)
@@ -2258,7 +2251,7 @@ func TestServer_GracefulShutdown(t *testing.T) {
 		return ctx, stopFunc
 	})
 	serverErr := make(chan error, 1)
-	pty := ptytest.New(t).Attach(root)
+	stdout := expecter.NewAttachedToInvocation(t, root)
 	go func() {
 		serverErr <- root.WithContext(ctx).Run()
 	}()
@@ -2266,7 +2259,7 @@ func TestServer_GracefulShutdown(t *testing.T) {
 	// It's fair to assume `stopFunc` isn't nil here, because the server
 	// has started and access URL is propagated.
 	stopFunc()
-	pty.ExpectMatch("waiting for provisioner jobs to complete")
+	stdout.ExpectMatchContext(ctx, "waiting for provisioner jobs to complete")
 	err := <-serverErr
 	require.NoError(t, err)
 }
@@ -2501,19 +2494,19 @@ func TestServer_TelemetryDisabled_FinalReport(t *testing.T) {
 		inv.Logger = inv.Logger.Named(opts.name)
 
 		errChan := make(chan error, 1)
-		pty := ptytest.New(t).Named(opts.name).Attach(inv)
+		stdout := expecter.NewAttachedToInvocation(t, inv)
 		go func() {
 			errChan <- inv.WithContext(ctx).Run()
 			// close the pty here so that we can start tearing down resources. This test creates multiple servers with
 			// associated ptys. There is a `t.Cleanup()` that does this, but it waits until the whole test is complete.
-			_ = pty.Close()
+			stdout.Close("invocation complete")
 		}()
 
 		if opts.waitForSnapshot {
-			pty.ExpectMatchContext(testutil.Context(t, testutil.WaitLong), "submitted snapshot")
+			stdout.ExpectMatchContext(testutil.Context(t, testutil.WaitLong), "submitted snapshot")
 		}
 		if opts.waitForTelemetryDisabledCheck {
-			pty.ExpectMatchContext(testutil.Context(t, testutil.WaitLong), "finished telemetry status check")
+			stdout.ExpectMatchContext(testutil.Context(t, testutil.WaitLong), "finished telemetry status check")
 		}
 		return errChan, cancelFunc
 	}