diff --git a/cli/exp_rpty_test.go b/cli/exp_rpty_test.go
index c7a0c47d18..9b5c0ffe22 100644
--- a/cli/exp_rpty_test.go
+++ b/cli/exp_rpty_test.go
@@ -90,7 +90,6 @@ func TestExpRpty(t *testing.T) {
 		wantLabel := "coder.devcontainers.TestExpRpty.Container"
 
 		client, workspace, agentToken := setupWorkspaceForAgent(t)
-		ctx := testutil.Context(t, testutil.WaitLong)
 		pool, err := dockertest.NewPool("")
 		require.NoError(t, err, "Could not connect to docker")
 		ct, err := pool.RunWithOptions(&dockertest.RunOptions{
@@ -128,14 +127,15 @@ func TestExpRpty(t *testing.T) {
 		clitest.SetupConfig(t, client, root)
 		pty := ptytest.New(t).Attach(inv)
 
+		ctx := testutil.Context(t, testutil.WaitLong)
 		cmdDone := tGo(t, func() {
 			err := inv.WithContext(ctx).Run()
 			assert.NoError(t, err)
 		})
 
-		pty.ExpectMatch(" #")
+		pty.ExpectMatchContext(ctx, " #")
 		pty.WriteLine("hostname")
-		pty.ExpectMatch(ct.Container.Config.Hostname)
+		pty.ExpectMatchContext(ctx, ct.Container.Config.Hostname)
 		pty.WriteLine("exit")
 		<-cmdDone
 	})
diff --git a/cli/ssh_test.go b/cli/ssh_test.go
index 7ce9d85258..2b3113a901 100644
--- a/cli/ssh_test.go
+++ b/cli/ssh_test.go
@@ -2052,7 +2052,6 @@ func TestSSH_Container(t *testing.T) {
 		t.Parallel()
 
 		client, workspace, agentToken := setupWorkspaceForAgent(t)
-		ctx := testutil.Context(t, testutil.WaitLong)
 		pool, err := dockertest.NewPool("")
 		require.NoError(t, err, "Could not connect to docker")
 		ct, err := pool.RunWithOptions(&dockertest.RunOptions{
@@ -2087,14 +2086,15 @@ func TestSSH_Container(t *testing.T) {
 		clitest.SetupConfig(t, client, root)
 		ptty := ptytest.New(t).Attach(inv)
 
+		ctx := testutil.Context(t, testutil.WaitLong)
 		cmdDone := tGo(t, func() {
 			err := inv.WithContext(ctx).Run()
 			assert.NoError(t, err)
 		})
 
-		ptty.ExpectMatch(" #")
+		ptty.ExpectMatchContext(ctx, " #")
 		ptty.WriteLine("hostname")
-		ptty.ExpectMatch(ct.Container.Config.Hostname)
+		ptty.ExpectMatchContext(ctx, ct.Container.Config.Hostname)
 		ptty.WriteLine("exit")
 		<-cmdDone
 	})
diff --git a/pty/ptytest/ptytest.go b/pty/ptytest/ptytest.go
index 3991bdeb04..5d15078094 100644
--- a/pty/ptytest/ptytest.go
+++ b/pty/ptytest/ptytest.go
@@ -145,6 +145,8 @@ type outExpecter struct {
 	runeReader *bufio.Reader
 }
 
+// Deprecated: use ExpectMatchContext instead.
+// This uses a background context, so will not respect the test's context.
 func (e *outExpecter) ExpectMatch(str string) string {
 	return e.expectMatchContextFunc(str, e.ExpectMatchContext)
 }