diff --git a/internal/controller/authenticator/jwtcachefiller/jwtcachefiller_test.go b/internal/controller/authenticator/jwtcachefiller/jwtcachefiller_test.go
index 3fdb7faf..6cc2bc76 100644
--- a/internal/controller/authenticator/jwtcachefiller/jwtcachefiller_test.go
+++ b/internal/controller/authenticator/jwtcachefiller/jwtcachefiller_test.go
@@ -486,7 +486,7 @@ func TestController(t *testing.T) {
 						authenticated bool
 						err           error
 					)
-					_ = wait.PollImmediate(10*time.Millisecond, 5*time.Second, func() (bool, error) {
+					_ = wait.PollUntilContextTimeout(context.Background(), 10*time.Millisecond, 5*time.Second, true, func(ctx context.Context) (bool, error) {
 						rsp, authenticated, err = cachedAuthenticator.AuthenticateToken(context.Background(), jwt)
 						return !isNotInitialized(err), nil
 					})
diff --git a/internal/dynamiccert/provider_test.go b/internal/dynamiccert/provider_test.go
index df744fc0..9dc05b70 100644
--- a/internal/dynamiccert/provider_test.go
+++ b/internal/dynamiccert/provider_test.go
@@ -4,6 +4,7 @@
 package dynamiccert
 
 import (
+	"context"
 	"crypto/tls"
 	"crypto/x509"
 	"net"
@@ -194,7 +195,7 @@ func TestProviderWithDynamicServingCertificateController(t *testing.T) {
 			var lastTLSConfig *tls.Config
 
 			// it will take some time for the controller to catch up
-			err = wait.PollImmediate(time.Second, 30*time.Second, func() (bool, error) {
+			err = wait.PollUntilContextTimeout(context.Background(), time.Second, 30*time.Second, true, func(ctx context.Context) (bool, error) {
 				actualTLSConfig, err := tlsConfig.GetConfigForClient(&tls.ClientHelloInfo{ServerName: "force-standard-sni"})
 				if err != nil {
 					return false, err
diff --git a/test/testlib/assertions.go b/test/testlib/assertions.go
index 877fdcfa..1178ed0e 100644
--- a/test/testlib/assertions.go
+++ b/test/testlib/assertions.go
@@ -1,11 +1,10 @@
-// Copyright 2021-2022 the Pinniped contributors. All Rights Reserved.
+// Copyright 2021-2023 the Pinniped contributors. All Rights Reserved.
 // SPDX-License-Identifier: Apache-2.0
 
 package testlib
 
 import (
 	"context"
-	"errors"
 	"fmt"
 	"testing"
 	"time"
@@ -88,7 +87,7 @@ func RequireEventually(
 	)
 
 	// Run the check until it completes with no assertion failures.
-	waitErr := wait.PollImmediate(tick, waitFor, func() (bool, error) {
+	waitErr := wait.PollUntilContextTimeout(context.Background(), tick, waitFor, true, func(ctx context.Context) (bool, error) {
 		t.Helper()
 		attempts++
 
@@ -133,7 +132,10 @@ func RequireEventuallyWithoutError(
 	msgAndArgs ...interface{},
 ) {
 	t.Helper()
-	require.NoError(t, wait.PollImmediate(tick, waitFor, f), msgAndArgs...)
+	// This previously used wait.PollImmediate (now deprecated), which did not take a ctx arg in the func.
+	// Hide this detail from the callers for now to keep the old signature.
+	fWithCtx := func(ctx context.Context) (bool, error) { return f() }
+	require.NoError(t, wait.PollUntilContextTimeout(context.Background(), tick, waitFor, true, fWithCtx), msgAndArgs...)
 }
 
 // RequireNeverWithoutError is similar to require.Never() except that it also allows the caller to
@@ -147,9 +149,11 @@ func RequireNeverWithoutError(
 	msgAndArgs ...interface{},
 ) {
 	t.Helper()
-	err := wait.PollImmediate(tick, waitFor, f)
-	isWaitTimeout := errors.Is(err, wait.ErrWaitTimeout)
-	if err != nil && !isWaitTimeout {
+	// This previously used wait.PollImmediate (now deprecated), which did not take a ctx arg in the func.
+	// Hide this detail from the callers for now to keep the old signature.
+	fWithCtx := func(ctx context.Context) (bool, error) { return f() }
+	err := wait.PollUntilContextTimeout(context.Background(), tick, waitFor, true, fWithCtx)
+	if err != nil && !wait.Interrupted(err) {
 		require.NoError(t, err, msgAndArgs...) // this will fail and throw the right error message
 	}
 	if err == nil {