diff --git a/diagnose_test.go b/diagnose_test.go
index 443e659..f178067 100644
--- a/diagnose_test.go
+++ b/diagnose_test.go
@@ -1,7 +1,6 @@
 package ngrok
 
 import (
-	"context"
 	"crypto/ecdsa"
 	"crypto/elliptic"
 	"crypto/rand"
@@ -20,6 +19,7 @@ import (
 
 	muxado "golang.ngrok.com/muxado/v2"
 
+	"golang.ngrok.com/ngrok/v2/internal/testcontext"
 	"golang.ngrok.com/ngrok/v2/internal/tunnel/proto"
 )
 
@@ -38,7 +38,7 @@ func TestDiagnoseTCPFailure(t *testing.T) {
 	d, ok := a.(Diagnoser)
 	require.True(t, ok, "agent should implement Diagnoser")
 
-	result, err := d.Diagnose(context.Background(), addr)
+	result, err := d.Diagnose(testcontext.ForTB(t), addr)
 	require.Error(t, err)
 	assert.True(t, IsTCPDiagnoseFailure(err))
 	assert.Equal(t, addr, result.Addr)
@@ -64,7 +64,7 @@ func TestDiagnoseTLSFailure(t *testing.T) {
 
 	d := a.(Diagnoser)
 
-	result, err := d.Diagnose(context.Background(), l.Addr().String())
+	result, err := d.Diagnose(testcontext.ForTB(t), l.Addr().String())
 	require.Error(t, err)
 	assert.True(t, IsTLSDiagnoseFailure(err))
 	assert.Equal(t, l.Addr().String(), result.Addr)
@@ -135,7 +135,7 @@ func TestDiagnoseMuxadoSuccess(t *testing.T) {
 
 	d := a.(Diagnoser)
 
-	result, err := d.Diagnose(context.Background(), l.Addr().String())
+	result, err := d.Diagnose(testcontext.ForTB(t), l.Addr().String())
 	require.NoError(t, err)
 	assert.Equal(t, l.Addr().String(), result.Addr)
 	assert.Equal(t, testRegion, result.Region)
@@ -167,8 +167,7 @@ func TestDiagnoseOnline(t *testing.T) {
 	d, ok := a.(Diagnoser)
 	require.True(t, ok)
 
-	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
-	defer cancel()
+	ctx := testcontext.ForTB(t)
 
 	result, err := d.Diagnose(ctx, serverAddr)
 	require.NoError(t, err)
diff --git a/internal/integration_tests/agent_tls_termination_test.go b/internal/integration_tests/agent_tls_termination_test.go
index dcbe26e..b8fc23f 100644
--- a/internal/integration_tests/agent_tls_termination_test.go
+++ b/internal/integration_tests/agent_tls_termination_test.go
@@ -22,8 +22,7 @@ func TestAgentTLSTerminationIntegration(t *testing.T) {
 	cert := CreateTestCertificate(t)
 
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Setup synchronization primitives
diff --git a/internal/integration_tests/early_response_test.go b/internal/integration_tests/early_response_test.go
index 48c1f06..d6b0cef 100644
--- a/internal/integration_tests/early_response_test.go
+++ b/internal/integration_tests/early_response_test.go
@@ -18,8 +18,7 @@ import (
 func TestEarlyResponseLargeUpload(t *testing.T) {
 	t.Parallel()
 
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	const maxBodySize = 1024
diff --git a/internal/integration_tests/endpoint_closing_test.go b/internal/integration_tests/endpoint_closing_test.go
index e2b991d..b45f1fe 100644
--- a/internal/integration_tests/endpoint_closing_test.go
+++ b/internal/integration_tests/endpoint_closing_test.go
@@ -15,8 +15,7 @@ func TestEndpointClosingIntegration(t *testing.T) {
 	t.Parallel()
 
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Create a listener endpoint
diff --git a/internal/integration_tests/error_code_test.go b/internal/integration_tests/error_code_test.go
index 4d231a7..67e1b3d 100644
--- a/internal/integration_tests/error_code_test.go
+++ b/internal/integration_tests/error_code_test.go
@@ -13,8 +13,7 @@ func TestErrorCode(t *testing.T) {
 	SkipIfOffline(t)
 	t.Parallel()
 
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 
 	// Create an endpoint with an invalid character ('@') in its URL
 	_, err := agent.Listen(ctx,
diff --git a/internal/integration_tests/event_handling_test.go b/internal/integration_tests/event_handling_test.go
index 631f62f..9797c63 100644
--- a/internal/integration_tests/event_handling_test.go
+++ b/internal/integration_tests/event_handling_test.go
@@ -1,7 +1,6 @@
 package integration_tests
 
 import (
-	"context"
 	"os"
 	"testing"
 	"time"
@@ -9,6 +8,7 @@ import (
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"golang.ngrok.com/ngrok/v2"
+	"golang.ngrok.com/ngrok/v2/internal/testcontext"
 )
 
 // TestEventHandlingIntegration tests that events are properly emitted and received
@@ -60,8 +60,7 @@ func TestEventHandlingIntegration(t *testing.T) {
 	require.NoError(t, err, "Failed to create agent")
 
 	// Create a context with timeout for the test
-	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
-	defer cancel()
+	ctx := testcontext.ForTB(t)
 
 	// Connect the agent (should trigger a connect event)
 	t.Log("Connecting agent...")
diff --git a/internal/integration_tests/forward_test.go b/internal/integration_tests/forward_test.go
index 09c3a70..f384042 100644
--- a/internal/integration_tests/forward_test.go
+++ b/internal/integration_tests/forward_test.go
@@ -18,8 +18,7 @@ func TestForward(t *testing.T) {
 	// Mark this test for parallel execution
 	t.Parallel()
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Create a channel to signal when the server is ready
diff --git a/internal/integration_tests/http2_test.go b/internal/integration_tests/http2_test.go
index b0b645e..903cfa1 100644
--- a/internal/integration_tests/http2_test.go
+++ b/internal/integration_tests/http2_test.go
@@ -24,8 +24,7 @@ func TestUpstreamProtocolHTTP2(t *testing.T) {
 		t.Parallel()
 
 		// Setup agent for this test
-		agent, ctx, cancel := SetupAgent(t)
-		defer cancel()
+		agent, ctx := SetupAgent(t)
 		defer func() { _ = agent.Disconnect() }()
 
 		// Set up a test HTTP/2 server
@@ -92,8 +91,7 @@ func TestUpstreamProtocolHTTP2(t *testing.T) {
 		t.Parallel()
 
 		// Setup agent for this test
-		agent, ctx, cancel := SetupAgent(t)
-		defer cancel()
+		agent, ctx := SetupAgent(t)
 		defer func() { _ = agent.Disconnect() }()
 
 		// Set up a test HTTP/2 server
diff --git a/internal/integration_tests/listen_http_test.go b/internal/integration_tests/listen_http_test.go
index cdd1149..bba7f27 100644
--- a/internal/integration_tests/listen_http_test.go
+++ b/internal/integration_tests/listen_http_test.go
@@ -15,8 +15,7 @@ func TestListenAndHTTPRequest(t *testing.T) {
 	// Mark this test for parallel execution
 	t.Parallel()
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Setup listener
diff --git a/internal/integration_tests/listen_http_url_test.go b/internal/integration_tests/listen_http_url_test.go
index 372329b..d0a0991 100644
--- a/internal/integration_tests/listen_http_url_test.go
+++ b/internal/integration_tests/listen_http_url_test.go
@@ -16,8 +16,7 @@ func TestListenWithHTTPURL(t *testing.T) {
 	// Mark this test for parallel execution
 	t.Parallel()
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Setup listener with HTTP URL
diff --git a/internal/integration_tests/listen_https_test.go b/internal/integration_tests/listen_https_test.go
index 610713b..0fa7bb0 100644
--- a/internal/integration_tests/listen_https_test.go
+++ b/internal/integration_tests/listen_https_test.go
@@ -16,8 +16,7 @@ func TestListenWithHTTPSURL(t *testing.T) {
 	// Mark this test for parallel execution
 	t.Parallel()
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Setup listener with HTTPS URL
diff --git a/internal/integration_tests/listen_tcp_test.go b/internal/integration_tests/listen_tcp_test.go
index 88e91b1..3fe9d08 100644
--- a/internal/integration_tests/listen_tcp_test.go
+++ b/internal/integration_tests/listen_tcp_test.go
@@ -16,8 +16,7 @@ func TestListenAndTCPConnection(t *testing.T) {
 	// Mark this test for parallel execution
 	t.Parallel()
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Setup TCP listener using the TCP scheme
diff --git a/internal/integration_tests/proxy_proto_test.go b/internal/integration_tests/proxy_proto_test.go
index 0fdb40b..9be6b27 100644
--- a/internal/integration_tests/proxy_proto_test.go
+++ b/internal/integration_tests/proxy_proto_test.go
@@ -221,10 +221,10 @@ func handleTCPConnection(t *testing.T, conn net.Conn, reader *bufio.Reader, srcA
 }
 
 // connectHTTPSClient connects to an HTTPS endpoint using an HTTP client
-func connectHTTPSClient(t *testing.T, endpointURL string) {
+func connectHTTPSClient(ctx context.Context, t *testing.T, endpointURL string) {
 	// Use MakeHTTPRequest to send test message
 	message := "Test message for PROXY protocol"
-	resp := MakeHTTPRequest(t, context.Background(), endpointURL, message)
+	resp := MakeHTTPRequest(t, ctx, endpointURL, message)
 	defer resp.Body.Close()
 
 	// Read the response
@@ -234,13 +234,13 @@ func connectHTTPSClient(t *testing.T, endpointURL string) {
 }
 
 // connectTCPClient connects to a TCP endpoint using a direct TCP connection
-func connectTCPClient(t *testing.T, endpointURL string) {
+func connectTCPClient(ctx context.Context, t *testing.T, endpointURL string) {
 	// For TCP, use direct TCP connection
 	u, err := url.Parse(endpointURL)
 	require.NoError(t, err, "Failed to parse URL")
 
 	// Connect to the endpoint using MakeTCPConnection
-	clientConn, err := MakeTCPConnection(t, context.Background(), u.Host)
+	clientConn, err := MakeTCPConnection(t, ctx, u.Host)
 	require.NoError(t, err, "Failed to connect to TCP endpoint")
 	defer clientConn.Close()
 
@@ -310,8 +310,7 @@ func TestProxyProtoIntegration(t *testing.T) {
 			t.Parallel()
 
 			// Setup agent
-			agent, ctx, cancel := SetupAgent(t)
-			defer cancel()
+			agent, ctx := SetupAgent(t)
 			defer func() { _ = agent.Disconnect() }()
 
 			// Create synchronization points
@@ -408,11 +407,11 @@ func TestProxyProtoIntegration(t *testing.T) {
 			// Connect to the endpoint with appropriate client based on scheme
 			switch {
 			case strings.HasPrefix(scheme, "https"):
-				connectHTTPSClient(t, endpointURL)
+				connectHTTPSClient(ctx, t, endpointURL)
 			case strings.HasPrefix(scheme, "tls"):
 				connectTLSClient(t, endpointURL)
 			default: // TCP
-				connectTCPClient(t, endpointURL)
+				connectTCPClient(ctx, t, endpointURL)
 			}
 
 			// Wait for the client address with timeout
diff --git a/internal/integration_tests/test_utils.go b/internal/integration_tests/test_utils.go
index 918385c..de43a6b 100644
--- a/internal/integration_tests/test_utils.go
+++ b/internal/integration_tests/test_utils.go
@@ -20,6 +20,7 @@ import (
 
 	"github.com/stretchr/testify/require"
 	"golang.ngrok.com/ngrok/v2"
+	"golang.ngrok.com/ngrok/v2/internal/testcontext"
 )
 
 // SkipIfOffline skips the test if NGROK_TEST_ONLINE environment variable is not set
@@ -30,7 +31,7 @@ func SkipIfOffline(t *testing.T) {
 }
 
 // SetupAgent creates and connects a new agent for testing
-func SetupAgent(t *testing.T) (ngrok.Agent, context.Context, context.CancelFunc) {
+func SetupAgent(t *testing.T) (ngrok.Agent, context.Context) {
 	// Skip if not running online tests
 	SkipIfOffline(t)
 
@@ -44,14 +45,13 @@ func SetupAgent(t *testing.T) (ngrok.Agent, context.Context, context.CancelFunc)
 	)
 	require.NoError(t, err, "Failed to create agent")
 
-	// Start a context with timeout
-	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+	ctx := testcontext.ForTB(t)
 
 	// Connect the agent
 	err = agent.Connect(ctx)
 	require.NoError(t, err, "Failed to connect agent")
 
-	return agent, ctx, cancel
+	return agent, ctx
 }
 
 // SetupListener sets up an ngrok listener with the specified options
diff --git a/internal/integration_tests/upstream_dialer_test.go b/internal/integration_tests/upstream_dialer_test.go
index 7537927..1d66e12 100644
--- a/internal/integration_tests/upstream_dialer_test.go
+++ b/internal/integration_tests/upstream_dialer_test.go
@@ -52,8 +52,7 @@ func TestUpstreamDialer(t *testing.T) {
 	t.Parallel()
 
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Create a custom dialer that returns an error and has synchronization
diff --git a/internal/integration_tests/url_pooling_test.go b/internal/integration_tests/url_pooling_test.go
index c8d85cb..a02df7e 100644
--- a/internal/integration_tests/url_pooling_test.go
+++ b/internal/integration_tests/url_pooling_test.go
@@ -23,8 +23,7 @@ func TestListenWithURLAndPooling(t *testing.T) {
 	t.Parallel()
 
 	// Setup agent
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer func() { _ = agent.Disconnect() }()
 
 	// Common URL for both endpoints - IMPORTANT: the exact same string must be used for both listeners
diff --git a/internal/integration_tests/websocket_test.go b/internal/integration_tests/websocket_test.go
index 672aa00..145637c 100644
--- a/internal/integration_tests/websocket_test.go
+++ b/internal/integration_tests/websocket_test.go
@@ -18,8 +18,7 @@ import (
 func TestWebSocketUpgrade(t *testing.T) {
 	t.Parallel()
 
-	agent, ctx, cancel := SetupAgent(t)
-	defer cancel()
+	agent, ctx := SetupAgent(t)
 	defer agent.Disconnect() //nolint:errcheck
 
 	// Start an upstream WebSocket server.
diff --git a/internal/legacy/online_test.go b/internal/legacy/online_test.go
index b0ef51e..32ff1d9 100644
--- a/internal/legacy/online_test.go
+++ b/internal/legacy/online_test.go
@@ -17,6 +17,7 @@ import (
 	"golang.org/x/net/websocket"
 
 	"golang.ngrok.com/ngrok/v2/internal/legacy/config"
+	"golang.ngrok.com/ngrok/v2/internal/testcontext"
 )
 
 func newTestLogger(t *testing.T) *slog.Logger {
@@ -86,7 +87,7 @@ func serveHTTP(ctx context.Context, t *testing.T, connectOpts []ConnectOption, o
 }
 
 func TestTunnel(t *testing.T) {
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 	sess := setupSession(ctx, t)
 
 	tun := startTunnel(ctx, t, sess, config.HTTPEndpoint(
@@ -101,7 +102,7 @@ func TestTunnel(t *testing.T) {
 }
 
 func TestTunnelConnMetadata(t *testing.T) {
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 	sess := setupSession(ctx, t)
 
 	tun := startTunnel(ctx, t, sess, config.HTTPEndpoint())
@@ -141,7 +142,7 @@ func (f failPanic) FailNow() {
 
 func TestTCP(t *testing.T) {
 	onlineTest(t)
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 
 	opts := config.TCPEndpoint()
 
@@ -168,7 +169,7 @@ func TestConnectionCallbacks(t *testing.T) {
 	// Don't run this one by default - it's timing-sensitive and prone to flakes
 	skipUnless(t, "NGROK_TEST_FLAKEY", "Skipping flakey network test")
 
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 	connects := 0
 	disconnectErrs := 0
 	disconnectNils := 0
@@ -201,7 +202,7 @@ type sketchyDialer struct {
 }
 
 func (sd *sketchyDialer) Dial(network, addr string) (net.Conn, error) {
-	return sd.DialContext(context.Background(), network, addr)
+	return sd.DialContext(context.TODO(), network, addr)
 }
 
 func (sd *sketchyDialer) DialContext(ctx context.Context, network, addr string) (net.Conn, error) {
@@ -218,7 +219,7 @@ func TestHeartbeatCallback(t *testing.T) {
 		t.Skip("Skipping long network test")
 	}
 
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 	heartbeats := 0
 	sess := setupSession(ctx, t,
 		WithHeartbeatHandler(func(ctx context.Context, sess Session, latency time.Duration) {
@@ -236,7 +237,7 @@ func TestHeartbeatCallback(t *testing.T) {
 func TestPermanentErrors(t *testing.T) {
 	onlineTest(t)
 	var err error
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 	token := os.Getenv("NGROK_AUTHTOKEN")
 
 	sess, err := Connect(ctx, WithAuthtoken(token))
@@ -253,7 +254,7 @@ func TestRetryableErrors(t *testing.T) {
 	onlineTest(t)
 	var err error
 	// Set global context with a longer timeout just to prevent test from hanging forever
-	ctx, cancel := context.WithTimeout(context.Background(), 8*time.Second)
+	ctx, cancel := context.WithTimeout(testcontext.ForTB(t), 8*time.Second)
 	defer cancel()
 
 	// Create a custom dialer with short timeout for invalid addresses
@@ -280,7 +281,7 @@ func TestRetryableErrors(t *testing.T) {
 }
 
 func TestNonExported(t *testing.T) {
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 
 	sess := setupSession(ctx, t)
 
@@ -294,7 +295,7 @@ func echo(ws *websocket.Conn) {
 func TestWebsockets(t *testing.T) {
 	onlineTest(t)
 
-	ctx := context.Background()
+	ctx := testcontext.ForTB(t)
 
 	srv := &http.ServeMux{}
 	srv.Handle("/", helloHandler)
diff --git a/internal/testcontext/testcontext.go b/internal/testcontext/testcontext.go
new file mode 100644
index 0000000..98b33fa
--- /dev/null
+++ b/internal/testcontext/testcontext.go
@@ -0,0 +1,37 @@
+// Package testcontext provides a function to obtain a [context.Context] in a test.
+package testcontext
+
+import (
+	"context"
+	"testing"
+	"time"
+)
+
+// ForTB returns a [context.Context] that is canceled
+// just before Cleanup-registered functions are called
+// or shortly before the test deadline,
+// whichever comes first.
+func ForTB(tb testing.TB) context.Context {
+	ctx := tb.Context()
+	deadline, ok := tbDeadline(tb)
+	if !ok {
+		return ctx
+	}
+	ctx, cancel := context.WithDeadline(ctx, deadline.Add(-10*time.Second))
+	tb.Cleanup(cancel)
+	return ctx
+}
+
+func tbDeadline(tb testing.TB) (deadline time.Time, ok bool) {
+	d, ok := tb.(deadliner)
+	if !ok {
+		return time.Time{}, false
+	}
+	return d.Deadline()
+}
+
+type deadliner interface {
+	Deadline() (deadline time.Time, ok bool)
+}
+
+var _ deadliner = (*testing.T)(nil)
diff --git a/internal/tunnel/client/raw_session_test.go b/internal/tunnel/client/raw_session_test.go
index 5f5926e..3275be8 100644
--- a/internal/tunnel/client/raw_session_test.go
+++ b/internal/tunnel/client/raw_session_test.go
@@ -8,6 +8,7 @@ import (
 	"time"
 
 	"golang.ngrok.com/muxado/v2"
+	"golang.ngrok.com/ngrok/v2/internal/testcontext"
 )
 
 type dummyStream struct{}
@@ -31,7 +32,7 @@ func TestHeartbeatTimeout(t *testing.T) {
 }
 
 func TestRawSessionCloseRace(t *testing.T) {
-	ctx, cancel := context.WithTimeout(context.Background(), time.Second*1)
+	ctx, cancel := context.WithTimeout(testcontext.ForTB(t), time.Second*1)
 	defer cancel()
 
 	// Since this is a race condition, run the test as many times as we can