diff --git a/cli/server.go b/cli/server.go
index 520f58454db29..e0d17838cde25 100644
--- a/cli/server.go
+++ b/cli/server.go
@@ -655,6 +655,10 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 				options.OIDCConfig = oc
 			}
 
+			// We'll read from this channel in the select below that tracks shutdown.  If it remains
+			// nil, that case of the select will just never fire, but it's important not to have a
+			// "bare" read on this channel.
+			var pubsubWatchdogTimeout <-chan struct{}
 			if vals.InMemoryDatabase {
 				// This is only used for testing.
 				options.Database = dbmem.New()
@@ -683,6 +687,9 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 					options.PrometheusRegistry.MustRegister(ps)
 				}
 				defer options.Pubsub.Close()
+				psWatchdog := pubsub.NewWatchdog(ctx, logger.Named("pswatch"), ps)
+				pubsubWatchdogTimeout = psWatchdog.Timeout()
+				defer psWatchdog.Close()
 			}
 
 			if options.DeploymentValues.Prometheus.Enable && options.DeploymentValues.Prometheus.CollectDBMetrics {
@@ -1031,6 +1038,8 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 				_, _ = io.WriteString(inv.Stdout, cliui.Bold("Interrupt caught, gracefully exiting. Use ctrl+\\ to force quit"))
 			case <-tunnelDone:
 				exitErr = xerrors.New("dev tunnel closed unexpectedly")
+			case <-pubsubWatchdogTimeout:
+				exitErr = xerrors.New("pubsub Watchdog timed out")
 			case exitErr = <-errCh:
 			}
 			if exitErr != nil && !xerrors.Is(exitErr, context.Canceled) {
diff --git a/coderd/database/pubsub/watchdog.go b/coderd/database/pubsub/watchdog.go
new file mode 100644
index 0000000000000..2b8d929fa7e38
--- /dev/null
+++ b/coderd/database/pubsub/watchdog.go
@@ -0,0 +1,141 @@
+package pubsub
+
+import (
+	"context"
+	"runtime/pprof"
+	"strings"
+	"sync"
+	"time"
+
+	"github.com/benbjohnson/clock"
+
+	"cdr.dev/slog"
+)
+
+const (
+	EventPubsubWatchdog = "pubsub_watchdog"
+	periodHeartbeat     = 15 * time.Second
+	// periodTimeout is the time without receiving a heartbeat (from any publisher) before we
+	// consider the watchdog to have timed out.  There is a tradeoff here between avoiding
+	// disruption due to a short-lived issue connecting to the postgres database, and restarting
+	// before the consequences of a non-working pubsub are noticed by end users (e.g. being unable
+	// to connect to their workspaces).
+	periodTimeout = 5 * time.Minute
+)
+
+type Watchdog struct {
+	ctx     context.Context
+	cancel  context.CancelFunc
+	logger  slog.Logger
+	ps      Pubsub
+	wg      sync.WaitGroup
+	timeout chan struct{}
+
+	// for testing
+	clock clock.Clock
+}
+
+func NewWatchdog(ctx context.Context, logger slog.Logger, ps Pubsub) *Watchdog {
+	return NewWatchdogWithClock(ctx, logger, ps, clock.New())
+}
+
+// NewWatchdogWithClock returns a watchdog with the given clock.  Product code should always call NewWatchDog.
+func NewWatchdogWithClock(ctx context.Context, logger slog.Logger, ps Pubsub, c clock.Clock) *Watchdog {
+	ctx, cancel := context.WithCancel(ctx)
+	w := &Watchdog{
+		ctx:     ctx,
+		cancel:  cancel,
+		logger:  logger,
+		ps:      ps,
+		timeout: make(chan struct{}),
+		clock:   c,
+	}
+	w.wg.Add(2)
+	go w.publishLoop()
+	go w.subscribeMonitor()
+	return w
+}
+
+func (w *Watchdog) Close() error {
+	w.cancel()
+	w.wg.Wait()
+	return nil
+}
+
+// Timeout returns a channel that is closed if the watchdog times out.  Note that the Timeout() chan
+// will NOT be closed if the Watchdog is Close'd or its context expires, so it is important to read
+// from the Timeout() chan in a select e.g.
+//
+// w := NewWatchDog(ctx, logger, ps)
+// select {
+// case <-ctx.Done():
+// case <-w.Timeout():
+//
+//	   FreakOut()
+//	}
+func (w *Watchdog) Timeout() <-chan struct{} {
+	return w.timeout
+}
+
+func (w *Watchdog) publishLoop() {
+	defer w.wg.Done()
+	tkr := w.clock.Ticker(periodHeartbeat)
+	defer tkr.Stop()
+	// immediate publish after starting the ticker.  This helps testing so that we can tell from
+	// the outside that the ticker is started.
+	err := w.ps.Publish(EventPubsubWatchdog, []byte{})
+	if err != nil {
+		w.logger.Warn(w.ctx, "failed to publish heartbeat on pubsub watchdog", slog.Error(err))
+	}
+	for {
+		select {
+		case <-w.ctx.Done():
+			w.logger.Debug(w.ctx, "context done; exiting publishLoop")
+			return
+		case <-tkr.C:
+			err := w.ps.Publish(EventPubsubWatchdog, []byte{})
+			if err != nil {
+				w.logger.Warn(w.ctx, "failed to publish heartbeat on pubsub watchdog", slog.Error(err))
+			}
+		}
+	}
+}
+
+func (w *Watchdog) subscribeMonitor() {
+	defer w.wg.Done()
+	beats := make(chan struct{})
+	unsub, err := w.ps.Subscribe(EventPubsubWatchdog, func(context.Context, []byte) {
+		w.logger.Debug(w.ctx, "got heartbeat for pubsub watchdog")
+		select {
+		case <-w.ctx.Done():
+		case beats <- struct{}{}:
+		}
+	})
+	if err != nil {
+		w.logger.Critical(w.ctx, "watchdog failed to subscribe", slog.Error(err))
+		close(w.timeout)
+		return
+	}
+	defer unsub()
+	tmr := w.clock.Timer(periodTimeout)
+	defer tmr.Stop()
+	for {
+		select {
+		case <-w.ctx.Done():
+			w.logger.Debug(w.ctx, "context done; exiting subscribeMonitor")
+			return
+		case <-beats:
+			// c.f. https://pkg.go.dev/time#Timer.Reset
+			if !tmr.Stop() {
+				<-tmr.C
+			}
+			tmr.Reset(periodTimeout)
+		case <-tmr.C:
+			buf := new(strings.Builder)
+			_ = pprof.Lookup("goroutine").WriteTo(buf, 1)
+			w.logger.Critical(w.ctx, "pubsub watchdog timeout", slog.F("goroutines", buf.String()))
+			close(w.timeout)
+			return
+		}
+	}
+}
diff --git a/coderd/database/pubsub/watchdog_test.go b/coderd/database/pubsub/watchdog_test.go
new file mode 100644
index 0000000000000..ddd5a864e2c66
--- /dev/null
+++ b/coderd/database/pubsub/watchdog_test.go
@@ -0,0 +1,124 @@
+package pubsub_test
+
+import (
+	"testing"
+	"time"
+
+	"github.com/benbjohnson/clock"
+	"github.com/stretchr/testify/require"
+
+	"cdr.dev/slog"
+	"cdr.dev/slog/sloggers/slogtest"
+	"github.com/coder/coder/v2/coderd/database/pubsub"
+	"github.com/coder/coder/v2/testutil"
+)
+
+func TestWatchdog_NoTimeout(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, time.Hour)
+	mClock := clock.NewMock()
+	start := time.Date(2024, 2, 5, 8, 7, 6, 5, time.UTC)
+	mClock.Set(start)
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fPS := newFakePubsub()
+	uut := pubsub.NewWatchdogWithClock(ctx, logger, fPS, mClock)
+
+	sub := testutil.RequireRecvCtx(ctx, t, fPS.subs)
+	require.Equal(t, pubsub.EventPubsubWatchdog, sub.event)
+	p := testutil.RequireRecvCtx(ctx, t, fPS.pubs)
+	require.Equal(t, pubsub.EventPubsubWatchdog, p)
+
+	// 5 min / 15 sec = 20, so do 21 ticks
+	for i := 0; i < 21; i++ {
+		mClock.Add(15 * time.Second)
+		p = testutil.RequireRecvCtx(ctx, t, fPS.pubs)
+		require.Equal(t, pubsub.EventPubsubWatchdog, p)
+		mClock.Add(30 * time.Millisecond) // reasonable round-trip
+		// forward the beat
+		sub.listener(ctx, []byte{})
+		// we shouldn't time out
+		select {
+		case <-uut.Timeout():
+			t.Fatal("watchdog tripped")
+		default:
+			// OK!
+		}
+	}
+
+	err := uut.Close()
+	require.NoError(t, err)
+}
+
+func TestWatchdog_Timeout(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitShort)
+	mClock := clock.NewMock()
+	start := time.Date(2024, 2, 5, 8, 7, 6, 5, time.UTC)
+	mClock.Set(start)
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fPS := newFakePubsub()
+	uut := pubsub.NewWatchdogWithClock(ctx, logger, fPS, mClock)
+
+	sub := testutil.RequireRecvCtx(ctx, t, fPS.subs)
+	require.Equal(t, pubsub.EventPubsubWatchdog, sub.event)
+	p := testutil.RequireRecvCtx(ctx, t, fPS.pubs)
+	require.Equal(t, pubsub.EventPubsubWatchdog, p)
+
+	// 5 min / 15 sec = 20, so do 19 ticks without timing out
+	for i := 0; i < 19; i++ {
+		mClock.Add(15 * time.Second)
+		p = testutil.RequireRecvCtx(ctx, t, fPS.pubs)
+		require.Equal(t, pubsub.EventPubsubWatchdog, p)
+		mClock.Add(30 * time.Millisecond) // reasonable round-trip
+		// we DO NOT forward the heartbeat
+		// we shouldn't time out
+		select {
+		case <-uut.Timeout():
+			t.Fatal("watchdog tripped")
+		default:
+			// OK!
+		}
+	}
+	mClock.Add(15 * time.Second)
+	p = testutil.RequireRecvCtx(ctx, t, fPS.pubs)
+	require.Equal(t, pubsub.EventPubsubWatchdog, p)
+	testutil.RequireRecvCtx(ctx, t, uut.Timeout())
+
+	err := uut.Close()
+	require.NoError(t, err)
+}
+
+type subscribe struct {
+	event    string
+	listener pubsub.Listener
+}
+
+type fakePubsub struct {
+	pubs chan string
+	subs chan subscribe
+}
+
+func (f *fakePubsub) Subscribe(event string, listener pubsub.Listener) (func(), error) {
+	f.subs <- subscribe{event, listener}
+	return func() {}, nil
+}
+
+func (*fakePubsub) SubscribeWithErr(string, pubsub.ListenerWithErr) (func(), error) {
+	panic("should not be called")
+}
+
+func (*fakePubsub) Close() error {
+	panic("should not be called")
+}
+
+func (f *fakePubsub) Publish(event string, _ []byte) error {
+	f.pubs <- event
+	return nil
+}
+
+func newFakePubsub() *fakePubsub {
+	return &fakePubsub{
+		pubs: make(chan string),
+		subs: make(chan subscribe),
+	}
+}