diff --git a/hscontrol/db/node.go b/hscontrol/db/node.go
index 002bde59..c983c841 100644
--- a/hscontrol/db/node.go
+++ b/hscontrol/db/node.go
@@ -498,6 +498,16 @@ func (e *EphemeralGarbageCollector) Cancel(nodeID types.NodeID) {
 	}
 }
 
+// IsScheduled reports whether a deletion timer is currently armed for nodeID.
+func (e *EphemeralGarbageCollector) IsScheduled(nodeID types.NodeID) bool {
+	e.mu.Lock()
+	defer e.mu.Unlock()
+
+	_, ok := e.toBeDeleted[nodeID]
+
+	return ok
+}
+
 // Start starts the garbage collector.
 func (e *EphemeralGarbageCollector) Start() {
 	for {
diff --git a/hscontrol/poll.go b/hscontrol/poll.go
index 35657026..656a2dad 100644
--- a/hscontrol/poll.go
+++ b/hscontrol/poll.go
@@ -96,12 +96,6 @@ func (m *mapSession) stopFromBatcher() {
 	}
 }
 
-func (m *mapSession) beforeServeLongPoll() {
-	if m.node.IsEphemeral() {
-		m.h.ephemeralGC.Cancel(m.node.ID)
-	}
-}
-
 // afterServeLongPoll is called when a long-polling session ends and the node
 // is disconnected.
 func (m *mapSession) afterServeLongPoll() {
@@ -144,8 +138,6 @@ func (m *mapSession) serve() {
 //
 //nolint:gocyclo
 func (m *mapSession) serveLongPoll() {
-	m.beforeServeLongPoll()
-
 	m.log.Trace().Caller().Msg("long poll session started")
 
 	// connectGen is set by [state.State.Connect] below and captured by the deferred cleanup closure.
@@ -248,6 +240,13 @@ func (m *mapSession) serveLongPoll() {
 
 	connectChanges, connectGen = m.h.state.Connect(m.node.ID)
 
+	// Cancel ephemeral GC only after Connect succeeds. Cancelling at the start
+	// of serveLongPoll left departed nodes without a deletion timer when a
+	// reconnect attempt failed before Connect (issue #3382).
+	if m.node.IsEphemeral() {
+		m.h.ephemeralGC.Cancel(m.node.ID)
+	}
+
 	m.log.Info().Caller().Str(zf.Chan, fmt.Sprintf("%p", m.ch)).Msg("node has connected")
 
 	// TODO(kradalby): Redo the comments here
diff --git a/hscontrol/poll_test.go b/hscontrol/poll_test.go
index 71ce08d9..ae936ec2 100644
--- a/hscontrol/poll_test.go
+++ b/hscontrol/poll_test.go
@@ -15,6 +15,7 @@ import (
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"tailscale.com/tailcfg"
+	"tailscale.com/types/key"
 )
 
 type delayedSuccessResponseWriter struct {
@@ -216,6 +217,67 @@ func TestServeLongPollWritesErrorWhenInitialMapFails(t *testing.T) {
 		"serveLongPoll must write an HTTP error response when the initial map cannot be built, not an empty 200")
 }
 
+// TestFailedReconnectDoesNotCancelEphemeralGC proves that a
+// long-poll reconnect attempt which fails before [state.State.Connect] must
+// not cancel a previously armed ephemeral GC timer. Cancelling at the start of
+// [mapSession.serveLongPoll] left departed ephemeral nodes stuck offline with
+// no deletion scheduled (https://github.com/juanfont/headscale/issues/3382).
+func TestFailedReconnectDoesNotCancelEphemeralGC(t *testing.T) {
+	t.Parallel()
+
+	app := createTestApp(t)
+	app.StartEphemeralGCForTest(t)
+
+	user := app.state.CreateUserForTest("eph-gc-cancel-user")
+	pak, err := app.state.CreatePreAuthKey(user.TypedID(), false, true, nil, nil)
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+
+	_, err = app.handleRegister(context.Background(), tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: pak.Key,
+		},
+		NodeKey: nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "eph-gc-cancel-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}, machineKey.Public())
+	require.NoError(t, err)
+
+	nodeView, ok := app.state.GetNodeByNodeKey(nodeKey.Public())
+	require.True(t, ok)
+	require.True(t, nodeView.IsEphemeral(), "node must be ephemeral so Cancel would arm on long-poll")
+
+	node := nodeView.AsStruct()
+
+	// Arm a long-lived deletion timer — the state after a normal disconnect
+	// has called afterServeLongPoll. A long expiry avoids racing the
+	// fail-before-Connect path below.
+	app.ephemeralGC.Schedule(node.ID, time.Hour)
+	require.True(t, app.ephemeralGC.IsScheduled(node.ID), "test sanity: GC timer must be armed")
+
+	// Drop the node from the NodeStore so UpdateNodeFromMapRequest fails before
+	// Connect, while the session still carries an ephemeral AuthKey (so the
+	// old Cancel-on-entry path would clear the timer).
+	app.state.DeleteNodeFromStoreForTest(node.ID)
+
+	writer := &recordingResponseWriter{}
+	session := app.newMapSession(context.Background(), tailcfg.MapRequest{
+		Stream:  true,
+		Version: tailcfg.CapabilityVersion(100),
+	}, writer, node)
+
+	session.serveLongPoll()
+
+	assert.GreaterOrEqual(t, writer.statusCode(), http.StatusInternalServerError,
+		"failed reconnect must write an HTTP error before Connect")
+	assert.True(t, app.ephemeralGC.IsScheduled(node.ID),
+		"failed reconnect must not cancel the ephemeral GC timer (issue #3382)")
+}
+
 // TestGitHubIssue3129_TransientlyBlockedWriteDoesNotLeaveLiveStaleSession
 // tests the scenario reported in
 // https://github.com/juanfont/headscale/issues/3129.
diff --git a/hscontrol/state/state.go b/hscontrol/state/state.go
index 88a38887..5b34c5d6 100644
--- a/hscontrol/state/state.go
+++ b/hscontrol/state/state.go
@@ -1458,6 +1458,13 @@ func (s *State) PutNodeInStoreForTest(node types.Node) types.NodeView {
 	return s.nodeStore.PutNode(node)
 }
 
+// DeleteNodeFromStoreForTest removes a node from the in-memory [NodeStore]
+// without touching the database. Used to force [State.UpdateNodeFromMapRequest]
+// failures in poll-session tests while keeping the DB row intact for later restore.
+func (s *State) DeleteNodeFromStoreForTest(id types.NodeID) {
+	s.nodeStore.DeleteNode(id)
+}
+
 // CreateRegisteredNodeForTest creates a test node with allocated IPs. This is a convenience wrapper around the database layer.
 func (s *State) CreateRegisteredNodeForTest(user *types.User, hostname ...string) *types.Node {
 	return s.db.CreateRegisteredNodeForTest(user, hostname...)