From 1ed2c5999793af4b21247449325f57f1310e5349 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Jos=C3=A9=20Almeida?=
 <57680069+zeval@users.noreply.github.com>
Date: Wed, 8 Jul 2026 12:11:28 +0100
Subject: [PATCH] feat: persist and expire quick chats (#1612)

* feat: persist and expire quick chats

* fix: address quick chat review feedback

* fix: resolve quick chat review findings

* fix: close remaining quick chat review gaps

* fix: avoid repeated quick chat expiration rechecks

* fix: guard quick chat expiration deletes

* fix: expire abandoned starting quick chats

* fix: ignore missing quick chat expiration candidates
---
 .../backend/internal/backendapp/boot_state.go | 209 ++++++++++++++++++
 .../internal/backendapp/helpers_test.go       | 137 ++++++++++++
 apps/backend/internal/backendapp/main.go      |   1 +
 .../internal/db/dialect/dialect_test.go       |  11 +
 apps/backend/internal/db/dialect/time.go      |  11 +
 .../task/handlers/process_handlers_test.go    |   6 +
 .../internal/task/repository/interface.go     |   3 +
 .../task/repository/repoerrors/errors.go      |   3 +
 .../internal/task/repository/sqlite/errors.go |   2 +-
 .../internal/task/repository/sqlite/task.go   |  96 ++++++++
 .../task/repository/task_repository_test.go   | 169 ++++++++++++++
 .../task/service/handoff_cascade_test.go      |   4 +
 .../task/service/handoff_workspace_test.go    |   8 +
 .../task/service/quick_chat_expiration.go     |  62 ++++++
 .../internal/task/service/service_tasks.go    |  40 +++-
 .../internal/task/service/service_test.go     | 108 +++++++++
 apps/web/app/page.tsx                         |  31 ++-
 apps/web/lib/api/domains/workspace-api.ts     |   2 +
 apps/web/lib/state/default-state.ts           |  17 +-
 apps/web/lib/state/hydration/hydrator.test.ts |  52 ++++-
 docs/plans/quick-chat-expiration/plan.md      | 195 ++++++++++++++++
 .../task-01-backend-candidate-query.md        |  42 ++++
 .../task-02-backend-expiration-service.md     |  42 ++++
 .../task-03-boot-hydration.md                 |  46 ++++
 .../task-04-e2e-and-verification.md           |  43 ++++
 docs/specs/INDEX.md                           |   1 +
 docs/specs/tasks/quick-chat-expiration.md     | 168 ++++++++++++++
 27 files changed, 1492 insertions(+), 17 deletions(-)
 create mode 100644 apps/backend/internal/task/service/quick_chat_expiration.go
 create mode 100644 docs/plans/quick-chat-expiration/plan.md
 create mode 100644 docs/plans/quick-chat-expiration/task-01-backend-candidate-query.md
 create mode 100644 docs/plans/quick-chat-expiration/task-02-backend-expiration-service.md
 create mode 100644 docs/plans/quick-chat-expiration/task-03-boot-hydration.md
 create mode 100644 docs/plans/quick-chat-expiration/task-04-e2e-and-verification.md
 create mode 100644 docs/specs/tasks/quick-chat-expiration.md

diff --git a/apps/backend/internal/backendapp/boot_state.go b/apps/backend/internal/backendapp/boot_state.go
index 96d2e4e85e..66e4acf60b 100644
--- a/apps/backend/internal/backendapp/boot_state.go
+++ b/apps/backend/internal/backendapp/boot_state.go
@@ -3,6 +3,8 @@ package backendapp
 import (
 	"context"
 	"net/http"
+	"sort"
+	"time"
 
 	agentsettingsdto "github.com/kandev/kandev/internal/agent/settings/dto"
 	taskdto "github.com/kandev/kandev/internal/task/dto"
@@ -16,6 +18,8 @@ import (
 const (
 	activeWorkspaceCookie       = "kandev-active-workspace"
 	legacyOfficeWorkspaceCookie = "office-active-workspace"
+	bootStateKeySessionID       = "sessionId"
+	bootStateKeyWorkspaceID     = "workspaceId"
 )
 
 func bootInitialState(
@@ -48,6 +52,7 @@ func bootInitialState(
 	if route.Route == webapp.RouteOffice {
 		builder.addOfficeRouteState(ctx, req, state)
 	}
+	builder.addQuickChatState(ctx, req, state)
 	return state
 }
 
@@ -261,6 +266,210 @@ func (b bootStateBuilder) addRepositoriesState(ctx context.Context, state map[st
 	}
 }
 
+func (b bootStateBuilder) addQuickChatState(ctx context.Context, req *http.Request, state map[string]any) {
+	workspaceID := b.resolveQuickChatWorkspaceID(ctx, req, state)
+	if workspaceID == "" {
+		return
+	}
+	quickChat, err := b.quickChatSessions(ctx, workspaceID)
+	if err != nil {
+		b.logBootError("list quick-chat sessions", err)
+		return
+	}
+	state["quickChat"] = map[string]any{
+		"isOpen":          false,
+		"sessions":        quickChat.sessions,
+		"activeSessionId": nil,
+	}
+	mergeBootTaskSessionItems(state, quickChat.taskSessions)
+}
+
+func (b bootStateBuilder) resolveQuickChatWorkspaceID(ctx context.Context, req *http.Request, state map[string]any) string {
+	if active := activeWorkspaceIDFromState(state); active != "" {
+		return active
+	}
+	if b.p.taskSvc == nil {
+		return ""
+	}
+	workspaces, err := b.p.taskSvc.ListWorkspaces(ctx)
+	if err != nil {
+		b.logBootError("list quick-chat workspaces", err)
+		return ""
+	}
+	settingsWorkspaceID := ""
+	if settings, ok := b.userSettings(ctx); ok {
+		settingsWorkspaceID = settings.Settings.WorkspaceID
+	}
+	return firstValidID(
+		workspaceIDSet(workspaces),
+		queryValue(req, "workspaceId"),
+		queryValue(req, "workspace"),
+		readActiveWorkspaceCookie(req),
+		settingsWorkspaceID,
+		firstWorkspaceID(workspaces),
+	)
+}
+
+func activeWorkspaceIDFromState(state map[string]any) string {
+	workspaces, ok := state["workspaces"].(map[string]any)
+	if !ok {
+		return ""
+	}
+	active, _ := workspaces["activeId"].(string)
+	return active
+}
+
+func (b bootStateBuilder) quickChatSessions(ctx context.Context, workspaceID string) (quickChatBootState, error) {
+	tasks, err := b.listQuickChatTasks(ctx, workspaceID)
+	if err != nil {
+		return quickChatBootState{}, err
+	}
+	if len(tasks) == 0 {
+		return quickChatBootState{sessions: []map[string]any{}}, nil
+	}
+	taskIDs := taskIDs(tasks)
+	sessionsByTask, err := b.p.taskSvc.BatchGetSessionsForTasks(ctx, taskIDs)
+	if err != nil {
+		return quickChatBootState{}, err
+	}
+	primaryByTask, err := b.p.taskSvc.GetPrimarySessionInfoForTasks(ctx, taskIDs)
+	if err != nil {
+		return quickChatBootState{}, err
+	}
+
+	items := make([]quickChatBootSession, 0, len(tasks))
+	taskSessions := make(map[string]taskdto.TaskSessionDTO, len(tasks))
+	for _, task := range tasks {
+		if !isRestorableQuickChatTask(task) {
+			continue
+		}
+		primary := primaryByTask[task.ID]
+		if primary == nil || primary.ID == "" {
+			continue
+		}
+		items = append(items, quickChatBootSession{
+			state:        mapQuickChatSessionState(task, primary),
+			lastActivity: quickChatLastActivity(task, sessionsByTask[task.ID]),
+		})
+		taskSessions[primary.ID] = taskdto.FromTaskSession(primary)
+	}
+	sort.SliceStable(items, func(i, j int) bool {
+		return items[i].lastActivity.After(items[j].lastActivity)
+	})
+	result := make([]map[string]any, 0, len(items))
+	for _, item := range items {
+		result = append(result, item.state)
+	}
+	return quickChatBootState{sessions: result, taskSessions: taskSessions}, nil
+}
+
+func (b bootStateBuilder) listQuickChatTasks(ctx context.Context, workspaceID string) ([]*taskmodels.Task, error) {
+	const pageSize = 1000
+	var all []*taskmodels.Task
+	for page := 1; ; page++ {
+		tasks, total, err := b.p.taskSvc.ListTasksByWorkspace(ctx, workspaceID, "", "", "", page, pageSize, "", false, false, true, true)
+		if err != nil {
+			return nil, err
+		}
+		all = append(all, tasks...)
+		if len(tasks) == 0 || len(all) >= total {
+			return all, nil
+		}
+	}
+}
+
+type quickChatBootSession struct {
+	state        map[string]any
+	lastActivity time.Time
+}
+
+type quickChatBootState struct {
+	sessions     []map[string]any
+	taskSessions map[string]taskdto.TaskSessionDTO
+}
+
+func mergeBootTaskSessionItems(state map[string]any, items map[string]taskdto.TaskSessionDTO) {
+	if len(items) == 0 {
+		return
+	}
+	taskSessions, ok := state["taskSessions"].(map[string]any)
+	if !ok {
+		state["taskSessions"] = map[string]any{"items": items}
+		return
+	}
+	merged := make(map[string]any, len(items))
+	switch existing := taskSessions["items"].(type) {
+	case map[string]taskdto.TaskSessionDTO:
+		for id, session := range existing {
+			merged[id] = session
+		}
+	case map[string]any:
+		for id, session := range existing {
+			merged[id] = session
+		}
+	}
+	for id, session := range items {
+		merged[id] = session
+	}
+	taskSessions["items"] = merged
+}
+
+func taskIDs(tasks []*taskmodels.Task) []string {
+	ids := make([]string, 0, len(tasks))
+	for _, task := range tasks {
+		if task != nil {
+			ids = append(ids, task.ID)
+		}
+	}
+	return ids
+}
+
+func isRestorableQuickChatTask(task *taskmodels.Task) bool {
+	return task != nil &&
+		task.IsEphemeral &&
+		task.WorkflowID == "" &&
+		task.Origin != taskmodels.TaskOriginAutomationRun
+}
+
+func mapQuickChatSessionState(task *taskmodels.Task, primary *taskmodels.TaskSession) map[string]any {
+	state := map[string]any{
+		bootStateKeySessionID:   primary.ID,
+		bootStateKeyWorkspaceID: task.WorkspaceID,
+	}
+	if task.Title != "" && task.Title != "Quick Chat" {
+		state["name"] = task.Title
+	}
+	if agentProfileID := quickChatAgentProfileID(task, primary); agentProfileID != "" {
+		state["agentProfileId"] = agentProfileID
+	}
+	return state
+}
+
+func quickChatAgentProfileID(task *taskmodels.Task, primary *taskmodels.TaskSession) string {
+	if task != nil {
+		if value, ok := task.Metadata[taskmodels.MetaKeyAgentProfileID].(string); ok {
+			return value
+		}
+	}
+	if primary != nil {
+		return primary.AgentProfileID
+	}
+	return ""
+}
+
+func quickChatLastActivity(task *taskmodels.Task, sessions []*taskmodels.TaskSession) time.Time {
+	last := time.Time{}
+	if task != nil {
+		last = task.UpdatedAt
+	}
+	for _, session := range sessions {
+		if session != nil && session.UpdatedAt.After(last) {
+			last = session.UpdatedAt
+		}
+	}
+	return last
+}
+
 func (b bootStateBuilder) addKanbanSnapshotsState(
 	ctx context.Context,
 	state map[string]any,
diff --git a/apps/backend/internal/backendapp/helpers_test.go b/apps/backend/internal/backendapp/helpers_test.go
index 0fc44ca207..094e1a3249 100644
--- a/apps/backend/internal/backendapp/helpers_test.go
+++ b/apps/backend/internal/backendapp/helpers_test.go
@@ -22,6 +22,7 @@ import (
 	taskdto "github.com/kandev/kandev/internal/task/dto"
 	"github.com/kandev/kandev/internal/task/models"
 	taskrepo "github.com/kandev/kandev/internal/task/repository"
+	sqlitetaskrepo "github.com/kandev/kandev/internal/task/repository/sqlite"
 	taskservice "github.com/kandev/kandev/internal/task/service"
 	usercontroller "github.com/kandev/kandev/internal/user/controller"
 	userservice "github.com/kandev/kandev/internal/user/service"
@@ -30,6 +31,7 @@ import (
 	workflowrepo "github.com/kandev/kandev/internal/workflow/repository"
 	workflowservice "github.com/kandev/kandev/internal/workflow/service"
 	"github.com/kandev/kandev/internal/worktree"
+	v1 "github.com/kandev/kandev/pkg/api/v1"
 	ws "github.com/kandev/kandev/pkg/websocket"
 )
 
@@ -612,6 +614,139 @@ func TestBootPayloadIncludesDebugRuntimeWhenDevMode(t *testing.T) {
 	}
 }
 
+func TestBootPayloadRestoresQuickChatSessions(t *testing.T) {
+	harness := newBootStateTestHarness(t)
+	ctx := context.Background()
+	repo := harness.taskRepo
+
+	if err := repo.CreateWorkspace(ctx, &models.Workspace{ID: "ws-qc", Name: "Quick Chats"}); err != nil {
+		t.Fatalf("CreateWorkspace: %v", err)
+	}
+	if err := repo.CreateWorkflow(ctx, &models.Workflow{ID: "wf-qc", WorkspaceID: "ws-qc", Name: "Workflow"}); err != nil {
+		t.Fatalf("CreateWorkflow: %v", err)
+	}
+	base := time.Date(2026, 7, 3, 12, 0, 0, 0, time.UTC)
+	seedBootQuickChatTask(t, repo, ctx, bootQuickChatFixture{
+		id: "task-old", title: "Older Chat", updatedAt: base.Add(-2 * time.Hour),
+		sessionUpdatedAt: base.Add(-90 * time.Minute), agentProfileID: "agent-old",
+	})
+	seedBootQuickChatTask(t, repo, ctx, bootQuickChatFixture{
+		id: "task-new", title: "Newer Chat", updatedAt: base.Add(-4 * time.Hour),
+		sessionUpdatedAt: base.Add(-10 * time.Minute), agentProfileID: "agent-new",
+	})
+	seedBootQuickChatTask(t, repo, ctx, bootQuickChatFixture{
+		id: "task-config", title: "Config", updatedAt: base, sessionUpdatedAt: base,
+		agentProfileID: "agent-config", metadata: map[string]interface{}{"config_mode": true},
+	})
+	seedBootQuickChatTask(t, repo, ctx, bootQuickChatFixture{
+		id: "task-automation", title: "Automation", updatedAt: base, sessionUpdatedAt: base,
+		agentProfileID: "agent-automation", origin: models.TaskOriginAutomationRun,
+	})
+	seedBootQuickChatTask(t, repo, ctx, bootQuickChatFixture{
+		id: "task-workflow", title: "Workflow Ephemeral", updatedAt: base, sessionUpdatedAt: base,
+		agentProfileID: "agent-workflow", workflowID: "wf-qc",
+	})
+
+	req := httptest.NewRequest(http.MethodGet, "/?workspaceId=ws-qc", nil)
+	payload := bootPayload(ctx, req, routeParams{
+		taskSvc:  harness.taskSvc,
+		services: &Services{Workflow: harness.workflowSvc},
+		userCtrl: harness.userCtrl,
+	}, webapp.ClassifyRoute("/"))
+
+	raw, err := json.Marshal(payload)
+	if err != nil {
+		t.Fatalf("Marshal payload: %v", err)
+	}
+	var decoded struct {
+		InitialState struct {
+			QuickChat struct {
+				Sessions []struct {
+					SessionID      string `json:"sessionId"`
+					WorkspaceID    string `json:"workspaceId"`
+					Name           string `json:"name"`
+					AgentProfileID string `json:"agentProfileId"`
+				} `json:"sessions"`
+				IsOpen bool `json:"isOpen"`
+			} `json:"quickChat"`
+			TaskSessions struct {
+				Items map[string]struct {
+					TaskID string `json:"task_id"`
+				} `json:"items"`
+			} `json:"taskSessions"`
+		} `json:"initialState"`
+	}
+	if err := json.Unmarshal(raw, &decoded); err != nil {
+		t.Fatalf("Unmarshal payload: %v", err)
+	}
+
+	sessions := decoded.InitialState.QuickChat.Sessions
+	if len(sessions) != 2 {
+		t.Fatalf("quickChat sessions = %#v, want 2 restored sessions", sessions)
+	}
+	if got := sessions[0].SessionID; got != "task-new-session" {
+		t.Fatalf("first restored session = %q, want newest task-new-session", got)
+	}
+	if sessions[0].AgentProfileID != "agent-new" || sessions[1].AgentProfileID != "agent-old" {
+		t.Fatalf("agent profile IDs = %#v", sessions)
+	}
+	if got := decoded.InitialState.TaskSessions.Items["task-new-session"].TaskID; got != "task-new" {
+		t.Fatalf("quick chat task session task_id = %q, want task-new", got)
+	}
+	if decoded.InitialState.QuickChat.IsOpen {
+		t.Fatal("quick chat should hydrate closed")
+	}
+}
+
+type bootQuickChatFixture struct {
+	id               string
+	title            string
+	workflowID       string
+	origin           string
+	agentProfileID   string
+	metadata         map[string]interface{}
+	updatedAt        time.Time
+	sessionUpdatedAt time.Time
+}
+
+func seedBootQuickChatTask(t *testing.T, repo *sqlitetaskrepo.Repository, ctx context.Context, f bootQuickChatFixture) {
+	t.Helper()
+	metadata := map[string]interface{}{models.MetaKeyAgentProfileID: f.agentProfileID}
+	for key, value := range f.metadata {
+		metadata[key] = value
+	}
+	if err := repo.CreateTask(ctx, &models.Task{
+		ID:          f.id,
+		WorkspaceID: "ws-qc",
+		WorkflowID:  f.workflowID,
+		Title:       f.title,
+		State:       v1.TaskStateTODO,
+		Priority:    "medium",
+		IsEphemeral: true,
+		Origin:      f.origin,
+		Metadata:    metadata,
+	}); err != nil {
+		t.Fatalf("CreateTask(%s): %v", f.id, err)
+	}
+	if _, err := repo.DB().ExecContext(ctx,
+		`UPDATE tasks SET created_at = ?, updated_at = ? WHERE id = ?`,
+		f.updatedAt.Add(-time.Hour), f.updatedAt, f.id,
+	); err != nil {
+		t.Fatalf("backdate task(%s): %v", f.id, err)
+	}
+	if err := repo.CreateTaskSession(ctx, &models.TaskSession{
+		ID:             f.id + "-session",
+		TaskID:         f.id,
+		AgentProfileID: f.agentProfileID,
+		State:          models.TaskSessionStateCompleted,
+		StartedAt:      f.sessionUpdatedAt.Add(-time.Hour),
+		UpdatedAt:      f.sessionUpdatedAt,
+		IsPrimary:      true,
+	}); err != nil {
+		t.Fatalf("CreateTaskSession(%s): %v", f.id, err)
+	}
+}
+
 func TestBootRouteDataIntegrationRouteIncludesOnlyLocalContext(t *testing.T) {
 	taskSvc, workflowSvc := newBootStateTestServices(t)
 	ctx := context.Background()
@@ -827,6 +962,7 @@ func TestQueryValueReadsRouteQueryFromAppStatePath(t *testing.T) {
 
 type bootStateTestHarness struct {
 	taskSvc     *taskservice.Service
+	taskRepo    *sqlitetaskrepo.Repository
 	workflowSvc *workflowservice.Service
 	userCtrl    *usercontroller.Controller
 	userSvc     *userservice.Service
@@ -901,6 +1037,7 @@ func newBootStateTestHarness(t *testing.T) bootStateTestHarness {
 	workflowSvc.SetWorkflowProvider(&workflowProviderAdapter{svc: taskSvc})
 	return bootStateTestHarness{
 		taskSvc:     taskSvc,
+		taskRepo:    taskRepo,
 		workflowSvc: workflowSvc,
 		userCtrl:    usercontroller.NewController(userSvc),
 		userSvc:     userSvc,
diff --git a/apps/backend/internal/backendapp/main.go b/apps/backend/internal/backendapp/main.go
index dd8feb9300..e587458324 100644
--- a/apps/backend/internal/backendapp/main.go
+++ b/apps/backend/internal/backendapp/main.go
@@ -700,6 +700,7 @@ func startGatewayAndServe(
 	}
 
 	services.Task.StartAutoArchiveLoop(ctx)
+	services.Task.StartQuickChatExpirationLoop(ctx)
 
 	// ============================================
 	// SYSTEM PAGES
diff --git a/apps/backend/internal/db/dialect/dialect_test.go b/apps/backend/internal/db/dialect/dialect_test.go
index f34e2315c5..d3b3d6e871 100644
--- a/apps/backend/internal/db/dialect/dialect_test.go
+++ b/apps/backend/internal/db/dialect/dialect_test.go
@@ -111,6 +111,17 @@ func TestNowMinusHours(t *testing.T) {
 	}
 }
 
+func TestGreatestTimestamp(t *testing.T) {
+	got := GreatestTimestamp(SQLite3, "t.updated_at", "MAX(ts.updated_at)")
+	if got != "max(t.updated_at, MAX(ts.updated_at))" {
+		t.Errorf("sqlite: got %q", got)
+	}
+	got = GreatestTimestamp(PGX, "t.updated_at", "MAX(ts.updated_at)")
+	if got != "GREATEST(t.updated_at, MAX(ts.updated_at))" {
+		t.Errorf("pgx: got %q", got)
+	}
+}
+
 func TestCurrentDate(t *testing.T) {
 	if CurrentDate(SQLite3) != "date('now')" {
 		t.Errorf("sqlite: got %q", CurrentDate(SQLite3))
diff --git a/apps/backend/internal/db/dialect/time.go b/apps/backend/internal/db/dialect/time.go
index 46c8db8651..3b56db4666 100644
--- a/apps/backend/internal/db/dialect/time.go
+++ b/apps/backend/internal/db/dialect/time.go
@@ -47,6 +47,17 @@ func NowMinusHours(driver, hoursExpr string) string {
 	return fmt.Sprintf("datetime('now', '-' || %s || ' hours')", hoursExpr)
 }
 
+// GreatestTimestamp returns the greater of two timestamp expressions.
+//
+//	SQLite:   max(left, right)
+//	Postgres: GREATEST(left, right)
+func GreatestTimestamp(driver, left, right string) string {
+	if IsPostgres(driver) {
+		return fmt.Sprintf("GREATEST(%s, %s)", left, right)
+	}
+	return fmt.Sprintf("max(%s, %s)", left, right)
+}
+
 // CurrentDate returns the SQL expression for the current date (no time component).
 //
 //	SQLite:   date('now')
diff --git a/apps/backend/internal/task/handlers/process_handlers_test.go b/apps/backend/internal/task/handlers/process_handlers_test.go
index f29eef0858..043e4d2404 100644
--- a/apps/backend/internal/task/handlers/process_handlers_test.go
+++ b/apps/backend/internal/task/handlers/process_handlers_test.go
@@ -83,6 +83,12 @@ func (m *mockRepository) ArchiveTask(ctx context.Context, id string) error {
 func (m *mockRepository) ListTasksForAutoArchive(ctx context.Context) ([]*models.Task, error) {
 	return nil, nil
 }
+func (m *mockRepository) ListExpiredQuickChatTasks(ctx context.Context, cutoff time.Time) ([]*models.Task, error) {
+	return nil, nil
+}
+func (m *mockRepository) DeleteExpiredQuickChatTask(ctx context.Context, id string, cutoff time.Time) (bool, error) {
+	return false, nil
+}
 func (m *mockRepository) CountOpenWatcherCreatedTasks(_ context.Context, _, _ string) (int, error) {
 	return 0, nil
 }
diff --git a/apps/backend/internal/task/repository/interface.go b/apps/backend/internal/task/repository/interface.go
index 0a3f20099f..fe47bc3a69 100644
--- a/apps/backend/internal/task/repository/interface.go
+++ b/apps/backend/internal/task/repository/interface.go
@@ -12,6 +12,7 @@ import (
 
 var ErrWorkspaceNameMismatch = repoerrors.ErrWorkspaceNameMismatch
 var ErrWorkspaceNotFound = repoerrors.ErrWorkspaceNotFound
+var ErrTaskNotFound = repoerrors.ErrTaskNotFound
 
 // WorkspaceRepository handles workspace CRUD.
 type WorkspaceRepository interface {
@@ -43,6 +44,8 @@ type TaskRepository interface {
 	// archived by the named cascade. Returns whether the row was updated.
 	UnarchiveTaskByCascade(ctx context.Context, id, cascadeID string) (bool, error)
 	ListTasksForAutoArchive(ctx context.Context) ([]*models.Task, error)
+	ListExpiredQuickChatTasks(ctx context.Context, cutoff time.Time) ([]*models.Task, error)
+	DeleteExpiredQuickChatTask(ctx context.Context, id string, cutoff time.Time) (bool, error)
 	// CountOpenWatcherCreatedTasks returns the number of open watcher-created
 	// tasks for a single watch, identified by the integration's task-metadata
 	// key (e.g. "sentry_issue_watch_id") and the watch id. Open = non-archived
diff --git a/apps/backend/internal/task/repository/repoerrors/errors.go b/apps/backend/internal/task/repository/repoerrors/errors.go
index 97c30abc21..29a7144328 100644
--- a/apps/backend/internal/task/repository/repoerrors/errors.go
+++ b/apps/backend/internal/task/repository/repoerrors/errors.go
@@ -8,3 +8,6 @@ var ErrWorkspaceNameMismatch = errors.New("workspace name mismatch")
 
 // ErrWorkspaceNotFound reports that no workspace row matched the supplied id.
 var ErrWorkspaceNotFound = errors.New("workspace not found")
+
+// ErrTaskNotFound reports that no task row matched the supplied id.
+var ErrTaskNotFound = errors.New("task not found")
diff --git a/apps/backend/internal/task/repository/sqlite/errors.go b/apps/backend/internal/task/repository/sqlite/errors.go
index 5dba6211c8..5db0f1a040 100644
--- a/apps/backend/internal/task/repository/sqlite/errors.go
+++ b/apps/backend/internal/task/repository/sqlite/errors.go
@@ -10,7 +10,7 @@ import (
 // DeleteTask, UpdateTaskState, …) when no row matches the supplied id.
 // Callers should classify via errors.Is rather than substring-matching the
 // formatted message, which includes the task id and is therefore brittle.
-var ErrTaskNotFound = errors.New("task not found")
+var ErrTaskNotFound = repoerrors.ErrTaskNotFound
 
 // ErrWorkspaceNotFound is returned by Repository workspace methods when no row
 // matches the supplied id.
diff --git a/apps/backend/internal/task/repository/sqlite/task.go b/apps/backend/internal/task/repository/sqlite/task.go
index d1975a721c..f1b6fdffa1 100644
--- a/apps/backend/internal/task/repository/sqlite/task.go
+++ b/apps/backend/internal/task/repository/sqlite/task.go
@@ -865,6 +865,102 @@ func (r *Repository) ListTasksForAutoArchive(ctx context.Context) ([]*models.Tas
 	return r.scanTasks(rows)
 }
 
+// ListExpiredQuickChatTasks returns quick-chat tasks whose last task/session
+// activity is older than cutoff. Active sessions are excluded so in-use chats
+// are never deleted by the idle sweeper.
+func (r *Repository) ListExpiredQuickChatTasks(ctx context.Context, cutoff time.Time) ([]*models.Task, error) {
+	drv := r.ro.DriverName()
+	sessionActivity := "COALESCE(MAX(ts.updated_at), t.updated_at)"
+	lastActivity := dialect.GreatestTimestamp(drv, "t.updated_at", sessionActivity)
+	query := fmt.Sprintf(`
+		WITH candidates AS (
+			SELECT t.id, %s AS last_activity
+			FROM tasks t
+			LEFT JOIN task_sessions ts ON ts.task_id = t.id
+			WHERE t.is_ephemeral = 1
+				AND COALESCE(t.workflow_id, '') = ''
+				AND COALESCE(t.origin, '') != ?
+				AND %s
+				AND t.archived_at IS NULL
+				AND NOT EXISTS (
+					SELECT 1 FROM task_sessions active
+					WHERE active.task_id = t.id
+						AND active.state IN (?, ?)
+				)
+			GROUP BY t.id, t.updated_at
+			HAVING %s < ?
+		)
+		SELECT %s
+		FROM tasks t
+		JOIN candidates c ON c.id = t.id
+		ORDER BY c.last_activity ASC
+	`,
+		lastActivity,
+		excludeConfigModePredicate(drv, "t.metadata"),
+		lastActivity,
+		taskSelectColumns("t"),
+	)
+	rows, err := r.ro.QueryContext(ctx, r.ro.Rebind(query),
+		models.TaskOriginAutomationRun,
+		models.TaskSessionStateRunning,
+		models.TaskSessionStateIdle,
+		cutoff,
+	)
+	if err != nil {
+		return nil, err
+	}
+	defer func() { _ = rows.Close() }()
+	return r.scanTasks(rows)
+}
+
+// DeleteExpiredQuickChatTask deletes id only when it still matches the expired
+// quick-chat predicate at delete time.
+func (r *Repository) DeleteExpiredQuickChatTask(ctx context.Context, id string, cutoff time.Time) (bool, error) {
+	drv := r.db.DriverName()
+	sessionActivity := "COALESCE(MAX(ts.updated_at), t.updated_at)"
+	lastActivity := dialect.GreatestTimestamp(drv, "t.updated_at", sessionActivity)
+	query := fmt.Sprintf(`
+		WITH candidate AS (
+			SELECT t.id, %s AS last_activity
+			FROM tasks t
+			LEFT JOIN task_sessions ts ON ts.task_id = t.id
+			WHERE t.id = ?
+				AND t.is_ephemeral = 1
+				AND COALESCE(t.workflow_id, '') = ''
+				AND COALESCE(t.origin, '') != ?
+				AND %s
+				AND t.archived_at IS NULL
+				AND NOT EXISTS (
+					SELECT 1 FROM task_sessions active
+					WHERE active.task_id = t.id
+						AND active.state IN (?, ?)
+				)
+			GROUP BY t.id, t.updated_at
+			HAVING %s < ?
+		)
+		DELETE FROM tasks
+		WHERE id = ?
+			AND EXISTS (SELECT 1 FROM candidate)
+	`,
+		lastActivity,
+		excludeConfigModePredicate(drv, "t.metadata"),
+		lastActivity,
+	)
+	result, err := r.db.ExecContext(ctx, r.db.Rebind(query),
+		id,
+		models.TaskOriginAutomationRun,
+		models.TaskSessionStateRunning,
+		models.TaskSessionStateIdle,
+		cutoff,
+		id,
+	)
+	if err != nil {
+		return false, err
+	}
+	rows, _ := result.RowsAffected()
+	return rows > 0, nil
+}
+
 // isSafeMetadataKey reports whether s is a safe JSON metadata key to splice
 // into a json_extract path. The key is concatenated into the SQL text (it
 // cannot be a bind parameter inside the '$.<key>' path literal), so it must be
diff --git a/apps/backend/internal/task/repository/task_repository_test.go b/apps/backend/internal/task/repository/task_repository_test.go
index 8bd2da9142..4ebbdf2b4e 100644
--- a/apps/backend/internal/task/repository/task_repository_test.go
+++ b/apps/backend/internal/task/repository/task_repository_test.go
@@ -182,6 +182,175 @@ func TestSQLiteRepository_UpdateTaskStateIfCurrentIn(t *testing.T) {
 	}
 }
 
+func TestSQLiteRepository_ListExpiredQuickChatTasks(t *testing.T) {
+	repo, cleanup := createTestSQLiteRepo(t)
+	defer cleanup()
+	ctx := context.Background()
+
+	if err := repo.CreateWorkspace(ctx, &models.Workspace{ID: "ws-quick", Name: "Quick"}); err != nil {
+		t.Fatalf("create workspace: %v", err)
+	}
+	if err := repo.CreateWorkflow(ctx, &models.Workflow{ID: "wf-quick", WorkspaceID: "ws-quick", Name: "Workflow"}); err != nil {
+		t.Fatalf("create workflow: %v", err)
+	}
+
+	now := time.Date(2026, 7, 3, 12, 0, 0, 0, time.UTC)
+	cutoff := now.Add(-7 * 24 * time.Hour)
+	old := cutoff.Add(-time.Hour)
+	older := cutoff.Add(-3 * time.Hour)
+	abandonedCreated := cutoff.Add(-2 * time.Hour)
+	abandonedStarting := cutoff.Add(-90 * time.Minute)
+	recent := cutoff.Add(time.Hour)
+
+	cases := []struct {
+		id             string
+		taskUpdated    time.Time
+		sessionUpdated time.Time
+		sessionState   models.TaskSessionState
+		ephemeral      bool
+		workflowID     string
+		archived       bool
+		origin         string
+		metadata       map[string]interface{}
+		wantExpired    bool
+	}{
+		{id: "expired-older", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateCompleted, ephemeral: true, wantExpired: true},
+		{id: "abandoned-created", taskUpdated: abandonedCreated, sessionUpdated: abandonedCreated, sessionState: models.TaskSessionStateCreated, ephemeral: true, wantExpired: true},
+		{id: "abandoned-starting", taskUpdated: abandonedStarting, sessionUpdated: abandonedStarting, sessionState: models.TaskSessionStateStarting, ephemeral: true, wantExpired: true},
+		{id: "expired-old", taskUpdated: old, sessionUpdated: old, sessionState: models.TaskSessionStateCompleted, ephemeral: true, wantExpired: true},
+		{id: "expired-waiting-input", taskUpdated: old, sessionUpdated: old, sessionState: models.TaskSessionStateWaitingForInput, ephemeral: true, wantExpired: true},
+		{id: "recent-task", taskUpdated: recent, sessionUpdated: old, sessionState: models.TaskSessionStateCompleted, ephemeral: true},
+		{id: "recent-session", taskUpdated: old, sessionUpdated: recent, sessionState: models.TaskSessionStateCompleted, ephemeral: true},
+		{id: "running-session", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateRunning, ephemeral: true},
+		{id: "idle-session", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateIdle, ephemeral: true},
+		{id: "config-mode", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateCompleted, ephemeral: true, metadata: map[string]interface{}{"config_mode": true}},
+		{id: "automation-run", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateCompleted, ephemeral: true, origin: models.TaskOriginAutomationRun},
+		{id: "kanban-task", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateCompleted, ephemeral: false, workflowID: "wf-quick"},
+		{id: "ephemeral-workflow", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateCompleted, ephemeral: true, workflowID: "wf-quick"},
+		{id: "archived", taskUpdated: older, sessionUpdated: older, sessionState: models.TaskSessionStateCompleted, ephemeral: true, archived: true},
+	}
+
+	for _, tc := range cases {
+		createQuickChatExpiryFixture(t, repo, ctx, tc.id, tc.workflowID, tc.origin, tc.metadata, tc.ephemeral, tc.archived, tc.taskUpdated, tc.sessionUpdated, tc.sessionState)
+	}
+
+	tasks, err := repo.ListExpiredQuickChatTasks(ctx, cutoff)
+	if err != nil {
+		t.Fatalf("ListExpiredQuickChatTasks: %v", err)
+	}
+
+	var got []string
+	for _, task := range tasks {
+		got = append(got, task.ID)
+	}
+	var want []string
+	for _, tc := range cases {
+		if tc.wantExpired {
+			want = append(want, tc.id)
+		}
+	}
+	if !slices.Equal(got, want) {
+		t.Fatalf("expired task IDs = %v, want %v", got, want)
+	}
+}
+
+func TestSQLiteRepository_DeleteExpiredQuickChatTask(t *testing.T) {
+	repo, cleanup := createTestSQLiteRepo(t)
+	defer cleanup()
+	ctx := context.Background()
+
+	if err := repo.CreateWorkspace(ctx, &models.Workspace{ID: "ws-quick", Name: "Quick"}); err != nil {
+		t.Fatalf("create workspace: %v", err)
+	}
+
+	now := time.Date(2026, 7, 3, 12, 0, 0, 0, time.UTC)
+	cutoff := now.Add(-7 * 24 * time.Hour)
+	old := cutoff.Add(-time.Hour)
+	recent := cutoff.Add(time.Hour)
+
+	createQuickChatExpiryFixture(t, repo, ctx, "expired", "", "", nil, true, false, old, old, models.TaskSessionStateCompleted)
+	createQuickChatExpiryFixture(t, repo, ctx, "active", "", "", nil, true, false, old, old, models.TaskSessionStateRunning)
+	createQuickChatExpiryFixture(t, repo, ctx, "recent", "", "", nil, true, false, old, recent, models.TaskSessionStateCompleted)
+
+	deleted, err := repo.DeleteExpiredQuickChatTask(ctx, "expired", cutoff)
+	if err != nil {
+		t.Fatalf("DeleteExpiredQuickChatTask expired: %v", err)
+	}
+	if !deleted {
+		t.Fatal("expected expired quick chat to be deleted")
+	}
+	if _, err := repo.GetTask(ctx, "expired"); err == nil {
+		t.Fatal("expired quick chat still exists after guarded delete")
+	}
+
+	for _, id := range []string{"active", "recent"} {
+		deleted, err := repo.DeleteExpiredQuickChatTask(ctx, id, cutoff)
+		if err != nil {
+			t.Fatalf("DeleteExpiredQuickChatTask %s: %v", id, err)
+		}
+		if deleted {
+			t.Fatalf("%s should not be deleted while ineligible", id)
+		}
+		if _, err := repo.GetTask(ctx, id); err != nil {
+			t.Fatalf("%s should still exist: %v", id, err)
+		}
+	}
+}
+
+func createQuickChatExpiryFixture(
+	t *testing.T,
+	repo *sqlite.Repository,
+	ctx context.Context,
+	id string,
+	workflowID string,
+	origin string,
+	metadata map[string]interface{},
+	ephemeral bool,
+	archived bool,
+	taskUpdated time.Time,
+	sessionUpdated time.Time,
+	sessionState models.TaskSessionState,
+) {
+	t.Helper()
+	task := &models.Task{
+		ID:          id,
+		WorkspaceID: "ws-quick",
+		WorkflowID:  workflowID,
+		Title:       id,
+		State:       v1.TaskStateTODO,
+		Priority:    "medium",
+		IsEphemeral: ephemeral,
+		Origin:      origin,
+		Metadata:    metadata,
+		CreatedAt:   taskUpdated.Add(-time.Hour),
+		UpdatedAt:   taskUpdated,
+	}
+	if archived {
+		archivedAt := taskUpdated.Add(time.Minute)
+		task.ArchivedAt = &archivedAt
+	}
+	if err := repo.CreateTask(ctx, task); err != nil {
+		t.Fatalf("CreateTask(%s): %v", id, err)
+	}
+	if _, err := repo.DB().ExecContext(ctx,
+		`UPDATE tasks SET created_at = ?, updated_at = ?, archived_at = ? WHERE id = ?`,
+		task.CreatedAt, taskUpdated, task.ArchivedAt, id,
+	); err != nil {
+		t.Fatalf("backdate task(%s): %v", id, err)
+	}
+	if err := repo.CreateTaskSession(ctx, &models.TaskSession{
+		ID:             id + "-session",
+		TaskID:         id,
+		AgentProfileID: "agent-1",
+		State:          sessionState,
+		StartedAt:      sessionUpdated.Add(-time.Hour),
+		UpdatedAt:      sessionUpdated,
+		IsPrimary:      true,
+	}); err != nil {
+		t.Fatalf("CreateTaskSession(%s): %v", id, err)
+	}
+}
+
 func TestSQLiteRepository_ListChildCompletionRows_ActiveChildren(t *testing.T) {
 	repo, cleanup := createTestSQLiteRepo(t)
 	defer cleanup()
diff --git a/apps/backend/internal/task/service/handoff_cascade_test.go b/apps/backend/internal/task/service/handoff_cascade_test.go
index 0fc7f3272c..4d198147be 100644
--- a/apps/backend/internal/task/service/handoff_cascade_test.go
+++ b/apps/backend/internal/task/service/handoff_cascade_test.go
@@ -327,6 +327,10 @@ func (r *fakeDeleteRepo) DeleteTask(_ context.Context, id string) error {
 	return nil
 }
 
+func (r *fakeDeleteRepo) DeleteExpiredQuickChatTask(context.Context, string, time.Time) (bool, error) {
+	panic("DeleteExpiredQuickChatTask should not be used by delete cascade tests")
+}
+
 // REGRESSION (post-review #4): a parent with already-archived children
 // must still have those children deleted by the cascade. The original
 // collectTaskTree used ListChildren which filtered archived rows; the
diff --git a/apps/backend/internal/task/service/handoff_workspace_test.go b/apps/backend/internal/task/service/handoff_workspace_test.go
index fe26d5409c..90a2fcb9fd 100644
--- a/apps/backend/internal/task/service/handoff_workspace_test.go
+++ b/apps/backend/internal/task/service/handoff_workspace_test.go
@@ -375,6 +375,14 @@ func (r *phase4TaskRepo) ListTasksForAutoArchive(context.Context) ([]*models.Tas
 	r.panicNotUsed("ListTasksForAutoArchive")
 	return nil, nil
 }
+func (r *phase4TaskRepo) ListExpiredQuickChatTasks(context.Context, time.Time) ([]*models.Task, error) {
+	r.panicNotUsed("ListExpiredQuickChatTasks")
+	return nil, nil
+}
+func (r *phase4TaskRepo) DeleteExpiredQuickChatTask(context.Context, string, time.Time) (bool, error) {
+	r.panicNotUsed("DeleteExpiredQuickChatTask")
+	return false, nil
+}
 func (r *phase4TaskRepo) CountOpenWatcherCreatedTasks(context.Context, string, string) (int, error) {
 	r.panicNotUsed("CountOpenWatcherCreatedTasks")
 	return 0, nil
diff --git a/apps/backend/internal/task/service/quick_chat_expiration.go b/apps/backend/internal/task/service/quick_chat_expiration.go
new file mode 100644
index 0000000000..fde4c137a1
--- /dev/null
+++ b/apps/backend/internal/task/service/quick_chat_expiration.go
@@ -0,0 +1,62 @@
+package service
+
+import (
+	"context"
+	"time"
+
+	"go.uber.org/zap"
+)
+
+const (
+	quickChatIdleRetention      = 7 * 24 * time.Hour
+	quickChatExpirationInterval = 24 * time.Hour
+)
+
+// StartQuickChatExpirationLoop starts a background goroutine that removes
+// abandoned quick chats after the retention window.
+func (s *Service) StartQuickChatExpirationLoop(ctx context.Context) {
+	ticker := time.NewTicker(quickChatExpirationInterval)
+	go func() {
+		defer ticker.Stop()
+		s.runQuickChatExpiration(ctx, time.Now())
+		for {
+			select {
+			case <-ctx.Done():
+				return
+			case now := <-ticker.C:
+				s.runQuickChatExpiration(ctx, now)
+			}
+		}
+	}()
+	s.logger.Info("quick-chat expiration loop started",
+		zap.Duration("interval", quickChatExpirationInterval),
+		zap.Duration("retention", quickChatIdleRetention))
+}
+
+func (s *Service) runQuickChatExpiration(ctx context.Context, now time.Time) {
+	cutoff := now.UTC().Add(-quickChatIdleRetention)
+	tasks, err := s.tasks.ListExpiredQuickChatTasks(ctx, cutoff)
+	if err != nil {
+		s.logger.Warn("quick-chat expiration: failed to list candidates", zap.Error(err))
+		return
+	}
+	if len(tasks) == 0 {
+		return
+	}
+
+	s.logger.Info("quick-chat expiration: found candidates", zap.Int("count", len(tasks)))
+	for _, task := range tasks {
+		deleted, err := s.deleteExpiredQuickChatTask(ctx, task.ID, cutoff)
+		if err != nil {
+			s.logger.Warn("quick-chat expiration: failed to delete task",
+				zap.String("task_id", task.ID),
+				zap.Error(err))
+			continue
+		}
+		if !deleted {
+			continue
+		}
+		s.logger.Info("quick-chat expiration: deleted task",
+			zap.String("task_id", task.ID))
+	}
+}
diff --git a/apps/backend/internal/task/service/service_tasks.go b/apps/backend/internal/task/service/service_tasks.go
index 932bd69f12..7872a154bd 100644
--- a/apps/backend/internal/task/service/service_tasks.go
+++ b/apps/backend/internal/task/service/service_tasks.go
@@ -18,6 +18,7 @@ import (
 	"github.com/kandev/kandev/internal/common/gitref"
 	"github.com/kandev/kandev/internal/events"
 	"github.com/kandev/kandev/internal/task/models"
+	taskrepo "github.com/kandev/kandev/internal/task/repository"
 	"github.com/kandev/kandev/internal/worktree"
 )
 
@@ -1006,12 +1007,37 @@ func (s *Service) DeleteTaskWithReason(ctx context.Context, id, reason string) e
 }
 
 func (s *Service) deleteTaskWithReason(ctx context.Context, id, reason string) error {
+	_, err := s.deleteTaskWithReasonAndDBDelete(ctx, id, reason, func(ctx context.Context, id string) (bool, error) {
+		if err := s.tasks.DeleteTask(ctx, id); err != nil {
+			return false, err
+		}
+		return true, nil
+	})
+	return err
+}
+
+func (s *Service) deleteExpiredQuickChatTask(ctx context.Context, id string, cutoff time.Time) (bool, error) {
+	deleted, err := s.deleteTaskWithReasonAndDBDelete(ctx, id, "", func(ctx context.Context, id string) (bool, error) {
+		return s.tasks.DeleteExpiredQuickChatTask(ctx, id, cutoff)
+	})
+	if errors.Is(err, taskrepo.ErrTaskNotFound) {
+		return false, nil
+	}
+	return deleted, err
+}
+
+func (s *Service) deleteTaskWithReasonAndDBDelete(
+	ctx context.Context,
+	id string,
+	reason string,
+	deleteFromDB func(context.Context, string) (bool, error),
+) (bool, error) {
 	start := time.Now()
 
 	// 1. Get task (sync, fast)
 	task, err := s.tasks.GetTask(ctx, id)
 	if err != nil {
-		return err
+		return false, err
 	}
 
 	// 2. Gather data needed for cleanup BEFORE delete (sync, fast)
@@ -1037,14 +1063,18 @@ func (s *Service) deleteTaskWithReason(ctx context.Context, id, reason string) e
 		}
 		stopTargets, err = s.buildStopTargets(ctx, id, activeSessions)
 		if err != nil {
-			return fmt.Errorf("list runtime cleanup inventory: %w", err)
+			return false, fmt.Errorf("list runtime cleanup inventory: %w", err)
 		}
 	}
 
 	// 4. Delete from DB (sync, fast)
-	if err := s.tasks.DeleteTask(ctx, id); err != nil {
+	deleted, err := deleteFromDB(ctx, id)
+	if err != nil {
 		s.logger.Error("failed to delete task", zap.String("task_id", id), zap.Error(err))
-		return err
+		return false, err
+	}
+	if !deleted {
+		return false, nil
 	}
 
 	// 5. Publish event (sync, fast) - frontend removes task immediately
@@ -1068,7 +1098,7 @@ func (s *Service) deleteTaskWithReason(ctx context.Context, id, reason string) e
 			"task deleted", "failed to stop session on task delete", "task cleanup completed")
 	}
 
-	return nil
+	return true, nil
 }
 
 // CleanupTaskResources tears down a task's runtime resources (container,
diff --git a/apps/backend/internal/task/service/service_test.go b/apps/backend/internal/task/service/service_test.go
index b4d664d2d9..93aaf1af87 100644
--- a/apps/backend/internal/task/service/service_test.go
+++ b/apps/backend/internal/task/service/service_test.go
@@ -1200,6 +1200,114 @@ func TestService_DeleteTaskCleansSuccessfulSessionResourcesOnPartialStopFailure(
 	}
 }
 
+func TestService_QuickChatExpirationDeletesExpiredCandidates(t *testing.T) {
+	svc, eventBus, repo := createTestService(t)
+	ctx := context.Background()
+	svc.setCleanupDoneForTestHook(make(chan struct{}, 1))
+	quickChatDir := t.TempDir()
+	svc.SetQuickChatDir(quickChatDir)
+
+	if err := repo.CreateWorkspace(ctx, &models.Workspace{ID: "ws-expire", Name: "Expire"}); err != nil {
+		t.Fatalf("create workspace: %v", err)
+	}
+	expiredTaskID := "quick-expired"
+	recentTaskID := "quick-recent"
+	now := time.Date(2026, 7, 3, 12, 0, 0, 0, time.UTC)
+
+	createQuickChatExpirationServiceFixture(t, repo, ctx, expiredTaskID, now.Add(-8*24*time.Hour))
+	createQuickChatExpirationServiceFixture(t, repo, ctx, recentTaskID, now.Add(-time.Hour))
+	expiredSessionDir := filepath.Join(quickChatDir, expiredTaskID+"-session")
+	if err := os.MkdirAll(expiredSessionDir, 0o755); err != nil {
+		t.Fatalf("mkdir expired session dir: %v", err)
+	}
+
+	svc.runQuickChatExpiration(ctx, now)
+	waitForCleanupDone(t, svc)
+
+	if _, err := repo.GetTask(ctx, expiredTaskID); err == nil {
+		t.Fatal("expired quick chat should be deleted")
+	}
+	if _, err := repo.GetTask(ctx, recentTaskID); err != nil {
+		t.Fatalf("recent quick chat should remain: %v", err)
+	}
+	if _, err := os.Stat(expiredSessionDir); !os.IsNotExist(err) {
+		t.Fatalf("expired quick-chat directory should be removed, got %v", err)
+	}
+	if !eventBusHasType(eventBus, "task.deleted") {
+		t.Fatalf("expected task.deleted event, got %#v", eventBus.GetPublishedEvents())
+	}
+}
+
+func TestService_QuickChatExpirationLoopRunsOnStartup(t *testing.T) {
+	svc, _, repo := createTestService(t)
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+	svc.setCleanupDoneForTestHook(make(chan struct{}, 1))
+
+	if err := repo.CreateWorkspace(ctx, &models.Workspace{ID: "ws-expire", Name: "Expire"}); err != nil {
+		t.Fatalf("create workspace: %v", err)
+	}
+	taskID := "quick-expired-startup"
+	createQuickChatExpirationServiceFixture(t, repo, ctx, taskID, time.Now().UTC().Add(-8*24*time.Hour))
+
+	svc.StartQuickChatExpirationLoop(ctx)
+	waitForCleanupDone(t, svc)
+
+	if _, err := repo.GetTask(context.Background(), taskID); err == nil {
+		t.Fatal("expired quick chat should be deleted by startup sweep")
+	}
+}
+
+func TestService_DeleteExpiredQuickChatTaskIgnoresMissingTask(t *testing.T) {
+	svc, _, _ := createTestService(t)
+
+	deleted, err := svc.deleteExpiredQuickChatTask(context.Background(), "missing", time.Now().UTC())
+	if err != nil {
+		t.Fatalf("deleteExpiredQuickChatTask missing task: %v", err)
+	}
+	if deleted {
+		t.Fatal("missing task should not be reported as deleted")
+	}
+}
+
+func createQuickChatExpirationServiceFixture(
+	t *testing.T,
+	repo *sqliterepo.Repository,
+	ctx context.Context,
+	taskID string,
+	updatedAt time.Time,
+) {
+	t.Helper()
+	if err := repo.CreateTask(ctx, &models.Task{
+		ID:          taskID,
+		WorkspaceID: "ws-expire",
+		Title:       taskID,
+		State:       v1.TaskStateTODO,
+		Priority:    "medium",
+		IsEphemeral: true,
+		CreatedAt:   updatedAt.Add(-time.Hour),
+		UpdatedAt:   updatedAt,
+	}); err != nil {
+		t.Fatalf("CreateTask(%s): %v", taskID, err)
+	}
+	if _, err := repo.DB().ExecContext(ctx,
+		`UPDATE tasks SET created_at = ?, updated_at = ? WHERE id = ?`,
+		updatedAt.Add(-time.Hour), updatedAt, taskID,
+	); err != nil {
+		t.Fatalf("backdate task(%s): %v", taskID, err)
+	}
+	if err := repo.CreateTaskSession(ctx, &models.TaskSession{
+		ID:        taskID + "-session",
+		TaskID:    taskID,
+		State:     models.TaskSessionStateCompleted,
+		StartedAt: updatedAt.Add(-time.Hour),
+		UpdatedAt: updatedAt,
+		IsPrimary: true,
+	}); err != nil {
+		t.Fatalf("CreateTaskSession(%s): %v", taskID, err)
+	}
+}
+
 func TestService_DeleteTaskCleansMissingSessionExecutorRowAfterStop(t *testing.T) {
 	svc, _, repo := createTestService(t)
 	ctx := context.Background()
diff --git a/apps/web/app/page.tsx b/apps/web/app/page.tsx
index dc86d04571..56692f7b3c 100644
--- a/apps/web/app/page.tsx
+++ b/apps/web/app/page.tsx
@@ -60,6 +60,27 @@ function readAgentProfileId(
   return typeof value === "string" ? value : undefined;
 }
 
+type QuickChatTask = Awaited<ReturnType<typeof listQuickChatSessions>>["tasks"][number];
+
+function mapQuickChatSessions(tasks: QuickChatTask[]): AppState["quickChat"]["sessions"] {
+  const quickChatUpdatedAt = (task: QuickChatTask) => Date.parse(task.updated_at ?? "") || 0;
+
+  return (
+    tasks
+      .filter((task) => task.primary_session_id)
+      .filter((task) => task.origin !== "automation_run")
+      // Legacy Next.js path only receives task.updated_at. The Go boot payload
+      // sorts by max(task/session updated_at) and is the authoritative SPA path.
+      .sort((a, b) => quickChatUpdatedAt(b) - quickChatUpdatedAt(a))
+      .map((task) => ({
+        sessionId: task.primary_session_id!,
+        workspaceId: task.workspace_id,
+        name: task.title !== "Quick Chat" ? task.title : undefined,
+        agentProfileId: readAgentProfileId(task.metadata),
+      }))
+  );
+}
+
 function buildBaseState(
   workspaces: ListWorkspacesResponse,
   userSettingsResponse: UserSettingsResponse | null,
@@ -181,15 +202,7 @@ export default async function Page({ searchParams }: PageProps) {
       workspaceWorkflows: workflowList.workflows,
     });
 
-    // Map quick chat tasks to sessions
-    const quickChatSessions = quickChatResponse.tasks
-      .filter((t) => t.primary_session_id) // Only include tasks with active sessions
-      .map((t) => ({
-        sessionId: t.primary_session_id!,
-        workspaceId: t.workspace_id,
-        name: t.title !== "Quick Chat" ? t.title : undefined,
-        agentProfileId: readAgentProfileId(t.metadata),
-      }));
+    const quickChatSessions = mapQuickChatSessions(quickChatResponse.tasks);
 
     initialState = {
       ...initialState,
diff --git a/apps/web/lib/api/domains/workspace-api.ts b/apps/web/lib/api/domains/workspace-api.ts
index 9e22d0986d..1e99d46f91 100644
--- a/apps/web/lib/api/domains/workspace-api.ts
+++ b/apps/web/lib/api/domains/workspace-api.ts
@@ -121,6 +121,8 @@ export async function listQuickChatSessions(workspaceId: string, options?: ApiRe
       workspace_id: string;
       primary_session_id?: string | null;
       metadata?: Record<string, unknown> | null;
+      origin?: string | null;
+      updated_at?: string;
     }>;
   }>(`/api/v1/workspaces/${workspaceId}/tasks?only_ephemeral=true&exclude_config=true`, options);
 }
diff --git a/apps/web/lib/state/default-state.ts b/apps/web/lib/state/default-state.ts
index 2bbc42df4a..802a64d967 100644
--- a/apps/web/lib/state/default-state.ts
+++ b/apps/web/lib/state/default-state.ts
@@ -14,6 +14,7 @@ import {
   defaultAutomationsState,
   defaultSystemState,
 } from "./slices";
+import { getStoredQuickChatNames } from "@/lib/local-storage";
 
 export const defaultState = {
   kanban: defaultKanbanState.kanban,
@@ -130,6 +131,20 @@ function mergeGitLabFields(
   };
 }
 
+function mergeQuickChatState(initialState: Partial<DefaultState>): DefaultState["quickChat"] {
+  const quickChat = { ...defaultState.quickChat, ...initialState.quickChat };
+  if (!initialState.quickChat?.sessions) return quickChat;
+
+  const storedNames = getStoredQuickChatNames();
+  return {
+    ...quickChat,
+    sessions: initialState.quickChat.sessions.map((session) => {
+      const localName = storedNames[session.sessionId];
+      return localName ? { ...session, name: localName } : session;
+    }),
+  };
+}
+
 export function mergeInitialState(initialState?: Partial<DefaultState>): DefaultState {
   if (!initialState) return defaultState;
 
@@ -220,7 +235,7 @@ export function mergeInitialState(initialState?: Partial<DefaultState>): Default
     chatInput: { ...defaultState.chatInput, ...initialState.chatInput },
     documentPanel: { ...defaultState.documentPanel, ...initialState.documentPanel },
     systemHealth: { ...defaultState.systemHealth, ...initialState.systemHealth },
-    quickChat: { ...defaultState.quickChat, ...initialState.quickChat },
+    quickChat: mergeQuickChatState(initialState),
     sessionFailureNotification:
       initialState.sessionFailureNotification ?? defaultState.sessionFailureNotification,
     bottomTerminal: { ...defaultState.bottomTerminal, ...initialState.bottomTerminal },
diff --git a/apps/web/lib/state/hydration/hydrator.test.ts b/apps/web/lib/state/hydration/hydrator.test.ts
index b57f868f09..8a563e2e4c 100644
--- a/apps/web/lib/state/hydration/hydrator.test.ts
+++ b/apps/web/lib/state/hydration/hydrator.test.ts
@@ -3,7 +3,7 @@ import { produce } from "immer";
 import type { Draft } from "immer";
 import { hydrateState, hydrateUI } from "./hydrator";
 import { defaultUIState } from "@/lib/state/slices/ui/ui-slice";
-import { defaultState } from "@/lib/state/default-state";
+import { defaultState, mergeInitialState } from "@/lib/state/default-state";
 import type { AppState } from "@/lib/state/store";
 
 function makeDraft(): AppState {
@@ -75,6 +75,56 @@ describe("hydrateUI — quick chat name overlay", () => {
 
     expect(result.quickChat.sessions.map((s) => s.name)).toEqual(["Renamed A", "Original B"]);
   });
+
+  it("clears stale quick chat sessions when the backend returns none", () => {
+    const result = produce(makeDraft(), (draft: Draft<AppState>) => {
+      draft.quickChat = {
+        isOpen: true,
+        activeSessionId: "stale-session",
+        sessions: [{ sessionId: "stale-session", workspaceId: "ws-1", name: "Stale" }],
+      };
+      hydrateUI(draft, {
+        quickChat: {
+          isOpen: false,
+          activeSessionId: null,
+          sessions: [],
+        },
+      });
+    });
+
+    expect(result.quickChat.sessions).toEqual([]);
+    expect(result.quickChat.isOpen).toBe(false);
+    expect(result.quickChat.activeSessionId).toBeNull();
+  });
+});
+
+describe("mergeInitialState — quick chat name overlay", () => {
+  beforeEach(() => {
+    window.localStorage.clear();
+  });
+
+  it("overlays locally-renamed names during boot payload merge", () => {
+    window.localStorage.setItem(
+      "kandev.quickChat.names",
+      JSON.stringify({ "sess-boot": "Local boot name" }),
+    );
+
+    const result = mergeInitialState({
+      quickChat: {
+        isOpen: false,
+        activeSessionId: null,
+        sessions: [
+          { sessionId: "sess-boot", workspaceId: "ws-1", name: "Backend task title" },
+          { sessionId: "sess-other", workspaceId: "ws-1", name: "Other title" },
+        ],
+      },
+    });
+
+    expect(result.quickChat.sessions.map((s) => s.name)).toEqual([
+      "Local boot name",
+      "Other title",
+    ]);
+  });
 });
 
 describe("hydrateState — sidebar views from user settings", () => {
diff --git a/docs/plans/quick-chat-expiration/plan.md b/docs/plans/quick-chat-expiration/plan.md
new file mode 100644
index 0000000000..da6a6dc709
--- /dev/null
+++ b/docs/plans/quick-chat-expiration/plan.md
@@ -0,0 +1,195 @@
+---
+spec: docs/specs/tasks/quick-chat-expiration.md
+created: 2026-07-03
+status: implemented
+---
+
+# Implementation Plan: Quick Chat Persistence & Expiration
+
+## Overview
+
+Restore quick-chat tabs from backend state during SPA boot, then add a backend-owned idle sweeper that deletes only true quick-chat tasks after 7 days of inactivity. The repository owns candidate selection because the filter depends on task metadata, task origin, workflow absence, active session state, and last activity across task/session timestamps. The service layer owns deletion so expiration reuses `Service.DeleteTask` and preserves existing cleanup and `task.deleted` behavior.
+
+---
+
+## Backend
+
+### Quick-chat candidate query
+
+Files:
+
+- `apps/backend/internal/task/repository/interface.go`
+- `apps/backend/internal/task/repository/sqlite/task.go`
+- `apps/backend/internal/task/repository/task_repository_test.go`
+- `apps/backend/internal/db/dialect/time.go` and `dialect_test.go` if a small `GreatestTimestamp` helper is needed
+
+Add a task repository method:
+
+```go
+ListExpiredQuickChatTasks(ctx context.Context, cutoff time.Time) ([]*models.Task, error)
+```
+
+The SQLite query must return only rows where:
+
+- `t.is_ephemeral = 1`
+- `COALESCE(t.workflow_id, '') = ''`
+- `COALESCE(t.origin, '') != models.TaskOriginAutomationRun`
+- `excludeConfigModePredicate(driver, "t.metadata")`
+- `t.archived_at IS NULL`
+- no session for the task has state in `('CREATED', 'STARTING', 'RUNNING', 'WAITING_FOR_INPUT')`
+- dialect-aware `last_activity = max/greatest(t.updated_at, COALESCE(MAX(ts.updated_at), t.updated_at)) < cutoff`
+
+Order by computed last activity ascending for deterministic deletion and tests.
+
+### Expiration service
+
+Files:
+
+- New `apps/backend/internal/task/service/quick_chat_expiration.go`
+- `apps/backend/internal/task/service/service_test.go`
+- `apps/backend/internal/backendapp/main.go`
+
+Add constants:
+
+```go
+const quickChatIdleRetention = 7 * 24 * time.Hour
+const quickChatExpirationInterval = 24 * time.Hour
+```
+
+Add service methods:
+
+```go
+func (s *Service) StartQuickChatExpirationLoop(ctx context.Context)
+func (s *Service) runQuickChatExpiration(ctx context.Context, now time.Time)
+```
+
+`runQuickChatExpiration` computes `cutoff := now.Add(-quickChatIdleRetention)`, calls `ListExpiredQuickChatTasks`, logs and returns without deleting on list errors, then iterates candidates and calls `s.DeleteTask(ctx, task.ID)`. A delete failure logs the task ID/error and continues with the rest.
+
+Wire `services.Task.StartQuickChatExpirationLoop(ctx)` next to `StartAutoArchiveLoop(ctx)` in `apps/backend/internal/backendapp/main.go`.
+
+### Boot-state quick-chat hydration
+
+Files:
+
+- `apps/backend/internal/backendapp/boot_state.go`
+- `apps/backend/internal/backendapp/boot_state_routes.go`
+- `apps/backend/internal/backendapp/helpers_test.go`
+- `apps/web/lib/api/domains/workspace-api.ts`
+- `apps/web/app/page.tsx`
+- `apps/web/lib/state/hydration/hydrator.test.ts`
+
+Add a boot-state helper that populates:
+
+```json
+"quickChat": {
+  "isOpen": false,
+  "sessions": [
+    {
+      "sessionId": "...",
+      "workspaceId": "...",
+      "name": "...",
+      "agentProfileId": "..."
+    }
+  ],
+  "activeSessionId": null
+}
+```
+
+The helper should:
+
+- resolve the active workspace from already-built boot state when possible, otherwise from query/cookie/user settings/first workspace using existing helpers;
+- fetch all pages of `ListTasksByWorkspace(ctx, workspaceID, "", "", "", page, pageSize, false, false, true, true)` so there is no count cap;
+- filter in Go to `workflow_id == ""`, `origin != automation_run`, and `primary_session_id != nil`;
+- use `BatchGetSessionsForTasks` and `GetPrimarySessionInfoForTasks` through `taskDTOsWithSessionInfo` or a small shared helper rather than adding a new endpoint;
+- compute last activity as `max(task.UpdatedAt, max(session.UpdatedAt))` and sort restored tabs newest first;
+- derive `agentProfileId` from `task.Metadata[models.MetaKeyAgentProfileID]`;
+- preserve local display-name overrides through the existing frontend `hydrateUI` quick-chat name overlay.
+
+Call this helper from SPA boot-state assembly so quick chats restore on `/`, `/tasks`, task-detail, local context routes (`/github`, `/gitlab`, `/jira`, `/linear`, `/stats`), `/office`, and settings routes when an active workspace can be resolved.
+
+Update the legacy `listQuickChatSessions` response typing and `app/page.tsx` mapping to include `origin`, `updated_at`, and the same automation-run filtering so stale Next-compatible code stays type-correct.
+
+---
+
+## Frontend
+
+No new visible controls are required. The frontend behavior change is boot-time state hydration: `QuickChatProvider` already mounts globally, and `hydrateUI` already overlays local quick-chat names from `localStorage`.
+
+State and tests:
+
+- Keep `QuickChatState` in `apps/web/lib/state/slices/ui/types.ts` unchanged unless the boot payload needs an explicit helper type.
+- Extend `apps/web/lib/state/hydration/hydrator.test.ts` if needed to assert that hydrated sessions replace the in-memory list, preserve local names, and clear the modal when the backend returns no sessions.
+- Add or update `apps/web/src/boot-payload.test.ts` only if TypeScript parsing/shape guards need to understand a narrower quick-chat payload.
+
+---
+
+## Tests
+
+- **What:** repository expiration query includes quick chats idle longer than cutoff.
+  **File:** `apps/backend/internal/task/repository/task_repository_test.go`
+  **How:** SQLite integration test with backdated `tasks.updated_at` and `task_sessions.updated_at`.
+
+- **What:** any new timestamp SQL dialect helper emits SQLite and Postgres fragments correctly.
+  **File:** `apps/backend/internal/db/dialect/dialect_test.go`
+  **How:** unit test for the helper only if Task 01 adds one.
+
+- **What:** repository query excludes active sessions, config-mode chats, automation-run ephemeral tasks, non-ephemeral tasks, archived tasks, and ephemeral tasks with a workflow.
+  **File:** `apps/backend/internal/task/repository/task_repository_test.go`
+  **How:** table-driven SQLite test seeding each row variant.
+
+- **What:** session activity keeps an old quick-chat task alive.
+  **File:** `apps/backend/internal/task/repository/task_repository_test.go`
+  **How:** set `tasks.updated_at` older than 7 days and primary `task_sessions.updated_at` newer than cutoff; assert no candidate.
+
+- **What:** expiration uses the service delete path, publishes `task.deleted`, and cleans quick-chat directories through existing async cleanup.
+  **File:** `apps/backend/internal/task/service/service_test.go`
+  **How:** service test with real SQLite repo, `SetQuickChatDir`, `cleanupDoneForTest`, and event-bus assertions.
+
+- **What:** expiration fails closed on candidate-list error and continues when a single delete fails.
+  **File:** `apps/backend/internal/task/service/quick_chat_expiration_test.go` or `service_test.go`
+  **How:** use a small fake repository/service seam if the real repo cannot simulate the list/delete errors cleanly.
+
+- **What:** boot payload contains quick-chat sessions ordered by last activity, excluding automation/config tasks.
+  **File:** `apps/backend/internal/backendapp/helpers_test.go`
+  **How:** use `newBootStateTestHarness`, create multiple ephemeral tasks/sessions, backdate rows with SQL, call `bootPayload`, and unmarshal `initialState.quickChat.sessions`.
+
+- **What:** frontend hydration overlays local quick-chat names onto backend-restored sessions.
+  **File:** `apps/web/lib/state/hydration/hydrator.test.ts`
+  **How:** existing jsdom localStorage tests extended for multiple restored sessions.
+
+---
+
+## E2E Tests
+
+- **Scenario:** GIVEN an open quick chat with a message, WHEN the user reloads the page, THEN the quick-chat tab restores and prior history is visible.
+  **File:** `apps/web/e2e/tests/chat/quick-chat.spec.ts`
+  **What to verify:** create a quick chat with `openQuickChatWithAgent`, send a mock-agent message, reload, reopen quick chat with the shortcut, assert the same response text appears without selecting a new agent.
+
+- **Scenario:** GIVEN multiple quick-chat tabs, WHEN the user reloads, THEN all tabs restore.
+  **File:** `apps/web/e2e/tests/chat/quick-chat.spec.ts`
+  **What to verify:** extend the existing multi-tab test or add a focused test that counts restored tab buttons after reload.
+
+Backend expiration is covered by Go integration tests rather than E2E because it has no new visible controls and depends on a 7-day idle clock.
+
+---
+
+## Implementation Waves
+
+Wave 1:
+
+- [x] [task-01-backend-candidate-query](task-01-backend-candidate-query.md)
+- [x] [task-03-boot-hydration](task-03-boot-hydration.md)
+
+Wave 2:
+
+- [x] [task-02-backend-expiration-service](task-02-backend-expiration-service.md)
+
+Wave 3:
+
+- [ ] [task-04-e2e-and-verification](task-04-e2e-and-verification.md)
+
+---
+
+## Open Questions
+
+- Confirm during implementation whether quick-chat messages update `tasks.updated_at`, `task_sessions.updated_at`, or only message/turn rows. The planned candidate query and hydration sort use `MAX(task.updated_at, session.updated_at)`, so the feature remains correct as long as at least one of those rows moves on activity.
diff --git a/docs/plans/quick-chat-expiration/task-01-backend-candidate-query.md b/docs/plans/quick-chat-expiration/task-01-backend-candidate-query.md
new file mode 100644
index 0000000000..c4311dd206
--- /dev/null
+++ b/docs/plans/quick-chat-expiration/task-01-backend-candidate-query.md
@@ -0,0 +1,42 @@
+---
+id: "01-backend-candidate-query"
+title: "Backend candidate query"
+status: done
+wave: 1
+depends_on: []
+plan: "plan.md"
+spec: "../../specs/tasks/quick-chat-expiration.md"
+---
+
+# Task 01: Backend Candidate Query
+
+## Acceptance
+
+- `repository.TaskRepository` exposes `ListExpiredQuickChatTasks(ctx, cutoff)` and SQLite implements it.
+- The query matches only true quick chats: ephemeral, no workflow, not archived, not config-mode, not automation-run origin, no active sessions.
+- Last activity uses the greater of `tasks.updated_at` and newest `task_sessions.updated_at`.
+
+## Verification
+
+- `cd apps/backend && go test ./internal/task/repository -run 'TestSQLiteRepository_ListExpiredQuickChatTasks'`
+
+## Files likely touched
+
+- `apps/backend/internal/task/repository/interface.go`
+- `apps/backend/internal/task/repository/sqlite/task.go`
+- `apps/backend/internal/task/repository/task_repository_test.go`
+- Optional `apps/backend/internal/db/dialect/time.go`
+- Optional `apps/backend/internal/db/dialect/dialect_test.go`
+
+## Dependencies
+
+None.
+
+## Inputs
+
+- Spec sections: Data model, API surface, Failure modes, Scenarios.
+- Existing patterns: `ListTasksForAutoArchive` in `apps/backend/internal/task/repository/sqlite/task.go`; `excludeConfigModePredicate` in the same file; active session state filters in `apps/backend/internal/task/repository/sqlite/session.go`; SQL portability helpers in `apps/backend/internal/db/dialect/`.
+
+## Output contract
+
+Update this task status to `done`, update the Wave 1 checkbox in `plan.md`, and report the files changed, tests run, and any discovered timestamp behavior.
diff --git a/docs/plans/quick-chat-expiration/task-02-backend-expiration-service.md b/docs/plans/quick-chat-expiration/task-02-backend-expiration-service.md
new file mode 100644
index 0000000000..066f549954
--- /dev/null
+++ b/docs/plans/quick-chat-expiration/task-02-backend-expiration-service.md
@@ -0,0 +1,42 @@
+---
+id: "02-backend-expiration-service"
+title: "Backend expiration service"
+status: done
+wave: 2
+depends_on: ["01-backend-candidate-query"]
+plan: "plan.md"
+spec: "../../specs/tasks/quick-chat-expiration.md"
+---
+
+# Task 02: Backend Expiration Service
+
+## Acceptance
+
+- The task service runs a daily quick-chat expiration loop with a hardcoded 7-day idle retention window.
+- Each expired candidate is deleted through `Service.DeleteTask`, preserving existing workspace directory cleanup and `task.deleted` publishing.
+- Candidate-list errors delete nothing; individual delete failures are logged and do not stop later candidates.
+
+## Verification
+
+- `cd apps/backend && go test ./internal/task/service -run 'TestService_QuickChatExpiration|TestService_DeleteTask'`
+- `cd apps/backend && go test ./internal/backendapp -run 'Test.*QuickChat'` if startup wiring gets focused coverage there.
+
+## Files likely touched
+
+- New `apps/backend/internal/task/service/quick_chat_expiration.go`
+- `apps/backend/internal/task/service/service_test.go`
+- Optional focused test file `apps/backend/internal/task/service/quick_chat_expiration_test.go`
+- `apps/backend/internal/backendapp/main.go`
+
+## Dependencies
+
+- Task 01 must land first so the service can call `ListExpiredQuickChatTasks`.
+
+## Inputs
+
+- Spec sections: What, State machine, Failure modes, Persistence guarantees.
+- Existing patterns: `StartAutoArchiveLoop` / `runAutoArchive` in `apps/backend/internal/task/service/auto_archive.go`; `DeleteTask` cleanup path in `apps/backend/internal/task/service/service_tasks.go`.
+
+## Output contract
+
+Update this task status to `done`, update the Wave 2 checkbox in `plan.md`, and report the files changed, tests run, and any cleanup/event behavior verified.
diff --git a/docs/plans/quick-chat-expiration/task-03-boot-hydration.md b/docs/plans/quick-chat-expiration/task-03-boot-hydration.md
new file mode 100644
index 0000000000..c3c9b79265
--- /dev/null
+++ b/docs/plans/quick-chat-expiration/task-03-boot-hydration.md
@@ -0,0 +1,46 @@
+---
+id: "03-boot-hydration"
+title: "Boot hydration"
+status: done
+wave: 1
+depends_on: []
+plan: "plan.md"
+spec: "../../specs/tasks/quick-chat-expiration.md"
+---
+
+# Task 03: Boot Hydration
+
+## Acceptance
+
+- SPA boot payload includes `initialState.quickChat.sessions` for the active workspace whenever an active workspace can be resolved.
+- Restored sessions exclude config-mode and automation-run ephemeral tasks, require a primary session, and are ordered by newest last activity first.
+- Frontend hydration keeps existing local quick-chat rename overlays and remains type-correct.
+
+## Verification
+
+- `cd apps/backend && go test ./internal/backendapp -run 'TestBoot.*QuickChat|TestBootPayload'`
+- `cd apps && pnpm --filter @kandev/web test -- --run lib/state/hydration/hydrator.test.ts src/boot-payload.test.ts`
+- `cd apps/web && pnpm run typecheck`
+
+## Files likely touched
+
+- `apps/backend/internal/backendapp/boot_state.go`
+- `apps/backend/internal/backendapp/boot_state_routes.go`
+- `apps/backend/internal/backendapp/helpers_test.go`
+- `apps/web/lib/api/domains/workspace-api.ts`
+- `apps/web/app/page.tsx`
+- `apps/web/lib/state/hydration/hydrator.test.ts`
+- Optional `apps/web/src/boot-payload.test.ts`
+
+## Dependencies
+
+None. This can proceed in parallel with Task 01 because it can use existing `ListTasksByWorkspace` plus session enrichment.
+
+## Inputs
+
+- Spec sections: API surface, Persistence guarantees, Scenarios.
+- Existing patterns: home/tasks boot-state helpers in `apps/backend/internal/backendapp/boot_state.go` and `boot_state_routes.go`; quick-chat local rename overlay in `apps/web/lib/state/hydration/hydrator.ts`.
+
+## Output contract
+
+Update this task status to `done`, update the Wave 1 checkbox in `plan.md`, and report the files changed, tests run, and any routes where quick-chat hydration intentionally no-ops.
diff --git a/docs/plans/quick-chat-expiration/task-04-e2e-and-verification.md b/docs/plans/quick-chat-expiration/task-04-e2e-and-verification.md
new file mode 100644
index 0000000000..4c83af4879
--- /dev/null
+++ b/docs/plans/quick-chat-expiration/task-04-e2e-and-verification.md
@@ -0,0 +1,43 @@
+---
+id: "04-e2e-and-verification"
+title: "E2E and verification"
+status: pending
+wave: 3
+depends_on: ["02-backend-expiration-service", "03-boot-hydration"]
+plan: "plan.md"
+spec: "../../specs/tasks/quick-chat-expiration.md"
+---
+
+# Task 04: E2E and Verification
+
+## Acceptance
+
+- Quick-chat E2E coverage proves a reload restores at least one existing quick-chat tab with prior history.
+- Multi-tab reload behavior is covered without adding a count cap.
+- Final verification runs targeted backend/frontend tests plus format/typecheck/lint commands appropriate for changed files.
+
+## Verification
+
+- `cd apps/web && pnpm e2e -- tests/chat/quick-chat.spec.ts`
+- `make -C apps/backend test`
+- `cd apps/web && pnpm run typecheck`
+- `cd apps && pnpm --filter @kandev/web lint`
+
+## Files likely touched
+
+- `apps/web/e2e/tests/chat/quick-chat.spec.ts`
+- Test helpers only if the reload flow needs a reusable selector/helper.
+
+## Dependencies
+
+- Task 02 for backend expiration coverage.
+- Task 03 for reload hydration behavior.
+
+## Inputs
+
+- Spec scenarios for reload restoration and 12-tab/no-cap behavior.
+- Existing quick-chat E2E helpers in `apps/web/e2e/tests/chat/quick-chat.spec.ts`.
+
+## Output contract
+
+Update this task status to `done`, update the Wave 3 checkbox in `plan.md`, and report tests run, any skipped checks, and residual risks.
diff --git a/docs/specs/INDEX.md b/docs/specs/INDEX.md
index 5bd7e90755..8410e9467c 100644
--- a/docs/specs/INDEX.md
+++ b/docs/specs/INDEX.md
@@ -49,6 +49,7 @@ Kandev's task model: documents, execution stages, labels, blocker escalation, su
 | [runtime-cleanup](tasks/runtime-cleanup.md) | draft |
 | [link-existing-task-github-issue](tasks/link-existing-task-github-issue.md) | building |
 | [multi-branch](tasks/multi-branch/spec.md) | shipped |
+| [quick-chat-expiration](tasks/quick-chat-expiration.md) | draft |
 
 ## agents/ — agent governance
 
diff --git a/docs/specs/tasks/quick-chat-expiration.md b/docs/specs/tasks/quick-chat-expiration.md
new file mode 100644
index 0000000000..d620eac80d
--- /dev/null
+++ b/docs/specs/tasks/quick-chat-expiration.md
@@ -0,0 +1,168 @@
+---
+status: draft
+created: 2026-07-02
+owner: José Almeida
+---
+
+# Quick Chat Persistence & Expiration
+
+## Why
+A user reported her quick chats "disappearing much faster." Quick chats are
+ephemeral tasks whose open-tab list lives only in the in-memory frontend store,
+so a page reload drops every tab even though the underlying task, session, and
+workspace directory still exist on the backend. Those now-unreachable rows and
+directories never get cleaned up, so they leak indefinitely. Users want their
+recent quick chats to survive a reload, and the system needs a bound so
+abandoned quick chats don't accumulate forever.
+
+## What
+- Open quick-chat tabs SHALL be restored after a full page reload, reconstructed
+  from backend state rather than client-only memory.
+- A quick chat that has been idle longer than the retention window SHALL be
+  deleted automatically (task row, its sessions, and its workspace directory),
+  the same as an explicit close.
+- The default retention window is **7 days** of inactivity, applied per quick
+  chat based on its last activity. The window is a hardcoded constant; it is not
+  user-configurable in this iteration.
+- Expiration SHALL reuse the existing quick-chat delete path so that workspace
+  directory cleanup and task-lifecycle events fire exactly as they do for a
+  user-initiated close.
+- Only quick chats expire. Config-mode chats, automation-run ephemeral tasks,
+  and non-ephemeral kanban/office tasks are untouched.
+- A quick chat that is actively in use (recent message or running session)
+  SHALL NOT expire, regardless of how old it is.
+
+## Data model
+No new tables. This feature operates on existing `tasks` and `task_sessions`
+rows. A **quick chat** is precisely the set of tasks matching:
+
+```
+tasks
+  is_ephemeral = 1
+  workflow_id  = ''                      -- ephemeral tasks carry no workflow
+  origin      != 'automation_run'        -- excludes run-mode ephemeral tasks
+  metadata.config_mode IS NOT 1          -- excludes config-mode settings chats
+  archived_at  IS NULL
+```
+
+This mirrors the existing list filters: `onlyEphemeral = true` plus the
+`excludeConfigModePredicate` (`json_extract(metadata,'$.config_mode') IS NOT 1`,
+`internal/task/repository/sqlite/task.go:62`) plus an `origin != 'automation_run'`
+guard. The `origin` guard distinguishes user-started quick chats (`origin =
+'manual'`) from automation run-mode ephemeral tasks.
+
+**Last-activity timestamp** for a quick chat is defined as:
+
+```
+last_activity = MAX(task.updated_at, MAX(session.updated_at) over its task_sessions)
+```
+
+Using the greater of the task row and its newest session row makes the metric
+robust to whichever row a message/turn bumps. A quick chat expires when
+`now - last_activity > 7 days`.
+
+## API surface
+- **Hydration (read):** reuse the existing workspace task listing rather than a
+  new endpoint. The frontend fetches quick chats via
+  `ListTasksByWorkspace(workspaceId, workflowID="", …, onlyEphemeral=true,
+  excludeConfig=true)` and filters out `origin == "automation_run"`, then
+  rebuilds the `quickChat.sessions` store slice (one tab per returned task, in
+  most-recently-active-first order). Each restored tab needs
+  `{ sessionId, workspaceId, agentProfileId }`, all resolvable from the task and
+  its primary session. The persisted display name is already available via
+  `getStoredQuickChatName` / `setStoredQuickChatName`.
+- **Deletion (expiration):** no new external contract. Expiration runs as a
+  backend background sweep that calls the existing `Service.DeleteTask` path
+  (which invokes `cleanupQuickChatDirs`, `internal/task/service/service_tasks.go:1402`,
+  and publishes `task.deleted`). Deleted quick chats propagate to any connected
+  client through the existing `task.deleted` WS handler.
+
+## State machine
+A quick chat task is created `active`, and reaches a terminal `deleted` state via
+one of these triggers (this feature adds only the last one):
+
+| Trigger | Actor | Existing? |
+|---|---|---|
+| User closes a tab (confirm) | user | yes (`use-quick-chat-modal.ts` `handleConfirmClose`) |
+| Rapid re-pick supersedes an in-flight start | frontend | yes (`useAgentSelection` orphan cleanup) |
+| Agent profile deleted | user | yes (`DeleteEphemeralTasksByAgentProfile`) |
+| **Idle longer than retention window** | **background sweep** | **new** |
+
+All four converge on `Service.DeleteTask`, so directory cleanup and event
+publishing are identical.
+
+## Failure modes
+- **Last-activity query fails / returns error:** the sweep fails closed — it
+  deletes nothing that pass and logs a warning. A transient DB error must never
+  cause an over-broad delete.
+- **A single quick chat delete fails** (dir busy, session stop error): the sweep
+  logs the failure, leaves that task in place, and continues with the rest. One
+  bad row does not abort the batch. The next sweep retries it.
+- **Hydration list query fails on boot:** quick chat tabs render empty (current
+  behavior); the app is otherwise unaffected. No error toast is required — this
+  degrades to today's behavior.
+- **A hydrated tab's backend session is already stopped/gone** (e.g. backend was
+  restarted between reloads): the tab still restores and shows its history;
+  sending a new message follows the normal resume/relaunch path. A tab whose
+  task no longer exists is simply not returned by the list and thus not shown.
+- **Clock skew / non-monotonic time:** expiration compares stored timestamps to
+  `now`; it does not assume monotonic wall clock beyond the 7-day granularity.
+
+## Persistence guarantees
+- **Survives reload:** open quick-chat tabs (restored from backend), quick-chat
+  task rows, sessions, and workspace directories — until they expire or are
+  closed.
+- **Survives backend restart:** quick-chat task rows and directories (subject to
+  the same 7-day idle expiration). Tab restoration on the client depends only on
+  the backend list, so it works across a backend restart as long as the task row
+  still exists.
+- **Does NOT survive:** a quick chat idle > 7 days (deleted on the next sweep).
+  The in-memory `quickChat.sessions` slice remains client-only and is rebuilt
+  from the backend on each load rather than persisted to `localStorage`.
+- **Retention window:** 7 days of inactivity, hardcoded. Sweep cadence is an
+  implementation detail (piggy-backing on an existing periodic job is
+  acceptable) but SHALL run at least daily so expiry is observed within roughly
+  a day of the window elapsing.
+
+## Scenarios
+- **GIVEN** an open quick chat with one or more tabs, **WHEN** the user reloads
+  the page, **THEN** the same tabs reappear, ordered most-recently-active first,
+  each showing its prior chat history and persisted name.
+- **GIVEN** a quick-chat task whose `last_activity` is 8 days ago, **WHEN** the
+  expiration sweep runs, **THEN** the task, its sessions, and its workspace
+  directory are deleted, a `task.deleted` event is published, and the tab
+  disappears from any connected client.
+- **GIVEN** a quick-chat task with a message sent 10 minutes ago (older than 7
+  days since creation but recently active), **WHEN** the sweep runs, **THEN** the
+  task is retained.
+- **GIVEN** a config-mode chat (`metadata.config_mode = 1`) idle for 30 days,
+  **WHEN** the sweep runs, **THEN** it is NOT deleted.
+- **GIVEN** an automation-run ephemeral task (`origin = 'automation_run'`) idle
+  for 30 days, **WHEN** the sweep runs, **THEN** it is NOT deleted.
+- **GIVEN** a non-ephemeral kanban task idle for a year, **WHEN** the sweep runs,
+  **THEN** it is NOT deleted.
+- **GIVEN** the last-activity query errors, **WHEN** the sweep runs, **THEN** no
+  quick chats are deleted and a warning is logged.
+- **GIVEN** two idle quick chats where deleting the first fails, **WHEN** the
+  sweep runs, **THEN** the second is still evaluated and deleted, and the failure
+  on the first is logged.
+- **GIVEN** the workspace has 12 quick chats within the retention window, **WHEN**
+  the user reloads, **THEN** all 12 tabs restore (no count cap in this
+  iteration).
+
+## Out of scope
+- A user-configurable retention window (per-workspace or global setting). Ships
+  as a hardcoded 7-day constant; revisit only if requested.
+- A hard count cap on number of quick chats (idle TTL only). If clutter becomes
+  a problem, a cap is a follow-up.
+- Persisting quick-chat tabs to `localStorage`. Backend is the source of truth;
+  no client-side durable store.
+- Archiving/soft-deleting expired quick chats — they are hard-deleted, matching
+  the existing close behavior.
+- Changing config-mode chat, automation-run, or kanban/office task lifecycles.
+
+## Open questions
+- Does a message/turn in a quick chat currently bump `tasks.updated_at`, or only
+  `task_sessions.updated_at` / turn rows? The `MAX(task, session)` definition is
+  chosen to be correct either way, but the implementation should confirm which
+  row actually moves so the sweep query reads the right column(s).