feat: add plan mode with restricted tool boundary (#24236)

> This PR was authored by Mux on behalf of Mike.

## Summary
- add persistent plan mode for chats and the chat-specific plan file
flow
- add structured planning tools such as `ask_user_question` and
`propose_plan`
- keep `write_file` and `edit_files` constrained to the chat-specific
plan file during plan turns
- allow shell exploration in plan mode, including subagents, via
`execute` and `process_output`
- block implementation-oriented, provider-native, MCP, dynamic, and
computer-use tools during plan turns
- update the chat UI, tests, and docs for the new planning flow

coderd/database/db2sdk/db2sdk.go

@@ -1601,6 +1601,9 @@ func Chat(c database.Chat, diffStatus *database.ChatDiffStatus, files []database
 	if c.LastError.Valid {
 		chat.LastError = &c.LastError.String
 	}
+	if c.PlanMode.Valid {
+		chat.PlanMode = codersdk.ChatPlanMode(c.PlanMode.ChatPlanMode)
+	}
 	if c.ParentChatID.Valid {
 		parentChatID := c.ParentChatID.UUID
 		chat.ParentChatID = &parentChatID

coderd/database/db2sdk/db2sdk_test.go

@@ -817,6 +817,7 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 		UpdatedAt:         now,
 		Archived:          true,
 		PinOrder:          1,
+		PlanMode:          database.NullChatPlanMode{ChatPlanMode: database.ChatPlanModePlan, Valid: true},
 		MCPServerIDs:      []uuid.UUID{uuid.New()},
 		Labels:            database.StringMap{"env": "prod"},
 		LastInjectedContext: pqtype.NullRawMessage{

coderd/database/dbauthz/dbauthz.go

@@ -2798,6 +2798,13 @@ func (q *querier) GetChatModelConfigsForTelemetry(ctx context.Context) ([]databa
 	return q.db.GetChatModelConfigsForTelemetry(ctx)
 }
 
+func (q *querier) GetChatPlanModeInstructions(ctx context.Context) (string, error) {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
+		return "", err
+	}
+	return q.db.GetChatPlanModeInstructions(ctx)
+}
+
 func (q *querier) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceDeploymentConfig); err != nil {
 		return database.ChatProvider{}, err
@@ -6090,6 +6097,17 @@ func (q *querier) UpdateChatPinOrder(ctx context.Context, arg database.UpdateCha
 	return q.db.UpdateChatPinOrder(ctx, arg)
 }
 
+func (q *querier) UpdateChatPlanModeByID(ctx context.Context, arg database.UpdateChatPlanModeByIDParams) (database.Chat, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ID)
+	if err != nil {
+		return database.Chat{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return database.Chat{}, err
+	}
+	return q.db.UpdateChatPlanModeByID(ctx, arg)
+}
+
 func (q *querier) UpdateChatProvider(ctx context.Context, arg database.UpdateChatProviderParams) (database.ChatProvider, error) {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return database.ChatProvider{}, err
@@ -7267,6 +7285,13 @@ func (q *querier) UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, incl
 	return q.db.UpsertChatIncludeDefaultSystemPrompt(ctx, includeDefaultSystemPrompt)
 }
 
+func (q *querier) UpsertChatPlanModeInstructions(ctx context.Context, value string) error {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
+		return err
+	}
+	return q.db.UpsertChatPlanModeInstructions(ctx, value)
+}
+
 func (q *querier) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err

coderd/database/dbauthz/dbauthz_test.go

@@ -834,6 +834,10 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().GetChatDesktopEnabled(gomock.Any()).Return(false, nil).AnyTimes()
 		check.Args().Asserts()
 	}))
+	s.Run("GetChatPlanModeInstructions", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().GetChatPlanModeInstructions(gomock.Any()).Return("", nil).AnyTimes()
+		check.Args().Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)
+	}))
 	s.Run("GetChatTemplateAllowlist", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		dbm.EXPECT().GetChatTemplateAllowlist(gomock.Any()).Return("", nil).AnyTimes()
 		check.Args().Asserts(rbac.ResourceDeploymentConfig, policy.ActionRead)
@@ -949,6 +953,16 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UpdateChatLastModelConfigByID(gomock.Any(), arg).Return(chat, nil).AnyTimes()
 		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(chat)
 	}))
+	s.Run("UpdateChatPlanModeByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.UpdateChatPlanModeByIDParams{
+			ID:       chat.ID,
+			PlanMode: database.NullChatPlanMode{ChatPlanMode: database.ChatPlanModePlan, Valid: true},
+		}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatPlanModeByID(gomock.Any(), arg).Return(chat, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(chat)
+	}))
 	s.Run("UpdateChatStatusPreserveUpdatedAt", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		arg := database.UpdateChatStatusPreserveUpdatedAtParams{
@@ -1115,6 +1129,10 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UpsertChatDesktopEnabled(gomock.Any(), false).Return(nil).AnyTimes()
 		check.Args(false).Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)
 	}))
+	s.Run("UpsertChatPlanModeInstructions", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().UpsertChatPlanModeInstructions(gomock.Any(), "").Return(nil).AnyTimes()
+		check.Args("").Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)
+	}))
 	s.Run("UpsertChatTemplateAllowlist", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		dbm.EXPECT().UpsertChatTemplateAllowlist(gomock.Any(), "").Return(nil).AnyTimes()
 		check.Args("").Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)

coderd/database/dbmetrics/querymetrics.go

@@ -1312,6 +1312,14 @@ func (m queryMetricsStore) GetChatModelConfigsForTelemetry(ctx context.Context)
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatPlanModeInstructions(ctx context.Context) (string, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatPlanModeInstructions(ctx)
+	m.queryLatencies.WithLabelValues("GetChatPlanModeInstructions").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatPlanModeInstructions").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatProviderByID(ctx, id)
@@ -4376,6 +4384,14 @@ func (m queryMetricsStore) UpdateChatPinOrder(ctx context.Context, arg database.
 	return r0
 }
 
+func (m queryMetricsStore) UpdateChatPlanModeByID(ctx context.Context, arg database.UpdateChatPlanModeByIDParams) (database.Chat, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatPlanModeByID(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatPlanModeByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatPlanModeByID").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpdateChatProvider(ctx context.Context, arg database.UpdateChatProviderParams) (database.ChatProvider, error) {
 	start := time.Now()
 	r0, r1 := m.s.UpdateChatProvider(ctx, arg)
@@ -5184,6 +5200,14 @@ func (m queryMetricsStore) UpsertChatIncludeDefaultSystemPrompt(ctx context.Cont
 	return r0
 }
 
+func (m queryMetricsStore) UpsertChatPlanModeInstructions(ctx context.Context, value string) error {
+	start := time.Now()
+	r0 := m.s.UpsertChatPlanModeInstructions(ctx, value)
+	m.queryLatencies.WithLabelValues("UpsertChatPlanModeInstructions").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertChatPlanModeInstructions").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
 	start := time.Now()
 	r0 := m.s.UpsertChatRetentionDays(ctx, retentionDays)

coderd/database/dbmock/dbmock.go

@@ -2417,6 +2417,21 @@ func (mr *MockStoreMockRecorder) GetChatModelConfigsForTelemetry(ctx any) *gomoc
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatModelConfigsForTelemetry", reflect.TypeOf((*MockStore)(nil).GetChatModelConfigsForTelemetry), ctx)
 }
 
+// GetChatPlanModeInstructions mocks base method.
+func (m *MockStore) GetChatPlanModeInstructions(ctx context.Context) (string, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatPlanModeInstructions", ctx)
+	ret0, _ := ret[0].(string)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatPlanModeInstructions indicates an expected call of GetChatPlanModeInstructions.
+func (mr *MockStoreMockRecorder) GetChatPlanModeInstructions(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatPlanModeInstructions", reflect.TypeOf((*MockStore)(nil).GetChatPlanModeInstructions), ctx)
+}
+
 // GetChatProviderByID mocks base method.
 func (m *MockStore) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	m.ctrl.T.Helper()
@@ -8282,6 +8297,21 @@ func (mr *MockStoreMockRecorder) UpdateChatPinOrder(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatPinOrder", reflect.TypeOf((*MockStore)(nil).UpdateChatPinOrder), ctx, arg)
 }
 
+// UpdateChatPlanModeByID mocks base method.
+func (m *MockStore) UpdateChatPlanModeByID(ctx context.Context, arg database.UpdateChatPlanModeByIDParams) (database.Chat, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatPlanModeByID", ctx, arg)
+	ret0, _ := ret[0].(database.Chat)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatPlanModeByID indicates an expected call of UpdateChatPlanModeByID.
+func (mr *MockStoreMockRecorder) UpdateChatPlanModeByID(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatPlanModeByID", reflect.TypeOf((*MockStore)(nil).UpdateChatPlanModeByID), ctx, arg)
+}
+
 // UpdateChatProvider mocks base method.
 func (m *MockStore) UpdateChatProvider(ctx context.Context, arg database.UpdateChatProviderParams) (database.ChatProvider, error) {
 	m.ctrl.T.Helper()
@@ -9741,6 +9771,20 @@ func (mr *MockStoreMockRecorder) UpsertChatIncludeDefaultSystemPrompt(ctx, inclu
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatIncludeDefaultSystemPrompt", reflect.TypeOf((*MockStore)(nil).UpsertChatIncludeDefaultSystemPrompt), ctx, includeDefaultSystemPrompt)
 }
 
+// UpsertChatPlanModeInstructions mocks base method.
+func (m *MockStore) UpsertChatPlanModeInstructions(ctx context.Context, value string) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpsertChatPlanModeInstructions", ctx, value)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpsertChatPlanModeInstructions indicates an expected call of UpsertChatPlanModeInstructions.
+func (mr *MockStoreMockRecorder) UpsertChatPlanModeInstructions(ctx, value any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatPlanModeInstructions", reflect.TypeOf((*MockStore)(nil).UpsertChatPlanModeInstructions), ctx, value)
+}
+
 // UpsertChatRetentionDays mocks base method.
 func (m *MockStore) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
 	m.ctrl.T.Helper()

coderd/database/dump.sql

@@ -287,6 +287,10 @@ CREATE TYPE chat_mode AS ENUM (
     'computer_use'
 );
 
+CREATE TYPE chat_plan_mode AS ENUM (
+    'plan'
+);
+
 CREATE TYPE chat_status AS ENUM (
     'waiting',
     'pending',
@@ -1470,7 +1474,8 @@ CREATE TABLE chats (
     last_read_message_id bigint,
     last_injected_context jsonb,
     dynamic_tools jsonb,
-    organization_id uuid NOT NULL
+    organization_id uuid NOT NULL,
+    plan_mode chat_plan_mode
 );
 
 CREATE TABLE connection_logs (

coderd/database/migrations/000469_chat_turn_mode.down.sql

@@ -0,0 +1,2 @@
+ALTER TABLE chats DROP COLUMN plan_mode;
+DROP TYPE chat_plan_mode;

coderd/database/migrations/000469_chat_turn_mode.up.sql

@@ -0,0 +1,2 @@
+CREATE TYPE chat_plan_mode AS ENUM ('plan');
+ALTER TABLE chats ADD COLUMN plan_mode chat_plan_mode;

coderd/database/modelqueries.go

@@ -800,6 +800,7 @@ func (q *sqlQuerier) GetAuthorizedChats(ctx context.Context, arg GetChatsParams,
 			&i.Chat.LastInjectedContext,
 			&i.Chat.DynamicTools,
 			&i.Chat.OrganizationID,
+			&i.Chat.PlanMode,
 			&i.HasUnread); err != nil {
 			return nil, err
 		}

coderd/database/models.go

@@ -1287,6 +1287,61 @@ func AllChatModeValues() []ChatMode {
 	}
 }
 
+type ChatPlanMode string
+
+const (
+	ChatPlanModePlan ChatPlanMode = "plan"
+)
+
+func (e *ChatPlanMode) Scan(src interface{}) error {
+	switch s := src.(type) {
+	case []byte:
+		*e = ChatPlanMode(s)
+	case string:
+		*e = ChatPlanMode(s)
+	default:
+		return fmt.Errorf("unsupported scan type for ChatPlanMode: %T", src)
+	}
+	return nil
+}
+
+type NullChatPlanMode struct {
+	ChatPlanMode ChatPlanMode `json:"chat_plan_mode"`
+	Valid        bool         `json:"valid"` // Valid is true if ChatPlanMode is not NULL
+}
+
+// Scan implements the Scanner interface.
+func (ns *NullChatPlanMode) Scan(value interface{}) error {
+	if value == nil {
+		ns.ChatPlanMode, ns.Valid = "", false
+		return nil
+	}
+	ns.Valid = true
+	return ns.ChatPlanMode.Scan(value)
+}
+
+// Value implements the driver Valuer interface.
+func (ns NullChatPlanMode) Value() (driver.Value, error) {
+	if !ns.Valid {
+		return nil, nil
+	}
+	return string(ns.ChatPlanMode), nil
+}
+
+func (e ChatPlanMode) Valid() bool {
+	switch e {
+	case ChatPlanModePlan:
+		return true
+	}
+	return false
+}
+
+func AllChatPlanModeValues() []ChatPlanMode {
+	return []ChatPlanMode{
+		ChatPlanModePlan,
+	}
+}
+
 type ChatStatus string
 
 const (
@@ -4247,6 +4302,7 @@ type Chat struct {
 	LastInjectedContext pqtype.NullRawMessage `db:"last_injected_context" json:"last_injected_context"`
 	DynamicTools        pqtype.NullRawMessage `db:"dynamic_tools" json:"dynamic_tools"`
 	OrganizationID      uuid.UUID             `db:"organization_id" json:"organization_id"`
+	PlanMode            NullChatPlanMode      `db:"plan_mode" json:"plan_mode"`
 }
 
 type ChatDebugRun struct {

coderd/database/querier.go

@@ -306,6 +306,7 @@ type sqlcQuerier interface {
 	GetChatModelConfigs(ctx context.Context) ([]ChatModelConfig, error)
 	// Returns all model configurations for telemetry snapshot collection.
 	GetChatModelConfigsForTelemetry(ctx context.Context) ([]GetChatModelConfigsForTelemetryRow, error)
+	GetChatPlanModeInstructions(ctx context.Context) (string, error)
 	GetChatProviderByID(ctx context.Context, id uuid.UUID) (ChatProvider, error)
 	GetChatProviderByProvider(ctx context.Context, provider string) (ChatProvider, error)
 	GetChatProviders(ctx context.Context) ([]ChatProvider, error)
@@ -982,6 +983,7 @@ type sqlcQuerier interface {
 	UpdateChatMessageByID(ctx context.Context, arg UpdateChatMessageByIDParams) (ChatMessage, error)
 	UpdateChatModelConfig(ctx context.Context, arg UpdateChatModelConfigParams) (ChatModelConfig, error)
 	UpdateChatPinOrder(ctx context.Context, arg UpdateChatPinOrderParams) error
+	UpdateChatPlanModeByID(ctx context.Context, arg UpdateChatPlanModeByIDParams) (Chat, error)
 	UpdateChatProvider(ctx context.Context, arg UpdateChatProviderParams) (ChatProvider, error)
 	UpdateChatStatus(ctx context.Context, arg UpdateChatStatusParams) (Chat, error)
 	UpdateChatStatusPreserveUpdatedAt(ctx context.Context, arg UpdateChatStatusPreserveUpdatedAtParams) (Chat, error)
@@ -1098,6 +1100,7 @@ type sqlcQuerier interface {
 	UpsertChatDiffStatus(ctx context.Context, arg UpsertChatDiffStatusParams) (ChatDiffStatus, error)
 	UpsertChatDiffStatusReference(ctx context.Context, arg UpsertChatDiffStatusReferenceParams) (ChatDiffStatus, error)
 	UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, includeDefaultSystemPrompt bool) error
+	UpsertChatPlanModeInstructions(ctx context.Context, value string) error
 	UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error
 	UpsertChatSystemPrompt(ctx context.Context, value string) error
 	UpsertChatTemplateAllowlist(ctx context.Context, templateAllowlist string) error

coderd/database/queries.sql.go

@@ -4816,7 +4816,7 @@ WHERE
             $3::int
     )
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type AcquireChatsParams struct {
@@ -4862,6 +4862,7 @@ func (q *sqlQuerier) AcquireChats(ctx context.Context, arg AcquireChatsParams) (
 			&i.LastInjectedContext,
 			&i.DynamicTools,
 			&i.OrganizationID,
+			&i.PlanMode,
 		); err != nil {
 			return nil, err
 		}
@@ -5000,9 +5001,9 @@ WITH chats AS (
     UPDATE chats
     SET archived = true, pin_order = 0, updated_at = NOW()
     WHERE id = $1::uuid OR root_chat_id = $1::uuid
-    RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 )
-SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 FROM chats
 ORDER BY (id = $1::uuid) DESC, created_at ASC, id ASC
 `
@@ -5042,6 +5043,7 @@ func (q *sqlQuerier) ArchiveChatByID(ctx context.Context, id uuid.UUID) ([]Chat,
 			&i.LastInjectedContext,
 			&i.DynamicTools,
 			&i.OrganizationID,
+			&i.PlanMode,
 		); err != nil {
 			return nil, err
 		}
@@ -5191,7 +5193,7 @@ func (q *sqlQuerier) DeleteOldChats(ctx context.Context, arg DeleteOldChatsParam
 }
 
 const getActiveChatsByAgentID = `-- name: GetActiveChatsByAgentID :many
-SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 FROM chats
 WHERE agent_id = $1::uuid
     AND archived = false
@@ -5237,6 +5239,7 @@ func (q *sqlQuerier) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.U
 			&i.LastInjectedContext,
 			&i.DynamicTools,
 			&i.OrganizationID,
+			&i.PlanMode,
 		); err != nil {
 			return nil, err
 		}
@@ -5253,7 +5256,7 @@ func (q *sqlQuerier) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.U
 
 const getChatByID = `-- name: GetChatByID :one
 SELECT
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 FROM
     chats
 WHERE
@@ -5289,12 +5292,13 @@ func (q *sqlQuerier) GetChatByID(ctx context.Context, id uuid.UUID) (Chat, error
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
 
 const getChatByIDForUpdate = `-- name: GetChatByIDForUpdate :one
-SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id FROM chats WHERE id = $1::uuid FOR UPDATE
+SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode FROM chats WHERE id = $1::uuid FOR UPDATE
 `
 
 func (q *sqlQuerier) GetChatByIDForUpdate(ctx context.Context, id uuid.UUID) (Chat, error) {
@@ -5326,6 +5330,7 @@ func (q *sqlQuerier) GetChatByIDForUpdate(ctx context.Context, id uuid.UUID) (Ch
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -6380,7 +6385,7 @@ func (q *sqlQuerier) GetChatUsageLimitUserOverride(ctx context.Context, userID u
 
 const getChats = `-- name: GetChats :many
 SELECT
-    chats.id, chats.owner_id, chats.workspace_id, chats.title, chats.status, chats.worker_id, chats.started_at, chats.heartbeat_at, chats.created_at, chats.updated_at, chats.parent_chat_id, chats.root_chat_id, chats.last_model_config_id, chats.archived, chats.last_error, chats.mode, chats.mcp_server_ids, chats.labels, chats.build_id, chats.agent_id, chats.pin_order, chats.last_read_message_id, chats.last_injected_context, chats.dynamic_tools, chats.organization_id,
+    chats.id, chats.owner_id, chats.workspace_id, chats.title, chats.status, chats.worker_id, chats.started_at, chats.heartbeat_at, chats.created_at, chats.updated_at, chats.parent_chat_id, chats.root_chat_id, chats.last_model_config_id, chats.archived, chats.last_error, chats.mode, chats.mcp_server_ids, chats.labels, chats.build_id, chats.agent_id, chats.pin_order, chats.last_read_message_id, chats.last_injected_context, chats.dynamic_tools, chats.organization_id, chats.plan_mode,
     EXISTS (
         SELECT 1 FROM chat_messages cm
         WHERE cm.chat_id = chats.id
@@ -6494,6 +6499,7 @@ func (q *sqlQuerier) GetChats(ctx context.Context, arg GetChatsParams) ([]GetCha
 			&i.Chat.LastInjectedContext,
 			&i.Chat.DynamicTools,
 			&i.Chat.OrganizationID,
+			&i.Chat.PlanMode,
 			&i.HasUnread,
 		); err != nil {
 			return nil, err
@@ -6510,7 +6516,7 @@ func (q *sqlQuerier) GetChats(ctx context.Context, arg GetChatsParams) ([]GetCha
 }
 
 const getChatsByWorkspaceIDs = `-- name: GetChatsByWorkspaceIDs :many
-SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 FROM chats
 WHERE archived = false
   AND workspace_id = ANY($1::uuid[])
@@ -6552,6 +6558,7 @@ func (q *sqlQuerier) GetChatsByWorkspaceIDs(ctx context.Context, ids []uuid.UUID
 			&i.LastInjectedContext,
 			&i.DynamicTools,
 			&i.OrganizationID,
+			&i.PlanMode,
 		); err != nil {
 			return nil, err
 		}
@@ -6679,7 +6686,7 @@ func (q *sqlQuerier) GetLastChatMessageByRole(ctx context.Context, arg GetLastCh
 
 const getStaleChats = `-- name: GetStaleChats :many
 SELECT
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 FROM
     chats
 WHERE
@@ -6728,6 +6735,7 @@ func (q *sqlQuerier) GetStaleChats(ctx context.Context, staleThreshold time.Time
 			&i.LastInjectedContext,
 			&i.DynamicTools,
 			&i.OrganizationID,
+			&i.PlanMode,
 		); err != nil {
 			return nil, err
 		}
@@ -6816,6 +6824,7 @@ INSERT INTO chats (
     last_model_config_id,
     title,
     mode,
+    plan_mode,
     status,
     mcp_server_ids,
     labels,
@@ -6831,13 +6840,14 @@ INSERT INTO chats (
     $8::uuid,
     $9::text,
     $10::chat_mode,
-    $11::chat_status,
-    COALESCE($12::uuid[], '{}'::uuid[]),
-    COALESCE($13::jsonb, '{}'::jsonb),
-    $14::jsonb
+    $11::chat_plan_mode,
+    $12::chat_status,
+    COALESCE($13::uuid[], '{}'::uuid[]),
+    COALESCE($14::jsonb, '{}'::jsonb),
+    $15::jsonb
 )
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type InsertChatParams struct {
@@ -6851,6 +6861,7 @@ type InsertChatParams struct {
 	LastModelConfigID uuid.UUID             `db:"last_model_config_id" json:"last_model_config_id"`
 	Title             string                `db:"title" json:"title"`
 	Mode              NullChatMode          `db:"mode" json:"mode"`
+	PlanMode          NullChatPlanMode      `db:"plan_mode" json:"plan_mode"`
 	Status            ChatStatus            `db:"status" json:"status"`
 	MCPServerIDs      []uuid.UUID           `db:"mcp_server_ids" json:"mcp_server_ids"`
 	Labels            pqtype.NullRawMessage `db:"labels" json:"labels"`
@@ -6869,6 +6880,7 @@ func (q *sqlQuerier) InsertChat(ctx context.Context, arg InsertChatParams) (Chat
 		arg.LastModelConfigID,
 		arg.Title,
 		arg.Mode,
+		arg.PlanMode,
 		arg.Status,
 		pq.Array(arg.MCPServerIDs),
 		arg.Labels,
@@ -6901,6 +6913,7 @@ func (q *sqlQuerier) InsertChat(ctx context.Context, arg InsertChatParams) (Chat
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -7429,9 +7442,9 @@ WITH chats AS (
         archived = false,
         updated_at = NOW()
     WHERE id = $1::uuid OR root_chat_id = $1::uuid
-    RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 )
-SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+SELECT id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 FROM chats
 ORDER BY (id = $1::uuid) DESC, created_at ASC, id ASC
 `
@@ -7475,6 +7488,7 @@ func (q *sqlQuerier) UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]Cha
 			&i.LastInjectedContext,
 			&i.DynamicTools,
 			&i.OrganizationID,
+			&i.PlanMode,
 		); err != nil {
 			return nil, err
 		}
@@ -7555,7 +7569,7 @@ UPDATE chats SET
     updated_at = NOW()
 WHERE
     id = $3::uuid
-RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatBuildAgentBindingParams struct {
@@ -7593,6 +7607,7 @@ func (q *sqlQuerier) UpdateChatBuildAgentBinding(ctx context.Context, arg Update
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -7606,7 +7621,7 @@ SET
 WHERE
     id = $2::uuid
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatByIDParams struct {
@@ -7643,6 +7658,7 @@ func (q *sqlQuerier) UpdateChatByID(ctx context.Context, arg UpdateChatByIDParam
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -7701,7 +7717,7 @@ SET
 WHERE
     id = $2::uuid
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatLabelsByIDParams struct {
@@ -7738,6 +7754,7 @@ func (q *sqlQuerier) UpdateChatLabelsByID(ctx context.Context, arg UpdateChatLab
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -7747,7 +7764,7 @@ UPDATE chats SET
     last_injected_context = $1::jsonb
 WHERE
     id = $2::uuid
-RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatLastInjectedContextParams struct {
@@ -7788,6 +7805,7 @@ func (q *sqlQuerier) UpdateChatLastInjectedContext(ctx context.Context, arg Upda
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -7801,7 +7819,7 @@ SET
 WHERE
     id = $2::uuid
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatLastModelConfigByIDParams struct {
@@ -7838,6 +7856,7 @@ func (q *sqlQuerier) UpdateChatLastModelConfigByID(ctx context.Context, arg Upda
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -7869,7 +7888,7 @@ SET
 WHERE
     id = $2::uuid
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatMCPServerIDsParams struct {
@@ -7906,6 +7925,7 @@ func (q *sqlQuerier) UpdateChatMCPServerIDs(ctx context.Context, arg UpdateChatM
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -8028,6 +8048,57 @@ func (q *sqlQuerier) UpdateChatPinOrder(ctx context.Context, arg UpdateChatPinOr
 	return err
 }
 
+const updateChatPlanModeByID = `-- name: UpdateChatPlanModeByID :one
+UPDATE
+    chats
+SET
+    -- NOTE: updated_at is intentionally NOT touched here to avoid changing list ordering.
+    plan_mode = $1::chat_plan_mode
+WHERE
+    id = $2::uuid
+RETURNING
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
+`
+
+type UpdateChatPlanModeByIDParams struct {
+	PlanMode NullChatPlanMode `db:"plan_mode" json:"plan_mode"`
+	ID       uuid.UUID        `db:"id" json:"id"`
+}
+
+func (q *sqlQuerier) UpdateChatPlanModeByID(ctx context.Context, arg UpdateChatPlanModeByIDParams) (Chat, error) {
+	row := q.db.QueryRowContext(ctx, updateChatPlanModeByID, arg.PlanMode, arg.ID)
+	var i Chat
+	err := row.Scan(
+		&i.ID,
+		&i.OwnerID,
+		&i.WorkspaceID,
+		&i.Title,
+		&i.Status,
+		&i.WorkerID,
+		&i.StartedAt,
+		&i.HeartbeatAt,
+		&i.CreatedAt,
+		&i.UpdatedAt,
+		&i.ParentChatID,
+		&i.RootChatID,
+		&i.LastModelConfigID,
+		&i.Archived,
+		&i.LastError,
+		&i.Mode,
+		pq.Array(&i.MCPServerIDs),
+		&i.Labels,
+		&i.BuildID,
+		&i.AgentID,
+		&i.PinOrder,
+		&i.LastReadMessageID,
+		&i.LastInjectedContext,
+		&i.DynamicTools,
+		&i.OrganizationID,
+		&i.PlanMode,
+	)
+	return i, err
+}
+
 const updateChatStatus = `-- name: UpdateChatStatus :one
 UPDATE
     chats
@@ -8041,7 +8112,7 @@ SET
 WHERE
     id = $6::uuid
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatStatusParams struct {
@@ -8089,6 +8160,7 @@ func (q *sqlQuerier) UpdateChatStatus(ctx context.Context, arg UpdateChatStatusP
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -8106,7 +8178,7 @@ SET
 WHERE
     id = $7::uuid
 RETURNING
-    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+    id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatStatusPreserveUpdatedAtParams struct {
@@ -8156,6 +8228,7 @@ func (q *sqlQuerier) UpdateChatStatusPreserveUpdatedAt(ctx context.Context, arg
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -8167,7 +8240,7 @@ UPDATE chats SET
     agent_id = $3::uuid,
     updated_at = NOW()
 WHERE id = $4::uuid
-RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id
+RETURNING id, owner_id, workspace_id, title, status, worker_id, started_at, heartbeat_at, created_at, updated_at, parent_chat_id, root_chat_id, last_model_config_id, archived, last_error, mode, mcp_server_ids, labels, build_id, agent_id, pin_order, last_read_message_id, last_injected_context, dynamic_tools, organization_id, plan_mode
 `
 
 type UpdateChatWorkspaceBindingParams struct {
@@ -8211,6 +8284,7 @@ func (q *sqlQuerier) UpdateChatWorkspaceBinding(ctx context.Context, arg UpdateC
 		&i.LastInjectedContext,
 		&i.DynamicTools,
 		&i.OrganizationID,
+		&i.PlanMode,
 	)
 	return i, err
 }
@@ -19839,6 +19913,18 @@ func (q *sqlQuerier) GetChatIncludeDefaultSystemPrompt(ctx context.Context) (boo
 	return include_default_system_prompt, err
 }
 
+const getChatPlanModeInstructions = `-- name: GetChatPlanModeInstructions :one
+SELECT
+	COALESCE((SELECT value FROM site_configs WHERE key = 'agents_chat_plan_mode_instructions'), '') :: text AS plan_mode_instructions
+`
+
+func (q *sqlQuerier) GetChatPlanModeInstructions(ctx context.Context) (string, error) {
+	row := q.db.QueryRowContext(ctx, getChatPlanModeInstructions)
+	var plan_mode_instructions string
+	err := row.Scan(&plan_mode_instructions)
+	return plan_mode_instructions, err
+}
+
 const getChatRetentionDays = `-- name: GetChatRetentionDays :one
 SELECT COALESCE(
     (SELECT value::integer FROM site_configs
@@ -20182,6 +20268,16 @@ func (q *sqlQuerier) UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, i
 	return err
 }
 
+const upsertChatPlanModeInstructions = `-- name: UpsertChatPlanModeInstructions :exec
+INSERT INTO site_configs (key, value) VALUES ('agents_chat_plan_mode_instructions', $1)
+ON CONFLICT (key) DO UPDATE SET value = $1 WHERE site_configs.key = 'agents_chat_plan_mode_instructions'
+`
+
+func (q *sqlQuerier) UpsertChatPlanModeInstructions(ctx context.Context, value string) error {
+	_, err := q.db.ExecContext(ctx, upsertChatPlanModeInstructions, value)
+	return err
+}
+
 const upsertChatRetentionDays = `-- name: UpsertChatRetentionDays :exec
 INSERT INTO site_configs (key, value)
 VALUES ('agents_chat_retention_days', CAST($1 AS integer)::text)

coderd/database/queries/chats.sql

@@ -402,6 +402,7 @@ INSERT INTO chats (
     last_model_config_id,
     title,
     mode,
+    plan_mode,
     status,
     mcp_server_ids,
     labels,
@@ -417,6 +418,7 @@ INSERT INTO chats (
     @last_model_config_id::uuid,
     @title::text,
     sqlc.narg('mode')::chat_mode,
+    sqlc.narg('plan_mode')::chat_plan_mode,
     @status::chat_status,
     COALESCE(@mcp_server_ids::uuid[], '{}'::uuid[]),
     COALESCE(sqlc.narg('labels')::jsonb, '{}'::jsonb),
@@ -518,6 +520,17 @@ WHERE
 RETURNING
     *;
 
+-- name: UpdateChatPlanModeByID :one
+UPDATE
+    chats
+SET
+    -- NOTE: updated_at is intentionally NOT touched here to avoid changing list ordering.
+    plan_mode = sqlc.narg('plan_mode')::chat_plan_mode
+WHERE
+    id = @id::uuid
+RETURNING
+    *;
+
 -- name: UpdateChatLastModelConfigByID :one
 UPDATE
     chats

coderd/database/queries/siteconfig.sql

@@ -159,6 +159,14 @@ SELECT
 INSERT INTO site_configs (key, value) VALUES ('agents_chat_system_prompt', $1)
 ON CONFLICT (key) DO UPDATE SET value = $1 WHERE site_configs.key = 'agents_chat_system_prompt';
 
+-- name: GetChatPlanModeInstructions :one
+SELECT
+	COALESCE((SELECT value FROM site_configs WHERE key = 'agents_chat_plan_mode_instructions'), '') :: text AS plan_mode_instructions;
+
+-- name: UpsertChatPlanModeInstructions :exec
+INSERT INTO site_configs (key, value) VALUES ('agents_chat_plan_mode_instructions', $1)
+ON CONFLICT (key) DO UPDATE SET value = $1 WHERE site_configs.key = 'agents_chat_plan_mode_instructions';
+
 -- name: GetChatDesktopEnabled :one
 SELECT
 	COALESCE((SELECT value = 'true' FROM site_configs WHERE key = 'agents_desktop_enabled'), false) :: boolean AS enable_desktop;