feat: add Cmd/Ctrl+Enter send setting (#25062)

Adds an Agents General setting to require Cmd/Ctrl+Enter before sending
chat messages. When enabled, plain Enter inserts a newline in agent chat
inputs while the send button remains available.

The preference is now persisted server-side through
`/api/v2/users/{user}/preferences`, alongside the existing user
preference settings, and is applied to both the create-agent input and
existing chat composer. Storybook and API coverage verify the setting,
keyboard behavior, validation, and persistence.

<details>
<summary>Coder Agents notes</summary>

Generated by Coder Agents from a Slack request. Dogfooded with
agent-browser against the Storybook settings and chat input stories.

</details>

coderd/apidoc/docs.go

@@ -14909,6 +14909,17 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.AgentChatSendShortcut": {
+            "type": "string",
+            "enum": [
+                "enter",
+                "modifier_enter"
+            ],
+            "x-enum-varnames": [
+                "AgentChatSendShortcutEnter",
+                "AgentChatSendShortcutModifierEnter"
+            ]
+        },
         "codersdk.AgentConnectionTiming": {
             "type": "object",
             "properties": {
@@ -23426,6 +23437,9 @@ const docTemplate = `{
         "codersdk.UpdateUserPreferenceSettingsRequest": {
             "type": "object",
             "properties": {
+                "agent_chat_send_shortcut": {
+                    "$ref": "#/definitions/codersdk.AgentChatSendShortcut"
+                },
                 "code_diff_display_mode": {
                     "$ref": "#/definitions/codersdk.AgentDisplayMode"
                 },
@@ -23899,6 +23913,9 @@ const docTemplate = `{
         "codersdk.UserPreferenceSettings": {
             "type": "object",
             "properties": {
+                "agent_chat_send_shortcut": {
+                    "$ref": "#/definitions/codersdk.AgentChatSendShortcut"
+                },
                 "code_diff_display_mode": {
                     "$ref": "#/definitions/codersdk.AgentDisplayMode"
                 },

coderd/apidoc/swagger.json

@@ -13375,6 +13375,14 @@
 				}
 			}
 		},
+		"codersdk.AgentChatSendShortcut": {
+			"type": "string",
+			"enum": ["enter", "modifier_enter"],
+			"x-enum-varnames": [
+				"AgentChatSendShortcutEnter",
+				"AgentChatSendShortcutModifierEnter"
+			]
+		},
 		"codersdk.AgentConnectionTiming": {
 			"type": "object",
 			"properties": {
@@ -21566,6 +21574,9 @@
 		"codersdk.UpdateUserPreferenceSettingsRequest": {
 			"type": "object",
 			"properties": {
+				"agent_chat_send_shortcut": {
+					"$ref": "#/definitions/codersdk.AgentChatSendShortcut"
+				},
 				"code_diff_display_mode": {
 					"$ref": "#/definitions/codersdk.AgentDisplayMode"
 				},
@@ -22010,6 +22021,9 @@
 		"codersdk.UserPreferenceSettings": {
 			"type": "object",
 			"properties": {
+				"agent_chat_send_shortcut": {
+					"$ref": "#/definitions/codersdk.AgentChatSendShortcut"
+				},
 				"code_diff_display_mode": {
 					"$ref": "#/definitions/codersdk.AgentDisplayMode"
 				},

coderd/database/dbauthz/dbauthz.go

@@ -4346,6 +4346,17 @@ func (q *querier) GetUserActivityInsights(ctx context.Context, arg database.GetU
 	return q.db.GetUserActivityInsights(ctx, arg)
 }
 
+func (q *querier) GetUserAgentChatSendShortcut(ctx context.Context, userID uuid.UUID) (string, error) {
+	user, err := q.db.GetUserByID(ctx, userID)
+	if err != nil {
+		return "", err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionReadPersonal, user); err != nil {
+		return "", err
+	}
+	return q.db.GetUserAgentChatSendShortcut(ctx, userID)
+}
+
 func (q *querier) GetUserByEmailOrUsername(ctx context.Context, arg database.GetUserByEmailOrUsernameParams) (database.User, error) {
 	return fetch(q.log, q.auth, q.db.GetUserByEmailOrUsername)(ctx, arg)
 }
@@ -7010,6 +7021,17 @@ func (q *querier) UpdateUsageEventsPostPublish(ctx context.Context, arg database
 	return q.db.UpdateUsageEventsPostPublish(ctx, arg)
 }
 
+func (q *querier) UpdateUserAgentChatSendShortcut(ctx context.Context, arg database.UpdateUserAgentChatSendShortcutParams) (string, error) {
+	user, err := q.db.GetUserByID(ctx, arg.UserID)
+	if err != nil {
+		return "", err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdatePersonal, user); err != nil {
+		return "", err
+	}
+	return q.db.UpdateUserAgentChatSendShortcut(ctx, arg)
+}
+
 func (q *querier) UpdateUserChatCompactionThreshold(ctx context.Context, arg database.UpdateUserChatCompactionThresholdParams) (database.UserConfig, error) {
 	u, err := q.db.GetUserByID(ctx, arg.UserID)
 	if err != nil {

coderd/database/dbauthz/dbauthz_test.go

@@ -2842,6 +2842,19 @@ func (s *MethodTestSuite) TestUser() {
 		dbm.EXPECT().UpdateUserCodeDiffDisplayMode(gomock.Any(), arg).Return("always_collapsed", nil).AnyTimes()
 		check.Args(arg).Asserts(u, policy.ActionUpdatePersonal).Returns("always_collapsed")
 	}))
+	s.Run("GetUserAgentChatSendShortcut", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().GetUserAgentChatSendShortcut(gomock.Any(), u.ID).Return("modifier_enter", nil).AnyTimes()
+		check.Args(u.ID).Asserts(u, policy.ActionReadPersonal).Returns("modifier_enter")
+	}))
+	s.Run("UpdateUserAgentChatSendShortcut", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.UpdateUserAgentChatSendShortcutParams{UserID: u.ID, AgentChatSendShortcut: "modifier_enter"}
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().UpdateUserAgentChatSendShortcut(gomock.Any(), arg).Return("modifier_enter", nil).AnyTimes()
+		check.Args(arg).Asserts(u, policy.ActionUpdatePersonal).Returns("modifier_enter")
+	}))
 	s.Run("ListUserChatCompactionThresholds", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		u := testutil.Fake(s.T(), faker, database.User{})
 		uc := database.UserConfig{UserID: u.ID, Key: codersdk.ChatCompactionThresholdKeyPrefix + "00000000-0000-0000-0000-000000000001", Value: "75"}

coderd/database/dbmetrics/querymetrics.go

@@ -2793,6 +2793,14 @@ func (m queryMetricsStore) GetUserActivityInsights(ctx context.Context, arg data
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetUserAgentChatSendShortcut(ctx context.Context, userID uuid.UUID) (string, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetUserAgentChatSendShortcut(ctx, userID)
+	m.queryLatencies.WithLabelValues("GetUserAgentChatSendShortcut").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetUserAgentChatSendShortcut").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetUserByEmailOrUsername(ctx context.Context, arg database.GetUserByEmailOrUsernameParams) (database.User, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetUserByEmailOrUsername(ctx, arg)
@@ -5001,6 +5009,14 @@ func (m queryMetricsStore) UpdateUsageEventsPostPublish(ctx context.Context, arg
 	return r0
 }
 
+func (m queryMetricsStore) UpdateUserAgentChatSendShortcut(ctx context.Context, arg database.UpdateUserAgentChatSendShortcutParams) (string, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateUserAgentChatSendShortcut(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateUserAgentChatSendShortcut").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateUserAgentChatSendShortcut").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpdateUserChatCompactionThreshold(ctx context.Context, arg database.UpdateUserChatCompactionThresholdParams) (database.UserConfig, error) {
 	start := time.Now()
 	r0, r1 := m.s.UpdateUserChatCompactionThreshold(ctx, arg)

coderd/database/dbmock/dbmock.go

@@ -5223,6 +5223,21 @@ func (mr *MockStoreMockRecorder) GetUserActivityInsights(ctx, arg any) *gomock.C
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserActivityInsights", reflect.TypeOf((*MockStore)(nil).GetUserActivityInsights), ctx, arg)
 }
 
+// GetUserAgentChatSendShortcut mocks base method.
+func (m *MockStore) GetUserAgentChatSendShortcut(ctx context.Context, userID uuid.UUID) (string, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetUserAgentChatSendShortcut", ctx, userID)
+	ret0, _ := ret[0].(string)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetUserAgentChatSendShortcut indicates an expected call of GetUserAgentChatSendShortcut.
+func (mr *MockStoreMockRecorder) GetUserAgentChatSendShortcut(ctx, userID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserAgentChatSendShortcut", reflect.TypeOf((*MockStore)(nil).GetUserAgentChatSendShortcut), ctx, userID)
+}
+
 // GetUserByEmailOrUsername mocks base method.
 func (m *MockStore) GetUserByEmailOrUsername(ctx context.Context, arg database.GetUserByEmailOrUsernameParams) (database.User, error) {
 	m.ctrl.T.Helper()
@@ -9427,6 +9442,21 @@ func (mr *MockStoreMockRecorder) UpdateUsageEventsPostPublish(ctx, arg any) *gom
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUsageEventsPostPublish", reflect.TypeOf((*MockStore)(nil).UpdateUsageEventsPostPublish), ctx, arg)
 }
 
+// UpdateUserAgentChatSendShortcut mocks base method.
+func (m *MockStore) UpdateUserAgentChatSendShortcut(ctx context.Context, arg database.UpdateUserAgentChatSendShortcutParams) (string, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateUserAgentChatSendShortcut", ctx, arg)
+	ret0, _ := ret[0].(string)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateUserAgentChatSendShortcut indicates an expected call of UpdateUserAgentChatSendShortcut.
+func (mr *MockStoreMockRecorder) UpdateUserAgentChatSendShortcut(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserAgentChatSendShortcut", reflect.TypeOf((*MockStore)(nil).UpdateUserAgentChatSendShortcut), ctx, arg)
+}
+
 // UpdateUserChatCompactionThreshold mocks base method.
 func (m *MockStore) UpdateUserChatCompactionThreshold(ctx context.Context, arg database.UpdateUserChatCompactionThresholdParams) (database.UserConfig, error) {
 	m.ctrl.T.Helper()

coderd/database/querier.go

@@ -699,6 +699,7 @@ type sqlcQuerier interface {
 	// produces a bloated value if a user has used multiple templates
 	// simultaneously.
 	GetUserActivityInsights(ctx context.Context, arg GetUserActivityInsightsParams) ([]GetUserActivityInsightsRow, error)
+	GetUserAgentChatSendShortcut(ctx context.Context, userID uuid.UUID) (string, error)
 	GetUserByEmailOrUsername(ctx context.Context, arg GetUserByEmailOrUsernameParams) (User, error)
 	GetUserByID(ctx context.Context, id uuid.UUID) (User, error)
 	GetUserChatCompactionThreshold(ctx context.Context, arg GetUserChatCompactionThresholdParams) (string, error)
@@ -1195,6 +1196,7 @@ type sqlcQuerier interface {
 	UpdateTemplateVersionFlagsByJobID(ctx context.Context, arg UpdateTemplateVersionFlagsByJobIDParams) error
 	UpdateTemplateWorkspacesLastUsedAt(ctx context.Context, arg UpdateTemplateWorkspacesLastUsedAtParams) error
 	UpdateUsageEventsPostPublish(ctx context.Context, arg UpdateUsageEventsPostPublishParams) error
+	UpdateUserAgentChatSendShortcut(ctx context.Context, arg UpdateUserAgentChatSendShortcutParams) (string, error)
 	UpdateUserChatCompactionThreshold(ctx context.Context, arg UpdateUserChatCompactionThresholdParams) (UserConfig, error)
 	UpdateUserChatCustomPrompt(ctx context.Context, arg UpdateUserChatCustomPromptParams) (UserConfig, error)
 	UpdateUserChatProviderKey(ctx context.Context, arg UpdateUserChatProviderKeyParams) (UserChatProviderKey, error)

coderd/database/queries.sql.go

@@ -25607,6 +25607,23 @@ func (q *sqlQuerier) GetAuthorizationUserRoles(ctx context.Context, userID uuid.
 	return i, err
 }
 
+const getUserAgentChatSendShortcut = `-- name: GetUserAgentChatSendShortcut :one
+SELECT
+	value AS agent_chat_send_shortcut
+FROM
+	user_configs
+WHERE
+	user_id = $1
+	AND key = 'preference_agent_chat_send_shortcut'
+`
+
+func (q *sqlQuerier) GetUserAgentChatSendShortcut(ctx context.Context, userID uuid.UUID) (string, error) {
+	row := q.db.QueryRowContext(ctx, getUserAgentChatSendShortcut, userID)
+	var agent_chat_send_shortcut string
+	err := row.Scan(&agent_chat_send_shortcut)
+	return agent_chat_send_shortcut, err
+}
+
 const getUserByEmailOrUsername = `-- name: GetUserByEmailOrUsername :one
 SELECT
 	id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, login_type, avatar_url, deleted, last_seen_at, quiet_hours_schedule, name, github_com_user_id, hashed_one_time_passcode, one_time_passcode_expires_at, is_system, is_service_account, chat_spend_limit_micros
@@ -26327,6 +26344,33 @@ func (q *sqlQuerier) UpdateInactiveUsersToDormant(ctx context.Context, arg Updat
 	return items, nil
 }
 
+const updateUserAgentChatSendShortcut = `-- name: UpdateUserAgentChatSendShortcut :one
+INSERT INTO
+	user_configs (user_id, key, value)
+VALUES
+	($1, 'preference_agent_chat_send_shortcut', $2::text)
+ON CONFLICT
+	ON CONSTRAINT user_configs_pkey
+DO UPDATE
+SET
+	value = $2
+WHERE user_configs.user_id = $1
+	AND user_configs.key = 'preference_agent_chat_send_shortcut'
+RETURNING value AS agent_chat_send_shortcut
+`
+
+type UpdateUserAgentChatSendShortcutParams struct {
+	UserID                uuid.UUID `db:"user_id" json:"user_id"`
+	AgentChatSendShortcut string    `db:"agent_chat_send_shortcut" json:"agent_chat_send_shortcut"`
+}
+
+func (q *sqlQuerier) UpdateUserAgentChatSendShortcut(ctx context.Context, arg UpdateUserAgentChatSendShortcutParams) (string, error) {
+	row := q.db.QueryRowContext(ctx, updateUserAgentChatSendShortcut, arg.UserID, arg.AgentChatSendShortcut)
+	var agent_chat_send_shortcut string
+	err := row.Scan(&agent_chat_send_shortcut)
+	return agent_chat_send_shortcut, err
+}
+
 const updateUserChatCompactionThreshold = `-- name: UpdateUserChatCompactionThreshold :one
 INSERT INTO user_configs (user_id, key, value)
 VALUES ($1, $2, ($3::int)::text)

coderd/database/queries/users.sql

@@ -327,6 +327,29 @@ WHERE user_configs.user_id = @user_id
 	AND user_configs.key = 'preference_code_diff_display_mode'
 RETURNING value AS code_diff_display_mode;
 
+-- name: GetUserAgentChatSendShortcut :one
+SELECT
+	value AS agent_chat_send_shortcut
+FROM
+	user_configs
+WHERE
+	user_id = @user_id
+	AND key = 'preference_agent_chat_send_shortcut';
+
+-- name: UpdateUserAgentChatSendShortcut :one
+INSERT INTO
+	user_configs (user_id, key, value)
+VALUES
+	(@user_id, 'preference_agent_chat_send_shortcut', @agent_chat_send_shortcut::text)
+ON CONFLICT
+	ON CONSTRAINT user_configs_pkey
+DO UPDATE
+SET
+	value = @agent_chat_send_shortcut
+WHERE user_configs.user_id = @user_id
+	AND user_configs.key = 'preference_agent_chat_send_shortcut'
+RETURNING value AS agent_chat_send_shortcut;
+
 -- name: UpdateUserRoles :one
 UPDATE
 	users

coderd/users.go

@@ -1257,10 +1257,20 @@ func (api *API) userPreferenceSettings(rw http.ResponseWriter, r *http.Request)
 		return
 	}
 
+	agentChatSendShortcut, err := api.Database.GetUserAgentChatSendShortcut(ctx, user.ID)
+	if err != nil && !errors.Is(err, sql.ErrNoRows) {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Error reading user preference settings.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+
 	httpapi.Write(ctx, rw, http.StatusOK, codersdk.UserPreferenceSettings{
 		TaskNotificationAlertDismissed: taskAlertDismissed,
 		ThinkingDisplayMode:            sanitizeThinkingDisplayMode(thinkingMode),
 		CodeDiffDisplayMode:            sanitizeAgentDisplayMode(codeDiffMode),
+		AgentChatSendShortcut:          sanitizeAgentChatSendShortcut(agentChatSendShortcut),
 	})
 }
 
@@ -1305,6 +1315,16 @@ func (api *API) putUserPreferenceSettings(rw http.ResponseWriter, r *http.Reques
 		})
 		return
 	}
+	if params.AgentChatSendShortcut != "" &&
+		!slices.Contains(codersdk.ValidAgentChatSendShortcuts, params.AgentChatSendShortcut) {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "Invalid agent chat send shortcut.",
+			Validations: []codersdk.ValidationError{
+				{Field: "agent_chat_send_shortcut", Detail: agentChatSendShortcutValidationDetail},
+			},
+		})
+		return
+	}
 	var settings codersdk.UserPreferenceSettings
 	err := api.Database.InTx(func(tx database.Store) error {
 		var err error
@@ -1356,6 +1376,23 @@ func (api *API) putUserPreferenceSettings(rw http.ResponseWriter, r *http.Reques
 			}
 			settings.CodeDiffDisplayMode = sanitizeAgentDisplayMode(stored)
 		}
+
+		if params.AgentChatSendShortcut != "" {
+			updated, err := tx.UpdateUserAgentChatSendShortcut(ctx, database.UpdateUserAgentChatSendShortcutParams{
+				UserID:                user.ID,
+				AgentChatSendShortcut: string(params.AgentChatSendShortcut),
+			})
+			if err != nil {
+				return newUserPreferenceSettingsAPIError("Internal error updating agent chat send shortcut.", err)
+			}
+			settings.AgentChatSendShortcut = sanitizeAgentChatSendShortcut(updated)
+		} else {
+			stored, err := tx.GetUserAgentChatSendShortcut(ctx, user.ID)
+			if err != nil && !errors.Is(err, sql.ErrNoRows) {
+				return newUserPreferenceSettingsAPIError("Error reading agent chat send shortcut.", err)
+			}
+			settings.AgentChatSendShortcut = sanitizeAgentChatSendShortcut(stored)
+		}
 		return nil
 	}, database.DefaultTXOptions().WithID("user_preference_settings"))
 	if err != nil {
@@ -1400,8 +1437,9 @@ func (e userPreferenceSettingsAPIError) Unwrap() error {
 }
 
 const (
-	thinkingDisplayModeValidationDetail = "must be one of: auto, preview, always_expanded, always_collapsed"
-	agentDisplayModeValidationDetail    = "must be one of: auto, always_expanded, always_collapsed"
+	thinkingDisplayModeValidationDetail   = "must be one of: auto, preview, always_expanded, always_collapsed"
+	agentDisplayModeValidationDetail      = "must be one of: auto, always_expanded, always_collapsed"
+	agentChatSendShortcutValidationDetail = "must be one of: enter, modifier_enter"
 )
 
 func sanitizeThinkingDisplayMode(raw string) codersdk.ThinkingDisplayMode {
@@ -1420,6 +1458,14 @@ func sanitizeAgentDisplayMode(raw string) codersdk.AgentDisplayMode {
 	return codersdk.AgentDisplayModeAuto
 }
 
+func sanitizeAgentChatSendShortcut(raw string) codersdk.AgentChatSendShortcut {
+	shortcut := codersdk.AgentChatSendShortcut(raw)
+	if slices.Contains(codersdk.ValidAgentChatSendShortcuts, shortcut) {
+		return shortcut
+	}
+	return codersdk.AgentChatSendShortcutEnter
+}
+
 func isValidFontName(font codersdk.TerminalFontName) bool {
 	return slices.Contains(codersdk.TerminalFontNames, font)
 }

coderd/users_test.go

@@ -1963,6 +1963,91 @@ func TestThinkingDisplayMode(t *testing.T) {
 	})
 }
 
+func TestAgentChatSendShortcutPreference(t *testing.T) {
+	t.Parallel()
+
+	adminClient := coderdtest.New(t, nil)
+	firstUser := coderdtest.CreateFirstUser(t, adminClient)
+
+	requireValidationField := func(t *testing.T, err error, field string) {
+		t.Helper()
+
+		var sdkErr *codersdk.Error
+		require.ErrorAs(t, err, &sdkErr)
+		require.Equal(t, http.StatusBadRequest, sdkErr.StatusCode())
+		require.Len(t, sdkErr.Validations, 1)
+		require.Equal(t, field, sdkErr.Validations[0].Field)
+	}
+
+	t.Run("defaults to enter", func(t *testing.T) {
+		t.Parallel()
+
+		client, _ := coderdtest.CreateAnotherUser(t, adminClient, firstUser.OrganizationID)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+		defer cancel()
+
+		settings, err := client.GetUserPreferenceSettings(ctx, codersdk.Me)
+		require.NoError(t, err)
+		require.Equal(t, codersdk.AgentChatSendShortcutEnter, settings.AgentChatSendShortcut)
+	})
+
+	t.Run("round-trips shortcut", func(t *testing.T) {
+		t.Parallel()
+
+		client, _ := coderdtest.CreateAnotherUser(t, adminClient, firstUser.OrganizationID)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+		defer cancel()
+
+		updated, err := client.UpdateUserPreferenceSettings(ctx, codersdk.Me, codersdk.UpdateUserPreferenceSettingsRequest{
+			AgentChatSendShortcut: codersdk.AgentChatSendShortcutModifierEnter,
+		})
+		require.NoError(t, err)
+		require.Equal(t, codersdk.AgentChatSendShortcutModifierEnter, updated.AgentChatSendShortcut)
+
+		settings, err := client.GetUserPreferenceSettings(ctx, codersdk.Me)
+		require.NoError(t, err)
+		require.Equal(t, codersdk.AgentChatSendShortcutModifierEnter, settings.AgentChatSendShortcut)
+	})
+
+	t.Run("rejects invalid shortcut", func(t *testing.T) {
+		t.Parallel()
+
+		client, _ := coderdtest.CreateAnotherUser(t, adminClient, firstUser.OrganizationID)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+		defer cancel()
+
+		_, err := client.UpdateUserPreferenceSettings(ctx, codersdk.Me, codersdk.UpdateUserPreferenceSettingsRequest{
+			AgentChatSendShortcut: codersdk.AgentChatSendShortcut("bogus"),
+		})
+		requireValidationField(t, err, "agent_chat_send_shortcut")
+	})
+
+	t.Run("updates preserve stored shortcut", func(t *testing.T) {
+		t.Parallel()
+
+		client, _ := coderdtest.CreateAnotherUser(t, adminClient, firstUser.OrganizationID)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+		defer cancel()
+
+		_, err := client.UpdateUserPreferenceSettings(ctx, codersdk.Me, codersdk.UpdateUserPreferenceSettingsRequest{
+			AgentChatSendShortcut: codersdk.AgentChatSendShortcutModifierEnter,
+			ThinkingDisplayMode:   codersdk.ThinkingDisplayModePreview,
+		})
+		require.NoError(t, err)
+
+		updated, err := client.UpdateUserPreferenceSettings(ctx, codersdk.Me, codersdk.UpdateUserPreferenceSettingsRequest{
+			ThinkingDisplayMode: codersdk.ThinkingDisplayModeAlwaysExpanded,
+		})
+		require.NoError(t, err)
+		require.Equal(t, codersdk.ThinkingDisplayModeAlwaysExpanded, updated.ThinkingDisplayMode)
+		require.Equal(t, codersdk.AgentChatSendShortcutModifierEnter, updated.AgentChatSendShortcut)
+	})
+}
+
 func TestAgentDisplayModePreferences(t *testing.T) {
 	t.Parallel()