diff --git a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_containers/HomeTodoContainer.tsx b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_containers/HomeTodoContainer.tsx
index f4524dca..28b6c677 100644
--- a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_containers/HomeTodoContainer.tsx
+++ b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_containers/HomeTodoContainer.tsx
@@ -64,6 +64,8 @@ export const HomeTodoContainer = () => {
     onStopFeedback: setFeedbackText,
     onPlayError: (message) =>
       setPlayErrorMessage(message ?? tToast("timerStartFailed")),
+    onUpdateError: (message) =>
+      setPlayErrorMessage(message ?? tToast("todoUpdateFailed")),
   });
 
   const handleConfirmPendingComplete = () => {
diff --git a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_hooks/use-home-todos-by-date.ts b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_hooks/use-home-todos-by-date.ts
index 2ecebfbd..cedc0fe9 100644
--- a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_hooks/use-home-todos-by-date.ts
+++ b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/home/_hooks/use-home-todos-by-date.ts
@@ -3,7 +3,9 @@
 import { useQueryClient } from "@tanstack/react-query";
 import { useEffect, useState } from "react";
 
+import type { ErrorType } from "@/api/client/custom-instance";
 import type { ApiError } from "@/api/error/api-error";
+import type { ErrorDto } from "@/api/generated/models";
 import type { HomeViewDay } from "@/app/[locale]/(main)/(with-time-sidebar)/home/_types/home-view-type";
 import type { Todo } from "@/app/[locale]/(main)/(with-time-sidebar)/home/_types/todo-type";
 
@@ -28,6 +30,7 @@ export interface UseHomeTodosByDateOptions {
   onTimerAlreadyRunning: () => void;
   onStopFeedback: (feedbackText: string | undefined) => void;
   onPlayError: (message: string | undefined) => void;
+  onUpdateError: (message: string | undefined) => void;
 }
 
 export const useHomeTodosByDate = (
@@ -37,6 +40,7 @@ export const useHomeTodosByDate = (
     onTimerAlreadyRunning,
     onStopFeedback,
     onPlayError,
+    onUpdateError,
   }: UseHomeTodosByDateOptions,
 ) => {
   const [todosByDate, setTodosByDate] = useState<Record<string, Todo[]>>({});
@@ -133,8 +137,9 @@ export const useHomeTodosByDate = (
           invalidateTodoDetail(dateKey, todoId);
           invalidateStatistics();
         },
-        onError: () => {
+        onError: (error: ErrorType<ErrorDto>) => {
           setTodosByDate((prev) => ({ ...prev, [dateKey]: previous }));
+          onUpdateError(error.response?.data.message);
         },
       },
     );
@@ -237,8 +242,9 @@ export const useHomeTodosByDate = (
           invalidateTodoDetail(dateKey, todoId);
           invalidateStatistics();
         },
-        onError: () => {
+        onError: (error: ErrorType<ErrorDto>) => {
           setTodosByDate((prev) => ({ ...prev, [dateKey]: previous }));
+          onUpdateError(error.response?.data.message);
         },
       },
     );
@@ -270,8 +276,9 @@ export const useHomeTodosByDate = (
       { todoId: movedTodo.todoId, data: { newIndex: toIndex, date: dateKey } },
       {
         onSuccess: invalidateHomeAndFocus,
-        onError: () => {
+        onError: (error: ErrorType<ErrorDto>) => {
           setTodosByDate((prev) => ({ ...prev, [dateKey]: previous }));
+          onUpdateError(error.response?.data.message);
         },
       },
     );
diff --git a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_containers/TodayTodoListContainer.tsx b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_containers/TodayTodoListContainer.tsx
index 09fd520c..988f923a 100644
--- a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_containers/TodayTodoListContainer.tsx
+++ b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_containers/TodayTodoListContainer.tsx
@@ -59,6 +59,8 @@ export const TodayTodoListContainer = () => {
     onStopFeedback: setFeedbackText,
     onPlayError: (message) =>
       setPlayErrorMessage(message ?? tToast("timerStartFailed")),
+    onUpdateError: (message) =>
+      setPlayErrorMessage(message ?? tToast("todoUpdateFailed")),
   });
 
   const handleConfirmPendingComplete = () => {
diff --git a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_hooks/useTodayTodoList.ts b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_hooks/useTodayTodoList.ts
index ed7b22ef..d263c2ac 100644
--- a/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_hooks/useTodayTodoList.ts
+++ b/apps/timo-web/app/[locale]/(main)/(with-time-sidebar)/today/_hooks/useTodayTodoList.ts
@@ -26,6 +26,7 @@ export interface UseTodayTodoListOptions {
   onTimerAlreadyRunning: () => void;
   onStopFeedback: (feedbackText: string | undefined) => void;
   onPlayError: (message: string | undefined) => void;
+  onUpdateError: (message: string | undefined) => void;
 }
 
 export const useTodayTodoList = (
@@ -35,6 +36,7 @@ export const useTodayTodoList = (
     onTimerAlreadyRunning,
     onStopFeedback,
     onPlayError,
+    onUpdateError,
   }: UseTodayTodoListOptions,
 ) => {
   const [todos, setTodos] = useState<TodayTodo[]>(initialTodos);
@@ -118,8 +120,9 @@ export const useTodayTodoList = (
           invalidateTodoDetail(todoId, dateKey);
           invalidateFocusTodo();
         },
-        onError: () => {
+        onError: (error: ErrorType<ErrorDto>) => {
           setTodos(previous);
+          onUpdateError(error.response?.data.message);
         },
       },
     );
@@ -237,8 +240,9 @@ export const useTodayTodoList = (
           invalidateTodoDetail(todoId, dateKey);
           invalidateFocusTodo();
         },
-        onError: () => {
+        onError: (error: ErrorType<ErrorDto>) => {
           setTodos(previous);
+          onUpdateError(error.response?.data.message);
         },
       },
     );
diff --git a/apps/timo-web/app/[locale]/(main)/focus/_hooks/use-focus-session.ts b/apps/timo-web/app/[locale]/(main)/focus/_hooks/use-focus-session.ts
index ff2d713e..66230d81 100644
--- a/apps/timo-web/app/[locale]/(main)/focus/_hooks/use-focus-session.ts
+++ b/apps/timo-web/app/[locale]/(main)/focus/_hooks/use-focus-session.ts
@@ -95,6 +95,7 @@ export const useFocusSession = ({
         invalidateHomeView();
         invalidateTimeBoxes();
         invalidateTodayView();
+        invalidateTodoDetail();
       },
       onError: onMutationError,
     },
@@ -108,6 +109,7 @@ export const useFocusSession = ({
         invalidateHomeView();
         invalidateTimeBoxes();
         invalidateTodayView();
+        invalidateTodoDetail();
       },
       onError: onMutationError,
     },
diff --git a/apps/timo-web/components/layout/sidebar/time/TimerPanel.tsx b/apps/timo-web/components/layout/sidebar/time/TimerPanel.tsx
index 636562ac..10ca10f6 100644
--- a/apps/timo-web/components/layout/sidebar/time/TimerPanel.tsx
+++ b/apps/timo-web/components/layout/sidebar/time/TimerPanel.tsx
@@ -35,6 +35,7 @@ export const TimerPanel = () => {
     invalidateTimeBoxes,
     invalidateTodayView,
     invalidateFocusTodo,
+    invalidateTodoDetail,
   } = useTimerQueryInvalidation();
 
   const { mutate: changeStatus } = useChangeStatus({
@@ -63,6 +64,7 @@ export const TimerPanel = () => {
         invalidateTimeBoxes();
         invalidateTodayView();
         invalidateFocusTodo();
+        if (response.data?.todoId) invalidateTodoDetail(response.data.todoId);
       },
     },
   });
@@ -75,6 +77,7 @@ export const TimerPanel = () => {
         invalidateTimeBoxes();
         invalidateTodayView();
         invalidateFocusTodo();
+        if (response.data?.todoId) invalidateTodoDetail(response.data.todoId);
       },
     },
   });
diff --git a/apps/timo-web/components/modal/OverlayModal.tsx b/apps/timo-web/components/modal/OverlayModal.tsx
index f925faaa..2f0d5972 100644
--- a/apps/timo-web/components/modal/OverlayModal.tsx
+++ b/apps/timo-web/components/modal/OverlayModal.tsx
@@ -114,19 +114,41 @@ export const OverlayModal = ({
         }}
       >
         <div
-          ref={dialogRef}
-          role="dialog"
-          aria-modal="true"
-          aria-label={ariaLabel}
-          tabIndex={-1}
+          className="fixed inset-0 overflow-y-auto"
           style={{ zIndex: panelZIndex }}
-          className={cn(
-            "fixed top-1/2 left-1/2 flex -translate-x-1/2 -translate-y-1/2 flex-col rounded-[4px] bg-white transition-all duration-200 ease-out",
-            isVisible ? "scale-100 opacity-100" : "scale-95 opacity-0",
-            className,
-          )}
         >
-          {children}
+          {/*
+            배경 클릭으로 모달을 닫는 영역이다. 포인터 전용 UX이며 키보드
+            사용자는 이미 Escape로 동일하게 닫을 수 있어(위 handleEscape),
+            여기서는 jsx-a11y의 인터랙션 규칙을 의도적으로 예외 처리한다.
+          */}
+          {/* eslint-disable-next-line jsx-a11y/no-static-element-interactions, jsx-a11y/click-events-have-key-events */}
+          <div
+            className="flex min-h-full items-center justify-center py-8"
+            onPointerDownCapture={() => {
+              wasFloatingLayerOpenRef.current = hasOpenFloatingLayer();
+            }}
+            onClick={(event) => {
+              if (event.target !== event.currentTarget) return;
+              if (wasFloatingLayerOpenRef.current) return;
+              onClose();
+            }}
+          >
+            <div
+              ref={dialogRef}
+              role="dialog"
+              aria-modal="true"
+              aria-label={ariaLabel}
+              tabIndex={-1}
+              className={cn(
+                "flex flex-col rounded-[4px] bg-white transition-all duration-200 ease-out",
+                isVisible ? "scale-100 opacity-100" : "scale-95 opacity-0",
+                className,
+              )}
+            >
+              {children}
+            </div>
+          </div>
         </div>
       </FocusTrap>
     </>,
diff --git a/apps/timo-web/hooks/timer/use-timer-query-invalidation.ts b/apps/timo-web/hooks/timer/use-timer-query-invalidation.ts
index 500c6cc3..e7c0cd05 100644
--- a/apps/timo-web/hooks/timer/use-timer-query-invalidation.ts
+++ b/apps/timo-web/hooks/timer/use-timer-query-invalidation.ts
@@ -9,6 +9,7 @@ import {
 } from "@/api/generated/endpoints/home/home";
 import { getGetTimeBoxesQueryKey } from "@/api/generated/endpoints/time-box/time-box";
 import { getGetActiveTimerQueryKey } from "@/api/generated/endpoints/timer/timer";
+import { getGetTodoDetailQueryKey } from "@/api/generated/endpoints/todo/todo";
 import { useStatisticsQueryInvalidation } from "@/hooks/statistics/use-statistics-query-invalidation";
 
 export const useTimerQueryInvalidation = () => {
@@ -25,6 +26,10 @@ export const useTimerQueryInvalidation = () => {
     queryClient.invalidateQueries({ queryKey: getGetTodayQueryKey() });
   const invalidateFocusTodo = () =>
     queryClient.invalidateQueries({ queryKey: getGetFocusTodoQueryKey() });
+  const invalidateTodoDetail = (todoId: number) =>
+    queryClient.invalidateQueries({
+      queryKey: getGetTodoDetailQueryKey(todoId),
+    });
   const invalidateTimerState = () => {
     invalidateActiveTimer();
     invalidateHomeView();
@@ -39,6 +44,7 @@ export const useTimerQueryInvalidation = () => {
     invalidateTimeBoxes,
     invalidateTodayView,
     invalidateFocusTodo,
+    invalidateTodoDetail,
     invalidateTimerState,
   };
 };
diff --git a/packages/timo-design-system/src/components/dropdown-view/DropdownView.tsx b/packages/timo-design-system/src/components/dropdown-view/DropdownView.tsx
index 7d2cfa0a..2973df80 100644
--- a/packages/timo-design-system/src/components/dropdown-view/DropdownView.tsx
+++ b/packages/timo-design-system/src/components/dropdown-view/DropdownView.tsx
@@ -49,7 +49,7 @@ export const DropdownView = ({
                 role="option"
                 aria-selected={isSelected}
                 onClick={() => onChange(item)}
-                className="typo-body-m-12 text-timo-gray-900 px-1.5 py-1"
+                className="typo-body-m-12 text-timo-gray-900 py-1"
               >
                 {item}
               </Dropdown.Item>
diff --git a/packages/timo-design-system/src/components/repeat/repeat-selector/RepeatSelector.tsx b/packages/timo-design-system/src/components/repeat/repeat-selector/RepeatSelector.tsx
index 50b36ea2..216f4649 100644
--- a/packages/timo-design-system/src/components/repeat/repeat-selector/RepeatSelector.tsx
+++ b/packages/timo-design-system/src/components/repeat/repeat-selector/RepeatSelector.tsx
@@ -44,6 +44,7 @@ export interface RepeatSelectorProps {
   frequencyHeading?: string;
   detailHeading: string;
   options: RepeatOption[];
+  isActive?: boolean;
   frequency: RepeatFrequency;
   onFrequencyChange?: (frequency: RepeatFrequency) => void;
   weekly: RepeatWeeklyDetail;
@@ -158,6 +159,7 @@ export const RepeatSelector = ({
   frequencyHeading = "반복 일정",
   detailHeading,
   options,
+  isActive = true,
   frequency,
   onFrequencyChange,
   weekly,
@@ -174,12 +176,18 @@ export const RepeatSelector = ({
   const draftFrequencyRef = useRef(frequency);
   const draftWeekdayIdsRef = useRef(weekly.selectedWeekdayIds);
   const draftRepeatDayRef = useRef(monthly.repeatDay);
+  // 반복이 꺼져 있을 때(isActive=false) frequency는 "DAILY"라는 기본값을 표시할
+  // 뿐 실제로 저장된 값이 아니다. 이 경우 "매일"을 선택해도 draft가 기본값과
+  // 같아서 "변경 없음"으로 오인되므로, 사용자가 실제로 클릭했는지를 별도로
+  // 추적해 그 경우엔 값이 같아도 반드시 커밋한다.
+  const hasSelectedFrequencyRef = useRef(false);
 
   const selectedLabel = options.find(
     (option) => option.frequency === draftFrequency,
   )?.label;
 
   const handleSelectFrequency = (value: RepeatFrequency) => {
+    hasSelectedFrequencyRef.current = true;
     draftFrequencyRef.current = value;
     setDraftFrequency(value);
     if (value !== "DAILY") setIsPicking(false);
@@ -201,6 +209,7 @@ export const RepeatSelector = ({
 
   const handleOpenChange = (isOpen: boolean) => {
     if (isOpen) {
+      hasSelectedFrequencyRef.current = false;
       draftFrequencyRef.current = frequency;
       setDraftFrequency(frequency);
       draftWeekdayIdsRef.current = weekly.selectedWeekdayIds;
@@ -210,7 +219,10 @@ export const RepeatSelector = ({
       return;
     }
 
-    if (draftFrequencyRef.current !== frequency) {
+    if (
+      hasSelectedFrequencyRef.current &&
+      (draftFrequencyRef.current !== frequency || !isActive)
+    ) {
       onFrequencyChange?.(draftFrequencyRef.current);
     }
     if (
diff --git a/packages/timo-design-system/src/components/todo/todo-toolbar/TodoToolbar.tsx b/packages/timo-design-system/src/components/todo/todo-toolbar/TodoToolbar.tsx
index e8057eb8..13028893 100644
--- a/packages/timo-design-system/src/components/todo/todo-toolbar/TodoToolbar.tsx
+++ b/packages/timo-design-system/src/components/todo/todo-toolbar/TodoToolbar.tsx
@@ -175,6 +175,7 @@ export const TodoToolbar = ({
 
       <RepeatSelector
         {...repeat}
+        isActive={isRepeatActive}
         trigger={(isOpen) =>
           isOpen ? (
             <RepeatBlueIcon />