diff --git a/apps/desktop/src/components/grid/DataGrid.vue b/apps/desktop/src/components/grid/DataGrid.vue
index 3d7dc43862..727e0c06bd 100644
--- a/apps/desktop/src/components/grid/DataGrid.vue
+++ b/apps/desktop/src/components/grid/DataGrid.vue
@@ -135,7 +135,7 @@ import { canFormatCellDetailJson, cellDetailEditorText, compactJsonText, default
 import { buildDataGridCellDetail, buildDataGridColumnDetail, buildDataGridRowDetail, CELL_DETAIL_VALUE_PREVIEW_MAX_LENGTH, dataGridColumnDetailJson, dataGridColumnDetailTsv, dataGridRowDetailJson, dataGridRowDetailTsv, type DataGridCellDetail } from "@/lib/dataGrid/dataGridDetail";
 import { applyColumnFormatter, buildColumnFormatterKey, getSupportedTimeZoneOptions, normalizeColumnFormatter, resolveColumnFormatter, type ColumnFormatterConfig, type DateTimeFormatterUnit, DateTimePatterns } from "@/lib/dataGrid/columnFormatter";
 import { temporalCellEditorConfig, type TemporalCellEditorConfig } from "@/lib/dataGrid/dataGridTemporalEditor";
-import { isBooleanCheckboxValue, isBooleanColumnType, isPointInBooleanCheckbox, normalizeBooleanCellValue } from "@/lib/dataGrid/dataGridBooleanColumn";
+import { BOOLEAN_CELL_EDITOR_VALUES, booleanCellEditorValue, isBooleanCellValue, isBooleanColumnType, parseBooleanCellEditorValue } from "@/lib/dataGrid/dataGridBooleanColumn";
 import { resolveDataGridColumnsByResultIndex } from "@/lib/dataGrid/dataGridColumnMetadata";
 import { isCancelSearchShortcut, isCopyCurrentRowShortcut, isDeleteCurrentRowShortcut, isFocusSearchShortcut, isModRShortcut, isSaveShortcut, isToggleTransposeShortcut } from "@/lib/editor/keyboardShortcuts";
 import { dataGridHeaderContentWidth, scrollbarGutterWidth } from "@/lib/dataGrid/dataGridScrollGutter";
@@ -2968,7 +2968,6 @@ const {
   startEdit,
   commitEdit,
   commitEditAndMaybeAutoSave,
-  cycleBooleanCellValue,
   commitEditFromBlur,
   applyCellValue,
   restoreCellValue,
@@ -3146,7 +3145,6 @@ function showReadonlyCellDetailsOnDblClick(item: RowItem, rowIndex: number, visi
 }
 
 function onDomCellDblClick(item: RowItem, rowIndex: number, visibleColIdx: number, actualColIdx: number, event: MouseEvent) {
-  if (isBooleanGridCell(item, actualColIdx) && canEditCellItem(item, actualColIdx)) return;
   if (showReadonlyCellDetailsOnDblClick(item, rowIndex, visibleColIdx, actualColIdx)) return;
   startDomCellEdit(item.id, actualColIdx, formatCellCached(item.data[actualColIdx], actualColIdx), event);
 }
@@ -3186,19 +3184,6 @@ function measureCellTextWidth(text: string, font: string): number {
   return width;
 }
 
-const cellTextWidthCache = new Map<string, number>();
-
-function measureCellTextWidthCached(text: string, font: string): number {
-  const key = `${font}|${text}`;
-  let width = cellTextWidthCache.get(key);
-  if (width === undefined) {
-    width = measureCellTextWidth(text, font);
-    if (cellTextWidthCache.size >= 200) cellTextWidthCache.clear();
-    cellTextWidthCache.set(key, width);
-  }
-  return width;
-}
-
 const tableColumnsByResultIndex = computed(() =>
   resolveDataGridColumnsByResultIndex({
     resultColumns: props.result.columns,
@@ -3232,7 +3217,7 @@ function isEnumGridColumnNullable(columnIndex: number): boolean {
   return tableColumnForGridColumn(columnIndex)?.is_nullable ?? false;
 }
 
-function isEnumEditorInitialNull(rowId: number | undefined, columnIndex: number): boolean {
+function isGridCellInitialNull(rowId: number | undefined, columnIndex: number): boolean {
   if (rowId === undefined) return false;
   return getRowItem(rowId)?.data[columnIndex] === null;
 }
@@ -3249,22 +3234,19 @@ function isBooleanGridColumn(columnIndex: number): boolean {
 }
 
 function isBooleanGridCell(item: RowItem | undefined, columnIndex: number): boolean {
-  return !!item && isBooleanGridColumn(columnIndex) && isBooleanCheckboxValue(item.data[columnIndex]);
+  return !!item && isBooleanGridColumn(columnIndex) && isBooleanCellValue(item.data[columnIndex]);
 }
 
 function isBooleanGridColumnNullable(columnIndex: number): boolean {
   return tableColumnForGridColumn(columnIndex)?.is_nullable ?? true;
 }
 
-function booleanCellChecked(value: unknown): boolean {
-  return normalizeBooleanCellValue(value) === true;
-}
-
-function cycleBooleanGridCell(item: RowItem | undefined, actualColIdx: number, event: MouseEvent) {
-  if (!item || !isBooleanGridCell(item, actualColIdx) || !canEditCellItem(item, actualColIdx)) return;
-  event.stopPropagation();
-  void cycleBooleanCellValue(item.id, actualColIdx, isBooleanGridColumnNullable(actualColIdx));
-}
+const booleanEditorModelValue = computed({
+  get: () => booleanCellEditorValue(editValue.value),
+  set: (value: string) => {
+    editValue.value = value;
+  },
+});
 
 function cellEditInputModeForColumn(columnIndex: number): "decimal" | "numeric" | undefined {
   const dataType = normalizedColumnDataType(tableColumnForGridColumn(columnIndex));
@@ -5079,8 +5061,7 @@ function onCanvasMouseMove(event: MouseEvent) {
   const next = hit && hitItem ? { rowIndex: hitItem.displayIndex, visibleColIdx: hit.rowNumber ? -1 : hit.visibleColIdx } : null;
   const actualColIdx = next ? visibleColumnIndexes.value[next.visibleColIdx] : undefined;
   if (canvasRef.value) {
-    const overBooleanInteractive = hit != null && !hit.rowNumber && hitItem != null && actualColIdx !== undefined && isBooleanGridCell(hitItem, actualColIdx) && canEditCellItem(hitItem, actualColIdx) && booleanInteractiveHitFromCanvasEvent(hitItem, hit, actualColIdx, event);
-    canvasRef.value.style.cursor = hit?.rowNumber ? "default" : overBooleanInteractive ? "pointer" : hitItem && actualColIdx !== undefined && canEditCellItem(hitItem, actualColIdx) ? "text" : "cell";
+    canvasRef.value.style.cursor = hit?.rowNumber ? "default" : hitItem && actualColIdx !== undefined && canEditCellItem(hitItem, actualColIdx) ? "text" : "cell";
   }
   if (next?.rowIndex === canvasHoverCell.value?.rowIndex && next?.visibleColIdx === canvasHoverCell.value?.visibleColIdx) {
     return;
@@ -5123,43 +5104,6 @@ function clearCanvasDetailHover(event?: MouseEvent) {
   onCanvasMouseLeave();
 }
 
-function booleanCheckboxHitFromCanvasEvent(item: RowItem, hit: { rowIndex: number; visibleColIdx: number }, actualColIdx: number, event: MouseEvent): boolean {
-  if (item.data[actualColIdx] === null) return false;
-  const canvas = canvasRef.value;
-  const canvasRect = canvas?.getBoundingClientRect();
-  const cellRect = canvasCellViewportRect(hit.rowIndex, hit.visibleColIdx);
-  if (!canvasRect || !cellRect) return false;
-  return isPointInBooleanCheckbox({ x: event.clientX - canvasRect.left, y: event.clientY - canvasRect.top }, { left: cellRect.left, top: cellRect.top, width: cellRect.width, height: cellRect.height });
-}
-
-function booleanNullTextHitFromCanvasEvent(item: RowItem, hit: { rowIndex: number; visibleColIdx: number }, actualColIdx: number, event: MouseEvent): boolean {
-  if (item.data[actualColIdx] !== null) return false;
-  const canvas = canvasRef.value;
-  const canvasRect = canvas?.getBoundingClientRect();
-  const cellRect = canvasCellViewportRect(hit.rowIndex, hit.visibleColIdx);
-  if (!canvasRect || !cellRect) return false;
-  const text = firstLineCellDisplayValue(formatCellCached(item.data[actualColIdx], actualColIdx));
-  if (!text) return false;
-  const textWidth = measureCellTextWidthCached(text, `italic 400 ${tableFontSize.value}px ${tableFontFamily.value}`);
-  if (textWidth <= 0) return false;
-  const left = cellRect.left + (cellRect.width - textWidth) / 2 - 2;
-  const right = left + textWidth + 4;
-  const x = event.clientX - canvasRect.left;
-  const y = event.clientY - canvasRect.top;
-  return x >= left && x <= right && y >= cellRect.top && y <= cellRect.top + cellRect.height;
-}
-
-function booleanInteractiveHitFromCanvasEvent(item: RowItem, hit: { rowIndex: number; visibleColIdx: number }, actualColIdx: number, event: MouseEvent): boolean {
-  return item.data[actualColIdx] === null ? booleanNullTextHitFromCanvasEvent(item, hit, actualColIdx, event) : booleanCheckboxHitFromCanvasEvent(item, hit, actualColIdx, event);
-}
-
-function tryCycleBooleanCheckboxOnCanvasMouseDown(item: RowItem, hit: { rowIndex: number; visibleColIdx: number }, actualColIdx: number, event: MouseEvent): boolean {
-  if (!isBooleanGridCell(item, actualColIdx) || !canEditCellItem(item, actualColIdx)) return false;
-  if (!booleanInteractiveHitFromCanvasEvent(item, hit, actualColIdx, event)) return false;
-  void cycleBooleanCellValue(item.id, actualColIdx, isBooleanGridColumnNullable(actualColIdx));
-  return true;
-}
-
 function onCanvasMouseDown(event: MouseEvent) {
   if (event.button !== 0) return;
   const hit = canvasHitTest(event);
@@ -5176,7 +5120,6 @@ function onCanvasMouseDown(event: MouseEvent) {
     onRowNumberMouseDown(item, event);
   } else {
     handleDataCellMousedown(item.displayIndex, hit.visibleColIdx, item.id, event);
-    if (actualColIdx !== undefined) tryCycleBooleanCheckboxOnCanvasMouseDown(item, hit, actualColIdx, event);
   }
   gridRef.value?.focus({ preventScroll: true });
   scheduleCanvasDraw();
@@ -5209,7 +5152,6 @@ function onCanvasDblClick(event: MouseEvent) {
   const actualColIdx = visibleColumnIndexes.value[hit.visibleColIdx];
   if (!item || actualColIdx === undefined) return;
   if (showReadonlyCellDetailsOnDblClick(item, item.displayIndex, hit.visibleColIdx, actualColIdx)) return;
-  if (isBooleanGridCell(item, actualColIdx) && canEditCellItem(item, actualColIdx)) return;
   startCellEdit(item.id, actualColIdx, canvasCellContentOverflows(item, actualColIdx, hit.visibleColIdx));
 }
 
@@ -5375,7 +5317,6 @@ function drawCanvasGrid() {
     searchMatchKeys: searchMatchSet.value,
     currentSearchMatch: currentSearchMatch.value,
     formatCell: formatCellCached,
-    columnIsBoolean: isBooleanGridColumn,
     draftCellPlaceholder: t("grid.quickEntryDraftPlaceholder"),
     isRowActive,
     rowCellsUseSelectionVisual,
@@ -5629,7 +5570,7 @@ function copyExtractorLabel(extractor: DataGridCopyExtractorId): string {
     "csv-with-headers": t("grid.copyExtractorWithHeaders", { format: "CSV" }),
     "pipe-separated": t("grid.copyExtractorPipeSeparated"),
     dsv: "DSV",
-    json: "JSON",
+    json: t("grid.copyExtractorJsonArray"),
     "json-lines": "JSON Lines",
     "one-row": t("grid.copyExtractorOneRow"),
     "sql-in-list": t("grid.copyExtractorSqlInList"),
@@ -5900,7 +5841,6 @@ function onTransposeCellDblClick(rowIndex: number, actualColIdx: number, display
     showTransposeCellDetails(rowIndex, actualColIdx);
     return;
   }
-  if (isBooleanGridCell(item, actualColIdx)) return;
   startDomCellEdit(item.id, actualColIdx, displayText, event);
 }
 
@@ -6401,10 +6341,6 @@ function editSelectedCell(): boolean {
   const item = displayItemAt(position.rowIndex);
   const actualColIndex = actualColumnIndex(position.colIndex);
   if (!item || !canEditCellItem(item, actualColIndex)) return false;
-  if (isBooleanGridCell(item, actualColIndex)) {
-    void cycleBooleanCellValue(item.id, actualColIndex, isBooleanGridColumnNullable(actualColIndex));
-    return true;
-  }
   startEdit(item.id, actualColIndex);
   return true;
 }
@@ -6444,10 +6380,23 @@ function deleteCurrentRow(): boolean {
   return true;
 }
 
-function commitGridEdit(value?: string | null) {
+function commitGridEdit(value?: CellValue) {
   void commitEditAndMaybeAutoSave(value === undefined ? undefined : { explicitValue: value }).finally(() => nextTick(() => gridRef.value?.focus({ preventScroll: true })));
 }
 
+function commitBooleanGridEdit(value?: string | null) {
+  if (value === undefined) {
+    commitGridEdit();
+    return;
+  }
+  const parsedValue = parseBooleanCellEditorValue(value);
+  if (parsedValue === undefined) {
+    commitGridEdit();
+    return;
+  }
+  commitGridEdit(parsedValue);
+}
+
 async function commitEditFromCellBlur() {
   const target = pendingQuickEntryDraftCellFocus.value;
   pendingQuickEntryDraftCellFocus.value = null;
@@ -8275,46 +8224,66 @@ function filterSubmenu(): ContextMenuItem {
 
 function buildExtractorContextItems(): ContextMenuItem[] {
   const items: ContextMenuItem[] = [];
+  let separatorPending = false;
   for (const extractor of DATA_GRID_COPY_EXTRACTOR_IDS) {
     const descriptor = DATA_GRID_COPY_EXTRACTOR_DESCRIPTORS[extractor];
     if (descriptor.separatorBefore) {
-      items.push({ label: "", separator: true });
+      separatorPending = items.length > 0;
     }
     const selected = extractor === selectedCopyExtractor.value;
+    const extractorItems: ContextMenuItem[] = [];
     if (extractor === "sql-inserts") {
       for (const excludePrimaryKeysFromInsert of [false, true]) {
+        if (selected && settingsStore.editorSettings.dataGridExtractorOptions.sql.excludePrimaryKeysFromInsert === excludePrimaryKeysFromInsert) continue;
         const options = sqlInsertExtractorOptions(excludePrimaryKeysFromInsert);
-        items.push({
+        extractorItems.push({
           label: t(excludePrimaryKeysFromInsert ? "grid.copyExtractorSqlInsertsWithoutPrimaryKeys" : "grid.copyExtractorSqlInsertsWithPrimaryKeys"),
           action: () => void copyWithExtractor(extractor, options),
           disabled: !canCopyWithExtractor(extractor, options),
-          checked: selected && settingsStore.editorSettings.dataGridExtractorOptions.sql.excludePrimaryKeysFromInsert === excludePrimaryKeysFromInsert,
         });
       }
-      continue;
+    } else if (!selected) {
+      extractorItems.push({
+        label: copyExtractorLabel(extractor),
+        action: () => {
+          // One-off copy as the chosen format; do NOT persist it as the default —
+          // the saved default stays controlled by the toolbar/settings dialog.
+          void copyWithExtractor(extractor);
+        },
+        disabled: !canCopyWithExtractor(extractor),
+      });
     }
-    items.push({
-      label: copyExtractorLabel(extractor),
-      action: () => {
-        // One-off copy as the chosen format; do NOT persist it as the default —
-        // the saved default stays controlled by the toolbar/settings dialog.
-        void copyWithExtractor(extractor);
-      },
-      disabled: !canCopyWithExtractor(extractor),
-      checked: selected,
-    });
+    if (extractorItems.length === 0) continue;
+    if (separatorPending) {
+      items.push({ label: "", separator: true });
+      separatorPending = false;
+    }
+    items.push(...extractorItems);
   }
-  items.push({ label: "", separator: true });
-  items.push({
-    label: t("grid.copyExtractorConfigure"),
-    icon: Settings2,
-    action: openExtractorConfiguration,
-  });
   return items;
 }
 
+function defaultExtractorContextItem(): ContextMenuItem {
+  const extractor = selectedCopyExtractor.value;
+  const extractorOptions = extractor === "sql-inserts" ? sqlInsertExtractorOptions(settingsStore.editorSettings.dataGridExtractorOptions.sql.excludePrimaryKeysFromInsert) : undefined;
+  return {
+    label: defaultCopyExtractorLabel.value,
+    action: () => void copyWithExtractor(extractor, extractorOptions),
+    disabled: !canCopyWithExtractor(extractor, extractorOptions),
+    checked: true,
+  };
+}
+
 function copySubmenu(): ContextMenuItem {
-  const items: ContextMenuItem[] = [];
+  const items: ContextMenuItem[] = [
+    {
+      label: t("grid.copyExtractorConfigure"),
+      icon: Settings2,
+      action: openExtractorConfiguration,
+    },
+    defaultExtractorContextItem(),
+    { label: "", separator: true },
+  ];
   if (contextColumn.value) {
     items.push({ label: t("grid.copyCell"), action: copyCell });
   }
@@ -8812,12 +8781,22 @@ const gridContextMenuItems = computed<ContextMenuItem[]>(() => {
                           @cancel="cancelEdit"
                           @commit="commitGridEdit"
                         />
+                        <EnumCellEditor
+                          v-else-if="isBooleanGridCell(displayItems[cell.recordIndex], cell.valueIndex)"
+                          v-model="booleanEditorModelValue"
+                          :values="BOOLEAN_CELL_EDITOR_VALUES"
+                          :nullable="isBooleanGridColumnNullable(cell.valueIndex)"
+                          :initial-null="isGridCellInitialNull(displayItems[cell.recordIndex]?.id, cell.valueIndex)"
+                          cell-layout="transpose"
+                          @cancel="cancelEdit"
+                          @commit="commitBooleanGridEdit"
+                        />
                         <EnumCellEditor
                           v-else-if="isEnumGridColumn(cell.valueIndex)"
                           v-model="editValue"
                           :values="enumValuesForGridColumn(cell.valueIndex)"
                           :nullable="isEnumGridColumnNullable(cell.valueIndex)"
-                          :initial-null="isEnumEditorInitialNull(displayItems[cell.recordIndex]?.id, cell.valueIndex)"
+                          :initial-null="isGridCellInitialNull(displayItems[cell.recordIndex]?.id, cell.valueIndex)"
                           cell-layout="transpose"
                           @cancel="cancelEdit"
                           @commit="commitGridEdit"
@@ -8858,22 +8837,6 @@ const gridContextMenuItems = computed<ContextMenuItem[]>(() => {
                         <template v-if="draftCellPlaceholder(displayItems[cell.recordIndex], cell.valueIndex)">
                           <span class="text-muted-foreground/70 italic">{{ draftCellPlaceholder(displayItems[cell.recordIndex], cell.valueIndex) }}</span>
                         </template>
-                        <template v-else-if="isBooleanGridCell(displayItems[cell.recordIndex], cell.valueIndex) && !cell.isNull">
-                          <span class="flex w-full justify-center">
-                            <span
-                              class="flex h-4 w-4 shrink-0 items-center justify-center rounded border"
-                              :class="[booleanCellChecked(displayItems[cell.recordIndex]?.data[cell.valueIndex]) ? 'border-primary bg-primary text-primary-foreground' : '', canEditCellItem(displayItems[cell.recordIndex], cell.valueIndex) ? 'cursor-pointer' : '']"
-                              @click="cycleBooleanGridCell(displayItems[cell.recordIndex], cell.valueIndex, $event)"
-                            >
-                              <Check v-if="booleanCellChecked(displayItems[cell.recordIndex]?.data[cell.valueIndex])" class="h-3 w-3" />
-                            </span>
-                          </span>
-                        </template>
-                        <template v-else-if="isBooleanGridCell(displayItems[cell.recordIndex], cell.valueIndex)">
-                          <span class="flex w-full justify-center">
-                            <span :class="canEditCellItem(displayItems[cell.recordIndex], cell.valueIndex) ? 'cursor-pointer' : ''" @click="cycleBooleanGridCell(displayItems[cell.recordIndex], cell.valueIndex, $event)">{{ firstLineCellDisplayValue(cell.display) }}</span>
-                          </span>
-                        </template>
                         <template v-else>{{ firstLineCellDisplayValue(cell.display) }}</template>
                         <div v-if="cellDetailButtonVisible(cell.recordIndex, cell.valueIndex)" class="absolute right-2 top-1/2 flex -translate-y-1/2 items-center gap-1">
                           <LightDropdownMenu
@@ -9330,12 +9293,21 @@ const gridContextMenuItems = computed<ContextMenuItem[]>(() => {
                         @cancel="cancelEdit"
                         @commit="commitGridEdit"
                       />
+                      <EnumCellEditor
+                        v-else-if="isBooleanGridCell(getRowItem(canvasEditingCell.rowId), canvasEditingCell.actualColIdx)"
+                        v-model="booleanEditorModelValue"
+                        :values="BOOLEAN_CELL_EDITOR_VALUES"
+                        :nullable="isBooleanGridColumnNullable(canvasEditingCell.actualColIdx)"
+                        :initial-null="isGridCellInitialNull(canvasEditingCell.rowId, canvasEditingCell.actualColIdx)"
+                        @cancel="cancelEdit"
+                        @commit="commitBooleanGridEdit"
+                      />
                       <EnumCellEditor
                         v-else-if="isEnumGridColumn(canvasEditingCell.actualColIdx)"
                         v-model="editValue"
                         :values="enumValuesForGridColumn(canvasEditingCell.actualColIdx)"
                         :nullable="isEnumGridColumnNullable(canvasEditingCell.actualColIdx)"
-                        :initial-null="isEnumEditorInitialNull(canvasEditingCell.rowId, canvasEditingCell.actualColIdx)"
+                        :initial-null="isGridCellInitialNull(canvasEditingCell.rowId, canvasEditingCell.actualColIdx)"
                         @cancel="cancelEdit"
                         @commit="commitGridEdit"
                       />
@@ -9497,12 +9469,21 @@ const gridContextMenuItems = computed<ContextMenuItem[]>(() => {
                           @cancel="cancelEdit"
                           @commit="commitGridEdit"
                         />
+                        <EnumCellEditor
+                          v-else-if="isBooleanGridCell(item, col.actualColIdx)"
+                          v-model="booleanEditorModelValue"
+                          :values="BOOLEAN_CELL_EDITOR_VALUES"
+                          :nullable="isBooleanGridColumnNullable(col.actualColIdx)"
+                          :initial-null="isGridCellInitialNull(item.id, col.actualColIdx)"
+                          @cancel="cancelEdit"
+                          @commit="commitBooleanGridEdit"
+                        />
                         <EnumCellEditor
                           v-else-if="isEnumGridColumn(col.actualColIdx)"
                           v-model="editValue"
                           :values="enumValuesForGridColumn(col.actualColIdx)"
                           :nullable="isEnumGridColumnNullable(col.actualColIdx)"
-                          :initial-null="isEnumEditorInitialNull(item.id, col.actualColIdx)"
+                          :initial-null="isGridCellInitialNull(item.id, col.actualColIdx)"
                           @cancel="cancelEdit"
                           @commit="commitGridEdit"
                         />
@@ -9542,22 +9523,6 @@ const gridContextMenuItems = computed<ContextMenuItem[]>(() => {
                         <template v-if="draftCellPlaceholder(item, col.actualColIdx)">
                           <span class="text-muted-foreground/70 italic">{{ draftCellPlaceholder(item, col.actualColIdx) }}</span>
                         </template>
-                        <template v-else-if="isBooleanGridCell(item, col.actualColIdx) && !isNull(item.data[col.actualColIdx])">
-                          <span class="flex w-full justify-center">
-                            <span
-                              class="flex h-4 w-4 shrink-0 items-center justify-center rounded border"
-                              :class="[booleanCellChecked(item.data[col.actualColIdx]) ? 'border-primary bg-primary text-primary-foreground' : '', canEditCellItem(item, col.actualColIdx) ? 'cursor-pointer' : '']"
-                              @click="cycleBooleanGridCell(item, col.actualColIdx, $event)"
-                            >
-                              <Check v-if="booleanCellChecked(item.data[col.actualColIdx])" class="h-3 w-3" />
-                            </span>
-                          </span>
-                        </template>
-                        <template v-else-if="isBooleanGridCell(item, col.actualColIdx)">
-                          <span class="flex w-full justify-center">
-                            <span :class="canEditCellItem(item, col.actualColIdx) ? 'cursor-pointer' : ''" @click="cycleBooleanGridCell(item, col.actualColIdx, $event)">{{ firstLineCellDisplayValue(formatCellCached(item.data[col.actualColIdx], col.actualColIdx)) }}</span>
-                          </span>
-                        </template>
                         <template v-else>{{ firstLineCellDisplayValue(formatCellCached(item.data[col.actualColIdx], col.actualColIdx)) }}</template>
                         <div v-if="cellDetailButtonVisible(item.displayIndex, col.actualColIdx)" class="absolute right-2 top-1/2 flex -translate-y-1/2 items-center gap-1">
                           <LightDropdownMenu
diff --git a/apps/desktop/src/components/grid/DataGridExtractorDialog.vue b/apps/desktop/src/components/grid/DataGridExtractorDialog.vue
index bb35b6d18a..3f23fae78c 100644
--- a/apps/desktop/src/components/grid/DataGridExtractorDialog.vue
+++ b/apps/desktop/src/components/grid/DataGridExtractorDialog.vue
@@ -141,7 +141,7 @@ function save() {
       <div class="grid gap-4 md:grid-cols-[260px_minmax(0,1fr)]">
         <div class="space-y-3">
           <div class="space-y-1.5">
-            <Label>{{ t("grid.copyExtractorFormat") }}</Label>
+            <Label>{{ t("grid.copyExtractorDefaultFormat") }}</Label>
             <Select v-model="draftExtractor">
               <SelectTrigger><SelectValue /></SelectTrigger>
               <SelectContent>
diff --git a/apps/desktop/src/components/ui/CustomContextMenu.vue b/apps/desktop/src/components/ui/CustomContextMenu.vue
index 6bbd9a7548..790ec7ca19 100644
--- a/apps/desktop/src/components/ui/CustomContextMenu.vue
+++ b/apps/desktop/src/components/ui/CustomContextMenu.vue
@@ -282,10 +282,10 @@ onBeforeUnmount(() => {
           </div>
           <button v-else :disabled="itemIsDisabled(item)" :class="[...itemButtonClass(item.variant), activeSubIndex === index ? 'bg-accent text-accent-foreground' : '']" @click="handleItemClick(item)" @mouseenter="(e) => onItemMouseEnter(index, e)" @mouseleave="onItemMouseLeave">
             <span class="flex size-4 shrink-0 items-center justify-center">
-              <component :is="item.icon" v-if="item.icon" :class="['size-4', item.iconClass]" />
+              <Check v-if="item.checked" class="size-4 text-primary" />
+              <component :is="item.icon" v-else-if="item.icon" :class="['size-4', item.iconClass]" />
             </span>
             <span class="flex-1 whitespace-nowrap">{{ item.label }}</span>
-            <Check v-if="item.checked" class="ml-4 size-4 shrink-0 text-primary" />
             <span v-if="item.shortcut" class="ml-8 inline-flex shrink-0 items-center gap-1 text-muted-foreground">
               <kbd v-for="key in shortcutKeys(item.shortcut)" :key="key" class="min-w-4 rounded border border-border/70 bg-muted/60 px-1 py-0.5 text-center font-mono text-[10px] leading-none text-muted-foreground shadow-xs">{{ key }}</kbd>
             </span>
@@ -313,10 +313,10 @@ onBeforeUnmount(() => {
           </div>
           <button v-else :disabled="itemIsDisabled(child)" :class="itemButtonClass(child.variant)" @click="handleSubItemClick(child)">
             <span class="flex size-4 shrink-0 items-center justify-center">
-              <component :is="child.icon" v-if="child.icon" :class="['size-4', child.iconClass]" />
+              <Check v-if="child.checked" class="size-4 text-primary" />
+              <component :is="child.icon" v-else-if="child.icon" :class="['size-4', child.iconClass]" />
             </span>
             <span class="flex-1 whitespace-nowrap">{{ child.label }}</span>
-            <Check v-if="child.checked" class="ml-4 size-4 shrink-0 text-primary" />
             <span v-if="child.shortcut" class="ml-8 inline-flex shrink-0 items-center gap-1 text-muted-foreground">
               <kbd v-for="key in shortcutKeys(child.shortcut)" :key="key" class="min-w-4 rounded border border-border/70 bg-muted/60 px-1 py-0.5 text-center font-mono text-[10px] leading-none text-muted-foreground shadow-xs">{{ key }}</kbd>
             </span>
diff --git a/apps/desktop/src/components/ui/__tests__/CustomContextMenu.spec.ts b/apps/desktop/src/components/ui/__tests__/CustomContextMenu.spec.ts
index 4f27cb6626..0d756d2f78 100644
--- a/apps/desktop/src/components/ui/__tests__/CustomContextMenu.spec.ts
+++ b/apps/desktop/src/components/ui/__tests__/CustomContextMenu.spec.ts
@@ -164,7 +164,7 @@ describe("CustomContextMenu lifecycle", () => {
     app.unmount();
   });
 
-  it("renders checked state after the menu label", async () => {
+  it("renders checked state in the leading icon slot", async () => {
     const root = defineComponent({
       setup() {
         return () =>
@@ -188,7 +188,8 @@ describe("CustomContextMenu lifecycle", () => {
 
     const current = Array.from(document.body.querySelectorAll("button")).find((button) => button.textContent?.includes("Current"));
     const other = Array.from(document.body.querySelectorAll("button")).find((button) => button.textContent?.includes("Other"));
-    expect(current?.lastElementChild?.tagName.toLowerCase()).toBe("svg");
+    expect(current?.firstElementChild?.querySelector("svg")).not.toBeNull();
+    expect(current?.lastElementChild?.tagName.toLowerCase()).toBe("span");
     expect(other?.querySelector("svg")).toBeNull();
 
     app.unmount();
diff --git a/apps/desktop/src/composables/useDataGridEditor.ts b/apps/desktop/src/composables/useDataGridEditor.ts
index f08efd72fb..64b944087d 100644
--- a/apps/desktop/src/composables/useDataGridEditor.ts
+++ b/apps/desktop/src/composables/useDataGridEditor.ts
@@ -2,7 +2,6 @@ import { ref, shallowRef, computed, nextTick, watch, getCurrentInstance, onActiv
 import * as api from "@/lib/backend/api";
 import type { CellValue } from "@/lib/dataGrid/cellValue";
 import { coerceDataGridCellValue, dataGridCellEditorText } from "@/lib/dataGrid/dataGridCellCoercion";
-import { nextBooleanCellValue } from "@/lib/dataGrid/dataGridBooleanColumn";
 import { focusDataGridEditorWithoutScrolling, preserveDataGridScrollPosition } from "@/lib/dataGrid/dataGridEditorFocus";
 import { normalizeDataGridSaveError } from "@/lib/dataGrid/dataGridSql";
 import { rowStatusFilterAfterAddingRow, type RowStatusFilter } from "@/lib/dataGrid/gridRowStatus";
@@ -793,19 +792,6 @@ export function useDataGridEditor(options: UseDataGridEditorOptions) {
     }
   }
 
-  async function cycleBooleanCellValue(rowId: number, col: number, nullable: boolean) {
-    if (!editable.value || !canEditColumn(col)) return;
-    const item = getRowItem(rowId);
-    if (!item || item.isDeleted) return;
-    if (!item.isNew && !item.isDraft && !canEditExistingRows.value) return;
-    if (isSavingNewRow(item)) return;
-    const newVal = nextBooleanCellValue(item.data[col], nullable);
-    isCancelling = false;
-    suppressNextBlurCommit = false;
-    editingCell.value = { rowId, col };
-    await commitEditAndMaybeAutoSave({ explicitValue: newVal });
-  }
-
   async function commitEditFromBlur(options: CommitEditOptions = {}) {
     if (suppressNextBlurCommit) {
       suppressNextBlurCommit = false;
@@ -1732,7 +1718,6 @@ export function useDataGridEditor(options: UseDataGridEditorOptions) {
     startEdit,
     commitEdit,
     commitEditAndMaybeAutoSave,
-    cycleBooleanCellValue,
     commitEditFromBlur,
     applyCellValue,
     restoreCellValue,
diff --git a/apps/desktop/src/i18n/locales/en.ts b/apps/desktop/src/i18n/locales/en.ts
index b759a5155f..db0eb41c37 100644
--- a/apps/desktop/src/i18n/locales/en.ts
+++ b/apps/desktop/src/i18n/locales/en.ts
@@ -1124,6 +1124,7 @@ export default {
     copy: "Copy",
     copyExtractorWithHeaders: "{format} with Headers",
     copyExtractorOneRow: "One-row",
+    copyExtractorJsonArray: "JSON Array",
     copyExtractorSqlInList: "SQL IN List",
     copyExtractorSqlInserts: "SQL Inserts",
     copyExtractorSqlInsertsWithPrimaryKeys: "SQL Inserts (with Primary Keys)",
@@ -1172,7 +1173,7 @@ export default {
     copyJson: "Copy JSON",
     copyDdl: "Copy DDL",
     copyCell: "Copy Cell",
-    copyRow: "Copy Row (JSON)",
+    copyRow: "Copy Entire Row (JSON Object)",
     copyColumnJson: "Copy Column (JSON)",
     copyColumnNames: "Copy Column Names",
     copyColumnNamesSelected: "Copy Selected Column Names ({count})",
@@ -1389,7 +1390,7 @@ export default {
     deleteRows: "Delete {count} Rows",
     cloneRows: "Clone {count} as New Rows",
     restoreRows: "Restore {count} Rows",
-    copyRows: "Copy {count} Rows (JSON)",
+    copyRows: "Copy {count} Rows (JSON Array)",
     copyColumnsJson: "Copy {count} Columns (JSON)",
     selectedRows: "{count} rows selected",
     restoreRow: "Restore Row",
diff --git a/apps/desktop/src/i18n/locales/es.ts b/apps/desktop/src/i18n/locales/es.ts
index 4366846d62..160168b463 100644
--- a/apps/desktop/src/i18n/locales/es.ts
+++ b/apps/desktop/src/i18n/locales/es.ts
@@ -1075,7 +1075,7 @@ export default withEnglishFallback({
     copyJson: "Copiar JSON",
     copyDdl: "Copiar DDL",
     copyCell: "Copiar celda",
-    copyRow: "Copiar fila (JSON)",
+    copyRow: "Copiar fila completa (objeto JSON)",
     copyColumnJson: "Copiar columna (JSON)",
     copyColumnNames: "Copiar nombres de columnas",
     copyColumnNamesSelected: "Copiar nombres de columnas seleccionadas ({count})",
@@ -1273,7 +1273,7 @@ export default withEnglishFallback({
     deleteRows: "Eliminar {count} filas",
     cloneRows: "Clonar {count} como filas nuevas",
     restoreRows: "Restaurar {count} filas",
-    copyRows: "Copiar {count} filas (JSON)",
+    copyRows: "Copiar {count} filas (array JSON)",
     copyColumnsJson: "Copiar {count} columnas (JSON)",
     selectedRows: "{count} filas seleccionadas",
     restoreRow: "Restaurar fila",
@@ -1443,6 +1443,7 @@ export default withEnglishFallback({
     filterBuilderNoMatchingColumns: "Sin columnas coincidentes",
     copyExtractorWithHeaders: "{format} (con encabezados)",
     copyExtractorOneRow: "CSV de una fila",
+    copyExtractorJsonArray: "Array JSON",
     copyExtractorSqlInList: "Lista SQL IN",
     copyExtractorSqlInserts: "Sentencias SQL INSERT",
     copyExtractorSqlInsertsWithPrimaryKeys: "Sentencias SQL INSERT (con claves primarias)",
diff --git a/apps/desktop/src/i18n/locales/it.ts b/apps/desktop/src/i18n/locales/it.ts
index a9604a4826..0f092cb04b 100644
--- a/apps/desktop/src/i18n/locales/it.ts
+++ b/apps/desktop/src/i18n/locales/it.ts
@@ -1073,7 +1073,7 @@ export default withEnglishFallback({
     copyJson: "Copia JSON",
     copyDdl: "Copia DDL",
     copyCell: "Copia Cella",
-    copyRow: "Copia Riga (JSON)",
+    copyRow: "Copia intera riga (oggetto JSON)",
     copyColumnJson: "Copia Colonna (JSON)",
     copyColumnNames: "Copia Nomi Colonne",
     copyColumnNamesSelected: "Copia Nomi Colonne Selezionate ({count})",
@@ -1271,7 +1271,7 @@ export default withEnglishFallback({
     deleteRows: "Elimina {count} Righe",
     cloneRows: "Clona {count} come Nuove Righe",
     restoreRows: "Ripristina {count} Righe",
-    copyRows: "Copia {count} Righe (JSON)",
+    copyRows: "Copia {count} righe (array JSON)",
     copyColumnsJson: "Copia {count} Colonne (JSON)",
     selectedRows: "{count} righe selezionate",
     restoreRow: "Ripristina Riga",
@@ -1441,6 +1441,7 @@ export default withEnglishFallback({
     filterBuilderNoMatchingColumns: "Nessun campo corrispondente",
     copyExtractorWithHeaders: "{format} (con intestazione)",
     copyExtractorOneRow: "CSV a riga singola",
+    copyExtractorJsonArray: "Array JSON",
     copyExtractorSqlInList: "Lista SQL IN",
     copyExtractorSqlInserts: "Istruzioni SQL INSERT",
     copyExtractorSqlInsertsWithPrimaryKeys: "Istruzioni SQL INSERT (con chiavi primarie)",
diff --git a/apps/desktop/src/i18n/locales/ja.ts b/apps/desktop/src/i18n/locales/ja.ts
index 0459018427..4438d81e66 100644
--- a/apps/desktop/src/i18n/locales/ja.ts
+++ b/apps/desktop/src/i18n/locales/ja.ts
@@ -1093,7 +1093,7 @@ export default withEnglishFallback({
     copyJson: "JSON をコピー",
     copyDdl: "DDLをコピー",
     copyCell: "セルをコピー",
-    copyRow: "行をコピー (JSON)",
+    copyRow: "行全体をコピー（JSON オブジェクト）",
     copyColumnJson: "列をコピー (JSON)",
     copyColumnNames: "すべての列名をコピー",
     copyColumnNamesSelected: "選択した列名をコピー（{count} 列）",
@@ -1289,7 +1289,7 @@ export default withEnglishFallback({
     deleteRows: "{count}行を削除",
     cloneRows: "{count}行を新しい行として複製",
     restoreRows: "{count}行を復元",
-    copyRows: "{count}行をコピー (JSON)",
+    copyRows: "{count}行をコピー（JSON 配列）",
     copyColumnsJson: "{count}列をコピー (JSON)",
     selectedRows: "{count}行選択中",
     restoreRow: "行を復元",
@@ -1463,6 +1463,7 @@ export default withEnglishFallback({
     filterBuilderNoMatchingColumns: "一致するフィールドがありません",
     copyExtractorWithHeaders: "{format}（ヘッダー付き）",
     copyExtractorOneRow: "単行CSV",
+    copyExtractorJsonArray: "JSON 配列",
     copyExtractorSqlInList: "SQL IN リスト",
     copyExtractorSqlInserts: "SQL INSERT 文",
     copyExtractorSqlInsertsWithPrimaryKeys: "SQL INSERT 文（主キーを含む）",
diff --git a/apps/desktop/src/i18n/locales/ko.ts b/apps/desktop/src/i18n/locales/ko.ts
index 4312f725f3..ed4e041dc0 100644
--- a/apps/desktop/src/i18n/locales/ko.ts
+++ b/apps/desktop/src/i18n/locales/ko.ts
@@ -1039,6 +1039,7 @@ export default withEnglishFallback({
     copy: "복사",
     copyExtractorWithHeaders: "머리글 포함 {format}",
     copyExtractorOneRow: "단일 행",
+    copyExtractorJsonArray: "JSON 배열",
     copyExtractorSqlInList: "SQL IN 목록",
     copyExtractorSqlInserts: "SQL INSERT",
     copyExtractorSqlInsertsWithPrimaryKeys: "SQL INSERT (기본 키 포함)",
@@ -1087,7 +1088,7 @@ export default withEnglishFallback({
     copyJson: "JSON 복사",
     copyDdl: "DDL 복사",
     copyCell: "셀 복사",
-    copyRow: "행 복사 (JSON)",
+    copyRow: "전체 행 복사(JSON 객체)",
     copyColumnJson: "컬럼 복사 (JSON)",
     copyColumnNames: "컬럼 이름 복사",
     copyColumnNamesSelected: "선택한 컬럼 이름 복사 ({count})",
@@ -1294,7 +1295,7 @@ export default withEnglishFallback({
     deleteRows: "{count}행 삭제",
     cloneRows: "{count}개를 새 행으로 복제",
     restoreRows: "{count}행 복원",
-    copyRows: "{count}행 복사 (JSON)",
+    copyRows: "{count}행 복사(JSON 배열)",
     copyColumnsJson: "{count}컬럼 복사 (JSON)",
     selectedRows: "{count}행 선택됨",
     restoreRow: "행 복원",
diff --git a/apps/desktop/src/i18n/locales/pt-BR.ts b/apps/desktop/src/i18n/locales/pt-BR.ts
index 8b0cdc96ca..f9450321af 100644
--- a/apps/desktop/src/i18n/locales/pt-BR.ts
+++ b/apps/desktop/src/i18n/locales/pt-BR.ts
@@ -1075,7 +1075,7 @@ export default withEnglishFallback({
     copyJson: "Copiar JSON",
     copyDdl: "Copiar DDL",
     copyCell: "Copiar Célula",
-    copyRow: "Copiar Linha (JSON)",
+    copyRow: "Copiar linha inteira (objeto JSON)",
     copyColumnJson: "Copiar Coluna (JSON)",
     copyColumnNames: "Copiar Nomes das Colunas",
     copyColumnNamesSelected: "Copiar Nomes das Colunas Selecionadas ({count})",
@@ -1273,7 +1273,7 @@ export default withEnglishFallback({
     deleteRows: "Excluir {count} Linhas",
     cloneRows: "Clonar {count} como Novas Linhas",
     restoreRows: "Restaurar {count} Linhas",
-    copyRows: "Copiar {count} Linhas (JSON)",
+    copyRows: "Copiar {count} linhas (array JSON)",
     copyColumnsJson: "Copiar {count} Colunas (JSON)",
     selectedRows: "{count} linhas selecionadas",
     restoreRow: "Restaurar Linha",
@@ -1443,6 +1443,7 @@ export default withEnglishFallback({
     filterBuilderNoMatchingColumns: "Nenhum campo correspondente",
     copyExtractorWithHeaders: "{format} (com cabeçalhos)",
     copyExtractorOneRow: "CSV de linha única",
+    copyExtractorJsonArray: "Array JSON",
     copyExtractorSqlInList: "Lista SQL IN",
     copyExtractorSqlInserts: "Instruções SQL INSERT",
     copyExtractorSqlInsertsWithPrimaryKeys: "Instruções SQL INSERT (com chaves primárias)",
diff --git a/apps/desktop/src/i18n/locales/zh-CN.ts b/apps/desktop/src/i18n/locales/zh-CN.ts
index d923d790fe..919f5eceb8 100644
--- a/apps/desktop/src/i18n/locales/zh-CN.ts
+++ b/apps/desktop/src/i18n/locales/zh-CN.ts
@@ -1125,6 +1125,7 @@ export default withEnglishFallback({
     copy: "复制",
     copyExtractorWithHeaders: "{format}（含表头）",
     copyExtractorOneRow: "单行 CSV",
+    copyExtractorJsonArray: "JSON 数组",
     copyExtractorSqlInList: "SQL IN 列表",
     copyExtractorSqlInserts: "SQL INSERT 语句",
     copyExtractorSqlInsertsWithPrimaryKeys: "SQL INSERT 语句（含主键）",
@@ -1133,7 +1134,7 @@ export default withEnglishFallback({
     copyExtractorWhereClause: "WHERE 条件",
     copyExtractorPipeSeparated: "竖线分隔",
     copyExtractorPretty: "表格文本",
-    copyExtractorConfigure: "配置数据提取器…",
+    copyExtractorConfigure: "设置复制格式…",
     copyExtractorDefaultFormat: "默认复制格式",
     copyExtractorFormat: "提取器",
     copyExtractorColumnSeparator: "列分隔符",
@@ -1173,7 +1174,7 @@ export default withEnglishFallback({
     copyJson: "复制 JSON",
     copyDdl: "复制 DDL",
     copyCell: "复制单元格",
-    copyRow: "复制行 (JSON)",
+    copyRow: "复制整行（JSON 对象）",
     copyColumnJson: "复制列 (JSON)",
     copyColumnNames: "复制全部列名",
     copyColumnNamesSelected: "复制选中列名（{count} 列）",
@@ -1390,7 +1391,7 @@ export default withEnglishFallback({
     deleteRows: "删除 {count} 行",
     cloneRows: "克隆 {count} 行为新行",
     restoreRows: "恢复 {count} 行",
-    copyRows: "复制 {count} 行 (JSON)",
+    copyRows: "复制 {count} 行（JSON 数组）",
     copyColumnsJson: "复制 {count} 列 (JSON)",
     selectedRows: "已选 {count} 行",
     restoreRow: "恢复行",
diff --git a/apps/desktop/src/i18n/locales/zh-TW.ts b/apps/desktop/src/i18n/locales/zh-TW.ts
index c50988b315..db4a42158a 100644
--- a/apps/desktop/src/i18n/locales/zh-TW.ts
+++ b/apps/desktop/src/i18n/locales/zh-TW.ts
@@ -1074,7 +1074,7 @@ export default withEnglishFallback({
     copyJson: "複製 JSON",
     copyDdl: "複製 DDL",
     copyCell: "複製儲存格",
-    copyRow: "複製整筆 (JSON)",
+    copyRow: "複製整筆（JSON 物件）",
     copyColumnJson: "複製欄 (JSON)",
     copyColumnNames: "複製全部欄名",
     copyColumnNamesSelected: "複製選取欄名（{count} 欄）",
@@ -1272,7 +1272,7 @@ export default withEnglishFallback({
     deleteRows: "刪除 {count} 筆",
     cloneRows: "複製 {count} 筆為新資料",
     restoreRows: "復原 {count} 筆",
-    copyRows: "複製 {count} 筆 (JSON)",
+    copyRows: "複製 {count} 筆（JSON 陣列）",
     copyColumnsJson: "複製 {count} 欄 (JSON)",
     selectedRows: "已選 {count} 筆",
     restoreRow: "復原資料",
@@ -1442,6 +1442,7 @@ export default withEnglishFallback({
     filterBuilderNoMatchingColumns: "沒有匹配的欄位",
     copyExtractorWithHeaders: "{format}（含表頭）",
     copyExtractorOneRow: "單行 CSV",
+    copyExtractorJsonArray: "JSON 陣列",
     copyExtractorSqlInList: "SQL IN 列表",
     copyExtractorSqlInserts: "SQL INSERT 語句",
     copyExtractorSqlInsertsWithPrimaryKeys: "SQL INSERT 語句（含主鍵）",
diff --git a/apps/desktop/src/lib/dataGrid/canvasDataGridRenderer.ts b/apps/desktop/src/lib/dataGrid/canvasDataGridRenderer.ts
index 7a3f16f663..1fc551c789 100644
--- a/apps/desktop/src/lib/dataGrid/canvasDataGridRenderer.ts
+++ b/apps/desktop/src/lib/dataGrid/canvasDataGridRenderer.ts
@@ -1,7 +1,6 @@
 import { firstLineCellDisplayValue, type CellValue } from "@/lib/dataGrid/cellValue";
 import type { RowStatus } from "@/lib/dataGrid/gridRowStatus";
 import { DATA_GRID_DARK_SEARCH_COLORS, resolveDataGridPaintTheme, type DataGridPaintTheme } from "@/lib/dataGrid/dataGridPaintTheme";
-import { BOOLEAN_CHECKBOX_SIZE, isBooleanCheckboxValue, normalizeBooleanCellValue } from "@/lib/dataGrid/dataGridBooleanColumn";
 
 export const CANVAS_DATA_GRID_ROW_HEIGHT = 26;
 
@@ -73,7 +72,6 @@ export interface DrawCanvasDataGridOptions {
   searchMatchKeys: ReadonlySet<number>;
   currentSearchMatch: CanvasSearchMatch | null;
   formatCell: (value: CellValue, columnIndex: number) => string;
-  columnIsBoolean?: (columnIndex: number) => boolean;
   draftCellPlaceholder?: string;
   isRowActive: (rowIndex: number) => boolean;
   rowCellsUseSelectionVisual: (rowId: number) => boolean;
@@ -228,29 +226,6 @@ function alignCanvasPixel(value: number, dpr: number): number {
   return Math.round(value * dpr) / dpr;
 }
 
-function drawBooleanCheckbox(ctx: CanvasRenderingContext2D, options: { drawX: number; y: number; colWidth: number; scaleX: number; scaleY: number; theme: DataGridPaintTheme; checked: boolean }): void {
-  const { drawX, y, colWidth, scaleX, scaleY, theme, checked } = options;
-  const size = BOOLEAN_CHECKBOX_SIZE;
-  const boxX = alignCanvasPixel(drawX + (colWidth - size) / 2, scaleX);
-  const boxY = alignCanvasPixel(y + (CANVAS_DATA_GRID_ROW_HEIGHT - size) / 2, scaleY);
-  ctx.lineWidth = 1;
-  if (checked) {
-    ctx.fillStyle = theme.primary;
-    ctx.fillRect(boxX, boxY, size, size);
-    ctx.strokeStyle = theme.background;
-    ctx.lineWidth = 2;
-    ctx.beginPath();
-    ctx.moveTo(boxX + 3, boxY + size / 2);
-    ctx.lineTo(boxX + size / 2 - 0.5, boxY + size - 3.5);
-    ctx.lineTo(boxX + size - 2.5, boxY + 3);
-    ctx.stroke();
-    ctx.lineWidth = 1;
-  } else {
-    ctx.strokeStyle = theme.mutedForeground;
-    ctx.strokeRect(boxX + 0.5, boxY + 0.5, size - 1, size - 1);
-  }
-}
-
 function crispCanvasLine(value: number, dpr: number): number {
   return alignCanvasPixel(value, dpr) + 0.5 / dpr;
 }
@@ -335,7 +310,6 @@ export function drawCanvasDataGrid(options: DrawCanvasDataGridOptions) {
     frozenColumnCount = 0,
     columnAligns,
     rightAlignedActionCell,
-    columnIsBoolean,
   } = options;
   const fallbackRatio = Math.max(1, options.pixelRatio ?? window.devicePixelRatio ?? 1);
   const { pixelWidth, pixelHeight, scaleX, scaleY } = resolveCanvasBackingStoreMetrics({
@@ -502,43 +476,26 @@ export function drawCanvasDataGrid(options: DrawCanvasDataGridOptions) {
       ctx.rect(clippedX, y, Math.min(cellPaintWidth, width - clippedX), CANVAS_DATA_GRID_ROW_HEIGHT);
       ctx.clip();
       const value = item.data[actualColIdx];
-      const isBooleanCell = columnIsBoolean?.(actualColIdx) === true && isBooleanCheckboxValue(value);
       const isRightAlign = columnAligns?.[visibleColIdx] === "right";
       const isEditingThisCell = editingCell?.rowId === item.id && editingCell.col === actualColIdx;
-      const isBooleanNullCell = isBooleanCell && value === null && !isEditingThisCell;
-      ctx.textAlign = isBooleanNullCell ? "center" : isRightAlign ? "right" : "left";
+      ctx.textAlign = isRightAlign ? "right" : "left";
       ctx.fillStyle = value === null ? theme.mutedForeground : theme.foreground;
       ctx.font = value === null ? italicFont : tabularFont;
       setCanvasNumericVariant(ctx, value === null ? "normal" : "tabular-nums");
       const reservedWidth = rightAlignedActionCell?.rowIndex === item.displayIndex && rightAlignedActionCell.visibleColIdx === visibleColIdx ? rightAlignedActionCell.reservedWidth : 0;
       const { textAnchorX, maxWidth: cellMaxWidth } = resolveCanvasCellTextLayout({ drawX, colWidth, dpr: scaleX, isRightAlign, reservedWidth });
-      if (isBooleanCell && value !== null && !isEditingThisCell) {
-        drawBooleanCheckbox(ctx, { drawX, y, colWidth, scaleX, scaleY, theme, checked: normalizeBooleanCellValue(value) === true });
-        if (item.isDeleted) {
-          const boxX = alignCanvasPixel(drawX + (colWidth - BOOLEAN_CHECKBOX_SIZE) / 2, scaleX);
-          const strikeY = alignCanvasPixel(y + CANVAS_DATA_GRID_ROW_HEIGHT / 2, scaleY);
-          ctx.strokeStyle = theme.foreground;
-          ctx.lineWidth = 1;
-          ctx.beginPath();
-          ctx.moveTo(boxX - 1, strikeY);
-          ctx.lineTo(alignCanvasPixel(boxX + BOOLEAN_CHECKBOX_SIZE + 1, scaleX), strikeY);
-          ctx.stroke();
-        }
-      } else {
-        const rawDisplayText = item.isDraft && value === null ? (draftCellPlaceholder ?? "") : formatCell(value, actualColIdx);
-        const displayText = isEditingThisCell ? "" : firstLineCellDisplayValue(rawDisplayText);
-        const text = isEditingThisCell ? displayText : fitCanvasText(ctx, displayText, cellMaxWidth, isBooleanNullCell ? "left" : isRightAlign ? "right" : "left");
-        const anchorX = isBooleanNullCell ? alignCanvasPixel(drawX + colWidth / 2, scaleX) : textAnchorX;
-        ctx.fillText(text, anchorX, textY);
-        if (item.isDeleted && text) {
-          const textWidth = ctx.measureText(text).width;
-          const lineStartX = isBooleanNullCell ? anchorX - textWidth / 2 : isRightAlign ? textAnchorX - textWidth : textAnchorX;
-          ctx.strokeStyle = theme.foreground;
-          ctx.beginPath();
-          ctx.moveTo(lineStartX, textY);
-          ctx.lineTo(alignCanvasPixel(lineStartX + textWidth, scaleX), textY);
-          ctx.stroke();
-        }
+      const rawDisplayText = item.isDraft && value === null ? (draftCellPlaceholder ?? "") : formatCell(value, actualColIdx);
+      const displayText = isEditingThisCell ? "" : firstLineCellDisplayValue(rawDisplayText);
+      const text = isEditingThisCell ? displayText : fitCanvasText(ctx, displayText, cellMaxWidth, isRightAlign ? "right" : "left");
+      ctx.fillText(text, textAnchorX, textY);
+      if (item.isDeleted && text) {
+        const textWidth = ctx.measureText(text).width;
+        const lineStartX = isRightAlign ? textAnchorX - textWidth : textAnchorX;
+        ctx.strokeStyle = theme.foreground;
+        ctx.beginPath();
+        ctx.moveTo(lineStartX, textY);
+        ctx.lineTo(alignCanvasPixel(lineStartX + textWidth, scaleX), textY);
+        ctx.stroke();
       }
       ctx.restore();
       setCanvasNumericVariant(ctx, "normal");
diff --git a/apps/desktop/src/lib/dataGrid/dataGridBooleanColumn.ts b/apps/desktop/src/lib/dataGrid/dataGridBooleanColumn.ts
index d75c9a9d90..2d29dcef9e 100644
--- a/apps/desktop/src/lib/dataGrid/dataGridBooleanColumn.ts
+++ b/apps/desktop/src/lib/dataGrid/dataGridBooleanColumn.ts
@@ -1,15 +1,12 @@
 import type { DatabaseType } from "@/types/database";
 
-export const BOOLEAN_CHECKBOX_SIZE = 13;
-
-const MYSQL_BIT_BOOLEAN_DATABASE_TYPES = new Set<DatabaseType>(["mysql"]);
+export const BOOLEAN_CELL_EDITOR_VALUES = ["true", "false"];
 
 export function isBooleanColumnType(dataType: string | undefined, databaseType?: DatabaseType): boolean {
   if (!dataType) return false;
   const normalized = dataType.trim().toLowerCase();
   if (normalized === "boolean" || normalized === "bool") return true;
   if (databaseType === "sqlserver") return normalized === "bit";
-  if (databaseType && MYSQL_BIT_BOOLEAN_DATABASE_TYPES.has(databaseType)) return normalized === "bit" || normalized === "bit(1)";
   return false;
 }
 
@@ -26,26 +23,20 @@ export function normalizeBooleanCellValue(value: unknown): boolean | null {
   return null;
 }
 
-export function isBooleanCheckboxValue(value: unknown): boolean {
+export function isBooleanCellValue(value: unknown): boolean {
   return value === null || normalizeBooleanCellValue(value) !== null;
 }
 
-export function nextBooleanCellValue(current: unknown, nullable: boolean): boolean | null {
-  const normalized = normalizeBooleanCellValue(current);
-  if (normalized === true) return false;
-  if (normalized === false) return nullable ? null : true;
-  return true;
+export function booleanCellEditorValue(value: unknown): string {
+  const normalized = normalizeBooleanCellValue(value);
+  if (normalized === true) return "true";
+  if (normalized === false) return "false";
+  return "";
 }
 
-export function booleanCheckboxRect(cell: { left: number; top: number; width: number; height: number }): { left: number; top: number; size: number } {
-  return {
-    left: cell.left + (cell.width - BOOLEAN_CHECKBOX_SIZE) / 2,
-    top: cell.top + (cell.height - BOOLEAN_CHECKBOX_SIZE) / 2,
-    size: BOOLEAN_CHECKBOX_SIZE,
-  };
-}
-
-export function isPointInBooleanCheckbox(point: { x: number; y: number }, cell: { left: number; top: number; width: number; height: number }): boolean {
-  const rect = booleanCheckboxRect(cell);
-  return point.x >= rect.left && point.x <= rect.left + rect.size && point.y >= rect.top && point.y <= rect.top + rect.size;
+export function parseBooleanCellEditorValue(value: string | null): boolean | null | undefined {
+  if (value === null) return null;
+  if (value === "true") return true;
+  if (value === "false") return false;
+  return undefined;
 }
diff --git a/packages/app-tests/dataGridBooleanColumn.test.ts b/packages/app-tests/dataGridBooleanColumn.test.ts
index f468b6a3c7..59f793ce71 100644
--- a/packages/app-tests/dataGridBooleanColumn.test.ts
+++ b/packages/app-tests/dataGridBooleanColumn.test.ts
@@ -1,7 +1,7 @@
 import { strict as assert } from "node:assert";
 import { readFileSync } from "node:fs";
 import { test } from "vitest";
-import { isBooleanCheckboxValue, isBooleanColumnType, nextBooleanCellValue, normalizeBooleanCellValue } from "../../apps/desktop/src/lib/dataGrid/dataGridBooleanColumn.ts";
+import { BOOLEAN_CELL_EDITOR_VALUES, booleanCellEditorValue, isBooleanCellValue, isBooleanColumnType, normalizeBooleanCellValue, parseBooleanCellEditorValue } from "../../apps/desktop/src/lib/dataGrid/dataGridBooleanColumn.ts";
 import { resolveDataGridColumnsByResultIndex } from "../../apps/desktop/src/lib/dataGrid/dataGridColumnMetadata.ts";
 import type { ColumnInfo } from "../../apps/desktop/src/types/database.ts";
 
@@ -20,18 +20,19 @@ test("detects boolean types using database semantics", () => {
   assert.equal(isBooleanColumnType("boolean"), true);
   assert.equal(isBooleanColumnType("bool", "postgres"), true);
   assert.equal(isBooleanColumnType("bit", "sqlserver"), true);
-  assert.equal(isBooleanColumnType("bit", "mysql"), true);
-  assert.equal(isBooleanColumnType("bit(1)", "mysql"), true);
+  assert.equal(isBooleanColumnType("boolean", "mysql"), true);
   assert.equal(isBooleanColumnType("  BOOLEAN ", "postgres"), true);
 });
 
-test("does not treat PostgreSQL bit strings or unknown bit semantics as boolean", () => {
+test("does not treat database bit strings or MySQL integer aliases as boolean", () => {
   assert.equal(isBooleanColumnType("bit", "postgres"), false);
   assert.equal(isBooleanColumnType("bit(1)", "postgres"), false);
   assert.equal(isBooleanColumnType("bit varying", "postgres"), false);
   assert.equal(isBooleanColumnType("varbit", "postgres"), false);
   assert.equal(isBooleanColumnType("bit", "opengauss"), false);
   assert.equal(isBooleanColumnType("bit", undefined), false);
+  assert.equal(isBooleanColumnType("bit", "mysql"), false);
+  assert.equal(isBooleanColumnType("bit(1)", "mysql"), false);
   assert.equal(isBooleanColumnType("bit(8)", "mysql"), false);
   assert.equal(isBooleanColumnType("tinyint(1)", "mysql"), false);
   assert.equal(isBooleanColumnType(undefined, "mysql"), false);
@@ -51,26 +52,31 @@ test("normalizes raw cell values to a tri-state boolean", () => {
   assert.equal(normalizeBooleanCellValue("maybe"), null);
 });
 
-test("shows checkboxes only for recognized boolean cell values", () => {
-  assert.equal(isBooleanCheckboxValue(true), true);
-  assert.equal(isBooleanCheckboxValue(0), true);
-  assert.equal(isBooleanCheckboxValue("false"), true);
-  assert.equal(isBooleanCheckboxValue(null), true);
-  assert.equal(isBooleanCheckboxValue(undefined), false);
-  assert.equal(isBooleanCheckboxValue("maybe"), false);
-  assert.equal(isBooleanCheckboxValue({}), false);
+test("opens boolean editors only for recognized boolean cell values", () => {
+  assert.equal(isBooleanCellValue(true), true);
+  assert.equal(isBooleanCellValue(0), true);
+  assert.equal(isBooleanCellValue("false"), true);
+  assert.equal(isBooleanCellValue(null), true);
+  assert.equal(isBooleanCellValue(undefined), false);
+  assert.equal(isBooleanCellValue("maybe"), false);
+  assert.equal(isBooleanCellValue({}), false);
 });
 
-test("cycles true -> false -> true for NOT NULL columns", () => {
-  assert.equal(nextBooleanCellValue(true, false), false);
-  assert.equal(nextBooleanCellValue(false, false), true);
-  assert.equal(nextBooleanCellValue(null, false), true);
+test("normalizes boolean values for the enum-style editor", () => {
+  assert.deepEqual(BOOLEAN_CELL_EDITOR_VALUES, ["true", "false"]);
+  assert.equal(booleanCellEditorValue(true), "true");
+  assert.equal(booleanCellEditorValue(1), "true");
+  assert.equal(booleanCellEditorValue(false), "false");
+  assert.equal(booleanCellEditorValue("0"), "false");
+  assert.equal(booleanCellEditorValue(null), "");
+  assert.equal(booleanCellEditorValue("maybe"), "");
 });
 
-test("cycles true -> false -> null -> true for nullable columns", () => {
-  assert.equal(nextBooleanCellValue(true, true), false);
-  assert.equal(nextBooleanCellValue(false, true), null);
-  assert.equal(nextBooleanCellValue(null, true), true);
+test("parses explicit enum-style boolean selections", () => {
+  assert.equal(parseBooleanCellEditorValue("true"), true);
+  assert.equal(parseBooleanCellEditorValue("false"), false);
+  assert.equal(parseBooleanCellEditorValue(null), null);
+  assert.equal(parseBooleanCellEditorValue("maybe"), undefined);
 });
 
 test("indexes table metadata once and resolves source-column aliases", () => {
@@ -87,18 +93,14 @@ test("indexes table metadata once and resolves source-column aliases", () => {
   assert.equal(resolved[2], undefined);
 });
 
-test("runs canvas selection before toggling a checkbox", () => {
-  const source = readFileSync("apps/desktop/src/components/grid/DataGrid.vue", "utf8");
-  const start = source.indexOf("function onCanvasMouseDown");
-  const end = source.indexOf("function onCanvasContext", start);
-  const handler = source.slice(start, end);
-  const selectionIndex = handler.indexOf("handleDataCellMousedown");
-  const toggleIndex = handler.indexOf("tryCycleBooleanCheckboxOnCanvasMouseDown");
+test("uses the enum editor for boolean cells without checkbox rendering or click cycling", () => {
+  const gridSource = readFileSync("apps/desktop/src/components/grid/DataGrid.vue", "utf8");
+  const rendererSource = readFileSync("apps/desktop/src/lib/dataGrid/canvasDataGridRenderer.ts", "utf8");
 
-  assert.ok(start >= 0 && end > start);
-  assert.ok(selectionIndex >= 0);
-  assert.ok(toggleIndex >= 0);
-  assert.ok(selectionIndex < toggleIndex);
+  assert.match(gridSource, /v-else-if="isBooleanGridCell\([^\n]+"[\s\S]*?v-model="booleanEditorModelValue"[\s\S]*?:values="BOOLEAN_CELL_EDITOR_VALUES"/);
+  assert.match(gridSource, /@commit="commitBooleanGridEdit"/);
+  assert.doesNotMatch(gridSource, /cycleBooleanCellValue|tryCycleBooleanCheckboxOnCanvasMouseDown|booleanCellChecked/);
+  assert.doesNotMatch(rendererSource, /drawBooleanCheckbox|BOOLEAN_CHECKBOX_SIZE|columnIsBoolean/);
 });
 
 test("uses the indexed metadata lookup in grid hot paths", () => {