diff --git a/apps/desktop/src/components/grid/DataGridFilterBuilder.vue b/apps/desktop/src/components/grid/DataGridFilterBuilder.vue
index 6d9a7f922..7fa21f1e4 100644
--- a/apps/desktop/src/components/grid/DataGridFilterBuilder.vue
+++ b/apps/desktop/src/components/grid/DataGridFilterBuilder.vue
@@ -1,4 +1,5 @@
 <script setup lang="ts">
+import { nextTick, ref, watch } from "vue";
 import { Eye, EyeOff, Plus, Search, Trash2 } from "@lucide/vue";
 import { useI18n } from "vue-i18n";
 import { Button } from "@/components/ui/button";
@@ -31,24 +32,168 @@ const emit = defineEmits<{
   updateRule: [id: string, patch: Partial<DataGridStructuredFilterRule>];
   "update:columnSearch": [value: string];
 }>();
+const columnSearchInputs = new Map<string, HTMLInputElement>();
+const filterRuleElements = new Map<string, HTMLElement>();
+const pendingValueFocus = new Set<string>();
+const pendingKeyboardAddFocus = new Set<string>();
+const openColumnSelectIds = ref(new Set<string>());
+const activeColumnIndexes = ref<Record<string, number>>({});
+let ruleIdsBeforeKeyboardAdd: Set<string> | undefined;
 
 function usesExpandedLayout(mode: DataGridContextFilterMode) {
   return filterModeUsesList(mode) || filterModeUsesRange(mode);
 }
 
-function updateRuleColumn(id: string, value: unknown) {
-  emit("updateRule", id, { columnName: String(value) });
+function updateRuleColumn(rule: DataGridStructuredFilterRule, value: unknown, focusValue = true) {
+  if (focusValue && filterModeNeedsValue(rule.mode)) pendingValueFocus.add(rule.id);
+  emit("updateRule", rule.id, { columnName: String(value) });
   emit("update:columnSearch", "");
 }
 
-function handleColumnSearchKeydown(event: KeyboardEvent) {
+function setColumnSearchInput(id: string, element: unknown) {
+  if (!(element instanceof HTMLInputElement)) {
+    columnSearchInputs.delete(id);
+    return;
+  }
+  columnSearchInputs.set(id, element);
+  if (openColumnSelectIds.value.has(id)) window.requestAnimationFrame(() => element.focus());
+}
+
+function setFilterRuleElement(id: string, element: unknown) {
+  if (element instanceof HTMLElement) filterRuleElements.set(id, element);
+  else filterRuleElements.delete(id);
+}
+
+function activeColumnIndex(id: string): number {
+  return activeColumnIndexes.value[id] ?? -1;
+}
+
+function setActiveColumnIndex(id: string, index: number) {
+  const count = props.filteredColumns.length;
+  const nextIndex = count ? ((index % count) + count) % count : -1;
+  activeColumnIndexes.value = { ...activeColumnIndexes.value, [id]: nextIndex };
+  window.requestAnimationFrame(() => {
+    const listbox = columnSearchInputs.get(id)?.closest('[role="listbox"]');
+    listbox?.querySelectorAll<HTMLElement>('[role="option"]')[nextIndex]?.scrollIntoView?.({ block: "nearest" });
+  });
+}
+
+function setColumnSelectOpen(id: string, open: boolean) {
+  const next = new Set(openColumnSelectIds.value);
+  if (open) {
+    next.clear();
+    next.add(id);
+  } else {
+    next.delete(id);
+  }
+  openColumnSelectIds.value = next;
+}
+
+async function handleColumnSelectOpen(rule: DataGridStructuredFilterRule, open: boolean) {
+  setColumnSelectOpen(rule.id, open);
+  if (!open) return;
+  const selectedIndex = props.filteredColumns.indexOf(rule.columnName);
+  setActiveColumnIndex(rule.id, selectedIndex >= 0 ? selectedIndex : 0);
+  await nextTick();
+  window.requestAnimationFrame(() => columnSearchInputs.get(rule.id)?.focus());
+}
+
+function handleColumnCloseAutoFocus(id: string, event: Event) {
+  if (pendingKeyboardAddFocus.delete(id)) {
+    event.preventDefault();
+    return;
+  }
+  if (!pendingValueFocus.delete(id)) return;
+  event.preventDefault();
+  void focusFilterRuleValue(id);
+}
+
+async function focusFilterRuleValue(id: string) {
+  await nextTick();
+  window.requestAnimationFrame(() => filterRuleElements.get(id)?.querySelector<HTMLElement>("[data-filter-value-editor]")?.focus());
+}
+
+function updateColumnSearch(id: string, event: Event) {
+  emit("update:columnSearch", (event.target as HTMLInputElement).value);
+  setActiveColumnIndex(id, 0);
+}
+
+function addRuleAndOpenColumnSelect() {
+  ruleIdsBeforeKeyboardAdd = new Set(props.rules.map((item) => item.id));
+  emit("add");
+}
+
+function selectActiveColumn(rule: DataGridStructuredFilterRule, addAnother: boolean) {
+  const column = props.filteredColumns[activeColumnIndex(rule.id)];
+  if (!column) return;
+  updateRuleColumn(rule, column, !addAnother);
+  if (addAnother) pendingKeyboardAddFocus.add(rule.id);
+  setColumnSelectOpen(rule.id, false);
+  if (!addAnother) return;
+  addRuleAndOpenColumnSelect();
+}
+
+function moveColumnSearchCaret(event: KeyboardEvent) {
+  if (event.shiftKey || event.altKey || event.ctrlKey || event.metaKey) return;
+  const input = event.currentTarget as HTMLInputElement;
+  if (typeof input.setSelectionRange !== "function") return;
+  const start = input.selectionStart ?? 0;
+  const end = input.selectionEnd ?? start;
+  const nextPosition = event.key === "ArrowLeft" ? (start === end ? Math.max(0, start - 1) : start) : start === end ? Math.min(input.value.length, end + 1) : end;
+  event.preventDefault();
+  event.stopPropagation();
+  input.setSelectionRange(nextPosition, nextPosition);
+}
+
+watch(
+  () => props.rules,
+  (rules) => {
+    if (!ruleIdsBeforeKeyboardAdd) return;
+    const addedRule = rules.find((item) => !ruleIdsBeforeKeyboardAdd?.has(item.id));
+    ruleIdsBeforeKeyboardAdd = undefined;
+    if (addedRule) void handleColumnSelectOpen(addedRule, true);
+  },
+);
+
+function handleColumnSearchKeydown(event: KeyboardEvent, rule: DataGridStructuredFilterRule) {
   if (event.isComposing || event.key === "Process") {
     event.stopPropagation();
     return;
   }
-  if (["Escape", "Tab", "ArrowUp", "ArrowDown", "Home", "End", "PageUp", "PageDown"].includes(event.key)) return;
+  if (event.key === "ArrowDown" || event.key === "ArrowUp") {
+    event.preventDefault();
+    event.stopPropagation();
+    setActiveColumnIndex(rule.id, activeColumnIndex(rule.id) + (event.key === "ArrowDown" ? 1 : -1));
+    return;
+  }
+  if (event.key === "Enter") {
+    event.preventDefault();
+    event.stopPropagation();
+    selectActiveColumn(rule, event.shiftKey);
+    return;
+  }
+  if (event.key === "ArrowLeft" || event.key === "ArrowRight") {
+    moveColumnSearchCaret(event);
+    return;
+  }
+  if (["Escape", "Tab"].includes(event.key)) return;
+  if (["Home", "End", "PageUp", "PageDown"].includes(event.key)) {
+    event.stopPropagation();
+    return;
+  }
   if (!event.ctrlKey && !event.metaKey && !event.altKey && (event.key.length === 1 || event.key === "Backspace" || event.key === "Delete")) event.stopPropagation();
 }
+
+function handleValueEditorKeydown(event: KeyboardEvent) {
+  if (event.key !== "Enter" || event.isComposing) return;
+  event.preventDefault();
+  if (!event.shiftKey) {
+    emit("apply");
+    return;
+  }
+  event.stopPropagation();
+  if (!event.repeat) addRuleAndOpenColumnSelect();
+}
 </script>
 
 <template>
@@ -63,38 +208,61 @@ function handleColumnSearchKeydown(event: KeyboardEvent) {
         <div v-if="index > 0" class="flex justify-center">
           <Button variant="ghost" size="sm" class="h-6 px-2 text-[11px]" @click="emit('updateRule', rule.id, { conjunction: rule.conjunction === 'AND' ? 'OR' : 'AND' })">{{ rule.conjunction }}</Button>
         </div>
-        <div class="grid items-center gap-2" :class="usesExpandedLayout(rule.mode) ? 'grid-cols-[minmax(0,1.2fr)_minmax(0,1fr)_auto]' : 'grid-cols-[minmax(0,1.2fr)_minmax(0,1fr)_minmax(0,1.2fr)_auto]'">
-          <Select :model-value="rule.columnName" :disabled="rule.disabled" @update:model-value="(value: any) => updateRuleColumn(rule.id, value)">
-            <SelectTrigger class="h-8 min-w-0 text-xs"><SelectValue :placeholder="t('grid.filterBuilderColumn')" /></SelectTrigger>
-            <SelectContent position="popper" class="max-h-72" :hide-scroll-buttons="true">
-              <SelectItem v-for="column in props.filteredColumns" :key="column" :value="column">{{ column }}</SelectItem>
+        <div :ref="(element) => setFilterRuleElement(rule.id, element)" class="grid items-center gap-2" :class="usesExpandedLayout(rule.mode) ? 'grid-cols-[minmax(0,1fr)_80px_auto]' : 'grid-cols-[minmax(0,1fr)_80px_minmax(0,1fr)_auto]'">
+          <Select :model-value="rule.columnName" :open="openColumnSelectIds.has(rule.id)" :disabled="rule.disabled" @update:model-value="(value: any) => updateRuleColumn(rule, value)" @update:open="(open: boolean) => handleColumnSelectOpen(rule, open)">
+            <SelectTrigger class="h-8 w-full min-w-0 overflow-hidden text-xs [&_[data-slot=select-value]]:min-w-0 [&_[data-slot=select-value]]:truncate">
+              <SelectValue v-if="rule.columnName">{{ rule.columnName }}</SelectValue>
+              <SelectValue v-else :placeholder="t('grid.filterBuilderColumn')" />
+            </SelectTrigger>
+            <SelectContent position="popper" class="max-h-72" :hide-scroll-buttons="true" @close-auto-focus="(event: Event) => handleColumnCloseAutoFocus(rule.id, event)">
+              <SelectItem
+                v-for="(column, columnIndex) in props.filteredColumns"
+                :key="column"
+                :value="column"
+                class="rounded-none"
+                :class="activeColumnIndex(rule.id) === columnIndex ? 'bg-accent text-accent-foreground' : ''"
+                :data-filter-active="activeColumnIndex(rule.id) === columnIndex ? '' : undefined"
+                @pointermove="setActiveColumnIndex(rule.id, columnIndex)"
+              >
+                {{ column }}
+              </SelectItem>
               <div v-if="!props.filteredColumns.length" class="px-2 py-2 text-xs text-muted-foreground">{{ t("grid.filterBuilderNoMatchingColumns") }}</div>
               <div class="sticky bottom-0 mt-1 flex items-center gap-1.5 border-t bg-popover px-2 py-1.5">
                 <Search class="h-3.5 w-3.5 text-muted-foreground" />
                 <input
+                  :ref="(element) => setColumnSearchInput(rule.id, element)"
                   :value="props.columnSearch"
                   class="h-7 min-w-0 flex-1 bg-transparent text-xs outline-none"
                   :placeholder="t('grid.filterBuilderSearchColumns')"
-                  @input="emit('update:columnSearch', ($event.target as HTMLInputElement).value)"
+                  @input="updateColumnSearch(rule.id, $event)"
                   @click.stop
-                  @keydown="handleColumnSearchKeydown"
+                  @keydown="handleColumnSearchKeydown($event, rule)"
                   @pointerdown.stop
                 />
               </div>
             </SelectContent>
           </Select>
           <Select :model-value="rule.mode" :disabled="rule.disabled" @update:model-value="(value: any) => emit('updateRule', rule.id, { mode: value as DataGridContextFilterMode })">
-            <SelectTrigger class="h-8 min-w-0 text-xs"><SelectValue /></SelectTrigger>
+            <SelectTrigger class="h-8 w-full min-w-0 overflow-hidden text-xs [&_[data-slot=select-value]]:min-w-0 [&_[data-slot=select-value]]:truncate"><SelectValue /></SelectTrigger>
             <SelectContent
-              ><SelectItem v-for="option in props.modeOptions" :key="option.value" :value="option.value">{{ t(option.labelKey) }}</SelectItem></SelectContent
+              ><SelectItem v-for="option in props.modeOptions" :key="option.value" :value="option.value" class="rounded-none">{{ t(option.labelKey) }}</SelectItem></SelectContent
             >
           </Select>
           <div v-if="filterModeUsesRange(rule.mode)" class="col-span-2 flex gap-2">
-            <Input :model-value="rule.rawValue" class="h-8 text-xs" :disabled="rule.disabled" :placeholder="t('grid.filterBuilderRangeStart')" @update:model-value="(value) => emit('updateRule', rule.id, { rawValue: String(value ?? '') })" @keydown.enter.prevent="emit('apply')" />
-            <Input :model-value="rule.rawEndValue" class="h-8 text-xs" :disabled="rule.disabled" :placeholder="t('grid.filterBuilderRangeEnd')" @update:model-value="(value) => emit('updateRule', rule.id, { rawEndValue: String(value ?? '') })" @keydown.enter.prevent="emit('apply')" />
+            <Input
+              data-filter-value-editor
+              :model-value="rule.rawValue"
+              class="h-8 text-xs"
+              :disabled="rule.disabled"
+              :placeholder="t('grid.filterBuilderRangeStart')"
+              @update:model-value="(value) => emit('updateRule', rule.id, { rawValue: String(value ?? '') })"
+              @keydown="handleValueEditorKeydown"
+            />
+            <Input :model-value="rule.rawEndValue" class="h-8 text-xs" :disabled="rule.disabled" :placeholder="t('grid.filterBuilderRangeEnd')" @update:model-value="(value) => emit('updateRule', rule.id, { rawEndValue: String(value ?? '') })" @keydown="handleValueEditorKeydown" />
           </div>
           <textarea
             v-else-if="filterModeUsesList(rule.mode)"
+            data-filter-value-editor
             :value="rule.rawValue"
             rows="2"
             class="col-span-2 min-h-14 resize-y rounded-md border bg-transparent px-2.5 py-1 text-xs outline-none"
@@ -106,12 +274,13 @@ function handleColumnSearchKeydown(event: KeyboardEvent) {
           />
           <Input
             v-else-if="filterModeNeedsValue(rule.mode)"
+            data-filter-value-editor
             :model-value="rule.rawValue"
             class="h-8 text-xs"
             :disabled="rule.disabled"
             :placeholder="t('grid.filterBuilderValue')"
             @update:model-value="(value) => emit('updateRule', rule.id, { rawValue: String(value ?? '') })"
-            @keydown.enter.prevent="emit('apply')"
+            @keydown="handleValueEditorKeydown"
           />
           <div v-else class="flex h-8 items-center rounded-md border border-dashed px-2 text-xs text-muted-foreground">{{ t("grid.filterBuilderNoValue") }}</div>
           <div class="flex items-center gap-1" :class="usesExpandedLayout(rule.mode) ? 'col-start-3 row-start-1 row-span-2' : ''">
diff --git a/apps/desktop/src/components/grid/DataGridQueryControls.vue b/apps/desktop/src/components/grid/DataGridQueryControls.vue
index 66d469fa3..2349300b9 100644
--- a/apps/desktop/src/components/grid/DataGridQueryControls.vue
+++ b/apps/desktop/src/components/grid/DataGridQueryControls.vue
@@ -130,7 +130,7 @@ onUnmounted(onResizeEnd);
             <span v-if="filterButtonCount" class="absolute -right-1 -top-1 flex h-3.5 min-w-3.5 items-center justify-center rounded-full bg-primary px-1 text-[9px] leading-none text-primary-foreground">{{ filterButtonCount }}</span>
           </button>
         </PopoverTrigger>
-        <PopoverContent align="start" class="w-[380px] max-w-[calc(100vw-24px)] gap-3 p-3">
+        <PopoverContent align="start" class="w-[480px] max-w-[calc(100vw-24px)] gap-3 p-3">
           <div class="flex items-center justify-between gap-3">
             <div class="text-xs font-medium text-foreground">{{ t("grid.filter") }}</div>
             <Button variant="ghost" size="sm" class="h-7 px-2 text-xs" @click="emit('addRule')"><Plus class="mr-1 h-3.5 w-3.5" />{{ t("grid.filterBuilderAddRule") }}</Button>
diff --git a/apps/desktop/src/components/grid/__tests__/DataGridSurfaces.spec.ts b/apps/desktop/src/components/grid/__tests__/DataGridSurfaces.spec.ts
index b8f61e540..47d91f21f 100644
--- a/apps/desktop/src/components/grid/__tests__/DataGridSurfaces.spec.ts
+++ b/apps/desktop/src/components/grid/__tests__/DataGridSurfaces.spec.ts
@@ -311,18 +311,185 @@ describe("DataGridColumnHeader", () => {
 });
 
 describe("DataGridFilterBuilder", () => {
-  it("isolates text-entry keys while preserving popup navigation keys", () => {
-    const mounted = mountComponent(DataGridFilterBuilder, { rules: [{ id: "r1", columnName: "id", mode: "equals", rawValue: "", rawEndValue: "", conjunction: "AND" }], columns: ["id"], filteredColumns: ["id"], modeOptions: [{ value: "equals", labelKey: "equals" }], columnSearch: "" });
+  it("clips long selected values inside the filter grid", () => {
+    const mounted = mountComponent(DataGridFilterBuilder, {
+      rules: [{ id: "r1", columnName: "appointmentStatusWithAnExceptionallyLongName", mode: "equals", rawValue: "", rawEndValue: "", conjunction: "AND" }],
+      columns: ["appointmentStatusWithAnExceptionallyLongName", "name"],
+      filteredColumns: ["name"],
+      modeOptions: [{ value: "equals", labelKey: "equals" }],
+      columnSearch: "",
+    });
+    const selects = findAll(mounted.root, (node) => node.props["data-stub"] === "Select");
+    const selectContents = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectContent");
+    const triggers = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectTrigger");
+    const selectValues = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectValue");
+    const items = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectItem");
+    const ruleGrid = findOne(mounted.root, (node) => String(node.props.class).includes("grid-cols-[minmax(0,1fr)_80px_minmax(0,1fr)_auto]"));
+    const searchInput = findOne(mounted.root, (node) => node.type === "input" && node.props.placeholder === "grid.filterBuilderSearchColumns");
+    const valueEditor = findOne(mounted.root, (node) => node.props["data-filter-value-editor"] === "");
+
+    expect(selects).toHaveLength(2);
+    expect(selects[0].props["onUpdate:open"]).toEqual(expect.any(Function));
+    expect(selects[0].props["onUpdate:modelValue"]).toEqual(expect.any(Function));
+    expect(selectContents[0].props.onCloseAutoFocus).toEqual(expect.any(Function));
+    expect(triggers).toHaveLength(2);
+    expect(hostText(selectValues[0])).toBe("appointmentStatusWithAnExceptionallyLongName");
+    expect(items).toHaveLength(2);
+    expect(items.every((item) => String(item.props.class).includes("rounded-none"))).toBe(true);
+    expect(searchInput.props.placeholder).toBe("grid.filterBuilderSearchColumns");
+    expect(valueEditor.props.placeholder).toBe("grid.filterBuilderValue");
+    expect(String(ruleGrid.props.class)).toContain("grid-cols-[minmax(0,1fr)_80px_minmax(0,1fr)_auto]");
+    for (const trigger of triggers) {
+      expect(String(trigger.props.class)).toContain("w-full");
+      expect(String(trigger.props.class)).toContain("overflow-hidden");
+      expect(String(trigger.props.class)).toContain("[&_[data-slot=select-value]]:min-w-0");
+      expect(String(trigger.props.class)).toContain("[&_[data-slot=select-value]]:truncate");
+    }
+  });
+
+  it("keeps search focus while navigating and selecting filtered columns", async () => {
+    const onUpdateRule = vi.fn();
+    const onAdd = vi.fn();
+    const mounted = mountComponent(DataGridFilterBuilder, {
+      rules: [{ id: "r1", columnName: "", mode: "equals", rawValue: "", rawEndValue: "", conjunction: "AND" }],
+      columns: ["id", "image_size_bytes"],
+      filteredColumns: ["id", "image_size_bytes"],
+      modeOptions: [{ value: "equals", labelKey: "equals" }],
+      columnSearch: "",
+      onUpdateRule,
+      onAdd,
+    });
+    const columnSelect = findAll(mounted.root, (node) => node.props["data-stub"] === "Select")[0];
     const searchInput = findOne(mounted.root, (node) => node.type === "input" && node.props.placeholder === "grid.filterBuilderSearchColumns");
 
+    columnSelect.props["onUpdate:open"](true);
+    await nextTick();
+
+    let columnItems = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectItem").slice(0, 2);
+    expect(columnItems[0].props["data-filter-active"]).toBe("");
     expect(dispatch(searchInput, "keydown", { key: "a" }).propagationStopped).toBe(true);
     expect(dispatch(searchInput, "keydown", { key: "Backspace" }).propagationStopped).toBe(true);
-    expect(dispatch(searchInput, "keydown", { key: "ArrowDown" }).propagationStopped).toBe(false);
+
+    const arrowDown = dispatch(searchInput, "keydown", { key: "ArrowDown" });
+    expect(arrowDown.defaultPrevented).toBe(true);
+    expect(arrowDown.propagationStopped).toBe(true);
+    await nextTick();
+    columnItems = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectItem").slice(0, 2);
+    expect(columnItems[1].props["data-filter-active"]).toBe("");
+
+    const leftInput = { value: "image_", selectionStart: 4, selectionEnd: 4, setSelectionRange: vi.fn() };
+    const leftArrow = dispatch(searchInput, "keydown", { key: "ArrowLeft", currentTarget: leftInput });
+    expect(leftArrow.defaultPrevented).toBe(true);
+    expect(leftArrow.propagationStopped).toBe(true);
+    expect(leftInput.setSelectionRange).toHaveBeenCalledWith(3, 3);
+
+    const rightInput = { value: "image_", selectionStart: 1, selectionEnd: 4, setSelectionRange: vi.fn() };
+    const rightArrow = dispatch(searchInput, "keydown", { key: "ArrowRight", currentTarget: rightInput });
+    expect(rightArrow.defaultPrevented).toBe(true);
+    expect(rightArrow.propagationStopped).toBe(true);
+    expect(rightInput.setSelectionRange).toHaveBeenCalledWith(4, 4);
+
+    const enter = dispatch(searchInput, "keydown", { key: "Enter" });
+    expect(enter.defaultPrevented).toBe(true);
+    expect(enter.propagationStopped).toBe(true);
+    expect(onUpdateRule).toHaveBeenCalledWith("r1", { columnName: "image_size_bytes" });
+    expect(onAdd).not.toHaveBeenCalled();
     expect(dispatch(searchInput, "keydown", { key: "Process", isComposing: true }).propagationStopped).toBe(true);
   });
+
+  it("adds another rule after selecting a column with shift-enter", async () => {
+    const onUpdateRule = vi.fn();
+    const secondRule = { id: "r2", columnName: "id", mode: "equals" as const, rawValue: "", rawEndValue: "", conjunction: "AND" as const };
+    let mounted: ReturnType<typeof mountComponent>;
+    const onAdd = vi.fn(() => {
+      void mounted.setProps({ rules: [{ id: "r1", columnName: "", mode: "equals", rawValue: "", rawEndValue: "", conjunction: "AND" }, secondRule] });
+    });
+    mounted = mountComponent(DataGridFilterBuilder, {
+      rules: [{ id: "r1", columnName: "", mode: "equals", rawValue: "", rawEndValue: "", conjunction: "AND" }],
+      columns: ["id"],
+      filteredColumns: ["id"],
+      modeOptions: [{ value: "equals", labelKey: "equals" }],
+      columnSearch: "",
+      onUpdateRule,
+      onAdd,
+    });
+    const columnSelect = findAll(mounted.root, (node) => node.props["data-stub"] === "Select")[0];
+    const searchInput = findOne(mounted.root, (node) => node.type === "input" && node.props.placeholder === "grid.filterBuilderSearchColumns");
+
+    columnSelect.props["onUpdate:open"](true);
+    await nextTick();
+    const shiftEnter = dispatch(searchInput, "keydown", { key: "Enter", shiftKey: true });
+
+    expect(shiftEnter.defaultPrevented).toBe(true);
+    expect(shiftEnter.propagationStopped).toBe(true);
+    expect(onUpdateRule).toHaveBeenCalledWith("r1", { columnName: "id" });
+    expect(onAdd).toHaveBeenCalledOnce();
+    await nextTick();
+    const columnSelects = findAll(mounted.root, (node) => node.props["data-stub"] === "Select").filter((_node, index) => index % 2 === 0);
+    const firstSelectContent = findAll(mounted.root, (node) => node.props["data-stub"] === "SelectContent")[0];
+    const closeAutoFocus = dispatch(firstSelectContent, "closeAutoFocus");
+    expect(closeAutoFocus.defaultPrevented).toBe(true);
+    expect(columnSelects).toHaveLength(2);
+    expect(columnSelects[0].props.open).toBe(false);
+    expect(columnSelects[1].props.open).toBe(true);
+  });
+
+  it("adds a rule instead of applying when shift-enter is pressed in a value editor", () => {
+    const onAdd = vi.fn();
+    const onApply = vi.fn();
+    const mounted = mountComponent(DataGridFilterBuilder, {
+      rules: [{ id: "r1", columnName: "id", mode: "equals", rawValue: "1", rawEndValue: "", conjunction: "AND" }],
+      columns: ["id"],
+      filteredColumns: ["id"],
+      modeOptions: [{ value: "equals", labelKey: "equals" }],
+      columnSearch: "",
+      onAdd,
+      onApply,
+    });
+    const valueEditor = findOne(mounted.root, (node) => node.props["data-filter-value-editor"] === "");
+
+    const shiftEnter = dispatch(valueEditor, "keydown", { key: "Enter", shiftKey: true, repeat: false });
+    expect(shiftEnter.defaultPrevented).toBe(true);
+    expect(shiftEnter.propagationStopped).toBe(true);
+    expect(onAdd).toHaveBeenCalledOnce();
+    expect(onApply).not.toHaveBeenCalled();
+
+    dispatch(valueEditor, "keydown", { key: "Enter", shiftKey: false });
+    expect(onApply).toHaveBeenCalledOnce();
+  });
 });
 
 describe("DataGridQueryControls", () => {
+  it("gives filter rules enough horizontal space for longer column names", () => {
+    const mounted = mountComponent(DataGridQueryControls, {
+      whereInput: "",
+      orderByInput: "",
+      columns: ["appointmentStatusWithAnExceptionallyLongName"],
+      conditionColumns: ["appointmentStatusWithAnExceptionallyLongName"],
+      historyScope: {},
+      canUseWhereSearch: true,
+      compact: false,
+      leadingBorder: false,
+      filterBuilderOpen: true,
+      filterButtonActive: false,
+      filterButtonCount: 0,
+      hasLocalColumnFilters: false,
+      localFilterCount: 0,
+      localFilterSummaries: [],
+      rules: [{ id: "r1", columnName: "appointmentStatusWithAnExceptionallyLongName", mode: "equals", rawValue: "", rawEndValue: "", conjunction: "AND" }],
+      filteredColumns: ["appointmentStatusWithAnExceptionallyLongName"],
+      modeOptions: [{ value: "equals", labelKey: "equals" }],
+      columnSearch: "",
+      applyWhere: vi.fn(),
+      applyOrderBy: vi.fn(),
+      clearOrderBy: vi.fn(),
+    });
+    const popoverContent = findOne(mounted.root, (node) => node.props["data-stub"] === "PopoverContent");
+
+    expect(String(popoverContent.props.class)).toContain("w-[480px]");
+    expect(String(popoverContent.props.class)).toContain("max-w-[calc(100vw-24px)]");
+  });
+
   it("keeps filter actions available in the popover", () => {
     const clearFilters = vi.fn();
     const applyFilters = vi.fn();