diff --git a/apps/desktop/src/components/editor/QueryEditor.vue b/apps/desktop/src/components/editor/QueryEditor.vue
index 4b3d0b4bf..737bbff65 100644
--- a/apps/desktop/src/components/editor/QueryEditor.vue
+++ b/apps/desktop/src/components/editor/QueryEditor.vue
@@ -350,6 +350,18 @@ function requestExecute() {
   return true;
 }
 
+function handleSqlSingleQuote(view: EditorViewType): boolean {
+  const { state } = view;
+  if (state.readOnly) return false;
+  if (state.selection.ranges.some((range) => !range.empty || range.from === 0 || state.doc.sliceString(range.from - 1, range.from) !== "'")) return false;
+  const transaction = state.changeByRange((range) => ({
+    changes: { from: range.from, insert: "'" },
+    range,
+  }));
+  view.dispatch(transaction, { userEvent: "input.type" });
+  return true;
+}
+
 function executionPickerAnchor(currentView: EditorViewType, cursorPos: number, candidateCount: number): { left: number; top: number } | undefined {
   const cursorRect = currentView.coordsAtPos(cursorPos);
   const rootRect = editorRef.value?.getBoundingClientRect();
@@ -1933,6 +1945,7 @@ onMounted(async () => {
       previewRangeComp.of(buildPreviewRangeExtension()),
       Prec.highest(
         keymap.of([
+          { key: "'", run: handleSqlSingleQuote },
           ...closeBracketsKeymap,
           { key: "Tab", run: handleTab },
           {
diff --git a/apps/desktop/src/components/grid/DataGrid.vue b/apps/desktop/src/components/grid/DataGrid.vue
index 7cc3729a5..1d183976e 100644
--- a/apps/desktop/src/components/grid/DataGrid.vue
+++ b/apps/desktop/src/components/grid/DataGrid.vue
@@ -141,6 +141,7 @@ import { useSettingsStore } from "@/stores/settingsStore";
 import type { DataGridSortDirection } from "@/lib/dataGridSort";
 import { getTableMetadataCapabilities } from "@/lib/tableMetadataCapabilities";
 import { forgetDataGridConditionHistory, loadDataGridConditionHistory, rememberDataGridConditionHistory } from "@/lib/dataGridConditionHistory";
+import { caretPositionInsideInsertedSqlSingleQuotes, insertedSqlSingleQuoteAtCaret } from "@/lib/sqlQuoteCaret";
 
 const SqlPreviewPanel = defineAsyncComponent(() => import("@/components/editor/SqlPreviewPanel.vue"));
 
@@ -453,6 +454,7 @@ const orderBySuggestionPosition = ref({ left: 0, top: 0 });
 const orderByInput = ref(props.initialOrderByInput ?? "");
 const hasOrderByInput = computed(() => orderByInput.value.trim().length > 0);
 const whereFilterInput = ref(props.initialWhereInput ?? "");
+let previousWhereFilterInputValue = whereFilterInput.value;
 const hasWhereFilterInput = computed(() => whereFilterInput.value.trim().length > 0);
 const conditionHistoryScope = computed(() => ({
   connectionId: props.connectionId,
@@ -1327,9 +1329,38 @@ function deleteWhereHistorySuggestion(value: string) {
   whereSuggestionIndex.value = whereSuggestions.value.length ? Math.min(whereSuggestionIndex.value, whereSuggestions.value.length - 1) : -1;
 }
 
+function onWhereFilterInput(event: Event) {
+  const input = event.target instanceof HTMLInputElement ? event.target : null;
+  if (!input) return;
+  const nextValue = input.value;
+  if (
+    insertedSqlSingleQuoteAtCaret({
+      previousValue: previousWhereFilterInputValue,
+      nextValue,
+      selectionStart: input.selectionStart,
+    })
+  ) {
+    const caret = input.selectionStart ?? nextValue.length;
+    const pairedValue = `${nextValue.slice(0, caret)}'${nextValue.slice(caret)}`;
+    whereFilterInput.value = pairedValue;
+    previousWhereFilterInputValue = pairedValue;
+    nextTick(() => input.setSelectionRange(caret, caret));
+    return;
+  }
+  const nextCaret = caretPositionInsideInsertedSqlSingleQuotes({
+    previousValue: previousWhereFilterInputValue,
+    nextValue,
+    selectionStart: input.selectionStart,
+  });
+  previousWhereFilterInputValue = nextValue;
+  if (nextCaret == null) return;
+  nextTick(() => input.setSelectionRange(nextCaret, nextCaret));
+}
+
 watch(whereFilterInput, (val) => {
   emit("update:whereInput", currentWhereInput() ?? "");
   persistStructuredFilterState();
+  previousWhereFilterInputValue = val;
   whereSuggestions.value = [];
   if (!props.tableMeta?.columns?.length) return;
   const trimmed = val.trim();
@@ -6603,6 +6634,7 @@ const gridContextMenuItems = computed<ContextMenuItem[]>(() => {
                     spellcheck="false"
                     class="flex-1 h-5 min-w-0 text-xs bg-transparent outline-none placeholder:text-muted-foreground/60"
                     placeholder=""
+                    @input="onWhereFilterInput"
                     @keydown="onWhereFilterKeydown"
                     @focus="showWhereHistorySuggestions"
                     @click="updateWhereSuggestionPosition"
diff --git a/apps/desktop/src/lib/sqlQuoteCaret.ts b/apps/desktop/src/lib/sqlQuoteCaret.ts
new file mode 100644
index 000000000..b1cb1e67f
--- /dev/null
+++ b/apps/desktop/src/lib/sqlQuoteCaret.ts
@@ -0,0 +1,26 @@
+export interface SqlSingleQuoteCaretOptions {
+  previousValue: string;
+  nextValue: string;
+  selectionStart: number | null | undefined;
+}
+
+export function insertedSqlSingleQuoteAtCaret(options: SqlSingleQuoteCaretOptions): boolean {
+  const { previousValue, nextValue, selectionStart } = options;
+  if (typeof selectionStart !== "number" || selectionStart < 1) return false;
+  if (nextValue.charAt(selectionStart - 1) !== "'") return false;
+  return nextValue.slice(0, selectionStart - 1) + nextValue.slice(selectionStart) === previousValue;
+}
+
+export function caretPositionInsideInsertedSqlSingleQuotes(options: SqlSingleQuoteCaretOptions): number | null {
+  const { previousValue, nextValue, selectionStart } = options;
+  if (typeof selectionStart !== "number" || selectionStart < 2) return null;
+  if (nextValue.slice(selectionStart - 2, selectionStart) !== "''") return null;
+
+  const singleQuoteInsertPrevious = nextValue.slice(0, selectionStart - 1) + nextValue.slice(selectionStart);
+  if (singleQuoteInsertPrevious === previousValue) return selectionStart - 1;
+
+  const pairInsertPrevious = nextValue.slice(0, selectionStart - 2) + nextValue.slice(selectionStart);
+  if (pairInsertPrevious === previousValue) return selectionStart - 1;
+
+  return null;
+}
diff --git a/packages/app-tests/sqlQuoteCaret.test.ts b/packages/app-tests/sqlQuoteCaret.test.ts
new file mode 100644
index 000000000..ccc125d09
--- /dev/null
+++ b/packages/app-tests/sqlQuoteCaret.test.ts
@@ -0,0 +1,63 @@
+import { strict as assert } from "node:assert";
+import { test } from "vitest";
+import { caretPositionInsideInsertedSqlSingleQuotes, insertedSqlSingleQuoteAtCaret } from "../../apps/desktop/src/lib/sqlQuoteCaret.ts";
+
+test("detects a newly typed SQL single quote", () => {
+  assert.equal(
+    insertedSqlSingleQuoteAtCaret({
+      previousValue: "name = ",
+      nextValue: "name = '",
+      selectionStart: 8,
+    }),
+    true,
+  );
+  assert.equal(
+    insertedSqlSingleQuoteAtCaret({
+      previousValue: "name = '",
+      nextValue: "name = ''",
+      selectionStart: 9,
+    }),
+    true,
+  );
+});
+
+test("moves the caret between SQL single quotes after typing the closing quote", () => {
+  assert.equal(
+    caretPositionInsideInsertedSqlSingleQuotes({
+      previousValue: "name = '",
+      nextValue: "name = ''",
+      selectionStart: 9,
+    }),
+    8,
+  );
+});
+
+test("moves the caret between pasted SQL single quotes", () => {
+  assert.equal(
+    caretPositionInsideInsertedSqlSingleQuotes({
+      previousValue: "name = ",
+      nextValue: "name = ''",
+      selectionStart: 9,
+    }),
+    8,
+  );
+});
+
+test("keeps the caret unchanged for ordinary quote edits", () => {
+  assert.equal(
+    caretPositionInsideInsertedSqlSingleQuotes({
+      previousValue: "name = ",
+      nextValue: "name = '",
+      selectionStart: 8,
+    }),
+    null,
+  );
+  assert.equal(
+    caretPositionInsideInsertedSqlSingleQuotes({
+      previousValue: "name = 'a",
+      nextValue: "name = 'a'",
+      selectionStart: 10,
+    }),
+    null,
+  );
+});