diff --git a/apps/desktop/src/components/grid/DataGridConditionEditor.vue b/apps/desktop/src/components/grid/DataGridConditionEditor.vue
index 3f8b709a2d..6c242ab7b8 100644
--- a/apps/desktop/src/components/grid/DataGridConditionEditor.vue
+++ b/apps/desktop/src/components/grid/DataGridConditionEditor.vue
@@ -134,8 +134,9 @@ function createTextProbe(input: HTMLTextAreaElement, wrap: boolean, options: { w
 
 function shouldExpand(input: HTMLTextAreaElement) {
   if (!input.value) return false;
+  const hasMultipleLines = /\r?\n/.test(input.value);
   const probe = createTextProbe(input, false);
-  const should = probe.getBoundingClientRect().width > input.clientWidth + 1;
+  const should = hasMultipleLines || probe.getBoundingClientRect().width > input.clientWidth + 1;
   probe.remove();
   return should;
 }
diff --git a/apps/desktop/src/components/grid/__tests__/DataGridConditionEditor.spec.ts b/apps/desktop/src/components/grid/__tests__/DataGridConditionEditor.spec.ts
index 47889a45b8..d87a2caf8e 100644
--- a/apps/desktop/src/components/grid/__tests__/DataGridConditionEditor.spec.ts
+++ b/apps/desktop/src/components/grid/__tests__/DataGridConditionEditor.spec.ts
@@ -390,6 +390,33 @@ describe("DataGridConditionEditor quote completion", () => {
     vi.unstubAllGlobals();
   });
 
+  it("expands when a multiline value is pasted even if each line fits", async () => {
+    vi.spyOn(HTMLElement.prototype, "getBoundingClientRect").mockImplementation(function (this: HTMLElement) {
+      const width = 320;
+      return { x: 0, y: 0, left: 0, top: 0, right: width, bottom: 24, width, height: 24, toJSON: () => ({}) } as DOMRect;
+    });
+    vi.spyOn(HTMLCanvasElement.prototype, "getContext").mockReturnValue(null);
+    vi.stubGlobal("requestAnimationFrame", (callback: FrameRequestCallback) => {
+      callback(0);
+      return 1;
+    });
+    const { input } = mountEditor("where", "where id in ()");
+    mockTextareaMetrics(input, { clientWidth: 320, scrollWidth: 320, clientHeight: 24, scrollHeight: 72 });
+    input.focus();
+    await nextTick();
+    expect(document.body.querySelector(".data-grid-topbar-condition-input--expanded")).toBeNull();
+
+    input.value = "where id in (60792411\n580019433\n1035062084)";
+    input.setSelectionRange(input.value.length, input.value.length);
+    input.dispatchEvent(new Event("input", { bubbles: true }));
+
+    await nextTick();
+    await nextTick();
+
+    expect(document.body.querySelector(".data-grid-topbar-condition-input--expanded")).toBeTruthy();
+    vi.unstubAllGlobals();
+  });
+
   it("preserves the caret offset when focus moves into the expanded textarea", async () => {
     vi.spyOn(HTMLElement.prototype, "getBoundingClientRect").mockImplementation(function (this: HTMLElement) {
       const width = this.classList.contains("data-grid-topbar-condition-pane--expanded") ? 160 : 140;