diff --git a/apps/desktop/src/components/grid/DataGrid.vue b/apps/desktop/src/components/grid/DataGrid.vue
index 8ef8edf4b..000af2d20 100644
--- a/apps/desktop/src/components/grid/DataGrid.vue
+++ b/apps/desktop/src/components/grid/DataGrid.vue
@@ -8683,18 +8683,15 @@ function copySubmenu(): ContextMenuItem {
       items.push({
         label: labels.insertNoPkMerged,
         action: () => copyRowAsInsertWithoutPrimaryKeys("merged"),
-        disabled: !canCopyRowAsInsertWithoutPrimaryKeys.value,
       });
       items.push({
         label: labels.insertNoPkRowByRow,
         action: () => copyRowAsInsertWithoutPrimaryKeys("row-by-row"),
-        disabled: !canCopyRowAsInsertWithoutPrimaryKeys.value,
       });
     } else {
       items.push({
         label: labels.insertNoPk,
         action: () => copyRowAsInsertWithoutPrimaryKeys(),
-        disabled: !canCopyRowAsInsertWithoutPrimaryKeys.value,
       });
     }
   }
diff --git a/packages/app-tests/useDataGridExport.test.ts b/packages/app-tests/useDataGridExport.test.ts
index 75ec16961..a8f354ed5 100644
--- a/packages/app-tests/useDataGridExport.test.ts
+++ b/packages/app-tests/useDataGridExport.test.ts
@@ -390,9 +390,7 @@ test("copy row as INSERT refreshes prepared SQL after row data changes", async (
     isDirtyCol: [false, false],
     status: "",
   };
-  apiMock.buildDataGridCopyInsertStatement
-    .mockResolvedValueOnce("INSERT INTO users (id, name) VALUES (1, 'before');")
-    .mockResolvedValueOnce("INSERT INTO users (id, name) VALUES (1, 'after');");
+  apiMock.buildDataGridCopyInsertStatement.mockResolvedValueOnce("INSERT INTO users (id, name) VALUES (1, 'before');").mockResolvedValueOnce("INSERT INTO users (id, name) VALUES (1, 'after');");
   const composable = useDataGridExport({
     columns: computed(() => ["id", "name"]),
     displayItems: computed(() => [row]),
@@ -426,14 +424,61 @@ test("copy row as INSERT refreshes prepared SQL after row data changes", async (
   await composable.copyRowAsInsert();
 
   assert.equal(apiMock.buildDataGridCopyInsertStatement.mock.calls.length, 2);
-  assert.deepEqual(apiMock.buildDataGridCopyInsertStatement.mock.calls.map((call) => call[0].rows), [
-    [[1, "before"]],
-    [[1, "after"]],
-  ]);
-  assert.deepEqual(clipboardMock.copyToClipboard.mock.calls.map((call) => call[0]), [
-    "INSERT INTO users (id, name) VALUES (1, 'before');",
-    "INSERT INTO users (id, name) VALUES (1, 'after');",
-  ]);
+  assert.deepEqual(
+    apiMock.buildDataGridCopyInsertStatement.mock.calls.map((call) => call[0].rows),
+    [[[1, "before"]], [[1, "after"]]],
+  );
+  assert.deepEqual(
+    clipboardMock.copyToClipboard.mock.calls.map((call) => call[0]),
+    ["INSERT INTO users (id, name) VALUES (1, 'before');", "INSERT INTO users (id, name) VALUES (1, 'after');"],
+  );
+});
+
+test("copy row as INSERT works without prior prefetch (first context-menu click)", async () => {
+  const contextCell = ref({ rowId: 1, rowIndex: 0, col: 0 });
+  const row = {
+    id: 1,
+    data: [1, "alice"],
+    isNew: false,
+    isDeleted: false,
+    isDirtyCol: [false, false],
+    status: "",
+  };
+  apiMock.buildDataGridCopyInsertStatement.mockResolvedValueOnce("INSERT INTO users (id, name) VALUES (1, 'alice');");
+  const composable = useDataGridExport({
+    columns: computed(() => ["id", "name"]),
+    displayItems: computed(() => [row]),
+    sql: computed(() => undefined),
+    tableMeta: computed(() => ({
+      tableName: "users",
+      primaryKeys: ["id"],
+    })),
+    databaseType: computed(() => "mysql"),
+    connectionId: computed(() => "conn-1"),
+    database: computed(() => "db"),
+    context: computed(() => "table-data"),
+    sourceColumns: computed(() => undefined),
+    columnTypes: computed(() => undefined),
+    whereInput: computed(() => undefined),
+    orderBy: computed(() => undefined),
+    exportBatchSize: computed(() => 1000),
+    hasCellSelection: computed(() => false),
+    selectedCells: computed(() => ({ columns: [], rows: [] })),
+    selectedRange: computed(() => null),
+    contextCell,
+    getRowItem: () => row,
+    selectedRowIds: ref(new Set<number>()),
+    hasRowSelection: computed(() => false),
+  });
+
+  assert.equal(composable.canCopyRowAsInsert.value, true);
+  assert.equal(composable.canCopyPreparedInsert(false), false);
+
+  await composable.copyRowAsInsert();
+
+  assert.equal(apiMock.buildDataGridCopyInsertStatement.mock.calls.length, 1);
+  assert.equal(clipboardMock.copyToClipboard.mock.calls[0][0], "INSERT INTO users (id, name) VALUES (1, 'alice');");
+  assert.equal(composable.canCopyPreparedInsert(false), true);
 });
 
 test("default data grid export file names use sanitized base names and compact local timestamps", () => {