diff --git a/apps/sim/lib/sim-search/live/read-window.test.ts b/apps/sim/lib/sim-search/live/read-window.test.ts
new file mode 100644
index 00000000000..e464a48d7ac
--- /dev/null
+++ b/apps/sim/lib/sim-search/live/read-window.test.ts
@@ -0,0 +1,16 @@
+/**
+ * @vitest-environment node
+ */
+import { describe, expect, it } from 'vitest'
+import { encodedWindowEnd } from '@/lib/sim-search/live/read-window'
+
+const encoded = (text: string) => JSON.stringify(text).length - 2
+
+describe('encodedWindowEnd', () => {
+  it('returns the longest window it found to fit when escapes lead the text', () => {
+    const content = `${'"'.repeat(1_000)}${'x'.repeat(20_000)}`
+    const end = encodedWindowEnd(content, 0, 20_000, 8_000)
+    expect(end).toBe(19_000)
+    expect(encoded(content.slice(0, end))).toBeLessThanOrEqual(20_000)
+  })
+})
diff --git a/apps/sim/lib/sim-search/live/read-window.ts b/apps/sim/lib/sim-search/live/read-window.ts
index 335f0d3c4df..eebaf6be4ba 100644
--- a/apps/sim/lib/sim-search/live/read-window.ts
+++ b/apps/sim/lib/sim-search/live/read-window.ts
@@ -1,6 +1,9 @@
 /** Characters one standard read returns, the page budget indexed document reads use. */
 export const READ_WINDOW_CHARACTERS = 8000
 
+/** Times a window is shortened to fit its budget before the minimum is used instead. */
+const MAX_SHRINKS = 3
+
 /**
  * Where a window of `content` from `start` ends so its text, as JSON encodes it, fits `budget`
  * characters. JSON escapes quotes, backslashes and line breaks, so a window is shortened until its
@@ -13,9 +16,10 @@ export function encodedWindowEnd(
   minimumEnd: number
 ): number {
   let end = Math.min(content.length, start + budget)
-  for (let attempt = 0; attempt < 3 && end > minimumEnd; attempt++) {
+  for (let shrinks = 0; end > minimumEnd; shrinks++) {
     const encoded = JSON.stringify(content.slice(start, end)).length - 2
     if (encoded <= budget) return end
+    if (shrinks === MAX_SHRINKS) break
     end = start + Math.floor(((end - start) * budget) / encoded)
   }
   return minimumEnd