diff --git a/src/providers/rag/chunking.test.ts b/src/providers/rag/chunking.test.ts
new file mode 100644
index 0000000..2cecd69
--- /dev/null
+++ b/src/providers/rag/chunking.test.ts
@@ -0,0 +1,92 @@
+import { describe, expect, test } from "bun:test"
+import { chunkText } from "./index"
+
+const CHUNK_SIZE = 1600
+const CHUNK_OVERLAP = 320
+
+// Every test that calls chunkText on unbreakable input gets an explicit timeout:
+// before the forward-progress fix these spin forever rather than failing.
+const HANG_TIMEOUT_MS = 5000
+
+/** A long unbroken token — a URL, base64 blob or minified payload — after one early space. */
+const UNBREAKABLE = "x".repeat(10) + " " + "a".repeat(5000)
+
+describe("chunkText", () => {
+  test("returns the whole text as one chunk when it fits", () => {
+    expect(chunkText("a short memory")).toEqual(["a short memory"])
+  })
+
+  test(
+    "terminates on text whose only break lies within the overlap of start",
+    () => {
+      const chunks = chunkText(UNBREAKABLE)
+
+      expect(chunks.length).toBeGreaterThan(0)
+      expect(chunks.length).toBeLessThan(20)
+    },
+    HANG_TIMEOUT_MS
+  )
+
+  test(
+    "emits full-size chunks rather than slivers when no break point qualifies",
+    () => {
+      const chunks = chunkText(UNBREAKABLE)
+
+      // Every chunk but the last should be a genuine chunk, not an 11-character
+      // sliver cut at the single early space.
+      for (const chunk of chunks.slice(0, -1)) {
+        expect(chunk.length).toBeGreaterThan(CHUNK_SIZE * 0.5)
+      }
+    },
+    HANG_TIMEOUT_MS
+  )
+
+  test(
+    "covers the whole input when no break point qualifies",
+    () => {
+      const chunks = chunkText(UNBREAKABLE)
+
+      // Chunks overlap, so concatenating them is longer than the input; what
+      // matters is that no region of the source is skipped.
+      expect(chunks.join("")).toContain("a".repeat(4000))
+      expect(chunks[0]).toStartWith("xxxxxxxxxx")
+      expect(chunks[chunks.length - 1]).toEndWith("a")
+    },
+    HANG_TIMEOUT_MS
+  )
+
+  test(
+    "terminates when the caller's overlap is larger than the chunk step",
+    () => {
+      const chunks = chunkText("word ".repeat(500), 100, 90)
+
+      expect(chunks.length).toBeGreaterThan(0)
+    },
+    HANG_TIMEOUT_MS
+  )
+
+  test("still breaks long prose on sentence boundaries", () => {
+    const sentence = "The orbital sensor array reported a thermal anomaly. "
+    const chunks = chunkText(sentence.repeat(100))
+
+    expect(chunks.length).toBeGreaterThan(1)
+    // The first break should land on a sentence end, not a hard cut at CHUNK_SIZE.
+    expect(chunks[0]).toEndWith("anomaly.")
+    expect(chunks[0].length).toBeLessThanOrEqual(CHUNK_SIZE + 1)
+  })
+
+  test("keeps overlapping context between consecutive chunks", () => {
+    const sentence = "The orbital sensor array reported a thermal anomaly. "
+    const chunks = chunkText(sentence.repeat(100))
+
+    // The tail of chunk 0 should reappear at the head of chunk 1.
+    const tail = chunks[0].slice(-(CHUNK_OVERLAP / 2))
+    expect(chunks[1]).toContain(tail)
+  })
+
+  test("never emits an empty chunk", () => {
+    for (const chunk of chunkText(UNBREAKABLE)) {
+      expect(chunk.length).toBeGreaterThan(0)
+    }
+  })
+})
diff --git a/src/providers/rag/index.ts b/src/providers/rag/index.ts
index c90b723..7dcc3b0 100644
--- a/src/providers/rag/index.ts
+++ b/src/providers/rag/index.ts
@@ -30,7 +30,11 @@ const EMBEDDING_MODEL = "text-embedding-3-small"
  * Split text into overlapping chunks, attempting to break on sentence boundaries.
  * Follows the chunking approach from OpenClaw/QMD: ~400 tokens with overlap.
  */
-function chunkText(text: string, chunkSize: number = CHUNK_SIZE, overlap: number = CHUNK_OVERLAP): string[] {
+export function chunkText(
+  text: string,
+  chunkSize: number = CHUNK_SIZE,
+  overlap: number = CHUNK_OVERLAP
+): string[] {
   if (text.length <= chunkSize) {
     return [text.trim()]
   }
@@ -46,22 +50,29 @@ function chunkText(text: string, chunkSize: number = CHUNK_SIZE, overlap: number
       break
     }
 
-    // Try to break on sentence boundary
+    // Try to break on sentence boundary, then newline, then word. A candidate is
+    // only usable if it fills at least half the chunk — the word fallback in
+    // particular can land just past `start` on text with a long unbroken token
+    // (a URL, a base64 blob, minified JSON), and a sliver chunk there leaves the
+    // window unable to move forward by the overlap.
+    const minBreakPoint = start + chunkSize * 0.5
+
     let breakPoint = text.lastIndexOf(". ", end)
-    if (breakPoint <= start || breakPoint < start + chunkSize * 0.5) {
+    if (breakPoint < minBreakPoint) {
       breakPoint = text.lastIndexOf("\n", end)
     }
-    if (breakPoint <= start || breakPoint < start + chunkSize * 0.5) {
+    if (breakPoint < minBreakPoint) {
       breakPoint = text.lastIndexOf(" ", end)
     }
-    if (breakPoint <= start) {
+    if (breakPoint < minBreakPoint) {
       breakPoint = end
     }
 
     chunks.push(text.slice(start, breakPoint + 1).trim())
-    start = breakPoint + 1 - overlap
 
-    if (start < 0) start = 0
+    // Always advance. The half-chunk floor above keeps this positive for the
+    // default sizes, but a caller-supplied overlap can still exceed the step.
+    start = Math.max(breakPoint + 1 - overlap, start + 1)
   }
 
   return chunks.filter((c) => c.length > 0)