diff --git a/packages/core/src/session/model-request.ts b/packages/core/src/session/model-request.ts
index 293c93a5e61..129456de6f7 100644
--- a/packages/core/src/session/model-request.ts
+++ b/packages/core/src/session/model-request.ts
@@ -188,30 +188,31 @@ export const unsupportedParts = (
 
 export const boundImages = (messages: LLMRequest["messages"]) => {
   const isImage = (mime: string) => mime.toLowerCase().startsWith("image/")
-  const imageBytes = messages.reduce(
-    (total, message) =>
-      total +
-      message.content.reduce((sum, part) => {
-        if (part.type === "media" && isImage(part.media.mediaType)) return sum + mediaBytes(part.media)
-        if (part.type !== "tool-result" || part.result.type !== "content") return sum
-        return (
-          sum +
-          part.result.value.reduce(
-            (bytes: number, item: Content) =>
-              bytes + (item.type === "file" && isImage(item.mime) ? Buffer.byteLength(item.uri) : 0),
-            0,
-          )
-        )
-      }, 0),
-    0,
+  const sizes = messages.flatMap((message) =>
+    message.content.flatMap((part) => {
+      if (part.type === "media") return isImage(part.media.mediaType) ? [mediaBytes(part.media)] : []
+      if (part.type !== "tool-result" || part.result.type !== "content") return []
+      return part.result.value.flatMap((item: Content) =>
+        item.type === "file" && isImage(item.mime) ? [Buffer.byteLength(item.uri)] : [],
+      )
+    }),
   )
-  if (imageBytes <= IMAGE_BYTES_TRIGGER) return messages
+  // Replay the images in order, dropping the oldest down to the target whenever the kept payload passes the trigger.
+  // A new image then moves the cut only every (trigger - target) bytes instead of on every request, so the replaced
+  // prefix, and with it the provider's prompt cache, stays the same between cuts.
+  let cut = 0
+  let kept = 0
+  for (const size of sizes) {
+    kept += size
+    if (kept <= IMAGE_BYTES_TRIGGER) continue
+    while (kept > IMAGE_BYTES_TARGET) kept -= sizes[cut++]!
+  }
+  if (cut === 0) return messages
 
-  let removed = 0
+  let index = 0
   return replaceMedia(messages, (media) => {
-    if (!isImage(media.mime) || imageBytes - removed <= IMAGE_BYTES_TARGET) return
-    removed += media.bytes()
-    return IMAGE_REMOVED
+    if (!isImage(media.mime)) return
+    return index++ < cut ? IMAGE_REMOVED : undefined
   })
 }
 
diff --git a/packages/core/test/session-model-request.test.ts b/packages/core/test/session-model-request.test.ts
index fb1837a5956..d1b2559f3bb 100644
--- a/packages/core/test/session-model-request.test.ts
+++ b/packages/core/test/session-model-request.test.ts
@@ -203,6 +203,21 @@ describe("SessionModelRequest.boundImages", () => {
     expect(result[3]).toBe(third)
   })
 
+  test("keeps the replaced prefix stable as new images arrive, so the prompt cache survives", () => {
+    const image = (name: string) =>
+      Message.user({ type: "media", media: Media.base64("a".repeat(3 * 1024 * 1024), "image/png"), filename: name })
+    const removed = (messages: ReturnType<typeof boundImages>) =>
+      messages.filter((message) => message.content[0]?.type === "text").length
+    const history = Array.from({ length: 9 }, (_, i) => image(`${i}.png`))
+
+    // 27 MiB passes the 25 MiB trigger: the oldest four go, leaving 15 MiB.
+    expect(removed(boundImages(history))).toBe(4)
+    // Each later image used to move the cut by one; now the cut holds until the kept payload passes the trigger again.
+    expect(removed(boundImages([...history, image("9.png")]))).toBe(4)
+    expect(removed(boundImages([...history, image("9.png"), image("10.png"), image("11.png")]))).toBe(4)
+    expect(removed(boundImages([...history, ...Array.from({ length: 4 }, (_, i) => image(`${9 + i}.png`))]))).toBe(8)
+  })
+
   test("replaces images nested in tool results", () => {
     const image = "a".repeat(13 * 1024 * 1024)
     const result = boundImages([