diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index c99110a4b3c1..51cb5f40da61 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -2812,7 +2812,8 @@ export async function runEmbeddedAttempt(
 
         try {
           // Idempotent cleanup for legacy sessions with persisted image payloads.
-          // Called each run; only mutates already-answered user turns that still carry image blocks.
+          // Only mutates user turns older than a few assistant replies so recent
+          // history stays byte-identical for prompt-cache prefix matching.
           const didPruneImages = pruneProcessedHistoryImages(activeSession.messages);
           if (didPruneImages) {
             activeSession.agent.replaceMessages(activeSession.messages);
diff --git a/src/agents/pi-embedded-runner/run/history-image-prune.test.ts b/src/agents/pi-embedded-runner/run/history-image-prune.test.ts
index 03e532eda2e4..f5045d7f8b7c 100644
--- a/src/agents/pi-embedded-runner/run/history-image-prune.test.ts
+++ b/src/agents/pi-embedded-runner/run/history-image-prune.test.ts
@@ -28,23 +28,44 @@ function expectPrunedImageMessage(
 
 describe("pruneProcessedHistoryImages", () => {
   const image: ImageContent = { type: "image", data: "abc", mimeType: "image/png" };
+  const assistantTurn = () => castAgentMessage({ role: "assistant", content: "ack" });
+  const userText = () => castAgentMessage({ role: "user", content: "more" });
 
-  it("prunes image blocks from user messages that already have assistant replies", () => {
+  it("prunes image blocks from user messages older than 3 assistant turns", () => {
     const messages: AgentMessage[] = [
       castAgentMessage({
         role: "user",
         content: [{ type: "text", text: "See /tmp/photo.png" }, { ...image }],
       }),
-      castAgentMessage({
-        role: "assistant",
-        content: "got it",
-      }),
+      assistantTurn(),
+      userText(),
+      assistantTurn(),
+      userText(),
+      assistantTurn(),
     ];
 
     const content = expectPrunedImageMessage(messages, "expected user array content");
     expect(content[0]?.type).toBe("text");
   });
 
+  it("keeps image blocks within the last 3 assistant turns to preserve prompt cache", () => {
+    const messages: AgentMessage[] = [
+      castAgentMessage({
+        role: "user",
+        content: [{ type: "text", text: "See /tmp/photo.png" }, { ...image }],
+      }),
+      assistantTurn(),
+      userText(),
+      assistantTurn(),
+    ];
+
+    const didMutate = pruneProcessedHistoryImages(messages);
+
+    expect(didMutate).toBe(false);
+    const content = expectArrayMessageContent(messages[0], "expected user array content");
+    expect(content[1]).toMatchObject({ type: "image", data: "abc" });
+  });
+
   it("does not prune latest user message when no assistant response exists yet", () => {
     const messages: AgentMessage[] = [
       castAgentMessage({
@@ -61,20 +82,47 @@ describe("pruneProcessedHistoryImages", () => {
     expect(content[1]).toMatchObject({ type: "image", data: "abc" });
   });
 
-  it("prunes image blocks from toolResult messages that already have assistant replies", () => {
+  it("prunes image blocks from toolResult messages older than 3 assistant turns", () => {
     const messages: AgentMessage[] = [
       castAgentMessage({
         role: "toolResult",
         toolName: "read",
         content: [{ type: "text", text: "screenshot bytes" }, { ...image }],
       }),
+      assistantTurn(),
+      userText(),
+      assistantTurn(),
+      userText(),
+      assistantTurn(),
+    ];
+
+    expectPrunedImageMessage(messages, "expected toolResult array content");
+  });
+
+  it("prunes only old images while preserving recent ones", () => {
+    const messages: AgentMessage[] = [
       castAgentMessage({
-        role: "assistant",
-        content: "ack",
+        role: "user",
+        content: [{ type: "text", text: "old" }, { ...image }],
       }),
+      assistantTurn(),
+      userText(),
+      assistantTurn(),
+      castAgentMessage({
+        role: "user",
+        content: [{ type: "text", text: "recent" }, { ...image }],
+      }),
+      assistantTurn(),
     ];
 
-    expectPrunedImageMessage(messages, "expected toolResult array content");
+    const didMutate = pruneProcessedHistoryImages(messages);
+    expect(didMutate).toBe(true);
+
+    const oldContent = expectArrayMessageContent(messages[0], "expected old user content");
+    expect(oldContent[1]).toMatchObject({ type: "text", text: PRUNED_HISTORY_IMAGE_MARKER });
+
+    const recentContent = expectArrayMessageContent(messages[4], "expected recent user content");
+    expect(recentContent[1]).toMatchObject({ type: "image", data: "abc" });
   });
 
   it("does not change messages when no assistant turn exists", () => {
diff --git a/src/agents/pi-embedded-runner/run/history-image-prune.ts b/src/agents/pi-embedded-runner/run/history-image-prune.ts
index 4e92bb08f01a..0138cc1ccdc6 100644
--- a/src/agents/pi-embedded-runner/run/history-image-prune.ts
+++ b/src/agents/pi-embedded-runner/run/history-image-prune.ts
@@ -2,24 +2,37 @@ import type { AgentMessage } from "@mariozechner/pi-agent-core";
 
 export const PRUNED_HISTORY_IMAGE_MARKER = "[image data removed - already processed by model]";
 
+/**
+ * Number of most-recent assistant turns whose preceding user/toolResult image blocks are
+ * kept intact. Pruning these would diverge the request bytes from what the provider
+ * cached on the previous turn, invalidating the prompt-cache prefix.
+ */
+const PRESERVE_RECENT_ASSISTANT_TURNS = 3;
+
 /**
  * Idempotent cleanup for legacy sessions that persisted image blocks in history.
- * Called each run; mutates only user turns that already have an assistant reply.
+ * Called each run; mutates only user turns that are older than
+ * {@link PRESERVE_RECENT_ASSISTANT_TURNS} assistant replies so recent turns remain
+ * byte-identical for prompt caching.
  */
 export function pruneProcessedHistoryImages(messages: AgentMessage[]): boolean {
-  let lastAssistantIndex = -1;
+  let assistantSeen = 0;
+  let pruneBeforeIndex = -1;
   for (let i = messages.length - 1; i >= 0; i--) {
     if (messages[i]?.role === "assistant") {
-      lastAssistantIndex = i;
-      break;
+      assistantSeen++;
+      if (assistantSeen >= PRESERVE_RECENT_ASSISTANT_TURNS) {
+        pruneBeforeIndex = i;
+        break;
+      }
     }
   }
-  if (lastAssistantIndex < 0) {
+  if (pruneBeforeIndex < 0) {
     return false;
   }
 
   let didMutate = false;
-  for (let i = 0; i < lastAssistantIndex; i++) {
+  for (let i = 0; i < pruneBeforeIndex; i++) {
     const message = messages[i];
     if (
       !message ||