diff --git a/src/agents/pi-extensions/compaction-safeguard.test.ts b/src/agents/pi-extensions/compaction-safeguard.test.ts
index ef294a4f4c9..8e0f0453196 100644
--- a/src/agents/pi-extensions/compaction-safeguard.test.ts
+++ b/src/agents/pi-extensions/compaction-safeguard.test.ts
@@ -445,6 +445,11 @@ describe("compaction-safeguard recent-turn preservation", () => {
         content: [{ type: "text", text: "recent result" }],
         timestamp: 6,
       } as unknown as AgentMessage,
+      {
+        role: "assistant",
+        content: [{ type: "text", text: "recent final answer" }],
+        timestamp: 7,
+      } as unknown as AgentMessage,
     ];
 
     const split = splitPreservedRecentTurns({
@@ -452,6 +457,17 @@ describe("compaction-safeguard recent-turn preservation", () => {
       recentTurnsPreserve: 1,
     });
 
+    expect(split.preservedMessages.map((msg) => msg.role)).toEqual([
+      "user",
+      "assistant",
+      "assistant",
+    ]);
+    expect(
+      split.preservedMessages.some(
+        (msg) => msg.role === "user" && (msg as { content?: unknown }).content === "recent ask",
+      ),
+    ).toBe(true);
+
     const summarizableToolResultIds = split.summarizableMessages
       .filter((msg) => msg.role === "toolResult")
       .map((msg) => (msg as { toolCallId?: unknown }).toolCallId);
@@ -459,6 +475,24 @@ describe("compaction-safeguard recent-turn preservation", () => {
     expect(summarizableToolResultIds).not.toContain("call_recent");
   });
 
+  it("formats preserved non-text messages with placeholders", () => {
+    const section = formatPreservedTurnsSection([
+      {
+        role: "user",
+        content: [{ type: "image", data: "abc", mimeType: "image/png" }],
+        timestamp: 1,
+      } as unknown as AgentMessage,
+      {
+        role: "assistant",
+        content: [{ type: "toolCall", id: "call_recent", name: "read", arguments: {} }],
+        timestamp: 2,
+      } as unknown as AgentMessage,
+    ]);
+
+    expect(section).toContain("- User: [non-text content: image]");
+    expect(section).toContain("- Assistant: [non-text content: toolCall]");
+  });
+
   it("clamps preserve count into a safe range", () => {
     expect(resolveRecentTurnsPreserve(undefined)).toBe(3);
     expect(resolveRecentTurnsPreserve(-1)).toBe(0);
diff --git a/src/agents/pi-extensions/compaction-safeguard.ts b/src/agents/pi-extensions/compaction-safeguard.ts
index a801fb800f6..68ab218f588 100644
--- a/src/agents/pi-extensions/compaction-safeguard.ts
+++ b/src/agents/pi-extensions/compaction-safeguard.ts
@@ -196,6 +196,54 @@ function extractMessageText(message: AgentMessage): string {
   return parts.join("\n").trim();
 }
 
+function formatNonTextPlaceholder(content: unknown): string | null {
+  if (content === null || content === undefined) {
+    return null;
+  }
+  if (!Array.isArray(content)) {
+    return "[non-text content]";
+  }
+  const typeCounts = new Map<string, number>();
+  for (const block of content) {
+    if (!block || typeof block !== "object") {
+      continue;
+    }
+    const typeRaw = (block as { type?: unknown }).type;
+    const type = typeof typeRaw === "string" && typeRaw.trim().length > 0 ? typeRaw : "unknown";
+    if (type === "text") {
+      continue;
+    }
+    typeCounts.set(type, (typeCounts.get(type) ?? 0) + 1);
+  }
+  if (typeCounts.size === 0) {
+    return "[non-text content]";
+  }
+  const parts = [...typeCounts.entries()].map(([type, count]) =>
+    count > 1 ? `${type} x${count}` : type,
+  );
+  return `[non-text content: ${parts.join(", ")}]`;
+}
+
+function findPreservedStartIndexByTurnBoundary(
+  messages: AgentMessage[],
+  preserveTurns: number,
+): number {
+  let seenUsers = 0;
+  let earliestSelectedUserIndex = -1;
+  for (let i = messages.length - 1; i >= 0; i -= 1) {
+    const role = (messages[i] as { role?: unknown }).role;
+    if (role !== "user") {
+      continue;
+    }
+    seenUsers += 1;
+    earliestSelectedUserIndex = i;
+    if (seenUsers >= preserveTurns) {
+      return i;
+    }
+  }
+  return earliestSelectedUserIndex;
+}
+
 function splitPreservedRecentTurns(params: {
   messages: AgentMessage[];
   recentTurnsPreserve: number;
@@ -207,21 +255,30 @@ function splitPreservedRecentTurns(params: {
   if (preserveTurns <= 0) {
     return { summarizableMessages: params.messages, preservedMessages: [] };
   }
-  const preserveMessages = preserveTurns * 2;
-  const candidateIndexes: number[] = [];
-  for (let i = params.messages.length - 1; i >= 0; i -= 1) {
-    const role = (params.messages[i] as { role?: unknown }).role;
-    if (role === "user" || role === "assistant") {
-      candidateIndexes.push(i);
+  const boundaryStartIndex = findPreservedStartIndexByTurnBoundary(params.messages, preserveTurns);
+  const preservedIndexSet = new Set<number>();
+  if (boundaryStartIndex >= 0) {
+    for (let i = boundaryStartIndex; i < params.messages.length; i += 1) {
+      const role = (params.messages[i] as { role?: unknown }).role;
+      if (role === "user" || role === "assistant") {
+        preservedIndexSet.add(i);
+      }
     }
-    if (candidateIndexes.length >= preserveMessages) {
-      break;
+  } else {
+    const fallbackMessageCount = preserveTurns * 2;
+    for (let i = params.messages.length - 1; i >= 0; i -= 1) {
+      const role = (params.messages[i] as { role?: unknown }).role;
+      if (role === "user" || role === "assistant") {
+        preservedIndexSet.add(i);
+      }
+      if (preservedIndexSet.size >= fallbackMessageCount) {
+        break;
+      }
     }
   }
-  if (candidateIndexes.length === 0) {
+  if (preservedIndexSet.size === 0) {
     return { summarizableMessages: params.messages, preservedMessages: [] };
   }
-  const preservedIndexSet = new Set(candidateIndexes);
   const summarizableMessages = params.messages.filter((_, idx) => !preservedIndexSet.has(idx));
   // Preserving recent assistant turns can orphan downstream toolResult messages.
   // Repair pairings here so compaction summarization doesn't trip strict providers.
@@ -243,13 +300,17 @@ function formatPreservedTurnsSection(messages: AgentMessage[]): string {
     .map((message) => {
       const role = message.role === "assistant" ? "Assistant" : "User";
       const text = extractMessageText(message);
-      if (!text) {
+      const nonTextPlaceholder = formatNonTextPlaceholder(
+        (message as { content?: unknown }).content,
+      );
+      const rendered = text || nonTextPlaceholder;
+      if (!rendered) {
         return null;
       }
       const trimmed =
-        text.length > MAX_RECENT_TURN_TEXT_CHARS
-          ? `${text.slice(0, MAX_RECENT_TURN_TEXT_CHARS)}...`
-          : text;
+        rendered.length > MAX_RECENT_TURN_TEXT_CHARS
+          ? `${rendered.slice(0, MAX_RECENT_TURN_TEXT_CHARS)}...`
+          : rendered;
       return `- ${role}: ${trimmed}`;
     })
     .filter((line): line is string => Boolean(line));