diff --git a/src/agents/anthropic-payload-policy.test.ts b/src/agents/anthropic-payload-policy.test.ts
index c3d26b3f6dfc..9c90aa56513e 100644
--- a/src/agents/anthropic-payload-policy.test.ts
+++ b/src/agents/anthropic-payload-policy.test.ts
@@ -14,6 +14,7 @@ type TestPayload = {
   messages: Array<{ role: string; content: unknown }>;
   service_tier?: string;
   system?: unknown;
+  tools?: unknown;
 };
 
 function textBlock(text: string, cache_control?: { type: "ephemeral"; ttl?: "1h" }) {
@@ -214,6 +215,55 @@ describe("anthropic payload policy", () => {
     });
   });
 
+  it("uses the latest tool result when only one message cache marker remains", () => {
+    const policy = resolveAnthropicPayloadPolicy({
+      provider: "anthropic",
+      api: "anthropic-messages",
+      baseUrl: "https://api.anthropic.com/v1",
+      cacheRetention: "short",
+      enableCacheControl: true,
+    });
+    const payload: TestPayload = {
+      system: [
+        { type: "text", text: "Claude Code identity." },
+        { type: "text", text: "Follow policy." },
+      ],
+      tools: [{ name: "Read", cache_control: { type: "ephemeral" } }],
+      messages: [
+        {
+          role: "user",
+          content: [{ type: "text", text: "Investigate the cache writes." }],
+        },
+        {
+          role: "assistant",
+          content: [{ type: "text", text: "I'll inspect the logs." }],
+        },
+        {
+          role: "user",
+          content: [{ type: "tool_result", tool_use_id: "tool_1", content: "log chunk" }],
+        },
+      ],
+    };
+
+    applyAnthropicPayloadPolicyToParams(payload, policy);
+
+    expect(payload.messages[0]).toEqual({
+      role: "user",
+      content: [{ type: "text", text: "Investigate the cache writes." }],
+    });
+    expect(payload.messages[2]).toEqual({
+      role: "user",
+      content: [
+        {
+          type: "tool_result",
+          tool_use_id: "tool_1",
+          content: "log chunk",
+          cache_control: { type: "ephemeral" },
+        },
+      ],
+    });
+  });
+
   it("denies proxied Anthropic service tier but honors explicit long TTL for custom hosts", () => {
     const policy = resolveAnthropicPayloadPolicy({
       provider: "anthropic",
diff --git a/src/agents/anthropic-payload-policy.ts b/src/agents/anthropic-payload-policy.ts
index c44c9ef1b0f3..8bf6db4715e3 100644
--- a/src/agents/anthropic-payload-policy.ts
+++ b/src/agents/anthropic-payload-policy.ts
@@ -27,6 +27,8 @@ type AnthropicPayloadPolicyInput = {
   serviceTier?: AnthropicServiceTier;
 };
 
+const ANTHROPIC_CACHE_CONTROL_LIMIT = 4;
+
 /** @deprecated Anthropic-family provider payload helper; do not use from third-party plugins. */
 export type AnthropicPayloadPolicy = {
   allowsServiceTier: boolean;
@@ -142,8 +144,9 @@ function stripAnthropicSystemPromptBoundary(system: unknown): void {
 function applyAnthropicCacheControlToMessages(
   messages: unknown,
   cacheControl: AnthropicEphemeralCacheControl,
+  markerLimit: number,
 ): void {
-  if (!Array.isArray(messages) || messages.length === 0) {
+  if (!Array.isArray(messages) || messages.length === 0 || markerLimit <= 0) {
     return;
   }
 
@@ -162,6 +165,10 @@ function applyAnthropicCacheControlToMessages(
 
     const content = record.content;
     if (typeof content === "string") {
+      if (fallbackToolResult && markerLimit === 1) {
+        fallbackToolResult.cache_control = cacheControl;
+        return;
+      }
       record.content = [
         {
           type: "text",
@@ -169,6 +176,9 @@ function applyAnthropicCacheControlToMessages(
           cache_control: cacheControl,
         },
       ];
+      if (fallbackToolResult && markerLimit > 1) {
+        fallbackToolResult.cache_control = cacheControl;
+      }
       return;
     }
 
@@ -184,8 +194,12 @@ function applyAnthropicCacheControlToMessages(
 
       const blockRecord = block as Record<string, unknown>;
       if (blockRecord.type === "text" || blockRecord.type === "image") {
+        if (fallbackToolResult && markerLimit === 1) {
+          fallbackToolResult.cache_control = cacheControl;
+          return;
+        }
         blockRecord.cache_control = cacheControl;
-        if (fallbackToolResult) {
+        if (fallbackToolResult && markerLimit > 1) {
           fallbackToolResult.cache_control = cacheControl;
         }
         return;
@@ -201,6 +215,20 @@ function applyAnthropicCacheControlToMessages(
   }
 }
 
+function countAnthropicCacheControlMarkers(blocks: unknown): number {
+  if (!Array.isArray(blocks)) {
+    return 0;
+  }
+
+  let count = 0;
+  for (const block of blocks) {
+    if (block && typeof block === "object" && "cache_control" in block) {
+      count += 1;
+    }
+  }
+  return count;
+}
+
 /** @deprecated Anthropic-family provider payload helper; do not use from third-party plugins. */
 export function resolveAnthropicPayloadPolicy(
   input: AnthropicPayloadPolicyInput,
@@ -246,7 +274,14 @@ export function applyAnthropicPayloadPolicyToParams(
     return;
   }
 
-  applyAnthropicCacheControlToMessages(payloadObj.messages, policy.cacheControl);
+  const usedMarkers =
+    countAnthropicCacheControlMarkers(payloadObj.system) +
+    countAnthropicCacheControlMarkers(payloadObj.tools);
+  applyAnthropicCacheControlToMessages(
+    payloadObj.messages,
+    policy.cacheControl,
+    ANTHROPIC_CACHE_CONTROL_LIMIT - usedMarkers,
+  );
 }
 
 /** @deprecated Anthropic-family provider payload helper; do not use from third-party plugins. */
diff --git a/src/llm/providers/anthropic.ts b/src/llm/providers/anthropic.ts
index b1a76d1452b9..11269e1dfc95 100644
--- a/src/llm/providers/anthropic.ts
+++ b/src/llm/providers/anthropic.ts
@@ -41,6 +41,8 @@ import { buildCopilotDynamicHeaders, hasCopilotVisionInput } from "./github-copi
 import { adjustMaxTokensForThinking, buildBaseOptions } from "./simple-options.js";
 import { transformMessages } from "./transform-messages.js";
 
+const ANTHROPIC_CACHE_CONTROL_LIMIT = 4;
+
 /**
  * Resolve cache retention preference.
  * Defaults to "short" and uses OPENCLAW_CACHE_RETENTION for backward compatibility.
@@ -939,9 +941,27 @@ function buildParams(
   options?: AnthropicOptions,
 ): MessageCreateParamsStreaming {
   const { cacheControl } = getCacheControl(model, options?.cacheRetention);
+  const systemCacheControlCount = !cacheControl
+    ? 0
+    : isOAuthTokenResult
+      ? 1 + (context.systemPrompt ? 1 : 0)
+      : context.systemPrompt
+        ? 1
+        : 0;
+  const toolCacheControlCount = cacheControl && context.tools?.length ? 1 : 0;
+  const messageCacheControlLimit = Math.max(
+    0,
+    ANTHROPIC_CACHE_CONTROL_LIMIT - systemCacheControlCount - toolCacheControlCount,
+  );
   const params: MessageCreateParamsStreaming = {
     model: model.id,
-    messages: convertMessages(context.messages, model, isOAuthTokenResult, cacheControl),
+    messages: convertMessages(
+      context.messages,
+      model,
+      isOAuthTokenResult,
+      cacheControl,
+      messageCacheControlLimit,
+    ),
     max_tokens: options?.maxTokens ?? model.maxTokens,
     stream: true,
   };
@@ -1041,6 +1061,7 @@ function convertMessages(
   model: Model<"anthropic-messages">,
   isOAuthTokenValue: boolean,
   cacheControl?: CacheControlEphemeral,
+  messageCacheControlLimit = 4,
 ): MessageParam[] {
   const params: MessageParam[] = [];
 
@@ -1178,7 +1199,7 @@ function convertMessages(
     }
   }
 
-  if (cacheControl && params.length > 0) {
+  if (cacheControl && params.length > 0 && messageCacheControlLimit > 0) {
     let fallbackToolResult: ContentBlockParam | undefined;
 
     for (let i = params.length - 1; i >= 0; i--) {
@@ -1191,14 +1212,13 @@ function convertMessages(
         for (let j = message.content.length - 1; j >= 0; j--) {
           const block = message.content[j];
           if (block.type === "text" || block.type === "image") {
-            (block as typeof block & { cache_control?: typeof cacheControl }).cache_control =
-              cacheControl;
-            if (fallbackToolResult) {
-              (
-                fallbackToolResult as typeof fallbackToolResult & {
-                  cache_control?: typeof cacheControl;
-                }
-              ).cache_control = cacheControl;
+            if (fallbackToolResult && messageCacheControlLimit === 1) {
+              applyContentBlockCacheControl(fallbackToolResult, cacheControl);
+              return params;
+            }
+            applyContentBlockCacheControl(block, cacheControl);
+            if (fallbackToolResult && messageCacheControlLimit > 1) {
+              applyContentBlockCacheControl(fallbackToolResult, cacheControl);
             }
             return params;
           }
@@ -1210,6 +1230,10 @@ function convertMessages(
       }
 
       if (typeof message.content === "string") {
+        if (fallbackToolResult && messageCacheControlLimit === 1) {
+          applyContentBlockCacheControl(fallbackToolResult, cacheControl);
+          return params;
+        }
         message.content = [
           {
             type: "text",
@@ -1217,16 +1241,15 @@ function convertMessages(
             cache_control: cacheControl,
           },
         ] as ContentBlockParam[];
+        if (fallbackToolResult && messageCacheControlLimit > 1) {
+          applyContentBlockCacheControl(fallbackToolResult, cacheControl);
+        }
         return params;
       }
     }
 
     if (fallbackToolResult) {
-      (
-        fallbackToolResult as typeof fallbackToolResult & {
-          cache_control?: typeof cacheControl;
-        }
-      ).cache_control = cacheControl;
+      applyContentBlockCacheControl(fallbackToolResult, cacheControl);
     }
   }
 
@@ -1268,6 +1291,14 @@ function buildSystemPromptBlocks(
   return blocks.length > 0 ? blocks : [{ type: "text", text: "" }];
 }
 
+function applyContentBlockCacheControl(
+  block: ContentBlockParam,
+  cacheControl: CacheControlEphemeral,
+): void {
+  (block as ContentBlockParam & { cache_control?: CacheControlEphemeral }).cache_control =
+    cacheControl;
+}
+
 function shouldUseFineGrainedToolStreamingBeta(
   model: Model<"anthropic-messages">,
   context: Context,