diff --git a/src/common/utils/ai/cacheStrategy.test.ts b/src/common/utils/ai/cacheStrategy.test.ts
index 24a25e64a..194d505b0 100644
--- a/src/common/utils/ai/cacheStrategy.test.ts
+++ b/src/common/utils/ai/cacheStrategy.test.ts
@@ -41,13 +41,22 @@ describe("cacheStrategy", () => {
       expect(result).toEqual(messages);
     });
 
-    it("should not modify messages if less than 2 messages", () => {
+    it("should add cache control to single message for Anthropic models", () => {
       const messages: ModelMessage[] = [{ role: "user", content: "Hello" }];
       const result = applyCacheControl(messages, "anthropic:claude-3-5-sonnet");
-      expect(result).toEqual(messages);
+      expect(result[0]).toEqual({
+        ...messages[0],
+        providerOptions: {
+          anthropic: {
+            cacheControl: {
+              type: "ephemeral",
+            },
+          },
+        },
+      });
     });
 
-    it("should add cache control to second-to-last message for Anthropic models", () => {
+    it("should add cache control to last message for Anthropic models", () => {
       const messages: ModelMessage[] = [
         { role: "user", content: "Hello" },
         { role: "assistant", content: "Hi there!" },
@@ -56,9 +65,10 @@ describe("cacheStrategy", () => {
       const result = applyCacheControl(messages, "anthropic:claude-3-5-sonnet");
 
       expect(result[0]).toEqual(messages[0]); // First message unchanged
-      expect(result[1]).toEqual({
-        // Second message has cache control
-        ...messages[1],
+      expect(result[1]).toEqual(messages[1]); // Second message unchanged
+      expect(result[2]).toEqual({
+        // Last message has cache control
+        ...messages[2],
         providerOptions: {
           anthropic: {
             cacheControl: {
@@ -67,7 +77,6 @@ describe("cacheStrategy", () => {
           },
         },
       });
-      expect(result[2]).toEqual(messages[2]); // Last message unchanged
     });
 
     it("should work with exactly 2 messages", () => {
@@ -77,9 +86,10 @@ describe("cacheStrategy", () => {
       ];
       const result = applyCacheControl(messages, "anthropic:claude-3-5-sonnet");
 
-      expect(result[0]).toEqual({
-        // First message gets cache control
-        ...messages[0],
+      expect(result[0]).toEqual(messages[0]); // First message unchanged
+      expect(result[1]).toEqual({
+        // Last message gets cache control
+        ...messages[1],
         providerOptions: {
           anthropic: {
             cacheControl: {
@@ -88,7 +98,6 @@ describe("cacheStrategy", () => {
           },
         },
       });
-      expect(result[1]).toEqual(messages[1]); // Last message unchanged
     });
 
     it("should add cache control to last content part for array content", () => {
@@ -108,17 +117,24 @@ describe("cacheStrategy", () => {
             { type: "text", text: "How can I help?" },
           ],
         },
-        { role: "user", content: "Final question" },
+        {
+          role: "user",
+          content: [
+            { type: "text", text: "Final" },
+            { type: "text", text: "question" },
+          ],
+        },
       ];
       const result = applyCacheControl(messages, "anthropic:claude-3-5-sonnet");
 
       expect(result[0]).toEqual(messages[0]); // First message unchanged
+      expect(result[1]).toEqual(messages[1]); // Second message unchanged
 
-      // Second message (array content): cache control on LAST content part only
-      const secondMsg = result[1];
-      expect(secondMsg.role).toBe("assistant");
-      expect(Array.isArray(secondMsg.content)).toBe(true);
-      const content = secondMsg.content as Array<{
+      // Last message (array content): cache control on LAST content part only
+      const lastMsg = result[2];
+      expect(lastMsg.role).toBe("user");
+      expect(Array.isArray(lastMsg.content)).toBe(true);
+      const content = lastMsg.content as Array<{
         type: string;
         text: string;
         providerOptions?: unknown;
@@ -127,8 +143,6 @@ describe("cacheStrategy", () => {
       expect(content[1].providerOptions).toEqual({
         anthropic: { cacheControl: { type: "ephemeral" } },
       }); // Last part has cache control
-
-      expect(result[2]).toEqual(messages[2]); // Last message unchanged
     });
   });
 
diff --git a/src/common/utils/ai/cacheStrategy.ts b/src/common/utils/ai/cacheStrategy.ts
index 70d82f5f3..c6fdc78e7 100644
--- a/src/common/utils/ai/cacheStrategy.ts
+++ b/src/common/utils/ai/cacheStrategy.ts
@@ -66,10 +66,10 @@ function addCacheControlToLastContentPart(msg: ModelMessage): ModelMessage {
 
 /**
  * Apply cache control to messages for Anthropic models.
- * Caches all messages except the last user message for optimal cache hits.
+ * Adds a cache marker to the last message so the entire conversation is cached.
  *
  * NOTE: The SDK requires providerOptions on content parts, not on the message.
- * We add cache_control to the last content part of the second-to-last message.
+ * We add cache_control to the last content part of the last message.
  */
 export function applyCacheControl(messages: ModelMessage[], modelString: string): ModelMessage[] {
   // Only apply cache control for Anthropic models
@@ -77,14 +77,13 @@ export function applyCacheControl(messages: ModelMessage[], modelString: string)
     return messages;
   }
 
-  // Need at least 2 messages to add a cache breakpoint
-  if (messages.length < 2) {
+  // Need at least 1 message to add a cache breakpoint
+  if (messages.length < 1) {
     return messages;
   }
 
-  // Add cache breakpoint at the second-to-last message
-  // This caches everything up to (but not including) the current user message
-  const cacheIndex = messages.length - 2;
+  // Add cache breakpoint at the last message
+  const cacheIndex = messages.length - 1;
 
   return messages.map((msg, index) => {
     if (index === cacheIndex) {
diff --git a/src/node/services/aiService.ts b/src/node/services/aiService.ts
index 2995d46fb..6fd672f06 100644
--- a/src/node/services/aiService.ts
+++ b/src/node/services/aiService.ts
@@ -102,7 +102,7 @@ if (typeof globalFetchWithExtras.certificate === "function") {
  *
  * Injects cache_control on:
  * 1. Last tool (caches all tool definitions)
- * 2. Second-to-last message's last content part (caches conversation history)
+ * 2. Last message's last content part (caches entire conversation)
  */
 function wrapFetchWithAnthropicCacheControl(baseFetch: typeof fetch): typeof fetch {
   const cachingFetch = async (
@@ -123,11 +123,11 @@ function wrapFetchWithAnthropicCacheControl(baseFetch: typeof fetch): typeof fet
         lastTool.cache_control ??= { type: "ephemeral" };
       }
 
-      // Inject cache_control on second-to-last message's last content part
-      // This caches conversation history up to (but not including) the current user message
-      if (Array.isArray(json.messages) && json.messages.length >= 2) {
-        const secondToLastMsg = json.messages[json.messages.length - 2] as Record<string, unknown>;
-        const content = secondToLastMsg.content;
+      // Inject cache_control on last message's last content part
+      // This caches the entire conversation
+      if (Array.isArray(json.messages) && json.messages.length >= 1) {
+        const lastMsg = json.messages[json.messages.length - 1] as Record<string, unknown>;
+        const content = lastMsg.content;
 
         if (Array.isArray(content) && content.length > 0) {
           // Array content: add cache_control to last part