diff --git a/api/app/clients/prompts/addCacheControl.js b/api/app/clients/prompts/addCacheControl.js
index 375e08e9b6..eed5910dc9 100644
--- a/api/app/clients/prompts/addCacheControl.js
+++ b/api/app/clients/prompts/addCacheControl.js
@@ -9,31 +9,31 @@ function addCacheControl(messages) {
   }
 
   const updatedMessages = [...messages];
-  let userMessagesFound = 0;
+  let userMessagesModified = 0;
 
-  for (let i = updatedMessages.length - 1; i >= 0 && userMessagesFound < 2; i--) {
-    if (updatedMessages[i].role === 'user') {
-      if (typeof updatedMessages[i].content === 'string') {
-        updatedMessages[i] = {
-          ...updatedMessages[i],
-          content: [
-            {
-              type: 'text',
-              text: updatedMessages[i].content,
-              cache_control: { type: 'ephemeral' },
-            },
-          ],
-        };
-      } else if (Array.isArray(updatedMessages[i].content)) {
-        updatedMessages[i] = {
-          ...updatedMessages[i],
-          content: updatedMessages[i].content.map((item) => ({
-            ...item,
-            cache_control: { type: 'ephemeral' },
-          })),
-        };
+  for (let i = updatedMessages.length - 1; i >= 0 && userMessagesModified < 2; i--) {
+    const message = updatedMessages[i];
+    if (message.role !== 'user') {
+      continue;
+    }
+
+    if (typeof message.content === 'string') {
+      message.content = [
+        {
+          type: 'text',
+          text: message.content,
+          cache_control: { type: 'ephemeral' },
+        },
+      ];
+      userMessagesModified++;
+    } else if (Array.isArray(message.content)) {
+      for (let j = message.content.length - 1; j >= 0; j--) {
+        if (message.content[j].type === 'text') {
+          message.content[j].cache_control = { type: 'ephemeral' };
+          userMessagesModified++;
+          break;
+        }
       }
-      userMessagesFound++;
     }
   }
 
diff --git a/api/app/clients/prompts/addCacheControl.spec.js b/api/app/clients/prompts/addCacheControl.spec.js
index d95ccaf34b..c46ffd95e3 100644
--- a/api/app/clients/prompts/addCacheControl.spec.js
+++ b/api/app/clients/prompts/addCacheControl.spec.js
@@ -116,6 +116,7 @@ describe('addCacheControl', () => {
         content: [
           { type: 'text', text: 'Hello' },
           { type: 'image', url: 'http://example.com/image.jpg' },
+          { type: 'text', text: 'This is an image' },
         ],
       },
       { role: 'assistant', content: 'Hi there' },
@@ -124,8 +125,9 @@ describe('addCacheControl', () => {
 
     const result = addCacheControl(messages);
 
-    expect(result[0].content[0].cache_control).toEqual({ type: 'ephemeral' });
-    expect(result[0].content[1].cache_control).toEqual({ type: 'ephemeral' });
+    expect(result[0].content[0]).not.toHaveProperty('cache_control');
+    expect(result[0].content[1]).not.toHaveProperty('cache_control');
+    expect(result[0].content[2].cache_control).toEqual({ type: 'ephemeral' });
     expect(result[2].content[0]).toEqual({
       type: 'text',
       text: 'How are you?',
@@ -143,7 +145,6 @@ describe('addCacheControl', () => {
     ];
 
     const result = addCacheControl(messages);
-    console.dir(result, { depth: null });
 
     expect(result[0].content).toEqual('Hello');
     expect(result[2].content[0]).toEqual({
@@ -161,4 +162,66 @@ describe('addCacheControl', () => {
     expect(result[1].content).toBe('Hi there');
     expect(result[3].content).toBe('I\'m doing well, thanks!');
   });
+
+  test('should handle edge case with multiple content types', () => {
+    const messages = [
+      {
+        role: 'user',
+        content: [
+          {
+            type: 'image',
+            source: { type: 'base64', media_type: 'image/png', data: 'some_base64_string' },
+          },
+          {
+            type: 'image',
+            source: { type: 'base64', media_type: 'image/png', data: 'another_base64_string' },
+          },
+          { type: 'text', text: 'what do all these images have in common' },
+        ],
+      },
+      { role: 'assistant', content: 'I see multiple images.' },
+      { role: 'user', content: 'Correct!' },
+    ];
+
+    const result = addCacheControl(messages);
+
+    expect(result[0].content[0]).not.toHaveProperty('cache_control');
+    expect(result[0].content[1]).not.toHaveProperty('cache_control');
+    expect(result[0].content[2].cache_control).toEqual({ type: 'ephemeral' });
+    expect(result[2].content[0]).toEqual({
+      type: 'text',
+      text: 'Correct!',
+      cache_control: { type: 'ephemeral' },
+    });
+  });
+
+  test('should handle user message with no text block', () => {
+    const messages = [
+      {
+        role: 'user',
+        content: [
+          {
+            type: 'image',
+            source: { type: 'base64', media_type: 'image/png', data: 'some_base64_string' },
+          },
+          {
+            type: 'image',
+            source: { type: 'base64', media_type: 'image/png', data: 'another_base64_string' },
+          },
+        ],
+      },
+      { role: 'assistant', content: 'I see two images.' },
+      { role: 'user', content: 'Correct!' },
+    ];
+
+    const result = addCacheControl(messages);
+
+    expect(result[0].content[0]).not.toHaveProperty('cache_control');
+    expect(result[0].content[1]).not.toHaveProperty('cache_control');
+    expect(result[2].content[0]).toEqual({
+      type: 'text',
+      text: 'Correct!',
+      cache_control: { type: 'ephemeral' },
+    });
+  });
 });