diff --git a/homeassistant/components/openai_conversation/ai_task.py b/homeassistant/components/openai_conversation/ai_task.py
index ff8c6e62520..5fc700a73ad 100644
--- a/homeassistant/components/openai_conversation/ai_task.py
+++ b/homeassistant/components/openai_conversation/ai_task.py
@@ -39,7 +39,10 @@ class OpenAITaskEntity(
 ):
     """OpenAI AI Task entity."""
 
-    _attr_supported_features = ai_task.AITaskEntityFeature.GENERATE_DATA
+    _attr_supported_features = (
+        ai_task.AITaskEntityFeature.GENERATE_DATA
+        | ai_task.AITaskEntityFeature.SUPPORT_ATTACHMENTS
+    )
 
     async def _async_generate_data(
         self,
diff --git a/homeassistant/components/openai_conversation/entity.py b/homeassistant/components/openai_conversation/entity.py
index db14480ec5f..7679bef83f1 100644
--- a/homeassistant/components/openai_conversation/entity.py
+++ b/homeassistant/components/openai_conversation/entity.py
@@ -345,6 +345,26 @@ class OpenAIBaseLLMEntity(Entity):
             for content in chat_log.content
             for m in _convert_content_to_param(content)
         ]
+
+        last_content = chat_log.content[-1]
+
+        # Handle attachments by adding them to the last user message
+        if last_content.role == "user" and last_content.attachments:
+            files = await async_prepare_files_for_prompt(
+                self.hass,
+                [a.path for a in last_content.attachments],
+            )
+            last_message = messages[-1]
+            assert (
+                last_message["type"] == "message"
+                and last_message["role"] == "user"
+                and isinstance(last_message["content"], str)
+            )
+            last_message["content"] = [
+                {"type": "input_text", "text": last_message["content"]},  # type: ignore[list-item]
+                *files,  # type: ignore[list-item]
+            ]
+
         if structure and structure_name:
             model_args["text"] = {
                 "format": {
diff --git a/tests/components/openai_conversation/test_ai_task.py b/tests/components/openai_conversation/test_ai_task.py
index 4541e11f5f8..14e3056c0e2 100644
--- a/tests/components/openai_conversation/test_ai_task.py
+++ b/tests/components/openai_conversation/test_ai_task.py
@@ -1,11 +1,12 @@
 """Test AI Task platform of OpenAI Conversation integration."""
 
-from unittest.mock import AsyncMock
+from pathlib import Path
+from unittest.mock import AsyncMock, patch
 
 import pytest
 import voluptuous as vol
 
-from homeassistant.components import ai_task
+from homeassistant.components import ai_task, media_source
 from homeassistant.core import HomeAssistant
 from homeassistant.exceptions import HomeAssistantError
 from homeassistant.helpers import entity_registry as er, selector
@@ -122,3 +123,86 @@ async def test_generate_invalid_structured_data(
                 },
             ),
         )
+
+
+@pytest.mark.usefixtures("mock_init_component")
+async def test_generate_data_with_attachments(
+    hass: HomeAssistant,
+    mock_config_entry: MockConfigEntry,
+    mock_create_stream: AsyncMock,
+    entity_registry: er.EntityRegistry,
+) -> None:
+    """Test AI Task data generation with attachments."""
+    entity_id = "ai_task.openai_ai_task"
+
+    # Mock the OpenAI response stream
+    mock_create_stream.return_value = [
+        create_message_item(id="msg_A", text="Hi there!", output_index=0)
+    ]
+
+    # Test with attachments
+    with (
+        patch(
+            "homeassistant.components.media_source.async_resolve_media",
+            side_effect=[
+                media_source.PlayMedia(
+                    url="http://example.com/doorbell_snapshot.jpg",
+                    mime_type="image/jpeg",
+                    path=Path("doorbell_snapshot.jpg"),
+                ),
+                media_source.PlayMedia(
+                    url="http://example.com/context.txt",
+                    mime_type="text/plain",
+                    path=Path("context.txt"),
+                ),
+            ],
+        ),
+        patch("pathlib.Path.exists", return_value=True),
+        # patch.object(hass.config, "is_allowed_path", return_value=True),
+        patch(
+            "homeassistant.components.openai_conversation.entity.guess_file_type",
+            return_value=("image/jpeg", None),
+        ),
+        patch("pathlib.Path.read_bytes", return_value=b"fake_image_data"),
+    ):
+        result = await ai_task.async_generate_data(
+            hass,
+            task_name="Test Task",
+            entity_id=entity_id,
+            instructions="Test prompt",
+            attachments=[
+                {"media_content_id": "media-source://media/doorbell_snapshot.jpg"},
+                {"media_content_id": "media-source://media/context.txt"},
+            ],
+        )
+
+    assert result.data == "Hi there!"
+
+    # Verify that the create stream was called with the correct parameters
+    # The last call should have the user message with attachments
+    call_args = mock_create_stream.call_args
+    assert call_args is not None
+
+    # Check that the input includes the attachments
+    input_messages = call_args[1]["input"]
+    assert len(input_messages) > 0
+
+    # Find the user message with attachments
+    user_message_with_attachments = input_messages[-2]
+
+    assert user_message_with_attachments is not None
+    assert isinstance(user_message_with_attachments["content"], list)
+    assert len(user_message_with_attachments["content"]) == 3  # Text + attachments
+    assert user_message_with_attachments["content"] == [
+        {"type": "input_text", "text": "Test prompt"},
+        {
+            "detail": "auto",
+            "image_url": "data:image/jpeg;base64,ZmFrZV9pbWFnZV9kYXRh",
+            "type": "input_image",
+        },
+        {
+            "detail": "auto",
+            "image_url": "data:image/jpeg;base64,ZmFrZV9pbWFnZV9kYXRh",
+            "type": "input_image",
+        },
+    ]