diff --git a/Dockerfile b/Dockerfile
index e90f3d4..fcc12a5 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,4 +1,4 @@
-FROM python:3.14.4-alpine3.23 AS python-base
+FROM python:3.14.5-alpine3.23 AS python-base
 
 LABEL Description="DiscordBot"
 
diff --git a/pyproject.toml b/pyproject.toml
index 0bb0f61..ef5ad7c 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "DiscordBot"
-version = "3.0.14"
+version = "3.0.15"
 description = "A simple Discord bot with OpenAI support and server administration tools"
 urls.Repository = "https://github.com/ddc/DiscordBot"
 urls.Homepage = "https://ddc.github.io/DiscordBot"
@@ -36,18 +36,18 @@ dependencies = [
   "ddcdatabases[postgres]>=4.0.1",
   "discord-py>=2.7.1",
   "gTTS>=2.5.4",
-  "openai>=2.36.0",
+  "openai>=2.38.0",
   "PyNaCl>=1.6.2",
   "pythonLogs>=7.0.1",
-  "uuid-utils>=0.14.1",
+  "uuid-utils>=0.16.0",
 ]
 
 [dependency-groups]
 dev = [
-    "coverage>=7.13.5",
-    "poethepoet>=0.45.0",
+    "coverage>=7.14.0",
+    "poethepoet>=0.46.0",
     "pytest-asyncio>=1.3.0",
-    "ruff>=0.15.12",
+    "ruff>=0.15.14",
     "testcontainers[postgres]>=4.14.2",
 ]
 
diff --git a/src/bot/cogs/open_ai.py b/src/bot/cogs/open_ai.py
index de678a2..e038a72 100644
--- a/src/bot/cogs/open_ai.py
+++ b/src/bot/cogs/open_ai.py
@@ -1,8 +1,11 @@
 import discord
+import time
 from discord.ext import commands
 from openai import AsyncOpenAI
-from openai.types.chat import ChatCompletionSystemMessageParam, ChatCompletionUserMessageParam
-from src.bot.constants.settings import get_bot_settings
+from openai.types.responses import WebSearchToolParam
+from openai.types.shared import ReasoningEffort
+from openai.types.shared_params import Reasoning
+from src.bot.constants.settings import BotSettings, get_bot_settings
 from src.bot.discord_bot import Bot
 from src.bot.tools import bot_utils
 from src.bot.tools.cooldowns import CoolDowns
@@ -12,9 +15,15 @@ class OpenAi(commands.Cog):
     """OpenAI-powered commands for AI assistance and text generation."""
 
     def __init__(self, bot: Bot) -> None:
-        self.bot = bot
-        self._bot_settings = get_bot_settings()
+        self.bot: Bot = bot
+        self._bot_settings: BotSettings = get_bot_settings()
         self._openai_client: AsyncOpenAI = AsyncOpenAI(api_key=self._bot_settings.openai_api_key)
+        self._effort: ReasoningEffort = "xhigh"
+        self._instructions: str = (
+            "You are a helpful AI assistant. When answering factual questions, use web search and base your "
+            "answer only on information directly supported by the sources. Do not invent or extrapolate specific "
+            "numbers, statistics, or breakdowns that the sources do not explicitly state. Cite the source URL(s)."
+        )
 
     @commands.command()
     @commands.cooldown(1, CoolDowns.OpenAI.value, commands.BucketType.user)
@@ -26,8 +35,17 @@ async def ai(self, ctx: commands.Context, *, msg_text: str) -> None:
             ai Write a haiku about programming
             ai Explain quantum computing in simple terms
         """
-        await ctx.message.channel.typing()
+        # Reasoning + web search can take a couple of minutes, so show a progress
+        # message immediately so the user knows the bot is working (not stuck).
+        progress_embed = discord.Embed(
+            description="🔄 **Please wait, I'm thinking and searching the web for an accurate answer...** "
+            "(this may take a moment)",
+            color=discord.Color.blurple(),
+        )
+        progress_embed.set_author(name=ctx.author.display_name, icon_url=getattr(ctx.author.avatar, "url", None))
+        progress_msg = await bot_utils.send_with_retry(ctx, ctx.send, embed=progress_embed)
 
+        start = time.monotonic()
         try:
             response_text = await self._get_ai_response(msg_text)
             color = discord.Color.green()
@@ -36,8 +54,15 @@ async def ai(self, ctx: commands.Context, *, msg_text: str) -> None:
             self.bot.log.error(f"OpenAI API error: {e}")
             color = discord.Color.red()
             description = f"Sorry, I encountered an error: {e}"
+        elapsed = time.monotonic() - start
+
+        # Remove the progress message before sending the final answer.
+        try:
+            await progress_msg.delete()
+        except discord.HTTPException:
+            pass
 
-        embeds = self._create_ai_embeds(ctx, description, color)
+        embeds = self._create_ai_embeds(ctx, description, color, elapsed)
         if len(embeds) == 1:
             await bot_utils.send_embed(ctx, embeds[0], False)
         else:
@@ -46,30 +71,32 @@ async def ai(self, ctx: commands.Context, *, msg_text: str) -> None:
 
     async def _get_ai_response(self, message: str) -> str:
         """Get response from OpenAI API."""
-        model = self._bot_settings.openai_model
 
-        # Create properly typed messages for OpenAI API
-        messages: list[ChatCompletionSystemMessageParam | ChatCompletionUserMessageParam] = [
-            ChatCompletionSystemMessageParam(
-                role="system",
-                content="You are a helpful AI assistant. Provide clear, concise, and accurate responses.",
-            ),
-            ChatCompletionUserMessageParam(role="user", content=message),
-        ]
-
-        # Use the correct OpenAI API endpoint (async — does not block the event loop)
-        response = await self._openai_client.chat.completions.create(
-            model=model,
-            messages=messages,
-            max_completion_tokens=1000,
+        response = await self._openai_client.responses.create(
+            instructions=self._instructions,
+            model=self._bot_settings.openai_model,
+            reasoning=Reasoning(effort=self._effort),
+            tools=[WebSearchToolParam(type="web_search")],
+            max_output_tokens=None,
+            input=message,
         )
 
-        content = response.choices[0].message.content
+        content = response.output_text
         return content.strip() if content else ""
 
-    def _create_ai_embeds(self, ctx: commands.Context, description: str, color: discord.Color) -> list[discord.Embed]:
+    @staticmethod
+    def _format_duration(seconds: float) -> str:
+        """Format an elapsed duration as e.g. '5ms' (sub-second) or '20s'."""
+        if seconds < 1:
+            return f"{round(seconds * 1000)}ms"
+        return f"{round(seconds)}s"
+
+    def _create_ai_embeds(
+        self, ctx: commands.Context, description: str, color: discord.Color, elapsed: float = 0.0
+    ) -> list[discord.Embed]:
         """Create formatted embed(s) for AI response, paginating if needed."""
         model = self._bot_settings.openai_model
+        duration = self._format_duration(elapsed)
         max_length = 2000
         chunks = []
 
@@ -92,7 +119,7 @@ def _create_ai_embeds(self, ctx: commands.Context, description: str, color: disc
                 name=ctx.author.display_name,
                 icon_url=getattr(ctx.author.avatar, "url", None),
             )
-            footer_text = f"{model} | {bot_utils.get_current_date_time_str_long()} UTC"
+            footer_text = f"{model} | {duration} | {bot_utils.get_current_date_time_str_long()} UTC"
             if len(chunks) > 1:
                 footer_text = f"Page {i + 1}/{len(chunks)} | {footer_text}"
             embed.set_footer(
diff --git a/tests/unit/bot/cogs/test_open_ai.py b/tests/unit/bot/cogs/test_open_ai.py
index 1524bc3..616b242 100644
--- a/tests/unit/bot/cogs/test_open_ai.py
+++ b/tests/unit/bot/cogs/test_open_ai.py
@@ -58,11 +58,9 @@ def mock_ctx():
 
 @pytest.fixture
 def mock_openai_response():
-    """Create a mock OpenAI response."""
+    """Create a mock OpenAI Responses API response."""
     response = MagicMock()
-    response.choices = [MagicMock()]
-    response.choices[0].message = MagicMock()
-    response.choices[0].message.content = "This is a mock AI response from OpenAI."
+    response.output_text = "This is a mock AI response from OpenAI."
     return response
 
 
@@ -98,7 +96,7 @@ async def test_ai_command_success(
         with patch.object(openai_cog, "_get_ai_response", return_value="AI response here"):
             await openai_cog.ai.callback(openai_cog, mock_ctx, msg_text="What is Python?")
 
-            mock_ctx.message.channel.typing.assert_called_once()
+            mock_ctx.send.assert_called_once()  # progress message was sent
             mock_send_embed.assert_called_once()
 
             # Check embed properties
@@ -118,7 +116,7 @@ async def test_ai_command_error(self, mock_send_embed, mock_get_settings, openai
         with patch.object(openai_cog, "_get_ai_response", side_effect=Exception("API Error")):
             await openai_cog.ai.callback(openai_cog, mock_ctx, msg_text="What is Python?")
 
-            mock_ctx.message.channel.typing.assert_called_once()
+            mock_ctx.send.assert_called_once()  # progress message was sent
             mock_send_embed.assert_called_once()
 
             # Check error embed properties
@@ -140,7 +138,7 @@ async def test_get_ai_response_success(
 
         # Mock the client instance directly
         mock_client = MagicMock()
-        mock_client.chat.completions.create = AsyncMock(return_value=mock_openai_response)
+        mock_client.responses.create = AsyncMock(return_value=mock_openai_response)
         openai_cog._openai_client = mock_client
 
         result = await openai_cog._get_ai_response("What is Python?")
@@ -148,19 +146,16 @@ async def test_get_ai_response_success(
         assert result == "This is a mock AI response from OpenAI."
 
         # Verify OpenAI API call
-        mock_client.chat.completions.create.assert_called_once()
-        call_args = mock_client.chat.completions.create.call_args
+        mock_client.responses.create.assert_called_once()
+        call_args = mock_client.responses.create.call_args
 
         assert call_args[1]["model"] == "gpt-3.5-turbo"
-        assert call_args[1]["max_completion_tokens"] == 1000
-        assert "temperature" not in call_args[1]
-
-        # Verify message types and content
-        messages = call_args[1]["messages"]
-        assert len(messages) == 2
-        assert messages[0]["role"] == "system"
-        assert messages[1]["role"] == "user"
-        assert messages[1]["content"] == "What is Python?"
+        assert call_args[1]["max_output_tokens"] is None
+        assert call_args[1]["instructions"] == openai_cog._instructions
+        assert call_args[1]["input"] == "What is Python?"
+        # Reasoning effort and web search are enabled
+        assert call_args[1]["reasoning"]["effort"] == "xhigh"
+        assert call_args[1]["tools"][0]["type"] == "web_search"
 
     @pytest.mark.asyncio
     @patch("src.bot.cogs.open_ai.get_bot_settings")
@@ -169,11 +164,11 @@ async def test_get_ai_response_with_leading_trailing_spaces(
     ):
         """Test _get_ai_response strips leading/trailing spaces."""
         mock_get_settings.return_value = mock_bot_settings
-        mock_openai_response.choices[0].message.content = "  Response with spaces  "
+        mock_openai_response.output_text = "  Response with spaces  "
 
         # Mock the client instance directly
         mock_client = MagicMock()
-        mock_client.chat.completions.create = AsyncMock(return_value=mock_openai_response)
+        mock_client.responses.create = AsyncMock(return_value=mock_openai_response)
         openai_cog._openai_client = mock_client
 
         result = await openai_cog._get_ai_response("Test message")
@@ -250,13 +245,13 @@ async def test_ai_command_with_different_models(self, mock_send_embed, openai_co
 
         # Mock the client instance directly
         mock_client = MagicMock()
-        mock_client.chat.completions.create = AsyncMock(return_value=mock_openai_response)
+        mock_client.responses.create = AsyncMock(return_value=mock_openai_response)
         openai_cog._openai_client = mock_client
 
         await openai_cog.ai.callback(openai_cog, mock_ctx, msg_text="Test question")
 
         # Verify correct model was used
-        call_args = mock_client.chat.completions.create.call_args
+        call_args = mock_client.responses.create.call_args
         assert call_args[1]["model"] == "gpt-4"
 
     @pytest.mark.asyncio
@@ -303,15 +298,14 @@ async def test_get_ai_response_system_message_content(
 
         # Mock the client instance directly
         mock_client = MagicMock()
-        mock_client.chat.completions.create = AsyncMock(return_value=mock_openai_response)
+        mock_client.responses.create = AsyncMock(return_value=mock_openai_response)
         openai_cog._openai_client = mock_client
 
         await openai_cog._get_ai_response("Test message")
 
-        messages = mock_client.chat.completions.create.call_args[1]["messages"]
-        system_message = messages[0]
-        expected_content = "You are a helpful AI assistant. Provide clear, concise, and accurate responses."
-        assert system_message["content"] == expected_content
+        call_args = mock_client.responses.create.call_args[1]
+        assert call_args["instructions"] == openai_cog._instructions
+        assert call_args["input"] == "Test message"
 
     @pytest.mark.asyncio
     @patch("src.bot.cogs.open_ai.get_bot_settings")
@@ -323,26 +317,39 @@ async def test_get_ai_response_api_parameters(
 
         # Mock the client instance directly
         mock_client = MagicMock()
-        mock_client.chat.completions.create = AsyncMock(return_value=mock_openai_response)
+        mock_client.responses.create = AsyncMock(return_value=mock_openai_response)
         openai_cog._openai_client = mock_client
 
         await openai_cog._get_ai_response("Test message")
 
-        call_args = mock_client.chat.completions.create.call_args[1]
-        assert call_args["max_completion_tokens"] == 1000
+        call_args = mock_client.responses.create.call_args[1]
+        assert call_args["max_output_tokens"] is None
+        assert call_args["reasoning"]["effort"] == "xhigh"
+        assert call_args["tools"][0]["type"] == "web_search"
         assert "temperature" not in call_args
         assert call_args["model"] == "gpt-3.5-turbo"
 
     @patch("src.bot.cogs.open_ai.bot_utils.get_current_date_time_str_long")
     def test_create_ai_embeds_footer(self, mock_get_datetime, openai_cog, mock_ctx):
-        """Test that embed footer contains correct timestamp and model name."""
+        """Test that embed footer contains model, duration, and timestamp."""
         mock_get_datetime.return_value = "2023-01-01 12:00:00"
 
-        embeds = openai_cog._create_ai_embeds(mock_ctx, "Test", discord.Color.blue())
+        embeds = openai_cog._create_ai_embeds(mock_ctx, "Test", discord.Color.blue(), elapsed=20.0)
 
-        assert embeds[0].footer.text == "gpt-3.5-turbo | 2023-01-01 12:00:00 UTC"
+        assert embeds[0].footer.text == "gpt-3.5-turbo | 20s | 2023-01-01 12:00:00 UTC"
         mock_get_datetime.assert_called_once()
 
+    def test_format_duration_milliseconds(self, openai_cog):
+        """Sub-second durations are shown in milliseconds."""
+        assert openai_cog._format_duration(0.005) == "5ms"
+        assert openai_cog._format_duration(0.5) == "500ms"
+
+    def test_format_duration_seconds(self, openai_cog):
+        """Durations of one second or more are shown in whole seconds."""
+        assert openai_cog._format_duration(1.0) == "1s"
+        assert openai_cog._format_duration(20.4) == "20s"
+        assert openai_cog._format_duration(119.6) == "120s"
+
     @pytest.mark.asyncio
     async def test_setup_function(self, mock_bot):
         """Test the setup function."""
@@ -406,15 +413,13 @@ async def test_get_ai_response_empty_response(self, mock_get_settings, openai_co
         """Test _get_ai_response with empty response from OpenAI."""
         mock_get_settings.return_value = mock_bot_settings
 
-        # Mock empty response
+        # Mock empty response (whitespace only)
         mock_response = MagicMock()
-        mock_response.choices = [MagicMock()]
-        mock_response.choices[0].message = MagicMock()
-        mock_response.choices[0].message.content = "   "  # Only whitespace
+        mock_response.output_text = "   "
 
         # Mock the client instance directly
         mock_client = MagicMock()
-        mock_client.chat.completions.create = AsyncMock(return_value=mock_response)
+        mock_client.responses.create = AsyncMock(return_value=mock_response)
         openai_cog._openai_client = mock_client
 
         result = await openai_cog._get_ai_response("Test message")
@@ -473,7 +478,8 @@ async def test_ai_command_pagination(
         with patch.object(openai_cog, "_get_ai_response", return_value=long_response):
             await openai_cog.ai.callback(openai_cog, mock_ctx, msg_text="Long question")
 
-            mock_ctx.send.assert_called_once()
-            call_kwargs = mock_ctx.send.call_args[1]
+            # ctx.send called twice: progress message, then the paginated first page
+            assert mock_ctx.send.call_count == 2
+            call_kwargs = mock_ctx.send.call_args[1]  # last call == paginated send
             assert "embed" in call_kwargs
             assert "view" in call_kwargs
diff --git a/uv.lock b/uv.lock
index 79a87b4..185b197 100644
--- a/uv.lock
+++ b/uv.lock
@@ -4,11 +4,11 @@ requires-python = ">=3.14"
 
 [[package]]
 name = "aiohappyeyeballs"
-version = "2.6.1"
+version = "2.6.2"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/26/30/f84a107a9c4331c14b2b586036f40965c128aa4fee4dda5d3d51cb14ad54/aiohappyeyeballs-2.6.1.tar.gz", hash = "sha256:c3f9d0113123803ccadfdf3f0faa505bc78e6a72d1cc4806cbd719826e943558", size = 22760, upload-time = "2025-03-12T01:42:48.764Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/33/c6/61a2d7b7572279226bb2e7f61d7a19ca7c90da0329c93fa0d560cbf288d8/aiohappyeyeballs-2.6.2.tar.gz", hash = "sha256:e202810ee718bd01fc6ef49e8ea53d023d5cb6b581076d7925aa499fa55dbe64", size = 22591, upload-time = "2026-05-20T15:12:24.631Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/0f/15/5bf3b99495fb160b63f95972b81750f18f7f4e02ad051373b669d17d44f2/aiohappyeyeballs-2.6.1-py3-none-any.whl", hash = "sha256:f349ba8f4b75cb25c99c5c2d84e997e485204d2902a9597802b0371f09331fb8", size = 15265, upload-time = "2025-03-12T01:42:47.083Z" },
+    { url = "https://files.pythonhosted.org/packages/5f/fc/a7bf5b6e4e617b45f90f2d9d2a68519c249c81dd4fc2658c7a2a61c4f4b7/aiohappyeyeballs-2.6.2-py3-none-any.whl", hash = "sha256:4708045e2d7a6c6bdf8aafa8ed39649eaf926a4543b54560659129e3365953c4", size = 15062, upload-time = "2026-05-20T15:12:23.328Z" },
 ]
 
 [[package]]
@@ -206,11 +206,11 @@ wheels = [
 
 [[package]]
 name = "certifi"
-version = "2026.4.22"
+version = "2026.5.20"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/25/ee/6caf7a40c36a1220410afe15a1cc64993a1f864871f698c0f93acb72842a/certifi-2026.4.22.tar.gz", hash = "sha256:8d455352a37b71bf76a79caa83a3d6c25afee4a385d632127b6afb3963f1c580", size = 137077, upload-time = "2026-04-22T11:26:11.191Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/f3/ce/ee2ecad540810a79593028e88299baeae54d346cc7a0d94b6199988b89b1/certifi-2026.5.20.tar.gz", hash = "sha256:69dea482ab64caa7b9f6aba1c6bf48bb6a5448d1c0f1b17ab42ad8c763a5344d", size = 135422, upload-time = "2026-05-20T11:46:50.073Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/22/30/7cd8fdcdfbc5b869528b079bfb76dcdf6056b1a2097a662e5e8c04f42965/certifi-2026.4.22-py3-none-any.whl", hash = "sha256:3cb2210c8f88ba2318d29b0388d1023c8492ff72ecdde4ebdaddbb13a31b1c4a", size = 135707, upload-time = "2026-04-22T11:26:09.372Z" },
+    { url = "https://files.pythonhosted.org/packages/59/8c/57e832b7af6d7c5abe66eb3fbe3a3a32f4d11ea23a1aa7131371035be991/certifi-2026.5.20-py3-none-any.whl", hash = "sha256:3c52e209ba0a4ad7aebe60436a4ab349c39e1e602e8c134221e546902ad25897", size = 134134, upload-time = "2026-05-20T11:46:48.578Z" },
 ]
 
 [[package]]
@@ -310,41 +310,41 @@ wheels = [
 
 [[package]]
 name = "coverage"
-version = "7.13.5"
-source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/9d/e0/70553e3000e345daff267cec284ce4cbf3fc141b6da229ac52775b5428f1/coverage-7.13.5.tar.gz", hash = "sha256:c81f6515c4c40141f83f502b07bbfa5c240ba25bbe73da7b33f1e5b6120ff179", size = 915967, upload-time = "2026-03-17T10:33:18.341Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/8e/77/39703f0d1d4b478bfd30191d3c14f53caf596fac00efb3f8f6ee23646439/coverage-7.13.5-cp314-cp314-macosx_10_15_x86_64.whl", hash = "sha256:fbabfaceaeb587e16f7008f7795cd80d20ec548dc7f94fbb0d4ec2e038ce563f", size = 219621, upload-time = "2026-03-17T10:32:08.589Z" },
-    { url = "https://files.pythonhosted.org/packages/e2/3e/51dff36d99ae14639a133d9b164d63e628532e2974d8b1edb99dd1ebc733/coverage-7.13.5-cp314-cp314-macosx_11_0_arm64.whl", hash = "sha256:9bb2a28101a443669a423b665939381084412b81c3f8c0fcfbac57f4e30b5b8e", size = 219953, upload-time = "2026-03-17T10:32:10.507Z" },
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 [[package]]
 name = "discordbot"
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+version = "3.0.15"
 source = { virtual = "." }
 dependencies = [
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-    { name = "uuid-utils", specifier = ">=0.14.1" },
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-    { name = "ruff", specifier = ">=0.15.12" },
+    { name = "ruff", specifier = ">=0.15.14" },
     { name = "testcontainers", extras = ["postgres"], specifier = ">=4.14.2" },
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