diff --git a/gptme/cli.py b/gptme/cli.py
index d8768ad3..2b542ef5 100644
--- a/gptme/cli.py
+++ b/gptme/cli.py
@@ -177,7 +177,8 @@ def main(
         tool_allowlist = [tool for tools in tool_allowlist for tool in tools.split(",")]
 
     config = get_config()
-    tool_format = tool_format or config.get_env("TOOL_TYPE") or "markdown"
+
+    tool_format = tool_format or config.get_env("TOOL_FORMAT") or "markdown"
 
     set_tool_format(tool_format)
 
diff --git a/gptme/llm/llm_openai.py b/gptme/llm/llm_openai.py
index e12d959f..9452b6ca 100644
--- a/gptme/llm/llm_openai.py
+++ b/gptme/llm/llm_openai.py
@@ -219,6 +219,8 @@ def _process_file(msg: dict) -> dict:
         else [{"type": "text", "text": message_content}]
     )
 
+    has_images = False
+
     for f in msg.get("files", []):
         f = Path(f)
         ext = f.suffix[1:]
@@ -263,8 +265,14 @@ def _process_file(msg: dict) -> dict:
                 "image_url": {"url": f"data:{media_type};base64,{data}"},
             }
         )
+        has_images = True
 
     msg["content"] = content
+
+    if msg["role"] == "system" and has_images:
+        # Images must come from user with openai
+        msg["role"] = "user"
+
     return msg
 
 
diff --git a/gptme/tools/base.py b/gptme/tools/base.py
index 89d822bf..26614126 100644
--- a/gptme/tools/base.py
+++ b/gptme/tools/base.py
@@ -2,10 +2,11 @@
 import json
 import logging
 import re
+import types
 from collections.abc import Callable, Generator
 from dataclasses import dataclass, field
 from textwrap import indent
-from typing import Any, Literal, Protocol, TypeAlias, cast
+from typing import Any, Literal, Protocol, TypeAlias, cast, get_origin
 
 from lxml import etree
 
@@ -71,6 +72,30 @@ class Parameter:
     required: bool = False
 
 
+# TODO: there must be a better way?
+def derive_type(t) -> str:
+    if get_origin(t) == Literal:
+        v = ", ".join(f'"{a}"' for a in t.__args__)
+        return f"Literal[{v}]"
+    elif get_origin(t) == types.UnionType:
+        v = ", ".join(derive_type(a) for a in t.__args__)
+        return f"Union[{v}]"
+    else:
+        return t.__name__
+
+
+def callable_signature(func: Callable) -> str:
+    # returns a signature f(arg1: type1, arg2: type2, ...) -> return_type
+    args = ", ".join(
+        f"{k}: {derive_type(v)}"
+        for k, v in func.__annotations__.items()
+        if k != "return"
+    )
+    ret_type = func.__annotations__.get("return")
+    ret = f" -> {derive_type(ret_type)}" if ret_type else ""
+    return f"{func.__name__}({args}){ret}"
+
+
 @dataclass(frozen=True, eq=False)
 class ToolSpec:
     """
@@ -139,6 +164,9 @@ def get_instructions(self, tool_format: ToolFormat):
         if tool_format in self.instructions_format:
             instructions.append(self.instructions_format[tool_format])
 
+        if self.functions:
+            instructions.append(self.get_functions_description())
+
         return "\n\n".join(instructions)
 
     def get_tool_prompt(self, examples: bool, tool_format: ToolFormat):
@@ -157,6 +185,19 @@ def get_examples(self, tool_format: ToolFormat = "markdown"):
             return self.examples(tool_format)
         return self.examples
 
+    def get_functions_description(self) -> str:
+        # return a prompt with a brief description of the available functions
+        if self.functions:
+            description = (
+                "The following Python functions can be called with `ipython` tool:\n\n"
+            )
+            return description + "\n".join(
+                f"{callable_signature(func)}: {func.__doc__ or 'No description'}"
+                for func in self.functions
+            )
+        else:
+            return "None"
+
 
 @dataclass(frozen=True)
 class ToolUse:
diff --git a/gptme/tools/browser.py b/gptme/tools/browser.py
index ce8ed393..6a9eb19b 100644
--- a/gptme/tools/browser.py
+++ b/gptme/tools/browser.py
@@ -46,10 +46,6 @@
 
 EngineType = Literal["google", "duckduckgo"]
 
-instructions = """
-To browse the web, you can use the `read_url`, `search`, and `screenshot_url` functions in Python with the `ipython` tool.
-""".strip()
-
 
 def examples(tool_format):
     return f"""
@@ -128,8 +124,7 @@ def screenshot_url(url: str, path: Path | str | None = None) -> Path:
 
 tool = ToolSpec(
     name="browser",
-    desc="Browse the web",
-    instructions=instructions,
+    desc="Browse, search or screenshot the web",
     examples=examples,
     functions=[read_url, search, screenshot_url],
     available=has_browser_tool(),
diff --git a/gptme/tools/chats.py b/gptme/tools/chats.py
index da3195b3..623a2dff 100644
--- a/gptme/tools/chats.py
+++ b/gptme/tools/chats.py
@@ -140,15 +140,6 @@ def read_chat(conversation: str, max_results: int = 5, incl_system=False) -> Non
         print(f"Conversation '{conversation}' not found.")
 
 
-instructions = """
-you can list, search and summarize past conversation logs by using the following Python functions
-with the `ipython` tool:
-- list_chats
-- search_chats
-- read_chat
-""".strip()
-
-
 def examples(tool_format):
     return f"""
 ### Search for a specific topic in past conversations
@@ -161,7 +152,6 @@ def examples(tool_format):
 tool = ToolSpec(
     name="chats",
     desc="List, search, and summarize past conversation logs",
-    instructions=instructions,
     examples=examples,
     functions=[list_chats, search_chats, read_chat],
 )
diff --git a/gptme/tools/computer.py b/gptme/tools/computer.py
index 3cbf1157..8a628e02 100644
--- a/gptme/tools/computer.py
+++ b/gptme/tools/computer.py
@@ -246,7 +246,7 @@ def computer(
 
 
 instructions = """
-Use the following Python function with the `ipython` tool to interact with the computer through X11.
+You can interact with the computer through X11 with the `computer` Python function.
 Available actions:
 - key: Send key sequence (e.g., "Return", "Control_L+c")
 - type: Type text with realistic delays
diff --git a/gptme/tools/python.py b/gptme/tools/python.py
index c93ea2d3..46b21656 100644
--- a/gptme/tools/python.py
+++ b/gptme/tools/python.py
@@ -8,14 +8,11 @@
 import functools
 import importlib.util
 import re
-import types
 from collections.abc import Callable, Generator
 from logging import getLogger
 from typing import (
     TYPE_CHECKING,
-    Literal,
     TypeVar,
-    get_origin,
 )
 
 from ..message import Message
@@ -49,38 +46,6 @@ def register_function(func: T) -> T:
     return func
 
 
-# TODO: there must be a better way?
-def derive_type(t) -> str:
-    if get_origin(t) == Literal:
-        v = ", ".join(f'"{a}"' for a in t.__args__)
-        return f"Literal[{v}]"
-    elif get_origin(t) == types.UnionType:
-        v = ", ".join(derive_type(a) for a in t.__args__)
-        return f"Union[{v}]"
-    else:
-        return t.__name__
-
-
-def callable_signature(func: Callable) -> str:
-    # returns a signature f(arg1: type1, arg2: type2, ...) -> return_type
-    args = ", ".join(
-        f"{k}: {derive_type(v)}"
-        for k, v in func.__annotations__.items()
-        if k != "return"
-    )
-    ret_type = func.__annotations__.get("return")
-    ret = f" -> {derive_type(ret_type)}" if ret_type else ""
-    return f"{func.__name__}({args}){ret}"
-
-
-def get_functions_prompt() -> str:
-    # return a prompt with a brief description of the available functions
-    return "\n".join(
-        f"- {callable_signature(func)}: {func.__doc__ or 'No description'}"
-        for func in registered_functions.values()
-    )
-
-
 def _get_ipython():
     global _ipython
     from IPython.terminal.embed import InteractiveShellEmbed  # fmt: skip
@@ -172,6 +137,10 @@ def get_installed_python_libraries() -> set[str]:
     return installed
 
 
+def get_functions():
+    return "\n".join([f"- {func.__name__}" for func in registered_functions.values()])
+
+
 instructions = """
 This tool execute Python code in an interactive IPython session.
 It will respond with the output and result of the execution.
@@ -218,9 +187,9 @@ def init() -> ToolSpec:
 The following libraries are available:
 {python_libraries_str}
 
-The following functions are available in the REPL:
-{get_functions_prompt()}
-    """.strip()
+The following functions are available:
+{get_functions()}
+""".strip()
 
     # create a copy with the updated instructions
     return dataclasses.replace(tool, instructions=_instructions)
diff --git a/gptme/tools/rag.py b/gptme/tools/rag.py
index ca112fec..f7b776f6 100644
--- a/gptme/tools/rag.py
+++ b/gptme/tools/rag.py
@@ -56,10 +56,7 @@
 logger = logging.getLogger(__name__)
 
 instructions = """
-Use RAG to index and search project documentation. Use `ipython` tool with the following Python functions:
-- rag_index
-- rag_search
-- rag_status
+Use RAG to index and search project documentation.
 """
 
 
diff --git a/gptme/tools/screenshot.py b/gptme/tools/screenshot.py
index 07462839..84c29824 100644
--- a/gptme/tools/screenshot.py
+++ b/gptme/tools/screenshot.py
@@ -42,6 +42,5 @@ def screenshot(path: Path | None = None) -> Path:
 tool = ToolSpec(
     name="screenshot",
     desc="Take a screenshot",
-    instructions="Use the `screenshot` Python function in `ipython` tool to capture a screenshot. You can optionally specify a filename.",
     functions=[screenshot],
 )
diff --git a/gptme/tools/subagent.py b/gptme/tools/subagent.py
index bf4aaae9..e3a0b6a7 100644
--- a/gptme/tools/subagent.py
+++ b/gptme/tools/subagent.py
@@ -156,10 +156,7 @@ def examples(tool_format):
 
 
 instructions = """
-You can use the following Python function with `ipython` tool to manage subagents:
-- subagent(sub_agent_name, prompt)
-- subagent_status(sub_agent_name)
-- subagent_wait(sub_agent_name)
+You can create, check status and wait for subagents.
 """.strip()
 
 tool = ToolSpec(
diff --git a/gptme/tools/vision.py b/gptme/tools/vision.py
index 8bd74ca5..dc73fdaa 100644
--- a/gptme/tools/vision.py
+++ b/gptme/tools/vision.py
@@ -20,7 +20,7 @@ def view_image(image_path: Path | str) -> Message:
 
 
 instructions = """
-You can use the `view_image(path)` Python function with `ipython` tool to open an image file.
+Use the `view_image` Python function with `ipython` tool to view an image file.
 """.strip()
 
 tool = ToolSpec(
diff --git a/gptme/tools/youtube.py b/gptme/tools/youtube.py
index 0b7077dc..3412bba9 100644
--- a/gptme/tools/youtube.py
+++ b/gptme/tools/youtube.py
@@ -28,17 +28,9 @@ def summarize_transcript(transcript: str) -> str:
     return llm_summarize(transcript).content
 
 
-instructions = """
-You can use the following Python functions with `ipython` tool:
-- `get_transcript(youtube_video_id)`
-- `summarize_transcript(youtube_video_id)`
-""".strip()
-
-
 tool: ToolSpec = ToolSpec(
     name="youtube",
     desc="Fetch and summarize YouTube video transcripts",
-    instructions=instructions,
     functions=[get_transcript, summarize_transcript],
     block_types=["youtube"],
     available=bool(YouTubeTranscriptApi),
diff --git a/tests/test_tools_python.py b/tests/test_tools_python.py
index 86fa98d5..ca6ade7b 100644
--- a/tests/test_tools_python.py
+++ b/tests/test_tools_python.py
@@ -1,6 +1,7 @@
 from typing import Literal, TypeAlias
 
-from gptme.tools.python import callable_signature, execute_python
+from gptme.tools.python import execute_python
+from gptme.tools.base import callable_signature
 
 
 def run(code):