diff --git a/gptme/cli.py b/gptme/cli.py
index 9f5d6db4..e932f6ac 100644
--- a/gptme/cli.py
+++ b/gptme/cli.py
@@ -22,6 +22,7 @@
 # The above may be used as a prompt for the agent.
 
 import atexit
+import errno
 import importlib.metadata
 import io
 import logging
@@ -194,15 +195,25 @@ def main(
     log.print()
     print("--- ^^^ past messages ^^^ ---")
 
+    def parse_prompt(prompt: str) -> str:
+        try:
+            f = Path(prompt).expanduser()
+            if f.exists() and f.is_file():
+                return f"```{prompt}\n{Path(prompt).expanduser().read_text()}\n```"
+        except OSError as oserr:
+            # some prompts are too long to be a path, so we can't read them
+            if oserr.errno != errno.ENAMETOOLONG:
+                pass
+        except UnicodeDecodeError:
+            # some files are not text files (images, audio, PDFs, binaries, etc), so we can't read them
+            # TODO: but can we handle them better than just printing the path? maybe with metadata from `file`?
+            pass
+        return prompt
+
     # check if any prompt is a full path, if so, replace it with the contents of that file
     # TODO: add support for directories
     # TODO: maybe do this for all prompts, not just those passed on cli
-    prompts = [
-        f"```{p}\n{Path(p).expanduser().read_text()}\n```"
-        if Path(p).expanduser().exists() and Path(p).expanduser().is_file()
-        else p
-        for p in prompts
-    ]
+    prompts = [parse_prompt(p) for p in prompts]
     # join prompts, grouped by `-` if present, since that's the separator for multiple-round prompts
     prompts = [p.strip() for p in "\n\n".join(prompts).split("\n\n-") if p]
 
diff --git a/gptme/llm.py b/gptme/llm.py
index f59b1d4c..38383b53 100644
--- a/gptme/llm.py
+++ b/gptme/llm.py
@@ -106,8 +106,13 @@ def print_clear():
             codeblock_started = "```" in delta_str[:-3]
             codeblock_finished = "```" in delta_str[-5:]
             if codeblock_started and codeblock_finished:
-                # if closing a code block, wait for user to run command
-                break
+                # noreorder
+                from .tools import is_supported_codeblock  # fmt: skip
+
+                # if closing a code block supported by tools, abort generation to let them run
+                if is_supported_codeblock(delta_str):
+                    print("\n")
+                    break
     except KeyboardInterrupt:
         return Message("assistant", deltas_to_str(deltas) + "... ^C Interrupted")
     finally:
diff --git a/gptme/logmanager.py b/gptme/logmanager.py
index f944fe8d..9e5834c8 100644
--- a/gptme/logmanager.py
+++ b/gptme/logmanager.py
@@ -92,7 +92,7 @@ def prepare_messages(self) -> list[Message]:
         msgs = self.log
         msgs_reduced = list(reduce_log(msgs))
 
-        if len(msgs) != len(msgs_reduced):
+        if len_tokens(msgs) != len_tokens(msgs_reduced):
             logger.info(
                 f"Reduced log from {len_tokens(msgs)//1} to {len_tokens(msgs_reduced)//1} tokens"
             )
diff --git a/gptme/tools/__init__.py b/gptme/tools/__init__.py
index bb81948d..8e076a4d 100644
--- a/gptme/tools/__init__.py
+++ b/gptme/tools/__init__.py
@@ -36,10 +36,11 @@ def execute_codeblock(codeblock: str, ask: bool) -> Generator[Message, None, Non
     codeblock_content = codeblock[len(lang_or_fn) :]
 
     is_filename = lang_or_fn.count(".") >= 1
+    assert is_supported_codeblock(codeblock), "Codeblock is not supported"
 
     if lang_or_fn in ["python", "py"]:
         yield from execute_python(codeblock_content, ask=ask)
-    elif lang_or_fn in ["terminal", "bash", "sh"]:
+    elif lang_or_fn in ["bash", "sh"]:
         yield from execute_shell(codeblock_content, ask=ask)
     elif lang_or_fn.startswith("patch "):
         fn = lang_or_fn[len("patch ") :]
@@ -52,6 +53,23 @@ def execute_codeblock(codeblock: str, ask: bool) -> Generator[Message, None, Non
         )
 
 
+def is_supported_codeblock(codeblock: str) -> bool:
+    """Returns whether a codeblock is supported by tools."""
+    lang_or_fn = codeblock.splitlines()[0].strip()
+    is_filename = lang_or_fn.count(".") >= 1
+
+    if lang_or_fn in ["python", "py"]:
+        return True
+    elif lang_or_fn in ["bash", "sh"]:
+        return True
+    elif lang_or_fn.startswith("patch "):
+        return True
+    elif is_filename:
+        return True
+    else:
+        return False
+
+
 def init_tools() -> None:
     """Runs initialization logic for tools."""
     init_python()
diff --git a/gptme/tools/patch.py b/gptme/tools/patch.py
index 95127683..d5258f8c 100644
--- a/gptme/tools/patch.py
+++ b/gptme/tools/patch.py
@@ -41,6 +41,7 @@ def apply(codeblock: str, content: str) -> str:
     """
     Applies the patch to the file.
     """
+    # TODO: support multiple patches in one file, or make it clear that this is not supported (one patch per codeblock)
     codeblock = codeblock.strip()
 
     # get the original chunk
diff --git a/gptme/util.py b/gptme/util.py
index ea743093..7ee9cb06 100644
--- a/gptme/util.py
+++ b/gptme/util.py
@@ -15,10 +15,12 @@
 
 
 # FIXME: model assumption
-def len_tokens(content: str | list[Message], model: str = "gpt-4") -> int:
-    """Get the number of tokens in a string."""
+def len_tokens(content: str | Message | list[Message], model: str = "gpt-4") -> int:
+    """Get the number of tokens in a string, message, or list of messages."""
     if isinstance(content, list):
         return sum(len_tokens(msg.content, model) for msg in content)
+    if isinstance(content, Message):
+        return len_tokens(content.content, model)
     return len(get_tokenizer(model).encode(content))
 
 
diff --git a/tests/test-integration.sh b/tests/test-integration.sh
index 326170cb..d41e2e47 100755
--- a/tests/test-integration.sh
+++ b/tests/test-integration.sh
@@ -43,6 +43,14 @@ gptme 'write a implementation of wireworld with curses to wireworld.py'
 gptme 'plot up to the 5rd degree taylor expansion of sin(x), save to sin.png'
 # works!
 
+# ask it to manipulate sin.png with imagemagick
+gptme 'rotate sin.png 90 degrees clockwise with imagemagick'
+# works!
+
+# ask it to manipulate sin.png with PIL
+gptme 'rotate sin.png 90 degrees clockwise with PIL'
+# needs PIL to be installed
+
 # write C code and apply patch
 gptme 'write a hello world program in c to hello.c, then patch it to ask for your name and print it'
 # works!