diff --git a/python/examples/drawing/__init__.py b/python/examples/drawing/__init__.py
new file mode 100644
index 00000000..b9584561
--- /dev/null
+++ b/python/examples/drawing/__init__.py
@@ -0,0 +1 @@
+# Let's draw some diagrams
diff --git a/python/examples/drawing/demo.py b/python/examples/drawing/demo.py
new file mode 100644
index 00000000..0f499084
--- /dev/null
+++ b/python/examples/drawing/demo.py
@@ -0,0 +1,60 @@
+import asyncio
+import sys
+import tkinter as tk
+
+from dotenv import dotenv_values
+
+import schema
+from render import render_drawing
+
+from typechat import (
+    Success,
+    Failure,
+    TypeChatJsonTranslator,
+    TypeChatValidator,
+    create_language_model,
+    process_requests,
+)
+
+
+async def main(file_path: str | None):
+    env_vals = dotenv_values()
+    model = create_language_model(env_vals)
+    validator = TypeChatValidator(schema.Drawing)
+    translator = TypeChatJsonTranslator(model, validator, schema.Drawing)
+    # print(translator._schema_str)
+
+    window = tk.Tk()
+    window.title("Click to continue...")
+    canvas = tk.Canvas(window, width=800, height=600, bg="white", highlightthickness=0)
+    canvas.pack(padx=10, pady=10)
+    canvas.bind("<Button-1>", lambda event: window.quit())
+
+    history: list[str] = []
+
+    async def request_handler(request: str):
+        print("[Sending request...]")
+        history.append(request)
+        result: Success[schema.Drawing] | Failure = await translator.translate("\n".join(history))
+        if isinstance(result, Failure):
+            print("Failure:", result.message)
+        else:
+            value: schema.Drawing = result.value
+            print(value)
+            if any(isinstance(item, schema.UnknownText) for item in value.items):
+                print("Unknown text detected. Please provide more context:")
+                for item in value.items:
+                    if isinstance(item, schema.UnknownText):
+                        print(" ", item.text)
+
+            canvas.delete("all")
+            render_drawing(canvas, value)
+            print("Click in drawing to continue...")
+            window.mainloop()
+
+    await process_requests("~> ", file_path, request_handler)
+
+
+if __name__ == "__main__":
+    file_path = sys.argv[1] if len(sys.argv) == 2 else None
+    asyncio.run(main(file_path))
diff --git a/python/examples/drawing/input.txt b/python/examples/drawing/input.txt
new file mode 100644
index 00000000..72f46146
--- /dev/null
+++ b/python/examples/drawing/input.txt
@@ -0,0 +1,5 @@
+draw three red squares in a diagonal
+red is the fill color
+make the corners touch
+add labels "foo", etc.
+make them pink
diff --git a/python/examples/drawing/render.py b/python/examples/drawing/render.py
new file mode 100644
index 00000000..41093e04
--- /dev/null
+++ b/python/examples/drawing/render.py
@@ -0,0 +1,105 @@
+import tkinter as tk
+
+from schema import Style, Box, Ellipse, Arrow, Drawing, UnknownText
+
+
+# Map line style to dash patterns
+dash_pattern = {
+    "solid": "",
+    "dashed": (4, 4),  # 4 pixels drawn, 4 pixels space
+    "dotted": (1, 1),  # 1 pixel drawn, 1 pixel space
+}
+
+
+def render_drawing(canvas: tk.Canvas, drawing: Drawing):
+
+    def draw_box(box: Box):
+        x1, y1 = box.x, box.y
+        x2, y2 = x1 + box.width, y1 + box.height
+        canvas.create_rectangle(
+            x1,
+            y1,
+            x2,
+            y2,
+            outline=getattr(box.style, "line_color", None) or "black",
+            fill=getattr(box.style, "fill_color", None) or "",
+        )
+        if box.text:
+            canvas.create_text((x1 + x2) / 2, (y1 + y2) / 2, text=box.text, fill="black")
+
+    def draw_ellipse(ellipse: Ellipse):
+        x1, y1 = ellipse.x, ellipse.y
+        x2, y2 = x1 + ellipse.width, y1 + ellipse.height
+        canvas.create_oval(
+            x1,
+            y1,
+            x2,
+            y2,
+            outline=getattr(ellipse.style, "line_color", None) or "black",
+            fill=getattr(ellipse.style, "fill_color", None) or "",
+        )
+        if ellipse.text:
+            canvas.create_text((x1 + x2) / 2, (y1 + y2) / 2, text=ellipse.text, fill="black")
+
+    def draw_arrow(arrow: Arrow):
+        canvas.create_line(
+            arrow.start_x,
+            arrow.start_y,
+            arrow.end_x,
+            arrow.end_y,
+            dash=dash_pattern[getattr(arrow.style, "line_style", None) or "solid"],
+            arrow=tk.LAST,
+            fill=getattr(arrow.style, "line_color", None) or "black",
+        )
+
+    for item in drawing.items:
+        match item:
+            case Box():
+                draw_box(item)
+            case Ellipse():
+                draw_ellipse(item)
+            case Arrow():
+                draw_arrow(item)
+            case UnknownText():
+                print(f"Unknown text: {item.text}")
+
+
+if __name__ == "__main__":
+    example_drawing = Drawing(
+        type="Drawing",
+        items=[
+            Box(
+                type="Box",
+                x=50,
+                y=50,
+                width=100,
+                height=100,
+                text="Hello",
+                style=Style(type="Style"),
+            ),
+            Ellipse(
+                type="Ellipse",
+                x=200,
+                y=50,
+                width=150,
+                height=100,
+                text="World",
+                style=Style(type="Style", fill_color="lightblue"),
+            ),
+            Arrow(
+                type="Arrow",
+                start_x=50,
+                start_y=200,
+                end_x=150,
+                end_y=200,
+                style=Style(type="Style", line_style="dashed"),
+            ),
+        ],
+    )
+
+    window = tk.Tk()
+    window.title("Drawing")
+    canvas = tk.Canvas(window, width=800, height=600, bg="white", highlightthickness=0)
+    canvas.pack(padx=10, pady=10)
+    render_drawing(canvas, example_drawing)
+    window.mainloop()
diff --git a/python/examples/drawing/schema.py b/python/examples/drawing/schema.py
new file mode 100644
index 00000000..035415f6
--- /dev/null
+++ b/python/examples/drawing/schema.py
@@ -0,0 +1,80 @@
+"""Schema for a drawing with boxes, ellipses, arrows, etc."""
+
+from dataclasses import dataclass
+from typing_extensions import Literal, Annotated, Doc, Optional
+
+
+@dataclass
+class Style:
+    """Style settings for drawing elements."""
+
+    type: Literal["Style"]
+
+    corners: Annotated[
+        Optional[Literal["rounded", "sharp"]],
+        Doc("Corner style of the drawing elements."),
+    ] = None
+    line_thickness: Annotated[Optional[int], Doc("Thickness of the lines.")] = None
+    line_color: Annotated[Optional[str], Doc("CSS-style color code for line color.")] = None
+    fill_color: Annotated[Optional[str], Doc("CSS-style color code for fill color.")] = None
+    line_style: Annotated[Optional[str], Doc("Style of the line: 'solid', 'dashed', 'dotted'.")] = None
+
+
+@dataclass
+class Box:
+    """A rectangular box defined by a coordinate system with the origin at the top left."""
+
+    type: Literal["Box"]
+
+    x: Annotated[int, Doc("X-coordinate of the top left corner.")]
+    y: Annotated[int, Doc("Y-coordinate of the top left corner.")]
+    width: Annotated[int, Doc("Width of the box.")]
+    height: Annotated[int, Doc("Height of the box.")]
+    text: Annotated[Optional[str], Doc("Optional text centered in the box.")] = None
+    style: Annotated[Optional[Style], Doc("Optional style settings for the box.")] = None
+
+
+@dataclass
+class Ellipse:
+    """An ellipse defined by its bounding box dimensions."""
+
+    type: Literal["Ellipse"]
+
+    x: Annotated[int, Doc("X-coordinate of the top left corner of the bounding box.")]
+    y: Annotated[int, Doc("Y-coordinate of the top left corner of the bounding box.")]
+    width: Annotated[int, Doc("Width of the bounding box.")]
+    height: Annotated[int, Doc("Height of the bounding box.")]
+    text: Annotated[Optional[str], Doc("Optional text centered in the box.")] = None
+    style: Annotated[Optional[Style], Doc("Optional style settings for the ellipse.")] = None
+
+
+@dataclass
+class Arrow:
+    """A line with a directional arrow at one or both ends, defined by start and end points."""
+
+    type: Literal["Arrow"]
+
+    start_x: Annotated[int, Doc("Starting X-coordinate.")]
+    start_y: Annotated[int, Doc("Starting Y-coordinate.")]
+    end_x: Annotated[int, Doc("Ending X-coordinate.")]
+    end_y: Annotated[int, Doc("Ending Y-coordinate.")]
+    style: Annotated[Optional[Style], Doc("Optional style settings for the arrow.")] = None
+    head_size: Annotated[Optional[int], Doc("Size of the arrowhead, if present.")] = None
+
+
+@dataclass
+class UnknownText:
+    """Used for input that does not match any other specified type."""
+
+    type: Literal["UnknownText"]
+
+    text: Annotated[str, Doc("The text that wasn't understood.")]
+
+
+@dataclass
+class Drawing:
+    """A collection of graphical elements including boxes, ellipses, arrows, and unrecognized text."""
+
+    type: Literal["Drawing"]
+
+    items: Annotated[list[Box | Arrow | Ellipse | UnknownText], Doc("List of drawable elements.")]
diff --git a/python/notebooks/coffeeShop.ipynb b/python/notebooks/coffeeShop.ipynb
index 9a95f51f..c5ecc602 100644
--- a/python/notebooks/coffeeShop.ipynb
+++ b/python/notebooks/coffeeShop.ipynb
@@ -7,7 +7,9 @@
    "outputs": [],
    "source": [
     "%pip install --upgrade setuptools\n",
-    "%pip install --upgrade gradio"
+    "%pip install --upgrade gradio\n",
+    "%pip install --upgrade python-dotenv\n",
+    "%pip install --upgrade tabulate"
    ]
   },
   {
diff --git a/python/src/typechat/_internal/interactive.py b/python/src/typechat/_internal/interactive.py
index 8ce7ca6d..d6f29595 100644
--- a/python/src/typechat/_internal/interactive.py
+++ b/python/src/typechat/_internal/interactive.py
@@ -20,8 +20,11 @@ async def process_requests(interactive_prompt: str, input_file_name: str | None,
                 print(interactive_prompt + line)
                 await process_request(line)
     else:
-        # Use readline to enable input editing and history
-        import readline  # type: ignore
+        try:
+            # Use readline to enable input editing and history
+            import readline  # type: ignore
+        except ImportError:
+            pass
         while True:
             try:
                 line = input(interactive_prompt)