diff --git a/src/timmy/agent.py b/src/timmy/agent.py
index 091f2355..2cac1fbb 100644
--- a/src/timmy/agent.py
+++ b/src/timmy/agent.py
@@ -16,6 +16,7 @@ Handoff Protocol maintains continuity across sessions.
 import logging
 from typing import TYPE_CHECKING, Union
 
+import httpx
 from agno.agent import Agent
 from agno.db.sqlite import SqliteDb
 from agno.models.ollama import Ollama
@@ -144,6 +145,32 @@ def _model_supports_tools(model_name: str) -> bool:
     return True
 
 
+def _warmup_model(model_name: str) -> bool:
+    """Warm up an Ollama model by sending a minimal generation request.
+
+    This prevents 'Server disconnected' errors on first request after cold model load.
+    Cold loads can take 30-40s, so we use a 60s timeout.
+
+    Args:
+        model_name: Name of the Ollama model to warm up
+
+    Returns:
+        True if warmup succeeded, False otherwise (does not raise)
+    """
+    try:
+        response = httpx.post(
+            f"{settings.ollama_url}/api/generate",
+            json={"model": model_name, "prompt": "hi", "options": {"num_predict": 1}},
+            timeout=60.0,
+        )
+        response.raise_for_status()
+        logger.info("Model %s warmed up successfully", model_name)
+        return True
+    except Exception as exc:
+        logger.warning("Model warmup failed: %s — first request may disconnect", exc)
+        return False
+
+
 def _resolve_backend(requested: str | None) -> str:
     """Return the backend name to use, resolving 'auto' and explicit overrides.
 
@@ -279,7 +306,7 @@ def create_timmy(
         logger.warning("Failed to load memory context: %s", exc)
         full_prompt = base_prompt
 
-    return Agent(
+    agent = Agent(
         name="Agent",
         model=Ollama(id=model_name, host=settings.ollama_url, timeout=300),
         db=SqliteDb(db_file=db_file),
@@ -291,6 +318,8 @@ def create_timmy(
         tool_call_limit=settings.max_agent_steps if use_tools else None,
         telemetry=settings.telemetry_enabled,
     )
+    _warmup_model(model_name)
+    return agent
 
 
 class TimmyWithMemory: