diff --git a/strix/runtime/docker_runtime.py b/strix/runtime/docker_runtime.py
index 2f53804..5b8a836 100644
--- a/strix/runtime/docker_runtime.py
+++ b/strix/runtime/docker_runtime.py
@@ -1,3 +1,4 @@
+import asyncio
 import contextlib
 import logging
 import os
@@ -22,6 +23,8 @@ from .runtime import AbstractRuntime, SandboxInfo
 STRIX_IMAGE = os.getenv("STRIX_IMAGE", "ghcr.io/usestrix/strix-sandbox:0.1.10")
 HOST_GATEWAY_HOSTNAME = "host.docker.internal"
 DOCKER_TIMEOUT = 60  # seconds
+TOOL_SERVER_HEALTH_TIMEOUT = 30  # seconds to wait for tool server to be healthy
+TOOL_SERVER_HEALTH_RETRIES = 10  # number of retries for health check
 logger = logging.getLogger(__name__)
 
 
@@ -300,7 +303,66 @@ class DockerRuntime(AbstractRuntime):
             user="pentester",
         )
 
-        time.sleep(5)
+        time.sleep(2)
+
+        self._wait_for_tool_server_health(tool_server_port)
+
+    def _wait_for_tool_server_health(
+        self,
+        port: int,
+        max_retries: int = TOOL_SERVER_HEALTH_RETRIES,
+        timeout: int = TOOL_SERVER_HEALTH_TIMEOUT,
+    ) -> None:
+        import httpx
+
+        host = self._resolve_docker_host()
+        health_url = f"http://{host}:{port}/health"
+
+        logger.info(f"Waiting for tool server health at {health_url}")
+
+        last_error: Exception | None = None
+        for attempt in range(max_retries):
+            try:
+                with httpx.Client(trust_env=False, timeout=timeout / max_retries) as client:
+                    response = client.get(health_url)
+                    response.raise_for_status()
+                    health_data = response.json()
+
+                    if health_data.get("status") == "healthy":
+                        logger.info(
+                            f"Tool server is healthy after {attempt + 1} attempt(s): {health_data}"
+                        )
+                        return
+
+                    logger.warning(f"Tool server returned unexpected status: {health_data}")
+
+            except httpx.ConnectError as e:
+                last_error = e
+                logger.debug(
+                    f"Tool server not ready (attempt {attempt + 1}/{max_retries}): "
+                    f"Connection refused"
+                )
+            except httpx.TimeoutException as e:
+                last_error = e
+                logger.debug(
+                    f"Tool server not ready (attempt {attempt + 1}/{max_retries}): "
+                    f"Request timed out"
+                )
+            except (httpx.RequestError, httpx.HTTPStatusError) as e:
+                last_error = e
+                logger.debug(f"Tool server not ready (attempt {attempt + 1}/{max_retries}): {e}")
+
+            sleep_time = min(2**attempt * 0.5, 5)
+            time.sleep(sleep_time)
+
+        error_detail = str(last_error) if last_error else "Unknown error"
+        raise SandboxInitializationError(
+            "Tool server failed to start",
+            f"Could not connect to tool server at {health_url} after {max_retries} attempts. "
+            f"Last error: {error_detail}. "
+            "Please ensure Docker Desktop is installed and running, "
+            "and try running strix again.",
+        )
 
     def _copy_local_directory_to_container(
         self, container: Container, local_path: str, target_name: str | None = None
@@ -377,6 +439,7 @@ class DockerRuntime(AbstractRuntime):
 
         api_url = await self.get_sandbox_url(container_id, self._tool_server_port)
 
+        await self._verify_tool_server_health(api_url)
         await self._register_agent_with_tool_server(api_url, agent_id, token)
 
         return {
@@ -387,6 +450,60 @@ class DockerRuntime(AbstractRuntime):
             "agent_id": agent_id,
         }
 
+    async def _verify_tool_server_health(
+        self,
+        api_url: str,
+        max_retries: int = 3,
+        timeout: int = 10,
+    ) -> None:
+        import httpx
+
+        health_url = f"{api_url}/health"
+        last_error: Exception | None = None
+
+        for attempt in range(max_retries):
+            try:
+                async with httpx.AsyncClient(trust_env=False, timeout=timeout) as client:
+                    response = await client.get(health_url)
+                    response.raise_for_status()
+                    health_data = response.json()
+
+                    if health_data.get("status") == "healthy":
+                        logger.debug(f"Tool server health verified: {health_data}")
+                        return
+
+                    logger.warning(f"Tool server returned unexpected status: {health_data}")
+
+            except httpx.ConnectError as e:
+                last_error = e
+                logger.debug(
+                    f"Tool server health check failed (attempt {attempt + 1}/{max_retries}): "
+                    f"Connection refused"
+                )
+            except httpx.TimeoutException as e:
+                last_error = e
+                logger.debug(
+                    f"Tool server health check failed (attempt {attempt + 1}/{max_retries}): "
+                    f"Request timed out"
+                )
+            except (httpx.RequestError, httpx.HTTPStatusError) as e:
+                last_error = e
+                logger.debug(
+                    f"Tool server health check failed (attempt {attempt + 1}/{max_retries}): {e}"
+                )
+
+            if attempt < max_retries - 1:
+                await asyncio.sleep(min(2**attempt, 4))
+
+        error_detail = str(last_error) if last_error else "Unknown error"
+        raise SandboxInitializationError(
+            "Tool server is not responding",
+            f"Could not connect to tool server at {health_url}. "
+            f"Last error: {error_detail}. "
+            "Please ensure Docker Desktop is installed and running, "
+            "and try running strix again.",
+        )
+
     async def _register_agent_with_tool_server(
         self, api_url: str, agent_id: str, token: str
     ) -> None: