diff --git a/tests/docker/test_dashboard.py b/tests/docker/test_dashboard.py
index ff2d2e42e0d..d68c81b2525 100644
--- a/tests/docker/test_dashboard.py
+++ b/tests/docker/test_dashboard.py
@@ -12,16 +12,36 @@ import subprocess
 import time
 
 
+def _poll(container: str, probe: str, *, deadline_s: float = 30.0,
+          interval_s: float = 0.5) -> tuple[bool, str]:
+    """Repeatedly run ``probe`` inside the container until it exits 0 or
+    ``deadline_s`` elapses. Returns (success, last stdout)."""
+    end = time.monotonic() + deadline_s
+    last = ""
+    while time.monotonic() < end:
+        r = subprocess.run(
+            ["docker", "exec", container, "sh", "-c", probe],
+            capture_output=True, text=True, timeout=10,
+        )
+        last = r.stdout
+        if r.returncode == 0:
+            return True, last
+        time.sleep(interval_s)
+    return False, last
+
+
 def test_dashboard_not_running_by_default(
     built_image: str, container_name: str,
 ) -> None:
     """Without HERMES_DASHBOARD, no dashboard process should be running."""
     subprocess.run(
         ["docker", "run", "-d", "--name", container_name, built_image,
-         "sleep", "30"],
+         "sleep", "60"],
         check=True, capture_output=True, timeout=30,
     )
-    time.sleep(3)
+    # Give the entrypoint enough time to finish bootstrap; if a dashboard
+    # were going to start it'd be visible by now.
+    time.sleep(5)
     r = subprocess.run(
         ["docker", "exec", container_name,
          "pgrep", "-f", "hermes dashboard"],
@@ -39,18 +59,16 @@ def test_dashboard_opt_in_starts(
     """With HERMES_DASHBOARD=1, a dashboard process should be visible."""
     subprocess.run(
         ["docker", "run", "-d", "--name", container_name,
-         "-e", "HERMES_DASHBOARD=1", built_image, "sleep", "30"],
+         "-e", "HERMES_DASHBOARD=1", built_image, "sleep", "120"],
         check=True, capture_output=True, timeout=30,
     )
-    time.sleep(5)
-    r = subprocess.run(
-        ["docker", "exec", container_name,
-         "pgrep", "-f", "hermes dashboard"],
-        capture_output=True, text=True, timeout=10,
-    )
-    assert r.returncode == 0, (
-        "Dashboard should be running with HERMES_DASHBOARD=1"
+    # Poll for the dashboard subprocess to appear — the entrypoint
+    # backgrounds it and bootstrap (skills sync etc.) can take a few
+    # seconds before the python process actually launches.
+    ok, _ = _poll(
+        container_name, "pgrep -f 'hermes dashboard'", deadline_s=30.0,
     )
+    assert ok, "Dashboard should be running with HERMES_DASHBOARD=1"
 
 
 def test_dashboard_port_override(
@@ -60,16 +78,17 @@ def test_dashboard_port_override(
     subprocess.run(
         ["docker", "run", "-d", "--name", container_name,
          "-e", "HERMES_DASHBOARD=1", "-e", "HERMES_DASHBOARD_PORT=9120",
-         built_image, "sleep", "30"],
+         built_image, "sleep", "120"],
         check=True, capture_output=True, timeout=30,
     )
-    time.sleep(5)
-    r = subprocess.run(
-        ["docker", "exec", container_name, "sh", "-c",
-         "ss -tlnp 2>/dev/null | grep ':9120' "
-         "|| netstat -tln 2>/dev/null | grep ':9120'"],
-        capture_output=True, text=True, timeout=10,
-    )
-    assert "9120" in r.stdout, (
-        f"Dashboard not listening on port 9120: stdout={r.stdout!r}"
+    # The dashboard process appearing in pgrep doesn't mean it's bound
+    # to the port yet — uvicorn takes another second or two to come up.
+    # The image doesn't ship ss/netstat, so probe /proc/net/tcp directly:
+    # port 9120 = 0x23A0, state 0A = LISTEN.
+    ok, stdout = _poll(
+        container_name,
+        "grep -E ' 0+:23A0 .* 0A ' /proc/net/tcp /proc/net/tcp6 "
+        "2>/dev/null",
+        deadline_s=60.0,
     )
+    assert ok, f"Dashboard not listening on port 9120: stdout={stdout!r}"