diff --git a/skills/continuous-learning-v2/agents/start-observer.sh b/skills/continuous-learning-v2/agents/start-observer.sh
index c3ada314..096a5d7b 100755
--- a/skills/continuous-learning-v2/agents/start-observer.sh
+++ b/skills/continuous-learning-v2/agents/start-observer.sh
@@ -215,8 +215,12 @@ case "$ACTION" in
       CLV2_OBSERVER_PROMPT_PATTERN="$CLV2_OBSERVER_PROMPT_PATTERN" \
       "$OBSERVER_LOOP_SCRIPT" >> "$LOG_FILE" 2>&1 &
 
-    # Wait for PID file
-    sleep 2
+    # Wait for PID file (poll up to 10s, exits early when it appears).
+    # Trade-off vs the old `sleep 2`: healthy startups return in iteration 1
+    # (no fixed latency), but a loop that crashes before writing the PID file
+    # is now detected in ~10s instead of ~2s. The longer ceiling is needed to
+    # tolerate slow filesystems where 2s under-waited and false-negatived.
+    for _i in $(seq 1 50); do [ -f "$PID_FILE" ] && break; sleep 0.2; done
 
     # Check for confirmation-seeking output in the observer log
     if tail -n +"$((start_line + 1))" "$LOG_FILE" 2>/dev/null | grep -E -i -q "$CLV2_OBSERVER_PROMPT_PATTERN"; then
diff --git a/tests/hooks/hooks.test.js b/tests/hooks/hooks.test.js
index f02bf4d1..8ccde106 100644
--- a/tests/hooks/hooks.test.js
+++ b/tests/hooks/hooks.test.js
@@ -3066,6 +3066,19 @@ async function runTests() {
     passed++;
   else failed++;
 
+  if (
+    test('start-observer waits for PID file via poll instead of fixed sleep (#2295)', () => {
+      const startObserverSource = fs.readFileSync(path.join(__dirname, '..', '..', 'skills', 'continuous-learning-v2', 'agents', 'start-observer.sh'), 'utf8');
+
+      assert.ok(!/^\s*sleep 2\s*$/m.test(startObserverSource), 'start-observer.sh should not use the fixed `sleep 2` wait after spawning the observer loop');
+      assert.ok(/\bseq 1 \d+\b/.test(startObserverSource), 'start-observer.sh should bound PID-file polling to a finite iteration count');
+      assert.ok(/\[ -f "\$PID_FILE" \] && break/.test(startObserverSource), 'start-observer.sh should exit polling as soon as $PID_FILE appears');
+      assert.ok(/sleep 0\.\d+/.test(startObserverSource), 'start-observer.sh should poll at sub-second intervals so healthy startups do not pay multi-second latency');
+    })
+  )
+    passed++;
+  else failed++;
+
   if (SKIP_BASH) {
     console.log('  ⊘ detect-project exports the resolved Python command (skipped on Windows)');
     passed++;