diff --git a/internal/agent/daemon.go b/internal/agent/daemon.go
index 53b4d18..9ef9c54 100644
--- a/internal/agent/daemon.go
+++ b/internal/agent/daemon.go
@@ -246,8 +246,12 @@ func (d *Daemon) Run(ctx context.Context) error {
 		}
 	}
 	d.sync.OnStreamRequest = func(req StreamRequest) {
+		// Off the sync loop: the handler does blocking I/O (os.Stat retries on
+		// NFS, then ffprobe in SetFile) — running it inline would stall task
+		// dispatch + status reporting for other items. The single-stream model
+		// (atomic SetFile swap, last-wins) tolerates concurrent requests.
 		if d.OnStreamRequested != nil {
-			d.OnStreamRequested(req)
+			go d.OnStreamRequested(req)
 		}
 	}
 	d.sync.OnStreamSession = func(sess StreamSession) {
diff --git a/internal/agent/types.go b/internal/agent/types.go
index 8a18687..58ecd38 100644
--- a/internal/agent/types.go
+++ b/internal/agent/types.go
@@ -134,6 +134,11 @@ type StatusUpdate struct {
 	StreamURL       string `json:"streamUrl,omitempty"`
 	StreamReady     bool   `json:"streamReady,omitempty"`
 	ErrorMessage    string `json:"errorMessage,omitempty"`
+	// StreamError reports a failed /stream attempt (path rejected, transient
+	// FS error, etc.) WITHOUT marking the download itself failed — the web
+	// clears streamRequested + surfaces this so the player fails fast with the
+	// real reason instead of a 20s "agent didn't respond" timeout.
+	StreamError string `json:"streamError,omitempty"`
 	// mode=seed_file: agent computes the info_hash from the local file
 	// and reports it back so the web player can target /stream/<hash>.
 	InfoHash string `json:"infoHash,omitempty"`
diff --git a/internal/cmd/daemon.go b/internal/cmd/daemon.go
index f27fbc9..2ffc459 100644
--- a/internal/cmd/daemon.go
+++ b/internal/cmd/daemon.go
@@ -563,33 +563,45 @@ func runDaemonStart() error {
 			return
 		}
 
+		// reportStreamError tells the web a /stream attempt failed WITHOUT
+		// marking the download failed (StreamError, not Status). The web clears
+		// streamRequested and surfaces this so the player fails fast with the
+		// real reason instead of polling out the 20s "agent didn't respond".
+		reportStreamError := func(reason string) {
+			go func() {
+				if _, err := agentClient.ReportStatus(ctx, agent.StatusUpdate{
+					TaskID:      sr.TaskID,
+					StreamError: reason,
+				}); err != nil {
+					log.Printf("[%s] stream error report failed: %v", agent.ShortID(sr.TaskID), err)
+				}
+			}()
+		}
+
 		filePath := filepath.Clean(sr.FilePath)
 		if !isAllowedStreamPath(filePath, cfg.Download.Dir, cfg.Library.ScanPath,
 			cfg.Organize.MoviesDir, cfg.Organize.TVShowsDir) {
 			log.Printf("[%s] stream request rejected: path outside allowed dirs: %s", agent.ShortID(sr.TaskID), filePath)
-			go func() {
-				if _, err := agentClient.ReportStatus(ctx, agent.StatusUpdate{
-					TaskID:       sr.TaskID,
-					Status:       "failed",
-					ErrorMessage: fmt.Sprintf("path outside allowed dirs: %s", filePath),
-				}); err != nil {
-					log.Printf("[%s] stream error report failed: %v", agent.ShortID(sr.TaskID), err)
-				}
-			}()
+			reportStreamError(fmt.Sprintf("path outside allowed dirs: %s", filePath))
 			return
 		}
-		info, err := os.Stat(filePath)
-		if err != nil {
-			log.Printf("[%s] stream request: file not found: %s", agent.ShortID(sr.TaskID), filePath)
-			go func() {
-				if _, err := agentClient.ReportStatus(ctx, agent.StatusUpdate{
-					TaskID:       sr.TaskID,
-					Status:       "failed",
-					ErrorMessage: fmt.Sprintf("file not found: %s", filePath),
-				}); err != nil {
-					log.Printf("[%s] stream error report failed: %v", agent.ShortID(sr.TaskID), err)
-				}
-			}()
+		// os.Stat over NFS can transiently fail (ESTALE/EAGAIN/timeout) right
+		// after a remount or under load. Retry a few times before giving up so
+		// a hiccup doesn't surface as a spurious "file not found" — this is the
+		// root of the intermittent "works on the 3rd try" stream failures.
+		var info os.FileInfo
+		var statErr error
+		for attempt := 0; attempt < 3; attempt++ {
+			if info, statErr = os.Stat(filePath); statErr == nil {
+				break
+			}
+			if attempt < 2 {
+				time.Sleep(300 * time.Millisecond)
+			}
+		}
+		if statErr != nil {
+			log.Printf("[%s] stream request: file not found after retries: %s (%v)", agent.ShortID(sr.TaskID), filePath, statErr)
+			reportStreamError(fmt.Sprintf("file not found: %s", filePath))
 			return
 		}
 
@@ -597,15 +609,7 @@ func runDaemonStart() error {
 			found := engine.FindVideoFile(filePath)
 			if found == "" {
 				log.Printf("[%s] stream request: no video file in directory: %s", agent.ShortID(sr.TaskID), filePath)
-				go func() {
-					if _, err := agentClient.ReportStatus(ctx, agent.StatusUpdate{
-						TaskID:       sr.TaskID,
-						Status:       "failed",
-						ErrorMessage: fmt.Sprintf("no video file in directory: %s", filePath),
-					}); err != nil {
-						log.Printf("[%s] stream error report failed: %v", agent.ShortID(sr.TaskID), err)
-					}
-				}()
+				reportStreamError(fmt.Sprintf("no video file in directory: %s", filePath))
 				return
 			}
 			filePath = found