diff --git a/internal/agent/loop_media.go b/internal/agent/loop_media.go
index ab6e1c6c..42255d42 100644
--- a/internal/agent/loop_media.go
+++ b/internal/agent/loop_media.go
@@ -65,9 +65,17 @@ func extractMediaFromContent(content, workspace string) []MediaResult {
 	if len(matches) == 0 {
 		return nil
 	}
+	// Resolve workspace to its real path (follows symlinks). Required because
+	// macOS uses symlinks for /tmp → /private/tmp; if we only Clean the
+	// workspace but EvalSymlinks the extracted paths, the Rel check below
+	// would spuriously fail even for legitimate files.
 	wsRoot := ""
 	if abs, err := filepath.Abs(workspace); err == nil {
-		wsRoot = filepath.Clean(abs)
+		if resolved, err := filepath.EvalSymlinks(abs); err == nil {
+			wsRoot = filepath.Clean(resolved)
+		} else {
+			wsRoot = filepath.Clean(abs)
+		}
 	}
 	if wsRoot == "" {
 		return nil
@@ -90,18 +98,24 @@ func extractMediaFromContent(content, workspace string) []MediaResult {
 			path = filepath.Join(wsRoot, path)
 		}
 		cleaned := filepath.Clean(path)
-		// Workspace containment check — blocks "../" escapes and absolute paths
-		// outside the agent's allowed area.
-		rel, err := filepath.Rel(wsRoot, cleaned)
-		if err != nil || rel == ".." || strings.HasPrefix(rel, ".."+string(filepath.Separator)) {
-			continue
-		}
-		// Existence + regular-file check prevents hallucinated paths and
-		// directory/symlink-device shenanigans from reaching the outbound queue.
+		// Existence + regular-file check. Lstat (not Stat) so a symlink at
+		// the leaf is rejected outright.
 		info, err := os.Lstat(cleaned)
 		if err != nil || !info.Mode().IsRegular() {
 			continue
 		}
+		// Resolve ancestor symlinks THEN check containment. A purely lexical
+		// Rel check would pass "<ws>/<symlink-dir>/secret" when symlink-dir
+		// points outside the workspace; EvalSymlinks closes that escape.
+		resolved, err := filepath.EvalSymlinks(cleaned)
+		if err != nil {
+			continue
+		}
+		rel, err := filepath.Rel(wsRoot, resolved)
+		if err != nil || rel == ".." || strings.HasPrefix(rel, ".."+string(filepath.Separator)) {
+			continue
+		}
+		cleaned = resolved
 		if _, dup := seen[cleaned]; dup {
 			continue
 		}
@@ -114,7 +128,12 @@ func extractMediaFromContent(content, workspace string) []MediaResult {
 	return results
 }
 
-// deduplicateMedia removes duplicate media results by path, keeping the first occurrence.
+// deduplicateMedia removes duplicate media results, normalizing each path
+// so legacy entries from parseMediaResult (raw tool output — may contain
+// "./" segments or relative forms) collapse cleanly with entries from
+// extractMediaFromContent (already Clean'd + Abs'd). Prevents double-send
+// when a tool returns MEDIA:./x.mp3 and the LLM echoes it back in a form
+// that resolves to the same file.
 func deduplicateMedia(media []MediaResult) []MediaResult {
 	if len(media) <= 1 {
 		return media
@@ -122,10 +141,16 @@ func deduplicateMedia(media []MediaResult) []MediaResult {
 	seen := make(map[string]bool, len(media))
 	result := make([]MediaResult, 0, len(media))
 	for _, m := range media {
-		if seen[m.Path] {
+		key := m.Path
+		if abs, err := filepath.Abs(key); err == nil {
+			key = filepath.Clean(abs)
+		} else {
+			key = filepath.Clean(key)
+		}
+		if seen[key] {
 			continue
 		}
-		seen[m.Path] = true
+		seen[key] = true
 		result = append(result, m)
 	}
 	return result
diff --git a/internal/agent/loop_media_test.go b/internal/agent/loop_media_test.go
index 4d4d65eb..7b32d06e 100644
--- a/internal/agent/loop_media_test.go
+++ b/internal/agent/loop_media_test.go
@@ -20,7 +20,13 @@ func writeTempFile(t *testing.T, workspace, relPath string) string {
 }
 
 func TestExtractMediaFromContent(t *testing.T) {
-	ws := t.TempDir()
+	wsRaw := t.TempDir()
+	// Resolve workspace symlinks up front (macOS has /var → /private/var) so
+	// expected paths match what the extractor returns after EvalSymlinks.
+	ws, err := filepath.EvalSymlinks(wsRaw)
+	if err != nil {
+		t.Fatal(err)
+	}
 	reportPath := writeTempFile(t, ws, "deliver/report.pdf")
 	audioA := writeTempFile(t, ws, "a.mp3")
 	audioB := writeTempFile(t, ws, "b.mp3")
@@ -33,6 +39,23 @@ func TestExtractMediaFromContent(t *testing.T) {
 		t.Fatal(err)
 	}
 
+	// Symlink inside workspace pointing to outside: must be rejected by
+	// EvalSymlinks-then-Rel containment. Covers the P0 ancestor-symlink
+	// escape the lexical-only Rel check would have allowed.
+	symlinkFile := filepath.Join(ws, "shortcut-to-leak.pdf")
+	if err := os.Symlink(outsidePath, symlinkFile); err != nil {
+		t.Skipf("symlink not supported: %v", err)
+	}
+	// Ancestor symlink case: dir symlink inside ws pointing outside.
+	symDirParent := t.TempDir()
+	if err := os.WriteFile(filepath.Join(symDirParent, "victim.pdf"), nil, 0o644); err != nil {
+		t.Fatal(err)
+	}
+	ancestorSym := filepath.Join(ws, "shared")
+	if err := os.Symlink(symDirParent, ancestorSym); err != nil {
+		t.Skipf("symlink not supported: %v", err)
+	}
+
 	tests := []struct {
 		name      string
 		content   string
@@ -84,6 +107,16 @@ func TestExtractMediaFromContent(t *testing.T) {
 			name:    "absolute path with no workspace dropped",
 			content: "MEDIA:" + reportPath,
 		},
+		{
+			name:      "symlink leaf rejected by Lstat",
+			content:   "MEDIA:shortcut-to-leak.pdf",
+			workspace: ws,
+		},
+		{
+			name:      "ancestor symlink escape blocked (P0)",
+			content:   "MEDIA:shared/victim.pdf",
+			workspace: ws,
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
diff --git a/internal/tools/tts.go b/internal/tools/tts.go
index e756de57..ed89cf49 100644
--- a/internal/tools/tts.go
+++ b/internal/tools/tts.go
@@ -242,11 +242,17 @@ func (t *TtsTool) Execute(ctx context.Context, args map[string]any) *Result {
 	// Set Result.Media explicitly (matching create_audio) so the agent loop's
 	// media collector uses the authoritative path even when the ForLLM
 	// MEDIA: prefix is reshaped by a provider bridge (e.g. claude_cli MCP).
+	// Prefer the provider-supplied MimeType ("audio/mpeg", "audio/ogg") over
+	// "audio/"+Extension — the latter yields the non-standard "audio/mp3".
+	mimeType := result.MimeType
+	if mimeType == "" {
+		mimeType = "audio/" + result.Extension
+	}
 	r := &Result{
 		ForLLM: forLLM,
 		Media: []bus.MediaFile{{
 			Path:     audioPath,
-			MimeType: "audio/" + result.Extension,
+			MimeType: mimeType,
 		}},
 	}
 	r.Deliverable = fmt.Sprintf("[Generated audio: %s]\nText: %s", filepath.Base(audioPath), text)