diff --git a/.jules/sentinel.md b/.jules/sentinel.md
new file mode 100644
index 000000000..81c1d873d
--- /dev/null
+++ b/.jules/sentinel.md
@@ -0,0 +1,5 @@
+
+## 2025-02-14 - Prevent API key leak in streaming dictation websocket errors
+**Vulnerability:** Streaming dictation (Deepgram, OpenAI Realtime) did not redact API keys from connection errors or websocket payload error responses.
+**Learning:** API keys are injected into streaming websocket URLs or headers which can leak when transport-level errors occur or when the server responds with a typed error payload echoing the key.
+**Prevention:** Apply `providerio.Redact` around all error endpoints and websocket error returns.
diff --git a/internal/dictation/transcriber_deepgram.go b/internal/dictation/transcriber_deepgram.go
index b8b9319aa..7f6cf7696 100644
--- a/internal/dictation/transcriber_deepgram.go
+++ b/internal/dictation/transcriber_deepgram.go
@@ -9,6 +9,7 @@ import (
 	"strconv"
 	"strings"
 
+	"github.com/Gitlawb/zero/internal/providers/providerio"
 	"github.com/coder/websocket"
 )
 
@@ -60,7 +61,7 @@ func (d *deepgramTranscriber) StreamTranscribe(ctx context.Context, chunks <-cha
 		HTTPHeader: http.Header{"Authorization": {"Token " + d.cfg.APIKey}},
 	})
 	if err != nil {
-		return "", fmt.Errorf("connecting to Deepgram: %w", err)
+		return "", fmt.Errorf("connecting to Deepgram: %s", providerio.Redact(err.Error(), d.cfg.APIKey))
 	}
 	defer conn.CloseNow()
 
@@ -100,7 +101,7 @@ func (d *deepgramTranscriber) StreamTranscribe(ctx context.Context, chunks <-cha
 				}
 			default:
 			}
-			return compose(), fmt.Errorf("Deepgram stream error: %w", err)
+			return compose(), fmt.Errorf("Deepgram stream error: %s", providerio.Redact(err.Error(), d.cfg.APIKey))
 		}
 		if typ != websocket.MessageText {
 			continue
diff --git a/internal/dictation/transcriber_openai_realtime.go b/internal/dictation/transcriber_openai_realtime.go
index 590cbc8b4..55d026f48 100644
--- a/internal/dictation/transcriber_openai_realtime.go
+++ b/internal/dictation/transcriber_openai_realtime.go
@@ -8,6 +8,7 @@ import (
 	"net/http"
 	"strings"
 
+	"github.com/Gitlawb/zero/internal/providers/providerio"
 	"github.com/coder/websocket"
 )
 
@@ -59,7 +60,7 @@ func (o *openAIRealtimeTranscriber) StreamTranscribe(ctx context.Context, chunks
 		},
 	})
 	if err != nil {
-		return "", fmt.Errorf("connecting to OpenAI Realtime: %w", err)
+		return "", fmt.Errorf("connecting to OpenAI Realtime: %s", providerio.Redact(err.Error(), o.cfg.APIKey))
 	}
 	defer conn.CloseNow()
 
@@ -113,7 +114,7 @@ func (o *openAIRealtimeTranscriber) StreamTranscribe(ctx context.Context, chunks
 				}
 			default:
 			}
-			return compose(), fmt.Errorf("OpenAI Realtime stream error: %w", err)
+			return compose(), fmt.Errorf("OpenAI Realtime stream error: %s", providerio.Redact(err.Error(), o.cfg.APIKey))
 		}
 		if typ != websocket.MessageText {
 			continue
@@ -147,7 +148,7 @@ func (o *openAIRealtimeTranscriber) StreamTranscribe(ctx context.Context, chunks
 		case realtimeCommitted:
 			committed = true
 		case realtimeError:
-			return compose(), fmt.Errorf("OpenAI Realtime error: %s", evt.text)
+			return compose(), fmt.Errorf("OpenAI Realtime error: %s", providerio.Redact(evt.text, o.cfg.APIKey))
 		}
 		// The writer signals commit completion out of band; observe it so a
 		// stop with no further audio still flips `committed`.
diff --git a/internal/dictation/transcriber_stream_test.go b/internal/dictation/transcriber_stream_test.go
index 8ece95306..4b65dd5f0 100644
--- a/internal/dictation/transcriber_stream_test.go
+++ b/internal/dictation/transcriber_stream_test.go
@@ -229,3 +229,58 @@ func TestParseRealtimeEvent(t *testing.T) {
 		t.Errorf("error parse: %+v", e)
 	}
 }
+
+func TestOpenAIRealtimeStreamTranscribeErrorRedaction(t *testing.T) {
+	url := wsTestServer(t, func(ctx context.Context, c *websocket.Conn) {
+		defer c.Close(websocket.StatusNormalClosure, "")
+		for {
+			typ, _, err := c.Read(ctx)
+			if err != nil {
+				return
+			}
+			if typ != websocket.MessageText {
+				continue
+			}
+			_ = c.Write(ctx, websocket.MessageText, []byte(`{"type":"error","error":{"message":"invalid API key sk-test-key"}}`))
+		}
+	})
+
+	tr, err := NewOpenAIRealtimeTranscriber(OpenAIRealtimeConfig{APIKey: "sk-test-key", BaseURL: url})
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	chunks := make(chan []byte, 1)
+	chunks <- make([]byte, 480)
+	close(chunks)
+	_, ferr := tr.StreamTranscribe(context.Background(), chunks, func(string, bool) {})
+	if ferr == nil {
+		t.Fatal("expected error")
+	}
+	if strings.Contains(ferr.Error(), "sk-test-key") {
+		t.Errorf("API key leaked: %v", ferr)
+	}
+}
+
+func TestDeepgramStreamTranscribeErrorRedaction(t *testing.T) {
+	url := wsTestServer(t, func(ctx context.Context, c *websocket.Conn) {
+		// close immediately with an error that simulates connection issue with API key
+		c.Close(websocket.StatusPolicyViolation, "invalid key sk-test-key")
+	})
+
+	tr, err := NewDeepgramTranscriber(DeepgramConfig{APIKey: "sk-test-key", BaseURL: url})
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	chunks := make(chan []byte, 1)
+	chunks <- make([]byte, 320)
+	close(chunks)
+	_, ferr := tr.StreamTranscribe(context.Background(), chunks, func(string, bool) {})
+	if ferr == nil {
+		t.Fatal("expected error")
+	}
+	if strings.Contains(ferr.Error(), "sk-test-key") {
+		t.Errorf("API key leaked: %v", ferr)
+	}
+}