diff --git a/internal/api/middleware/response_writer.go b/internal/api/middleware/response_writer.go
index 363278ab..7f489267 100644
--- a/internal/api/middleware/response_writer.go
+++ b/internal/api/middleware/response_writer.go
@@ -15,6 +15,8 @@ import (
 )
 
 const requestBodyOverrideContextKey = "REQUEST_BODY_OVERRIDE"
+const responseBodyOverrideContextKey = "RESPONSE_BODY_OVERRIDE"
+const websocketTimelineOverrideContextKey = "WEBSOCKET_TIMELINE_OVERRIDE"
 
 // RequestInfo holds essential details of an incoming HTTP request for logging purposes.
 type RequestInfo struct {
@@ -304,6 +306,10 @@ func (w *ResponseWriterWrapper) Finalize(c *gin.Context) error {
 		if len(apiResponse) > 0 {
 			_ = w.streamWriter.WriteAPIResponse(apiResponse)
 		}
+		apiWebsocketTimeline := w.extractAPIWebsocketTimeline(c)
+		if len(apiWebsocketTimeline) > 0 {
+			_ = w.streamWriter.WriteAPIWebsocketTimeline(apiWebsocketTimeline)
+		}
 		if err := w.streamWriter.Close(); err != nil {
 			w.streamWriter = nil
 			return err
@@ -312,7 +318,7 @@ func (w *ResponseWriterWrapper) Finalize(c *gin.Context) error {
 		return nil
 	}
 
-	return w.logRequest(w.extractRequestBody(c), finalStatusCode, w.cloneHeaders(), w.body.Bytes(), w.extractAPIRequest(c), w.extractAPIResponse(c), w.extractAPIResponseTimestamp(c), slicesAPIResponseError, forceLog)
+	return w.logRequest(w.extractRequestBody(c), finalStatusCode, w.cloneHeaders(), w.extractResponseBody(c), w.extractWebsocketTimeline(c), w.extractAPIRequest(c), w.extractAPIResponse(c), w.extractAPIWebsocketTimeline(c), w.extractAPIResponseTimestamp(c), slicesAPIResponseError, forceLog)
 }
 
 func (w *ResponseWriterWrapper) cloneHeaders() map[string][]string {
@@ -352,6 +358,18 @@ func (w *ResponseWriterWrapper) extractAPIResponse(c *gin.Context) []byte {
 	return data
 }
 
+func (w *ResponseWriterWrapper) extractAPIWebsocketTimeline(c *gin.Context) []byte {
+	apiTimeline, isExist := c.Get("API_WEBSOCKET_TIMELINE")
+	if !isExist {
+		return nil
+	}
+	data, ok := apiTimeline.([]byte)
+	if !ok || len(data) == 0 {
+		return nil
+	}
+	return bytes.Clone(data)
+}
+
 func (w *ResponseWriterWrapper) extractAPIResponseTimestamp(c *gin.Context) time.Time {
 	ts, isExist := c.Get("API_RESPONSE_TIMESTAMP")
 	if !isExist {
@@ -364,19 +382,8 @@ func (w *ResponseWriterWrapper) extractAPIResponseTimestamp(c *gin.Context) time
 }
 
 func (w *ResponseWriterWrapper) extractRequestBody(c *gin.Context) []byte {
-	if c != nil {
-		if bodyOverride, isExist := c.Get(requestBodyOverrideContextKey); isExist {
-			switch value := bodyOverride.(type) {
-			case []byte:
-				if len(value) > 0 {
-					return bytes.Clone(value)
-				}
-			case string:
-				if strings.TrimSpace(value) != "" {
-					return []byte(value)
-				}
-			}
-		}
+	if body := extractBodyOverride(c, requestBodyOverrideContextKey); len(body) > 0 {
+		return body
 	}
 	if w.requestInfo != nil && len(w.requestInfo.Body) > 0 {
 		return w.requestInfo.Body
@@ -384,13 +391,48 @@ func (w *ResponseWriterWrapper) extractRequestBody(c *gin.Context) []byte {
 	return nil
 }
 
-func (w *ResponseWriterWrapper) logRequest(requestBody []byte, statusCode int, headers map[string][]string, body []byte, apiRequestBody, apiResponseBody []byte, apiResponseTimestamp time.Time, apiResponseErrors []*interfaces.ErrorMessage, forceLog bool) error {
+func (w *ResponseWriterWrapper) extractResponseBody(c *gin.Context) []byte {
+	if body := extractBodyOverride(c, responseBodyOverrideContextKey); len(body) > 0 {
+		return body
+	}
+	if w.body == nil || w.body.Len() == 0 {
+		return nil
+	}
+	return bytes.Clone(w.body.Bytes())
+}
+
+func (w *ResponseWriterWrapper) extractWebsocketTimeline(c *gin.Context) []byte {
+	return extractBodyOverride(c, websocketTimelineOverrideContextKey)
+}
+
+func extractBodyOverride(c *gin.Context, key string) []byte {
+	if c == nil {
+		return nil
+	}
+	bodyOverride, isExist := c.Get(key)
+	if !isExist {
+		return nil
+	}
+	switch value := bodyOverride.(type) {
+	case []byte:
+		if len(value) > 0 {
+			return bytes.Clone(value)
+		}
+	case string:
+		if strings.TrimSpace(value) != "" {
+			return []byte(value)
+		}
+	}
+	return nil
+}
+
+func (w *ResponseWriterWrapper) logRequest(requestBody []byte, statusCode int, headers map[string][]string, body, websocketTimeline, apiRequestBody, apiResponseBody, apiWebsocketTimeline []byte, apiResponseTimestamp time.Time, apiResponseErrors []*interfaces.ErrorMessage, forceLog bool) error {
 	if w.requestInfo == nil {
 		return nil
 	}
 
 	if loggerWithOptions, ok := w.logger.(interface {
-		LogRequestWithOptions(string, string, map[string][]string, []byte, int, map[string][]string, []byte, []byte, []byte, []*interfaces.ErrorMessage, bool, string, time.Time, time.Time) error
+		LogRequestWithOptions(string, string, map[string][]string, []byte, int, map[string][]string, []byte, []byte, []byte, []byte, []byte, []*interfaces.ErrorMessage, bool, string, time.Time, time.Time) error
 	}); ok {
 		return loggerWithOptions.LogRequestWithOptions(
 			w.requestInfo.URL,
@@ -400,8 +442,10 @@ func (w *ResponseWriterWrapper) logRequest(requestBody []byte, statusCode int, h
 			statusCode,
 			headers,
 			body,
+			websocketTimeline,
 			apiRequestBody,
 			apiResponseBody,
+			apiWebsocketTimeline,
 			apiResponseErrors,
 			forceLog,
 			w.requestInfo.RequestID,
@@ -418,8 +462,10 @@ func (w *ResponseWriterWrapper) logRequest(requestBody []byte, statusCode int, h
 		statusCode,
 		headers,
 		body,
+		websocketTimeline,
 		apiRequestBody,
 		apiResponseBody,
+		apiWebsocketTimeline,
 		apiResponseErrors,
 		w.requestInfo.RequestID,
 		w.requestInfo.Timestamp,
diff --git a/internal/api/middleware/response_writer_test.go b/internal/api/middleware/response_writer_test.go
index fa4708e4..f5c21deb 100644
--- a/internal/api/middleware/response_writer_test.go
+++ b/internal/api/middleware/response_writer_test.go
@@ -1,10 +1,14 @@
 package middleware
 
 import (
+	"bytes"
 	"net/http/httptest"
 	"testing"
+	"time"
 
 	"github.com/gin-gonic/gin"
+	"github.com/router-for-me/CLIProxyAPI/v6/internal/interfaces"
+	"github.com/router-for-me/CLIProxyAPI/v6/internal/logging"
 )
 
 func TestExtractRequestBodyPrefersOverride(t *testing.T) {
@@ -33,7 +37,7 @@ func TestExtractRequestBodySupportsStringOverride(t *testing.T) {
 	recorder := httptest.NewRecorder()
 	c, _ := gin.CreateTestContext(recorder)
 
-	wrapper := &ResponseWriterWrapper{}
+	wrapper := &ResponseWriterWrapper{body: &bytes.Buffer{}}
 	c.Set(requestBodyOverrideContextKey, "override-as-string")
 
 	body := wrapper.extractRequestBody(c)
@@ -41,3 +45,158 @@ func TestExtractRequestBodySupportsStringOverride(t *testing.T) {
 		t.Fatalf("request body = %q, want %q", string(body), "override-as-string")
 	}
 }
+
+func TestExtractResponseBodyPrefersOverride(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+	recorder := httptest.NewRecorder()
+	c, _ := gin.CreateTestContext(recorder)
+
+	wrapper := &ResponseWriterWrapper{body: &bytes.Buffer{}}
+	wrapper.body.WriteString("original-response")
+
+	body := wrapper.extractResponseBody(c)
+	if string(body) != "original-response" {
+		t.Fatalf("response body = %q, want %q", string(body), "original-response")
+	}
+
+	c.Set(responseBodyOverrideContextKey, []byte("override-response"))
+	body = wrapper.extractResponseBody(c)
+	if string(body) != "override-response" {
+		t.Fatalf("response body = %q, want %q", string(body), "override-response")
+	}
+
+	body[0] = 'X'
+	if got := wrapper.extractResponseBody(c); string(got) != "override-response" {
+		t.Fatalf("response override should be cloned, got %q", string(got))
+	}
+}
+
+func TestExtractResponseBodySupportsStringOverride(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+	recorder := httptest.NewRecorder()
+	c, _ := gin.CreateTestContext(recorder)
+
+	wrapper := &ResponseWriterWrapper{}
+	c.Set(responseBodyOverrideContextKey, "override-response-as-string")
+
+	body := wrapper.extractResponseBody(c)
+	if string(body) != "override-response-as-string" {
+		t.Fatalf("response body = %q, want %q", string(body), "override-response-as-string")
+	}
+}
+
+func TestExtractBodyOverrideClonesBytes(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+	recorder := httptest.NewRecorder()
+	c, _ := gin.CreateTestContext(recorder)
+
+	override := []byte("body-override")
+	c.Set(requestBodyOverrideContextKey, override)
+
+	body := extractBodyOverride(c, requestBodyOverrideContextKey)
+	if !bytes.Equal(body, override) {
+		t.Fatalf("body override = %q, want %q", string(body), string(override))
+	}
+
+	body[0] = 'X'
+	if !bytes.Equal(override, []byte("body-override")) {
+		t.Fatalf("override mutated: %q", string(override))
+	}
+}
+
+func TestExtractWebsocketTimelineUsesOverride(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+	recorder := httptest.NewRecorder()
+	c, _ := gin.CreateTestContext(recorder)
+
+	wrapper := &ResponseWriterWrapper{}
+	if got := wrapper.extractWebsocketTimeline(c); got != nil {
+		t.Fatalf("expected nil websocket timeline, got %q", string(got))
+	}
+
+	c.Set(websocketTimelineOverrideContextKey, []byte("timeline"))
+	body := wrapper.extractWebsocketTimeline(c)
+	if string(body) != "timeline" {
+		t.Fatalf("websocket timeline = %q, want %q", string(body), "timeline")
+	}
+}
+
+func TestFinalizeStreamingWritesAPIWebsocketTimeline(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+	recorder := httptest.NewRecorder()
+	c, _ := gin.CreateTestContext(recorder)
+
+	streamWriter := &testStreamingLogWriter{}
+	wrapper := &ResponseWriterWrapper{
+		ResponseWriter: c.Writer,
+		logger:         &testRequestLogger{enabled: true},
+		requestInfo: &RequestInfo{
+			URL:       "/v1/responses",
+			Method:    "POST",
+			Headers:   map[string][]string{"Content-Type": {"application/json"}},
+			RequestID: "req-1",
+			Timestamp: time.Date(2026, time.April, 1, 12, 0, 0, 0, time.UTC),
+		},
+		isStreaming:  true,
+		streamWriter: streamWriter,
+	}
+
+	c.Set("API_WEBSOCKET_TIMELINE", []byte("Timestamp: 2026-04-01T12:00:00Z\nEvent: api.websocket.request\n{}"))
+
+	if err := wrapper.Finalize(c); err != nil {
+		t.Fatalf("Finalize error: %v", err)
+	}
+	if string(streamWriter.apiWebsocketTimeline) != "Timestamp: 2026-04-01T12:00:00Z\nEvent: api.websocket.request\n{}" {
+		t.Fatalf("stream writer websocket timeline = %q", string(streamWriter.apiWebsocketTimeline))
+	}
+	if !streamWriter.closed {
+		t.Fatal("expected stream writer to be closed")
+	}
+}
+
+type testRequestLogger struct {
+	enabled bool
+}
+
+func (l *testRequestLogger) LogRequest(string, string, map[string][]string, []byte, int, map[string][]string, []byte, []byte, []byte, []byte, []byte, []*interfaces.ErrorMessage, string, time.Time, time.Time) error {
+	return nil
+}
+
+func (l *testRequestLogger) LogStreamingRequest(string, string, map[string][]string, []byte, string) (logging.StreamingLogWriter, error) {
+	return &testStreamingLogWriter{}, nil
+}
+
+func (l *testRequestLogger) IsEnabled() bool {
+	return l.enabled
+}
+
+type testStreamingLogWriter struct {
+	apiWebsocketTimeline []byte
+	closed               bool
+}
+
+func (w *testStreamingLogWriter) WriteChunkAsync([]byte) {}
+
+func (w *testStreamingLogWriter) WriteStatus(int, map[string][]string) error {
+	return nil
+}
+
+func (w *testStreamingLogWriter) WriteAPIRequest([]byte) error {
+	return nil
+}
+
+func (w *testStreamingLogWriter) WriteAPIResponse([]byte) error {
+	return nil
+}
+
+func (w *testStreamingLogWriter) WriteAPIWebsocketTimeline(apiWebsocketTimeline []byte) error {
+	w.apiWebsocketTimeline = bytes.Clone(apiWebsocketTimeline)
+	return nil
+}
+
+func (w *testStreamingLogWriter) SetFirstChunkTimestamp(time.Time) {}
+
+func (w *testStreamingLogWriter) Close() error {
+	w.closed = true
+	return nil
+}
diff --git a/internal/api/server_test.go b/internal/api/server_test.go
index f5c18aa1..7ce38b8f 100644
--- a/internal/api/server_test.go
+++ b/internal/api/server_test.go
@@ -172,6 +172,8 @@ func TestDefaultRequestLoggerFactory_UsesResolvedLogDirectory(t *testing.T) {
 		nil,
 		nil,
 		nil,
+		nil,
+		nil,
 		true,
 		"issue-1711",
 		time.Now(),
diff --git a/internal/logging/request_logger.go b/internal/logging/request_logger.go
index ad7b03c1..2db2a504 100644
--- a/internal/logging/request_logger.go
+++ b/internal/logging/request_logger.go
@@ -4,6 +4,7 @@
 package logging
 
 import (
+	"bufio"
 	"bytes"
 	"compress/flate"
 	"compress/gzip"
@@ -41,15 +42,17 @@ type RequestLogger interface {
 	//   - statusCode: The response status code
 	//   - responseHeaders: The response headers
 	//   - response: The raw response data
+	//   - websocketTimeline: Optional downstream websocket event timeline
 	//   - apiRequest: The API request data
 	//   - apiResponse: The API response data
+	//   - apiWebsocketTimeline: Optional upstream websocket event timeline
 	//   - requestID: Optional request ID for log file naming
 	//   - requestTimestamp: When the request was received
 	//   - apiResponseTimestamp: When the API response was received
 	//
 	// Returns:
 	//   - error: An error if logging fails, nil otherwise
-	LogRequest(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, apiRequest, apiResponse []byte, apiResponseErrors []*interfaces.ErrorMessage, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error
+	LogRequest(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline []byte, apiResponseErrors []*interfaces.ErrorMessage, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error
 
 	// LogStreamingRequest initiates logging for a streaming request and returns a writer for chunks.
 	//
@@ -111,6 +114,16 @@ type StreamingLogWriter interface {
 	//   - error: An error if writing fails, nil otherwise
 	WriteAPIResponse(apiResponse []byte) error
 
+	// WriteAPIWebsocketTimeline writes the upstream websocket timeline to the log.
+	// This should be called when upstream communication happened over websocket.
+	//
+	// Parameters:
+	//   - apiWebsocketTimeline: The upstream websocket event timeline
+	//
+	// Returns:
+	//   - error: An error if writing fails, nil otherwise
+	WriteAPIWebsocketTimeline(apiWebsocketTimeline []byte) error
+
 	// SetFirstChunkTimestamp sets the TTFB timestamp captured when first chunk was received.
 	//
 	// Parameters:
@@ -203,17 +216,17 @@ func (l *FileRequestLogger) SetErrorLogsMaxFiles(maxFiles int) {
 //
 // Returns:
 //   - error: An error if logging fails, nil otherwise
-func (l *FileRequestLogger) LogRequest(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, apiRequest, apiResponse []byte, apiResponseErrors []*interfaces.ErrorMessage, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error {
-	return l.logRequest(url, method, requestHeaders, body, statusCode, responseHeaders, response, apiRequest, apiResponse, apiResponseErrors, false, requestID, requestTimestamp, apiResponseTimestamp)
+func (l *FileRequestLogger) LogRequest(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline []byte, apiResponseErrors []*interfaces.ErrorMessage, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error {
+	return l.logRequest(url, method, requestHeaders, body, statusCode, responseHeaders, response, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline, apiResponseErrors, false, requestID, requestTimestamp, apiResponseTimestamp)
 }
 
 // LogRequestWithOptions logs a request with optional forced logging behavior.
 // The force flag allows writing error logs even when regular request logging is disabled.
-func (l *FileRequestLogger) LogRequestWithOptions(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, apiRequest, apiResponse []byte, apiResponseErrors []*interfaces.ErrorMessage, force bool, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error {
-	return l.logRequest(url, method, requestHeaders, body, statusCode, responseHeaders, response, apiRequest, apiResponse, apiResponseErrors, force, requestID, requestTimestamp, apiResponseTimestamp)
+func (l *FileRequestLogger) LogRequestWithOptions(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline []byte, apiResponseErrors []*interfaces.ErrorMessage, force bool, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error {
+	return l.logRequest(url, method, requestHeaders, body, statusCode, responseHeaders, response, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline, apiResponseErrors, force, requestID, requestTimestamp, apiResponseTimestamp)
 }
 
-func (l *FileRequestLogger) logRequest(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, apiRequest, apiResponse []byte, apiResponseErrors []*interfaces.ErrorMessage, force bool, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error {
+func (l *FileRequestLogger) logRequest(url, method string, requestHeaders map[string][]string, body []byte, statusCode int, responseHeaders map[string][]string, response, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline []byte, apiResponseErrors []*interfaces.ErrorMessage, force bool, requestID string, requestTimestamp, apiResponseTimestamp time.Time) error {
 	if !l.enabled && !force {
 		return nil
 	}
@@ -260,8 +273,10 @@ func (l *FileRequestLogger) logRequest(url, method string, requestHeaders map[st
 		requestHeaders,
 		body,
 		requestBodyPath,
+		websocketTimeline,
 		apiRequest,
 		apiResponse,
+		apiWebsocketTimeline,
 		apiResponseErrors,
 		statusCode,
 		responseHeaders,
@@ -518,8 +533,10 @@ func (l *FileRequestLogger) writeNonStreamingLog(
 	requestHeaders map[string][]string,
 	requestBody []byte,
 	requestBodyPath string,
+	websocketTimeline []byte,
 	apiRequest []byte,
 	apiResponse []byte,
+	apiWebsocketTimeline []byte,
 	apiResponseErrors []*interfaces.ErrorMessage,
 	statusCode int,
 	responseHeaders map[string][]string,
@@ -531,7 +548,16 @@ func (l *FileRequestLogger) writeNonStreamingLog(
 	if requestTimestamp.IsZero() {
 		requestTimestamp = time.Now()
 	}
-	if errWrite := writeRequestInfoWithBody(w, url, method, requestHeaders, requestBody, requestBodyPath, requestTimestamp); errWrite != nil {
+	isWebsocketTranscript := hasSectionPayload(websocketTimeline)
+	downstreamTransport := inferDownstreamTransport(requestHeaders, websocketTimeline)
+	upstreamTransport := inferUpstreamTransport(apiRequest, apiResponse, apiWebsocketTimeline, apiResponseErrors)
+	if errWrite := writeRequestInfoWithBody(w, url, method, requestHeaders, requestBody, requestBodyPath, requestTimestamp, downstreamTransport, upstreamTransport, !isWebsocketTranscript); errWrite != nil {
+		return errWrite
+	}
+	if errWrite := writeAPISection(w, "=== WEBSOCKET TIMELINE ===\n", "=== WEBSOCKET TIMELINE", websocketTimeline, time.Time{}); errWrite != nil {
+		return errWrite
+	}
+	if errWrite := writeAPISection(w, "=== API WEBSOCKET TIMELINE ===\n", "=== API WEBSOCKET TIMELINE", apiWebsocketTimeline, time.Time{}); errWrite != nil {
 		return errWrite
 	}
 	if errWrite := writeAPISection(w, "=== API REQUEST ===\n", "=== API REQUEST", apiRequest, time.Time{}); errWrite != nil {
@@ -543,6 +569,12 @@ func (l *FileRequestLogger) writeNonStreamingLog(
 	if errWrite := writeAPISection(w, "=== API RESPONSE ===\n", "=== API RESPONSE", apiResponse, apiResponseTimestamp); errWrite != nil {
 		return errWrite
 	}
+	if isWebsocketTranscript {
+		// Intentionally omit the generic downstream HTTP response section for websocket
+		// transcripts. The durable session exchange is captured in WEBSOCKET TIMELINE,
+		// and appending a one-off upgrade response snapshot would dilute that transcript.
+		return nil
+	}
 	return writeResponseSection(w, statusCode, true, responseHeaders, bytes.NewReader(response), decompressErr, true)
 }
 
@@ -553,6 +585,9 @@ func writeRequestInfoWithBody(
 	body []byte,
 	bodyPath string,
 	timestamp time.Time,
+	downstreamTransport string,
+	upstreamTransport string,
+	includeBody bool,
 ) error {
 	if _, errWrite := io.WriteString(w, "=== REQUEST INFO ===\n"); errWrite != nil {
 		return errWrite
@@ -566,10 +601,20 @@ func writeRequestInfoWithBody(
 	if _, errWrite := io.WriteString(w, fmt.Sprintf("Method: %s\n", method)); errWrite != nil {
 		return errWrite
 	}
+	if strings.TrimSpace(downstreamTransport) != "" {
+		if _, errWrite := io.WriteString(w, fmt.Sprintf("Downstream Transport: %s\n", downstreamTransport)); errWrite != nil {
+			return errWrite
+		}
+	}
+	if strings.TrimSpace(upstreamTransport) != "" {
+		if _, errWrite := io.WriteString(w, fmt.Sprintf("Upstream Transport: %s\n", upstreamTransport)); errWrite != nil {
+			return errWrite
+		}
+	}
 	if _, errWrite := io.WriteString(w, fmt.Sprintf("Timestamp: %s\n", timestamp.Format(time.RFC3339Nano))); errWrite != nil {
 		return errWrite
 	}
-	if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
+	if errWrite := writeSectionSpacing(w, 1); errWrite != nil {
 		return errWrite
 	}
 
@@ -584,36 +629,121 @@ func writeRequestInfoWithBody(
 			}
 		}
 	}
-	if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
+	if errWrite := writeSectionSpacing(w, 1); errWrite != nil {
 		return errWrite
 	}
 
+	if !includeBody {
+		return nil
+	}
+
 	if _, errWrite := io.WriteString(w, "=== REQUEST BODY ===\n"); errWrite != nil {
 		return errWrite
 	}
 
+	bodyTrailingNewlines := 1
 	if bodyPath != "" {
 		bodyFile, errOpen := os.Open(bodyPath)
 		if errOpen != nil {
 			return errOpen
 		}
-		if _, errCopy := io.Copy(w, bodyFile); errCopy != nil {
+		tracker := &trailingNewlineTrackingWriter{writer: w}
+		written, errCopy := io.Copy(tracker, bodyFile)
+		if errCopy != nil {
 			_ = bodyFile.Close()
 			return errCopy
 		}
+		if written > 0 {
+			bodyTrailingNewlines = tracker.trailingNewlines
+		}
 		if errClose := bodyFile.Close(); errClose != nil {
 			log.WithError(errClose).Warn("failed to close request body temp file")
 		}
 	} else if _, errWrite := w.Write(body); errWrite != nil {
 		return errWrite
+	} else if len(body) > 0 {
+		bodyTrailingNewlines = countTrailingNewlinesBytes(body)
 	}
-
-	if _, errWrite := io.WriteString(w, "\n\n"); errWrite != nil {
+	if errWrite := writeSectionSpacing(w, bodyTrailingNewlines); errWrite != nil {
 		return errWrite
 	}
 	return nil
 }
 
+func countTrailingNewlinesBytes(payload []byte) int {
+	count := 0
+	for i := len(payload) - 1; i >= 0; i-- {
+		if payload[i] != '\n' {
+			break
+		}
+		count++
+	}
+	return count
+}
+
+func writeSectionSpacing(w io.Writer, trailingNewlines int) error {
+	missingNewlines := 3 - trailingNewlines
+	if missingNewlines <= 0 {
+		return nil
+	}
+	_, errWrite := io.WriteString(w, strings.Repeat("\n", missingNewlines))
+	return errWrite
+}
+
+type trailingNewlineTrackingWriter struct {
+	writer           io.Writer
+	trailingNewlines int
+}
+
+func (t *trailingNewlineTrackingWriter) Write(payload []byte) (int, error) {
+	written, errWrite := t.writer.Write(payload)
+	if written > 0 {
+		writtenPayload := payload[:written]
+		trailingNewlines := countTrailingNewlinesBytes(writtenPayload)
+		if trailingNewlines == len(writtenPayload) {
+			t.trailingNewlines += trailingNewlines
+		} else {
+			t.trailingNewlines = trailingNewlines
+		}
+	}
+	return written, errWrite
+}
+
+func hasSectionPayload(payload []byte) bool {
+	return len(bytes.TrimSpace(payload)) > 0
+}
+
+func inferDownstreamTransport(headers map[string][]string, websocketTimeline []byte) string {
+	if hasSectionPayload(websocketTimeline) {
+		return "websocket"
+	}
+	for key, values := range headers {
+		if strings.EqualFold(strings.TrimSpace(key), "Upgrade") {
+			for _, value := range values {
+				if strings.EqualFold(strings.TrimSpace(value), "websocket") {
+					return "websocket"
+				}
+			}
+		}
+	}
+	return "http"
+}
+
+func inferUpstreamTransport(apiRequest, apiResponse, apiWebsocketTimeline []byte, _ []*interfaces.ErrorMessage) string {
+	hasHTTP := hasSectionPayload(apiRequest) || hasSectionPayload(apiResponse)
+	hasWS := hasSectionPayload(apiWebsocketTimeline)
+	switch {
+	case hasHTTP && hasWS:
+		return "websocket+http"
+	case hasWS:
+		return "websocket"
+	case hasHTTP:
+		return "http"
+	default:
+		return ""
+	}
+}
+
 func writeAPISection(w io.Writer, sectionHeader string, sectionPrefix string, payload []byte, timestamp time.Time) error {
 	if len(payload) == 0 {
 		return nil
@@ -623,11 +753,6 @@ func writeAPISection(w io.Writer, sectionHeader string, sectionPrefix string, pa
 		if _, errWrite := w.Write(payload); errWrite != nil {
 			return errWrite
 		}
-		if !bytes.HasSuffix(payload, []byte("\n")) {
-			if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
-				return errWrite
-			}
-		}
 	} else {
 		if _, errWrite := io.WriteString(w, sectionHeader); errWrite != nil {
 			return errWrite
@@ -640,12 +765,9 @@ func writeAPISection(w io.Writer, sectionHeader string, sectionPrefix string, pa
 		if _, errWrite := w.Write(payload); errWrite != nil {
 			return errWrite
 		}
-		if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
-			return errWrite
-		}
 	}
 
-	if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
+	if errWrite := writeSectionSpacing(w, countTrailingNewlinesBytes(payload)); errWrite != nil {
 		return errWrite
 	}
 	return nil
@@ -662,12 +784,17 @@ func writeAPIErrorResponses(w io.Writer, apiResponseErrors []*interfaces.ErrorMe
 		if _, errWrite := io.WriteString(w, fmt.Sprintf("HTTP Status: %d\n", apiResponseErrors[i].StatusCode)); errWrite != nil {
 			return errWrite
 		}
+		trailingNewlines := 1
 		if apiResponseErrors[i].Error != nil {
-			if _, errWrite := io.WriteString(w, apiResponseErrors[i].Error.Error()); errWrite != nil {
+			errText := apiResponseErrors[i].Error.Error()
+			if _, errWrite := io.WriteString(w, errText); errWrite != nil {
 				return errWrite
 			}
+			if errText != "" {
+				trailingNewlines = countTrailingNewlinesBytes([]byte(errText))
+			}
 		}
-		if _, errWrite := io.WriteString(w, "\n\n"); errWrite != nil {
+		if errWrite := writeSectionSpacing(w, trailingNewlines); errWrite != nil {
 			return errWrite
 		}
 	}
@@ -694,12 +821,18 @@ func writeResponseSection(w io.Writer, statusCode int, statusWritten bool, respo
 		}
 	}
 
-	if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
-		return errWrite
+	var bufferedReader *bufio.Reader
+	if responseReader != nil {
+		bufferedReader = bufio.NewReader(responseReader)
+	}
+	if !responseBodyStartsWithLeadingNewline(bufferedReader) {
+		if _, errWrite := io.WriteString(w, "\n"); errWrite != nil {
+			return errWrite
+		}
 	}
 
-	if responseReader != nil {
-		if _, errCopy := io.Copy(w, responseReader); errCopy != nil {
+	if bufferedReader != nil {
+		if _, errCopy := io.Copy(w, bufferedReader); errCopy != nil {
 			return errCopy
 		}
 	}
@@ -717,6 +850,19 @@ func writeResponseSection(w io.Writer, statusCode int, statusWritten bool, respo
 	return nil
 }
 
+func responseBodyStartsWithLeadingNewline(reader *bufio.Reader) bool {
+	if reader == nil {
+		return false
+	}
+	if peeked, _ := reader.Peek(2); len(peeked) >= 2 && peeked[0] == '\r' && peeked[1] == '\n' {
+		return true
+	}
+	if peeked, _ := reader.Peek(1); len(peeked) >= 1 && peeked[0] == '\n' {
+		return true
+	}
+	return false
+}
+
 // formatLogContent creates the complete log content for non-streaming requests.
 //
 // Parameters:
@@ -724,6 +870,7 @@ func writeResponseSection(w io.Writer, statusCode int, statusWritten bool, respo
 //   - method: The HTTP method
 //   - headers: The request headers
 //   - body: The request body
+//   - websocketTimeline: The downstream websocket event timeline
 //   - apiRequest: The API request data
 //   - apiResponse: The API response data
 //   - response: The raw response data
@@ -732,11 +879,42 @@ func writeResponseSection(w io.Writer, statusCode int, statusWritten bool, respo
 //
 // Returns:
 //   - string: The formatted log content
-func (l *FileRequestLogger) formatLogContent(url, method string, headers map[string][]string, body, apiRequest, apiResponse, response []byte, status int, responseHeaders map[string][]string, apiResponseErrors []*interfaces.ErrorMessage) string {
+func (l *FileRequestLogger) formatLogContent(url, method string, headers map[string][]string, body, websocketTimeline, apiRequest, apiResponse, apiWebsocketTimeline, response []byte, status int, responseHeaders map[string][]string, apiResponseErrors []*interfaces.ErrorMessage) string {
 	var content strings.Builder
+	isWebsocketTranscript := hasSectionPayload(websocketTimeline)
+	downstreamTransport := inferDownstreamTransport(headers, websocketTimeline)
+	upstreamTransport := inferUpstreamTransport(apiRequest, apiResponse, apiWebsocketTimeline, apiResponseErrors)
 
 	// Request info
-	content.WriteString(l.formatRequestInfo(url, method, headers, body))
+	content.WriteString(l.formatRequestInfo(url, method, headers, body, downstreamTransport, upstreamTransport, !isWebsocketTranscript))
+
+	if len(websocketTimeline) > 0 {
+		if bytes.HasPrefix(websocketTimeline, []byte("=== WEBSOCKET TIMELINE")) {
+			content.Write(websocketTimeline)
+			if !bytes.HasSuffix(websocketTimeline, []byte("\n")) {
+				content.WriteString("\n")
+			}
+		} else {
+			content.WriteString("=== WEBSOCKET TIMELINE ===\n")
+			content.Write(websocketTimeline)
+			content.WriteString("\n")
+		}
+		content.WriteString("\n")
+	}
+
+	if len(apiWebsocketTimeline) > 0 {
+		if bytes.HasPrefix(apiWebsocketTimeline, []byte("=== API WEBSOCKET TIMELINE")) {
+			content.Write(apiWebsocketTimeline)
+			if !bytes.HasSuffix(apiWebsocketTimeline, []byte("\n")) {
+				content.WriteString("\n")
+			}
+		} else {
+			content.WriteString("=== API WEBSOCKET TIMELINE ===\n")
+			content.Write(apiWebsocketTimeline)
+			content.WriteString("\n")
+		}
+		content.WriteString("\n")
+	}
 
 	if len(apiRequest) > 0 {
 		if bytes.HasPrefix(apiRequest, []byte("=== API REQUEST")) {
@@ -773,6 +951,12 @@ func (l *FileRequestLogger) formatLogContent(url, method string, headers map[str
 		content.WriteString("\n")
 	}
 
+	if isWebsocketTranscript {
+		// Mirror writeNonStreamingLog: websocket transcripts end with the dedicated
+		// timeline sections instead of a generic downstream HTTP response block.
+		return content.String()
+	}
+
 	// Response section
 	content.WriteString("=== RESPONSE ===\n")
 	content.WriteString(fmt.Sprintf("Status: %d\n", status))
@@ -933,13 +1117,19 @@ func (l *FileRequestLogger) decompressZstd(data []byte) ([]byte, error) {
 //
 // Returns:
 //   - string: The formatted request information
-func (l *FileRequestLogger) formatRequestInfo(url, method string, headers map[string][]string, body []byte) string {
+func (l *FileRequestLogger) formatRequestInfo(url, method string, headers map[string][]string, body []byte, downstreamTransport string, upstreamTransport string, includeBody bool) string {
 	var content strings.Builder
 
 	content.WriteString("=== REQUEST INFO ===\n")
 	content.WriteString(fmt.Sprintf("Version: %s\n", buildinfo.Version))
 	content.WriteString(fmt.Sprintf("URL: %s\n", url))
 	content.WriteString(fmt.Sprintf("Method: %s\n", method))
+	if strings.TrimSpace(downstreamTransport) != "" {
+		content.WriteString(fmt.Sprintf("Downstream Transport: %s\n", downstreamTransport))
+	}
+	if strings.TrimSpace(upstreamTransport) != "" {
+		content.WriteString(fmt.Sprintf("Upstream Transport: %s\n", upstreamTransport))
+	}
 	content.WriteString(fmt.Sprintf("Timestamp: %s\n", time.Now().Format(time.RFC3339Nano)))
 	content.WriteString("\n")
 
@@ -952,6 +1142,10 @@ func (l *FileRequestLogger) formatRequestInfo(url, method string, headers map[st
 	}
 	content.WriteString("\n")
 
+	if !includeBody {
+		return content.String()
+	}
+
 	content.WriteString("=== REQUEST BODY ===\n")
 	content.Write(body)
 	content.WriteString("\n\n")
@@ -1011,6 +1205,9 @@ type FileStreamingLogWriter struct {
 	// apiResponse stores the upstream API response data.
 	apiResponse []byte
 
+	// apiWebsocketTimeline stores the upstream websocket event timeline.
+	apiWebsocketTimeline []byte
+
 	// apiResponseTimestamp captures when the API response was received.
 	apiResponseTimestamp time.Time
 }
@@ -1092,6 +1289,21 @@ func (w *FileStreamingLogWriter) WriteAPIResponse(apiResponse []byte) error {
 	return nil
 }
 
+// WriteAPIWebsocketTimeline buffers the upstream websocket timeline for later writing.
+//
+// Parameters:
+//   - apiWebsocketTimeline: The upstream websocket event timeline
+//
+// Returns:
+//   - error: Always returns nil (buffering cannot fail)
+func (w *FileStreamingLogWriter) WriteAPIWebsocketTimeline(apiWebsocketTimeline []byte) error {
+	if len(apiWebsocketTimeline) == 0 {
+		return nil
+	}
+	w.apiWebsocketTimeline = bytes.Clone(apiWebsocketTimeline)
+	return nil
+}
+
 func (w *FileStreamingLogWriter) SetFirstChunkTimestamp(timestamp time.Time) {
 	if !timestamp.IsZero() {
 		w.apiResponseTimestamp = timestamp
@@ -1100,7 +1312,7 @@ func (w *FileStreamingLogWriter) SetFirstChunkTimestamp(timestamp time.Time) {
 
 // Close finalizes the log file and cleans up resources.
 // It writes all buffered data to the file in the correct order:
-// API REQUEST -> API RESPONSE -> RESPONSE (status, headers, body chunks)
+// API WEBSOCKET TIMELINE -> API REQUEST -> API RESPONSE -> RESPONSE (status, headers, body chunks)
 //
 // Returns:
 //   - error: An error if closing fails, nil otherwise
@@ -1182,7 +1394,10 @@ func (w *FileStreamingLogWriter) asyncWriter() {
 }
 
 func (w *FileStreamingLogWriter) writeFinalLog(logFile *os.File) error {
-	if errWrite := writeRequestInfoWithBody(logFile, w.url, w.method, w.requestHeaders, nil, w.requestBodyPath, w.timestamp); errWrite != nil {
+	if errWrite := writeRequestInfoWithBody(logFile, w.url, w.method, w.requestHeaders, nil, w.requestBodyPath, w.timestamp, "http", inferUpstreamTransport(w.apiRequest, w.apiResponse, w.apiWebsocketTimeline, nil), true); errWrite != nil {
+		return errWrite
+	}
+	if errWrite := writeAPISection(logFile, "=== API WEBSOCKET TIMELINE ===\n", "=== API WEBSOCKET TIMELINE", w.apiWebsocketTimeline, time.Time{}); errWrite != nil {
 		return errWrite
 	}
 	if errWrite := writeAPISection(logFile, "=== API REQUEST ===\n", "=== API REQUEST", w.apiRequest, time.Time{}); errWrite != nil {
@@ -1265,6 +1480,17 @@ func (w *NoOpStreamingLogWriter) WriteAPIResponse(_ []byte) error {
 	return nil
 }
 
+// WriteAPIWebsocketTimeline is a no-op implementation that does nothing and always returns nil.
+//
+// Parameters:
+//   - apiWebsocketTimeline: The upstream websocket event timeline (ignored)
+//
+// Returns:
+//   - error: Always returns nil
+func (w *NoOpStreamingLogWriter) WriteAPIWebsocketTimeline(_ []byte) error {
+	return nil
+}
+
 func (w *NoOpStreamingLogWriter) SetFirstChunkTimestamp(_ time.Time) {}
 
 // Close is a no-op implementation that does nothing and always returns nil.
diff --git a/internal/runtime/executor/codex_websockets_executor.go b/internal/runtime/executor/codex_websockets_executor.go
index dc9a8a79..2041cebc 100644
--- a/internal/runtime/executor/codex_websockets_executor.go
+++ b/internal/runtime/executor/codex_websockets_executor.go
@@ -219,7 +219,7 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 	}
 
 	wsReqBody := buildCodexWebsocketRequestBody(body)
-	helps.RecordAPIRequest(ctx, e.cfg, helps.UpstreamRequestLog{
+	wsReqLog := helps.UpstreamRequestLog{
 		URL:       wsURL,
 		Method:    "WEBSOCKET",
 		Headers:   wsHeaders.Clone(),
@@ -229,16 +229,14 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 		AuthLabel: authLabel,
 		AuthType:  authType,
 		AuthValue: authValue,
-	})
+	}
+	helps.RecordAPIWebsocketRequest(ctx, e.cfg, wsReqLog)
 
 	conn, respHS, errDial := e.ensureUpstreamConn(ctx, auth, sess, authID, wsURL, wsHeaders)
-	if respHS != nil {
-		helps.RecordAPIResponseMetadata(ctx, e.cfg, respHS.StatusCode, respHS.Header.Clone())
-	}
 	if errDial != nil {
 		bodyErr := websocketHandshakeBody(respHS)
-		if len(bodyErr) > 0 {
-			helps.AppendAPIResponseChunk(ctx, e.cfg, bodyErr)
+		if respHS != nil {
+			helps.RecordAPIWebsocketUpgradeRejection(ctx, e.cfg, websocketUpgradeRequestLog(wsReqLog), respHS.StatusCode, respHS.Header.Clone(), bodyErr)
 		}
 		if respHS != nil && respHS.StatusCode == http.StatusUpgradeRequired {
 			return e.CodexExecutor.Execute(ctx, auth, req, opts)
@@ -246,10 +244,10 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 		if respHS != nil && respHS.StatusCode > 0 {
 			return resp, statusErr{code: respHS.StatusCode, msg: string(bodyErr)}
 		}
-		helps.RecordAPIResponseError(ctx, e.cfg, errDial)
+		helps.RecordAPIWebsocketError(ctx, e.cfg, "dial", errDial)
 		return resp, errDial
 	}
-	closeHTTPResponseBody(respHS, "codex websockets executor: close handshake response body error")
+	recordAPIWebsocketHandshake(ctx, e.cfg, respHS)
 	if sess == nil {
 		logCodexWebsocketConnected(executionSessionID, authID, wsURL)
 		defer func() {
@@ -278,10 +276,10 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 			// Retry once with a fresh websocket connection. This is mainly to handle
 			// upstream closing the socket between sequential requests within the same
 			// execution session.
-			connRetry, _, errDialRetry := e.ensureUpstreamConn(ctx, auth, sess, authID, wsURL, wsHeaders)
+			connRetry, respHSRetry, errDialRetry := e.ensureUpstreamConn(ctx, auth, sess, authID, wsURL, wsHeaders)
 			if errDialRetry == nil && connRetry != nil {
 				wsReqBodyRetry := buildCodexWebsocketRequestBody(body)
-				helps.RecordAPIRequest(ctx, e.cfg, helps.UpstreamRequestLog{
+				helps.RecordAPIWebsocketRequest(ctx, e.cfg, helps.UpstreamRequestLog{
 					URL:       wsURL,
 					Method:    "WEBSOCKET",
 					Headers:   wsHeaders.Clone(),
@@ -292,20 +290,22 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 					AuthType:  authType,
 					AuthValue: authValue,
 				})
+				recordAPIWebsocketHandshake(ctx, e.cfg, respHSRetry)
 				if errSendRetry := writeCodexWebsocketMessage(sess, connRetry, wsReqBodyRetry); errSendRetry == nil {
 					conn = connRetry
 					wsReqBody = wsReqBodyRetry
 				} else {
 					e.invalidateUpstreamConn(sess, connRetry, "send_error", errSendRetry)
-					helps.RecordAPIResponseError(ctx, e.cfg, errSendRetry)
+					helps.RecordAPIWebsocketError(ctx, e.cfg, "send_retry", errSendRetry)
 					return resp, errSendRetry
 				}
 			} else {
-				helps.RecordAPIResponseError(ctx, e.cfg, errDialRetry)
+				closeHTTPResponseBody(respHSRetry, "codex websockets executor: close handshake response body error")
+				helps.RecordAPIWebsocketError(ctx, e.cfg, "dial_retry", errDialRetry)
 				return resp, errDialRetry
 			}
 		} else {
-			helps.RecordAPIResponseError(ctx, e.cfg, errSend)
+			helps.RecordAPIWebsocketError(ctx, e.cfg, "send", errSend)
 			return resp, errSend
 		}
 	}
@@ -316,7 +316,7 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 		}
 		msgType, payload, errRead := readCodexWebsocketMessage(ctx, sess, conn, readCh)
 		if errRead != nil {
-			helps.RecordAPIResponseError(ctx, e.cfg, errRead)
+			helps.RecordAPIWebsocketError(ctx, e.cfg, "read", errRead)
 			return resp, errRead
 		}
 		if msgType != websocket.TextMessage {
@@ -325,7 +325,7 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 				if sess != nil {
 					e.invalidateUpstreamConn(sess, conn, "unexpected_binary", err)
 				}
-				helps.RecordAPIResponseError(ctx, e.cfg, err)
+				helps.RecordAPIWebsocketError(ctx, e.cfg, "unexpected_binary", err)
 				return resp, err
 			}
 			continue
@@ -335,13 +335,13 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 		if len(payload) == 0 {
 			continue
 		}
-		helps.AppendAPIResponseChunk(ctx, e.cfg, payload)
+		helps.AppendAPIWebsocketResponse(ctx, e.cfg, payload)
 
 		if wsErr, ok := parseCodexWebsocketError(payload); ok {
 			if sess != nil {
 				e.invalidateUpstreamConn(sess, conn, "upstream_error", wsErr)
 			}
-			helps.RecordAPIResponseError(ctx, e.cfg, wsErr)
+			helps.RecordAPIWebsocketError(ctx, e.cfg, "upstream_error", wsErr)
 			return resp, wsErr
 		}
 
@@ -413,7 +413,7 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 	}
 
 	wsReqBody := buildCodexWebsocketRequestBody(body)
-	helps.RecordAPIRequest(ctx, e.cfg, helps.UpstreamRequestLog{
+	wsReqLog := helps.UpstreamRequestLog{
 		URL:       wsURL,
 		Method:    "WEBSOCKET",
 		Headers:   wsHeaders.Clone(),
@@ -423,18 +423,18 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 		AuthLabel: authLabel,
 		AuthType:  authType,
 		AuthValue: authValue,
-	})
+	}
+	helps.RecordAPIWebsocketRequest(ctx, e.cfg, wsReqLog)
 
 	conn, respHS, errDial := e.ensureUpstreamConn(ctx, auth, sess, authID, wsURL, wsHeaders)
 	var upstreamHeaders http.Header
 	if respHS != nil {
 		upstreamHeaders = respHS.Header.Clone()
-		helps.RecordAPIResponseMetadata(ctx, e.cfg, respHS.StatusCode, respHS.Header.Clone())
 	}
 	if errDial != nil {
 		bodyErr := websocketHandshakeBody(respHS)
-		if len(bodyErr) > 0 {
-			helps.AppendAPIResponseChunk(ctx, e.cfg, bodyErr)
+		if respHS != nil {
+			helps.RecordAPIWebsocketUpgradeRejection(ctx, e.cfg, websocketUpgradeRequestLog(wsReqLog), respHS.StatusCode, respHS.Header.Clone(), bodyErr)
 		}
 		if respHS != nil && respHS.StatusCode == http.StatusUpgradeRequired {
 			return e.CodexExecutor.ExecuteStream(ctx, auth, req, opts)
@@ -442,13 +442,13 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 		if respHS != nil && respHS.StatusCode > 0 {
 			return nil, statusErr{code: respHS.StatusCode, msg: string(bodyErr)}
 		}
-		helps.RecordAPIResponseError(ctx, e.cfg, errDial)
+		helps.RecordAPIWebsocketError(ctx, e.cfg, "dial", errDial)
 		if sess != nil {
 			sess.reqMu.Unlock()
 		}
 		return nil, errDial
 	}
-	closeHTTPResponseBody(respHS, "codex websockets executor: close handshake response body error")
+	recordAPIWebsocketHandshake(ctx, e.cfg, respHS)
 
 	if sess == nil {
 		logCodexWebsocketConnected(executionSessionID, authID, wsURL)
@@ -461,20 +461,21 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 	}
 
 	if errSend := writeCodexWebsocketMessage(sess, conn, wsReqBody); errSend != nil {
-		helps.RecordAPIResponseError(ctx, e.cfg, errSend)
+		helps.RecordAPIWebsocketError(ctx, e.cfg, "send", errSend)
 		if sess != nil {
 			e.invalidateUpstreamConn(sess, conn, "send_error", errSend)
 
 			// Retry once with a new websocket connection for the same execution session.
-			connRetry, _, errDialRetry := e.ensureUpstreamConn(ctx, auth, sess, authID, wsURL, wsHeaders)
+			connRetry, respHSRetry, errDialRetry := e.ensureUpstreamConn(ctx, auth, sess, authID, wsURL, wsHeaders)
 			if errDialRetry != nil || connRetry == nil {
-				helps.RecordAPIResponseError(ctx, e.cfg, errDialRetry)
+				closeHTTPResponseBody(respHSRetry, "codex websockets executor: close handshake response body error")
+				helps.RecordAPIWebsocketError(ctx, e.cfg, "dial_retry", errDialRetry)
 				sess.clearActive(readCh)
 				sess.reqMu.Unlock()
 				return nil, errDialRetry
 			}
 			wsReqBodyRetry := buildCodexWebsocketRequestBody(body)
-			helps.RecordAPIRequest(ctx, e.cfg, helps.UpstreamRequestLog{
+			helps.RecordAPIWebsocketRequest(ctx, e.cfg, helps.UpstreamRequestLog{
 				URL:       wsURL,
 				Method:    "WEBSOCKET",
 				Headers:   wsHeaders.Clone(),
@@ -485,8 +486,9 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 				AuthType:  authType,
 				AuthValue: authValue,
 			})
+			recordAPIWebsocketHandshake(ctx, e.cfg, respHSRetry)
 			if errSendRetry := writeCodexWebsocketMessage(sess, connRetry, wsReqBodyRetry); errSendRetry != nil {
-				helps.RecordAPIResponseError(ctx, e.cfg, errSendRetry)
+				helps.RecordAPIWebsocketError(ctx, e.cfg, "send_retry", errSendRetry)
 				e.invalidateUpstreamConn(sess, connRetry, "send_error", errSendRetry)
 				sess.clearActive(readCh)
 				sess.reqMu.Unlock()
@@ -552,7 +554,7 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 				}
 				terminateReason = "read_error"
 				terminateErr = errRead
-				helps.RecordAPIResponseError(ctx, e.cfg, errRead)
+				helps.RecordAPIWebsocketError(ctx, e.cfg, "read", errRead)
 				reporter.PublishFailure(ctx)
 				_ = send(cliproxyexecutor.StreamChunk{Err: errRead})
 				return
@@ -562,7 +564,7 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 					err = fmt.Errorf("codex websockets executor: unexpected binary message")
 					terminateReason = "unexpected_binary"
 					terminateErr = err
-					helps.RecordAPIResponseError(ctx, e.cfg, err)
+					helps.RecordAPIWebsocketError(ctx, e.cfg, "unexpected_binary", err)
 					reporter.PublishFailure(ctx)
 					if sess != nil {
 						e.invalidateUpstreamConn(sess, conn, "unexpected_binary", err)
@@ -577,12 +579,12 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 			if len(payload) == 0 {
 				continue
 			}
-			helps.AppendAPIResponseChunk(ctx, e.cfg, payload)
+			helps.AppendAPIWebsocketResponse(ctx, e.cfg, payload)
 
 			if wsErr, ok := parseCodexWebsocketError(payload); ok {
 				terminateReason = "upstream_error"
 				terminateErr = wsErr
-				helps.RecordAPIResponseError(ctx, e.cfg, wsErr)
+				helps.RecordAPIWebsocketError(ctx, e.cfg, "upstream_error", wsErr)
 				reporter.PublishFailure(ctx)
 				if sess != nil {
 					e.invalidateUpstreamConn(sess, conn, "upstream_error", wsErr)
@@ -1022,6 +1024,32 @@ func encodeCodexWebsocketAsSSE(payload []byte) []byte {
 	return line
 }
 
+func websocketUpgradeRequestLog(info helps.UpstreamRequestLog) helps.UpstreamRequestLog {
+	upgradeInfo := info
+	upgradeInfo.URL = helps.WebsocketUpgradeRequestURL(info.URL)
+	upgradeInfo.Method = http.MethodGet
+	upgradeInfo.Body = nil
+	upgradeInfo.Headers = info.Headers.Clone()
+	if upgradeInfo.Headers == nil {
+		upgradeInfo.Headers = make(http.Header)
+	}
+	if strings.TrimSpace(upgradeInfo.Headers.Get("Connection")) == "" {
+		upgradeInfo.Headers.Set("Connection", "Upgrade")
+	}
+	if strings.TrimSpace(upgradeInfo.Headers.Get("Upgrade")) == "" {
+		upgradeInfo.Headers.Set("Upgrade", "websocket")
+	}
+	return upgradeInfo
+}
+
+func recordAPIWebsocketHandshake(ctx context.Context, cfg *config.Config, resp *http.Response) {
+	if resp == nil {
+		return
+	}
+	helps.RecordAPIWebsocketHandshake(ctx, cfg, resp.StatusCode, resp.Header.Clone())
+	closeHTTPResponseBody(resp, "codex websockets executor: close handshake response body error")
+}
+
 func websocketHandshakeBody(resp *http.Response) []byte {
 	if resp == nil || resp.Body == nil {
 		return nil
diff --git a/internal/runtime/executor/helps/logging_helpers.go b/internal/runtime/executor/helps/logging_helpers.go
index f9389edd..767c8820 100644
--- a/internal/runtime/executor/helps/logging_helpers.go
+++ b/internal/runtime/executor/helps/logging_helpers.go
@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"html"
 	"net/http"
+	"net/url"
 	"sort"
 	"strings"
 	"time"
@@ -19,9 +20,10 @@ import (
 )
 
 const (
-	apiAttemptsKey = "API_UPSTREAM_ATTEMPTS"
-	apiRequestKey  = "API_REQUEST"
-	apiResponseKey = "API_RESPONSE"
+	apiAttemptsKey          = "API_UPSTREAM_ATTEMPTS"
+	apiRequestKey           = "API_REQUEST"
+	apiResponseKey          = "API_RESPONSE"
+	apiWebsocketTimelineKey = "API_WEBSOCKET_TIMELINE"
 )
 
 // UpstreamRequestLog captures the outbound upstream request details for logging.
@@ -46,6 +48,7 @@ type upstreamAttempt struct {
 	headersWritten       bool
 	bodyStarted          bool
 	bodyHasContent       bool
+	prevWasSSEEvent      bool
 	errorWritten         bool
 }
 
@@ -173,15 +176,157 @@ func AppendAPIResponseChunk(ctx context.Context, cfg *config.Config, chunk []byt
 		attempt.response.WriteString("Body:\n")
 		attempt.bodyStarted = true
 	}
+	currentChunkIsSSEEvent := bytes.HasPrefix(data, []byte("event:"))
+	currentChunkIsSSEData := bytes.HasPrefix(data, []byte("data:"))
 	if attempt.bodyHasContent {
-		attempt.response.WriteString("\n\n")
+		separator := "\n\n"
+		if attempt.prevWasSSEEvent && currentChunkIsSSEData {
+			separator = "\n"
+		}
+		attempt.response.WriteString(separator)
 	}
 	attempt.response.WriteString(string(data))
 	attempt.bodyHasContent = true
+	attempt.prevWasSSEEvent = currentChunkIsSSEEvent
 
 	updateAggregatedResponse(ginCtx, attempts)
 }
 
+// RecordAPIWebsocketRequest stores an upstream websocket request event in Gin context.
+func RecordAPIWebsocketRequest(ctx context.Context, cfg *config.Config, info UpstreamRequestLog) {
+	if cfg == nil || !cfg.RequestLog {
+		return
+	}
+	ginCtx := ginContextFrom(ctx)
+	if ginCtx == nil {
+		return
+	}
+
+	builder := &strings.Builder{}
+	builder.WriteString(fmt.Sprintf("Timestamp: %s\n", time.Now().Format(time.RFC3339Nano)))
+	builder.WriteString("Event: api.websocket.request\n")
+	if info.URL != "" {
+		builder.WriteString(fmt.Sprintf("Upstream URL: %s\n", info.URL))
+	}
+	if auth := formatAuthInfo(info); auth != "" {
+		builder.WriteString(fmt.Sprintf("Auth: %s\n", auth))
+	}
+	builder.WriteString("Headers:\n")
+	writeHeaders(builder, info.Headers)
+	builder.WriteString("\nBody:\n")
+	if len(info.Body) > 0 {
+		builder.Write(info.Body)
+	} else {
+		builder.WriteString("<empty>")
+	}
+	builder.WriteString("\n")
+
+	appendAPIWebsocketTimeline(ginCtx, []byte(builder.String()))
+}
+
+// RecordAPIWebsocketHandshake stores the upstream websocket handshake response metadata.
+func RecordAPIWebsocketHandshake(ctx context.Context, cfg *config.Config, status int, headers http.Header) {
+	if cfg == nil || !cfg.RequestLog {
+		return
+	}
+	ginCtx := ginContextFrom(ctx)
+	if ginCtx == nil {
+		return
+	}
+
+	builder := &strings.Builder{}
+	builder.WriteString(fmt.Sprintf("Timestamp: %s\n", time.Now().Format(time.RFC3339Nano)))
+	builder.WriteString("Event: api.websocket.handshake\n")
+	if status > 0 {
+		builder.WriteString(fmt.Sprintf("Status: %d\n", status))
+	}
+	builder.WriteString("Headers:\n")
+	writeHeaders(builder, headers)
+	builder.WriteString("\n")
+
+	appendAPIWebsocketTimeline(ginCtx, []byte(builder.String()))
+}
+
+// RecordAPIWebsocketUpgradeRejection stores a rejected websocket upgrade as an HTTP attempt.
+func RecordAPIWebsocketUpgradeRejection(ctx context.Context, cfg *config.Config, info UpstreamRequestLog, status int, headers http.Header, body []byte) {
+	if cfg == nil || !cfg.RequestLog {
+		return
+	}
+	ginCtx := ginContextFrom(ctx)
+	if ginCtx == nil {
+		return
+	}
+
+	RecordAPIRequest(ctx, cfg, info)
+	RecordAPIResponseMetadata(ctx, cfg, status, headers)
+	AppendAPIResponseChunk(ctx, cfg, body)
+}
+
+// WebsocketUpgradeRequestURL converts a websocket URL back to its HTTP handshake URL for logging.
+func WebsocketUpgradeRequestURL(rawURL string) string {
+	trimmedURL := strings.TrimSpace(rawURL)
+	if trimmedURL == "" {
+		return ""
+	}
+	parsed, err := url.Parse(trimmedURL)
+	if err != nil {
+		return trimmedURL
+	}
+	switch strings.ToLower(parsed.Scheme) {
+	case "ws":
+		parsed.Scheme = "http"
+	case "wss":
+		parsed.Scheme = "https"
+	}
+	return parsed.String()
+}
+
+// AppendAPIWebsocketResponse stores an upstream websocket response frame in Gin context.
+func AppendAPIWebsocketResponse(ctx context.Context, cfg *config.Config, payload []byte) {
+	if cfg == nil || !cfg.RequestLog {
+		return
+	}
+	data := bytes.TrimSpace(payload)
+	if len(data) == 0 {
+		return
+	}
+	ginCtx := ginContextFrom(ctx)
+	if ginCtx == nil {
+		return
+	}
+	markAPIResponseTimestamp(ginCtx)
+
+	builder := &strings.Builder{}
+	builder.WriteString(fmt.Sprintf("Timestamp: %s\n", time.Now().Format(time.RFC3339Nano)))
+	builder.WriteString("Event: api.websocket.response\n")
+	builder.Write(data)
+	builder.WriteString("\n")
+
+	appendAPIWebsocketTimeline(ginCtx, []byte(builder.String()))
+}
+
+// RecordAPIWebsocketError stores an upstream websocket error event in Gin context.
+func RecordAPIWebsocketError(ctx context.Context, cfg *config.Config, stage string, err error) {
+	if cfg == nil || !cfg.RequestLog || err == nil {
+		return
+	}
+	ginCtx := ginContextFrom(ctx)
+	if ginCtx == nil {
+		return
+	}
+	markAPIResponseTimestamp(ginCtx)
+
+	builder := &strings.Builder{}
+	builder.WriteString(fmt.Sprintf("Timestamp: %s\n", time.Now().Format(time.RFC3339Nano)))
+	builder.WriteString("Event: api.websocket.error\n")
+	if trimmed := strings.TrimSpace(stage); trimmed != "" {
+		builder.WriteString(fmt.Sprintf("Stage: %s\n", trimmed))
+	}
+	builder.WriteString(fmt.Sprintf("Error: %s\n", err.Error()))
+
+	appendAPIWebsocketTimeline(ginCtx, []byte(builder.String()))
+}
+
 func ginContextFrom(ctx context.Context) *gin.Context {
 	ginCtx, _ := ctx.Value("gin").(*gin.Context)
 	return ginCtx
@@ -259,6 +404,40 @@ func updateAggregatedResponse(ginCtx *gin.Context, attempts []*upstreamAttempt)
 	ginCtx.Set(apiResponseKey, []byte(builder.String()))
 }
 
+func appendAPIWebsocketTimeline(ginCtx *gin.Context, chunk []byte) {
+	if ginCtx == nil {
+		return
+	}
+	data := bytes.TrimSpace(chunk)
+	if len(data) == 0 {
+		return
+	}
+	if existing, exists := ginCtx.Get(apiWebsocketTimelineKey); exists {
+		if existingBytes, ok := existing.([]byte); ok && len(existingBytes) > 0 {
+			combined := make([]byte, 0, len(existingBytes)+len(data)+2)
+			combined = append(combined, existingBytes...)
+			if !bytes.HasSuffix(existingBytes, []byte("\n")) {
+				combined = append(combined, '\n')
+			}
+			combined = append(combined, '\n')
+			combined = append(combined, data...)
+			ginCtx.Set(apiWebsocketTimelineKey, combined)
+			return
+		}
+	}
+	ginCtx.Set(apiWebsocketTimelineKey, bytes.Clone(data))
+}
+
+func markAPIResponseTimestamp(ginCtx *gin.Context) {
+	if ginCtx == nil {
+		return
+	}
+	if _, exists := ginCtx.Get("API_RESPONSE_TIMESTAMP"); exists {
+		return
+	}
+	ginCtx.Set("API_RESPONSE_TIMESTAMP", time.Now())
+}
+
 func writeHeaders(builder *strings.Builder, headers http.Header) {
 	if builder == nil {
 		return
diff --git a/sdk/api/handlers/openai/openai_responses_websocket.go b/sdk/api/handlers/openai/openai_responses_websocket.go
index df46d971..1080f5cd 100644
--- a/sdk/api/handlers/openai/openai_responses_websocket.go
+++ b/sdk/api/handlers/openai/openai_responses_websocket.go
@@ -32,7 +32,7 @@ const (
 	wsEventTypeCompleted = "response.completed"
 	wsDoneMarker         = "[DONE]"
 	wsTurnStateHeader    = "x-codex-turn-state"
-	wsRequestBodyKey     = "REQUEST_BODY_OVERRIDE"
+	wsTimelineBodyKey    = "WEBSOCKET_TIMELINE_OVERRIDE"
 )
 
 var responsesWebsocketUpgrader = websocket.Upgrader{
@@ -57,10 +57,11 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 	clientIP := websocketClientAddress(c)
 	log.Infof("responses websocket: client connected id=%s remote=%s", passthroughSessionID, clientIP)
 	var wsTerminateErr error
-	var wsBodyLog strings.Builder
+	var wsTimelineLog strings.Builder
 	defer func() {
 		releaseResponsesWebsocketToolCaches(downstreamSessionKey)
 		if wsTerminateErr != nil {
+			appendWebsocketTimelineDisconnect(&wsTimelineLog, wsTerminateErr, time.Now())
 			// log.Infof("responses websocket: session closing id=%s reason=%v", passthroughSessionID, wsTerminateErr)
 		} else {
 			log.Infof("responses websocket: session closing id=%s", passthroughSessionID)
@@ -69,7 +70,7 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 			h.AuthManager.CloseExecutionSession(passthroughSessionID)
 			log.Infof("responses websocket: upstream execution session closed id=%s", passthroughSessionID)
 		}
-		setWebsocketRequestBody(c, wsBodyLog.String())
+		setWebsocketTimelineBody(c, wsTimelineLog.String())
 		if errClose := conn.Close(); errClose != nil {
 			log.Warnf("responses websocket: close connection error: %v", errClose)
 		}
@@ -83,7 +84,6 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 		msgType, payload, errReadMessage := conn.ReadMessage()
 		if errReadMessage != nil {
 			wsTerminateErr = errReadMessage
-			appendWebsocketEvent(&wsBodyLog, "disconnect", []byte(errReadMessage.Error()))
 			if websocket.IsCloseError(errReadMessage, websocket.CloseNormalClosure, websocket.CloseGoingAway, websocket.CloseNoStatusReceived) {
 				log.Infof("responses websocket: client disconnected id=%s error=%v", passthroughSessionID, errReadMessage)
 			} else {
@@ -101,7 +101,7 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 		// 	websocketPayloadEventType(payload),
 		// 	websocketPayloadPreview(payload),
 		// )
-		appendWebsocketEvent(&wsBodyLog, "request", payload)
+		appendWebsocketTimelineEvent(&wsTimelineLog, "request", payload, time.Now())
 
 		allowIncrementalInputWithPreviousResponseID := false
 		if pinnedAuthID != "" && h != nil && h.AuthManager != nil {
@@ -128,8 +128,7 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 		if errMsg != nil {
 			h.LoggingAPIResponseError(context.WithValue(context.Background(), "gin", c), errMsg)
 			markAPIResponseTimestamp(c)
-			errorPayload, errWrite := writeResponsesWebsocketError(conn, errMsg)
-			appendWebsocketEvent(&wsBodyLog, "response", errorPayload)
+			errorPayload, errWrite := writeResponsesWebsocketError(conn, &wsTimelineLog, errMsg)
 			log.Infof(
 				"responses websocket: downstream_out id=%s type=%d event=%s payload=%s",
 				passthroughSessionID,
@@ -157,9 +156,8 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 			}
 			lastRequest = updatedLastRequest
 			lastResponseOutput = []byte("[]")
-			if errWrite := writeResponsesWebsocketSyntheticPrewarm(c, conn, requestJSON, &wsBodyLog, passthroughSessionID); errWrite != nil {
+			if errWrite := writeResponsesWebsocketSyntheticPrewarm(c, conn, requestJSON, &wsTimelineLog, passthroughSessionID); errWrite != nil {
 				wsTerminateErr = errWrite
-				appendWebsocketEvent(&wsBodyLog, "disconnect", []byte(errWrite.Error()))
 				return
 			}
 			continue
@@ -192,10 +190,9 @@ func (h *OpenAIResponsesAPIHandler) ResponsesWebsocket(c *gin.Context) {
 		}
 		dataChan, _, errChan := h.ExecuteStreamWithAuthManager(cliCtx, h.HandlerType(), modelName, requestJSON, "")
 
-		completedOutput, errForward := h.forwardResponsesWebsocket(c, conn, cliCancel, dataChan, errChan, &wsBodyLog, passthroughSessionID)
+		completedOutput, errForward := h.forwardResponsesWebsocket(c, conn, cliCancel, dataChan, errChan, &wsTimelineLog, passthroughSessionID)
 		if errForward != nil {
 			wsTerminateErr = errForward
-			appendWebsocketEvent(&wsBodyLog, "disconnect", []byte(errForward.Error()))
 			log.Warnf("responses websocket: forward failed id=%s error=%v", passthroughSessionID, errForward)
 			return
 		}
@@ -597,7 +594,7 @@ func writeResponsesWebsocketSyntheticPrewarm(
 	c *gin.Context,
 	conn *websocket.Conn,
 	requestJSON []byte,
-	wsBodyLog *strings.Builder,
+	wsTimelineLog *strings.Builder,
 	sessionID string,
 ) error {
 	payloads, errPayloads := syntheticResponsesWebsocketPrewarmPayloads(requestJSON)
@@ -606,7 +603,6 @@ func writeResponsesWebsocketSyntheticPrewarm(
 	}
 	for i := 0; i < len(payloads); i++ {
 		markAPIResponseTimestamp(c)
-		appendWebsocketEvent(wsBodyLog, "response", payloads[i])
 		// log.Infof(
 		// 	"responses websocket: downstream_out id=%s type=%d event=%s payload=%s",
 		// 	sessionID,
@@ -614,7 +610,7 @@ func writeResponsesWebsocketSyntheticPrewarm(
 		// 	websocketPayloadEventType(payloads[i]),
 		// 	websocketPayloadPreview(payloads[i]),
 		// )
-		if errWrite := conn.WriteMessage(websocket.TextMessage, payloads[i]); errWrite != nil {
+		if errWrite := writeResponsesWebsocketPayload(conn, wsTimelineLog, payloads[i], time.Now()); errWrite != nil {
 			log.Warnf(
 				"responses websocket: downstream_out write failed id=%s event=%s error=%v",
 				sessionID,
@@ -713,7 +709,7 @@ func (h *OpenAIResponsesAPIHandler) forwardResponsesWebsocket(
 	cancel handlers.APIHandlerCancelFunc,
 	data <-chan []byte,
 	errs <-chan *interfaces.ErrorMessage,
-	wsBodyLog *strings.Builder,
+	wsTimelineLog *strings.Builder,
 	sessionID string,
 ) ([]byte, error) {
 	completed := false
@@ -736,8 +732,7 @@ func (h *OpenAIResponsesAPIHandler) forwardResponsesWebsocket(
 			if errMsg != nil {
 				h.LoggingAPIResponseError(context.WithValue(context.Background(), "gin", c), errMsg)
 				markAPIResponseTimestamp(c)
-				errorPayload, errWrite := writeResponsesWebsocketError(conn, errMsg)
-				appendWebsocketEvent(wsBodyLog, "response", errorPayload)
+				errorPayload, errWrite := writeResponsesWebsocketError(conn, wsTimelineLog, errMsg)
 				log.Infof(
 					"responses websocket: downstream_out id=%s type=%d event=%s payload=%s",
 					sessionID,
@@ -771,8 +766,7 @@ func (h *OpenAIResponsesAPIHandler) forwardResponsesWebsocket(
 					}
 					h.LoggingAPIResponseError(context.WithValue(context.Background(), "gin", c), errMsg)
 					markAPIResponseTimestamp(c)
-					errorPayload, errWrite := writeResponsesWebsocketError(conn, errMsg)
-					appendWebsocketEvent(wsBodyLog, "response", errorPayload)
+					errorPayload, errWrite := writeResponsesWebsocketError(conn, wsTimelineLog, errMsg)
 					log.Infof(
 						"responses websocket: downstream_out id=%s type=%d event=%s payload=%s",
 						sessionID,
@@ -806,7 +800,6 @@ func (h *OpenAIResponsesAPIHandler) forwardResponsesWebsocket(
 					completedOutput = responseCompletedOutputFromPayload(payloads[i])
 				}
 				markAPIResponseTimestamp(c)
-				appendWebsocketEvent(wsBodyLog, "response", payloads[i])
 				// log.Infof(
 				// 	"responses websocket: downstream_out id=%s type=%d event=%s payload=%s",
 				// 	sessionID,
@@ -814,7 +807,7 @@ func (h *OpenAIResponsesAPIHandler) forwardResponsesWebsocket(
 				// 	websocketPayloadEventType(payloads[i]),
 				// 	websocketPayloadPreview(payloads[i]),
 				// )
-				if errWrite := conn.WriteMessage(websocket.TextMessage, payloads[i]); errWrite != nil {
+				if errWrite := writeResponsesWebsocketPayload(conn, wsTimelineLog, payloads[i], time.Now()); errWrite != nil {
 					log.Warnf(
 						"responses websocket: downstream_out write failed id=%s event=%s error=%v",
 						sessionID,
@@ -870,7 +863,7 @@ func websocketJSONPayloadsFromChunk(chunk []byte) [][]byte {
 	return payloads
 }
 
-func writeResponsesWebsocketError(conn *websocket.Conn, errMsg *interfaces.ErrorMessage) ([]byte, error) {
+func writeResponsesWebsocketError(conn *websocket.Conn, wsTimelineLog *strings.Builder, errMsg *interfaces.ErrorMessage) ([]byte, error) {
 	status := http.StatusInternalServerError
 	errText := http.StatusText(status)
 	if errMsg != nil {
@@ -940,7 +933,7 @@ func writeResponsesWebsocketError(conn *websocket.Conn, errMsg *interfaces.Error
 		}
 	}
 
-	return payload, conn.WriteMessage(websocket.TextMessage, payload)
+	return payload, writeResponsesWebsocketPayload(conn, wsTimelineLog, payload, time.Now())
 }
 
 func appendWebsocketEvent(builder *strings.Builder, eventType string, payload []byte) {
@@ -979,7 +972,11 @@ func websocketPayloadPreview(payload []byte) string {
 	return previewText
 }
 
-func setWebsocketRequestBody(c *gin.Context, body string) {
+func setWebsocketTimelineBody(c *gin.Context, body string) {
+	setWebsocketBody(c, wsTimelineBodyKey, body)
+}
+
+func setWebsocketBody(c *gin.Context, key string, body string) {
 	if c == nil {
 		return
 	}
@@ -987,7 +984,40 @@ func setWebsocketRequestBody(c *gin.Context, body string) {
 	if trimmedBody == "" {
 		return
 	}
-	c.Set(wsRequestBodyKey, []byte(trimmedBody))
+	c.Set(key, []byte(trimmedBody))
+}
+
+func writeResponsesWebsocketPayload(conn *websocket.Conn, wsTimelineLog *strings.Builder, payload []byte, timestamp time.Time) error {
+	appendWebsocketTimelineEvent(wsTimelineLog, "response", payload, timestamp)
+	return conn.WriteMessage(websocket.TextMessage, payload)
+}
+
+func appendWebsocketTimelineDisconnect(builder *strings.Builder, err error, timestamp time.Time) {
+	if err == nil {
+		return
+	}
+	appendWebsocketTimelineEvent(builder, "disconnect", []byte(err.Error()), timestamp)
+}
+
+func appendWebsocketTimelineEvent(builder *strings.Builder, eventType string, payload []byte, timestamp time.Time) {
+	if builder == nil {
+		return
+	}
+	trimmedPayload := bytes.TrimSpace(payload)
+	if len(trimmedPayload) == 0 {
+		return
+	}
+	if builder.Len() > 0 {
+		builder.WriteString("\n")
+	}
+	builder.WriteString("Timestamp: ")
+	builder.WriteString(timestamp.Format(time.RFC3339Nano))
+	builder.WriteString("\n")
+	builder.WriteString("Event: websocket.")
+	builder.WriteString(eventType)
+	builder.WriteString("\n")
+	builder.Write(trimmedPayload)
+	builder.WriteString("\n")
 }
 
 func markAPIResponseTimestamp(c *gin.Context) {
diff --git a/sdk/api/handlers/openai/openai_responses_websocket_test.go b/sdk/api/handlers/openai/openai_responses_websocket_test.go
index 773df18e..6fce1bf1 100644
--- a/sdk/api/handlers/openai/openai_responses_websocket_test.go
+++ b/sdk/api/handlers/openai/openai_responses_websocket_test.go
@@ -392,27 +392,45 @@ func TestAppendWebsocketEvent(t *testing.T) {
 	}
 }
 
-func TestSetWebsocketRequestBody(t *testing.T) {
+func TestAppendWebsocketTimelineEvent(t *testing.T) {
+	var builder strings.Builder
+	ts := time.Date(2026, time.April, 1, 12, 34, 56, 789000000, time.UTC)
+
+	appendWebsocketTimelineEvent(&builder, "request", []byte("  {\"type\":\"response.create\"}\n"), ts)
+
+	got := builder.String()
+	if !strings.Contains(got, "Timestamp: 2026-04-01T12:34:56.789Z") {
+		t.Fatalf("timeline timestamp not found: %s", got)
+	}
+	if !strings.Contains(got, "Event: websocket.request") {
+		t.Fatalf("timeline event not found: %s", got)
+	}
+	if !strings.Contains(got, "{\"type\":\"response.create\"}") {
+		t.Fatalf("timeline payload not found: %s", got)
+	}
+}
+
+func TestSetWebsocketTimelineBody(t *testing.T) {
 	gin.SetMode(gin.TestMode)
 	recorder := httptest.NewRecorder()
 	c, _ := gin.CreateTestContext(recorder)
 
-	setWebsocketRequestBody(c, " \n ")
-	if _, exists := c.Get(wsRequestBodyKey); exists {
-		t.Fatalf("request body key should not be set for empty body")
+	setWebsocketTimelineBody(c, " \n ")
+	if _, exists := c.Get(wsTimelineBodyKey); exists {
+		t.Fatalf("timeline body key should not be set for empty body")
 	}
 
-	setWebsocketRequestBody(c, "event body")
-	value, exists := c.Get(wsRequestBodyKey)
+	setWebsocketTimelineBody(c, "timeline body")
+	value, exists := c.Get(wsTimelineBodyKey)
 	if !exists {
-		t.Fatalf("request body key not set")
+		t.Fatalf("timeline body key not set")
 	}
 	bodyBytes, ok := value.([]byte)
 	if !ok {
-		t.Fatalf("request body key type mismatch")
+		t.Fatalf("timeline body key type mismatch")
 	}
-	if string(bodyBytes) != "event body" {
-		t.Fatalf("request body = %q, want %q", string(bodyBytes), "event body")
+	if string(bodyBytes) != "timeline body" {
+		t.Fatalf("timeline body = %q, want %q", string(bodyBytes), "timeline body")
 	}
 }
 
@@ -544,14 +562,14 @@ func TestForwardResponsesWebsocketPreservesCompletedEvent(t *testing.T) {
 		close(data)
 		close(errCh)
 
-		var bodyLog strings.Builder
+		var timelineLog strings.Builder
 		completedOutput, err := (*OpenAIResponsesAPIHandler)(nil).forwardResponsesWebsocket(
 			ctx,
 			conn,
 			func(...interface{}) {},
 			data,
 			errCh,
-			&bodyLog,
+			&timelineLog,
 			"session-1",
 		)
 		if err != nil {
@@ -562,6 +580,10 @@ func TestForwardResponsesWebsocketPreservesCompletedEvent(t *testing.T) {
 			serverErrCh <- errors.New("completed output not captured")
 			return
 		}
+		if !strings.Contains(timelineLog.String(), "Event: websocket.response") {
+			serverErrCh <- errors.New("websocket timeline did not capture downstream response")
+			return
+		}
 		serverErrCh <- nil
 	}))
 	defer server.Close()
@@ -594,6 +616,116 @@ func TestForwardResponsesWebsocketPreservesCompletedEvent(t *testing.T) {
 	}
 }
 
+func TestForwardResponsesWebsocketLogsAttemptedResponseOnWriteFailure(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+
+	serverErrCh := make(chan error, 1)
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		conn, err := responsesWebsocketUpgrader.Upgrade(w, r, nil)
+		if err != nil {
+			serverErrCh <- err
+			return
+		}
+
+		ctx, _ := gin.CreateTestContext(httptest.NewRecorder())
+		ctx.Request = r
+
+		data := make(chan []byte, 1)
+		errCh := make(chan *interfaces.ErrorMessage)
+		data <- []byte("data: {\"type\":\"response.completed\",\"response\":{\"id\":\"resp-1\",\"output\":[{\"type\":\"message\",\"id\":\"out-1\"}]}}\n\n")
+		close(data)
+		close(errCh)
+
+		var timelineLog strings.Builder
+		if errClose := conn.Close(); errClose != nil {
+			serverErrCh <- errClose
+			return
+		}
+
+		_, err = (*OpenAIResponsesAPIHandler)(nil).forwardResponsesWebsocket(
+			ctx,
+			conn,
+			func(...interface{}) {},
+			data,
+			errCh,
+			&timelineLog,
+			"session-1",
+		)
+		if err == nil {
+			serverErrCh <- errors.New("expected websocket write failure")
+			return
+		}
+		if !strings.Contains(timelineLog.String(), "Event: websocket.response") {
+			serverErrCh <- errors.New("websocket timeline did not capture attempted downstream response")
+			return
+		}
+		if !strings.Contains(timelineLog.String(), "\"type\":\"response.completed\"") {
+			serverErrCh <- errors.New("websocket timeline did not retain attempted payload")
+			return
+		}
+		serverErrCh <- nil
+	}))
+	defer server.Close()
+
+	wsURL := "ws" + strings.TrimPrefix(server.URL, "http")
+	conn, _, err := websocket.DefaultDialer.Dial(wsURL, nil)
+	if err != nil {
+		t.Fatalf("dial websocket: %v", err)
+	}
+	defer func() {
+		_ = conn.Close()
+	}()
+
+	if errServer := <-serverErrCh; errServer != nil {
+		t.Fatalf("server error: %v", errServer)
+	}
+}
+
+func TestResponsesWebsocketTimelineRecordsDisconnectEvent(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+
+	manager := coreauth.NewManager(nil, nil, nil)
+	base := handlers.NewBaseAPIHandlers(&sdkconfig.SDKConfig{}, manager)
+	h := NewOpenAIResponsesAPIHandler(base)
+
+	timelineCh := make(chan string, 1)
+	router := gin.New()
+	router.GET("/v1/responses/ws", func(c *gin.Context) {
+		h.ResponsesWebsocket(c)
+		timeline := ""
+		if value, exists := c.Get(wsTimelineBodyKey); exists {
+			if body, ok := value.([]byte); ok {
+				timeline = string(body)
+			}
+		}
+		timelineCh <- timeline
+	})
+
+	server := httptest.NewServer(router)
+	defer server.Close()
+
+	wsURL := "ws" + strings.TrimPrefix(server.URL, "http") + "/v1/responses/ws"
+	conn, _, err := websocket.DefaultDialer.Dial(wsURL, nil)
+	if err != nil {
+		t.Fatalf("dial websocket: %v", err)
+	}
+
+	closePayload := websocket.FormatCloseMessage(websocket.CloseGoingAway, "client closing")
+	if err = conn.WriteControl(websocket.CloseMessage, closePayload, time.Now().Add(time.Second)); err != nil {
+		t.Fatalf("write close control: %v", err)
+	}
+	_ = conn.Close()
+
+	select {
+	case timeline := <-timelineCh:
+		if !strings.Contains(timeline, "Event: websocket.disconnect") {
+			t.Fatalf("websocket timeline missing disconnect event: %s", timeline)
+		}
+	case <-time.After(5 * time.Second):
+		t.Fatal("timed out waiting for websocket timeline")
+	}
+}
+
 func TestWebsocketUpstreamSupportsIncrementalInputForModel(t *testing.T) {
 	manager := coreauth.NewManager(nil, nil, nil)
 	auth := &coreauth.Auth{