diff --git a/cmd/cloudflared/tunnel/cmd.go b/cmd/cloudflared/tunnel/cmd.go
index 1a975bec..61ce6c83 100644
--- a/cmd/cloudflared/tunnel/cmd.go
+++ b/cmd/cloudflared/tunnel/cmd.go
@@ -534,7 +534,7 @@ func tunnelFlags(shouldHide bool) []cli.Flag {
 		altsrc.NewStringFlag(&cli.StringFlag{
 			Name:    "loglevel",
 			Value:   "info",
-			Usage:   "Application logging level {panic, fatal, error, warn, info, debug}",
+			Usage:   "Application logging level {panic, fatal, error, warn, info, debug}. " + debugLevelWarning,
 			EnvVars: []string{"TUNNEL_LOGLEVEL"},
 			Hidden:  shouldHide,
 		}),
diff --git a/cmd/cloudflared/tunnel/logger.go b/cmd/cloudflared/tunnel/logger.go
index cb28af97..cc92001c 100644
--- a/cmd/cloudflared/tunnel/logger.go
+++ b/cmd/cloudflared/tunnel/logger.go
@@ -13,6 +13,9 @@ import (
 	"github.com/pkg/errors"
 )
 
+const debugLevelWarning = "At debug level, request URL, method, protocol, content legnth and header will be logged. " +
+	"Response status, content length and header will also be logged in debug level."
+
 var logger = log.CreateLogger()
 
 func configMainLogger(c *cli.Context) error {
@@ -22,6 +25,9 @@ func configMainLogger(c *cli.Context) error {
 		return errors.Wrap(err, "Unknown logging level specified")
 	}
 	logger.SetLevel(logLevel)
+	if logLevel == logrus.DebugLevel {
+		logger.Warn(debugLevelWarning)
+	}
 	return nil
 }
 
diff --git a/origin/tunnel.go b/origin/tunnel.go
index 67cc30ad..084455ac 100644
--- a/origin/tunnel.go
+++ b/origin/tunnel.go
@@ -636,25 +636,41 @@ func (h *TunnelHandler) logError(stream *h2mux.MuxedStream, err error) {
 }
 
 func (h *TunnelHandler) logRequest(req *http.Request, cfRay string, lbProbe bool) {
+	logger := log.NewEntry(h.logger)
 	if cfRay != "" {
-		h.logger.WithField("CF-RAY", cfRay).Debugf("%s %s %s", req.Method, req.URL, req.Proto)
+		logger = logger.WithField("CF-RAY", cfRay)
+		logger.Debugf("%s %s %s", req.Method, req.URL, req.Proto)
 	} else if lbProbe {
-		h.logger.Debugf("Load Balancer health check %s %s %s", req.Method, req.URL, req.Proto)
+		logger.Debugf("Load Balancer health check %s %s %s", req.Method, req.URL, req.Proto)
 	} else {
-		h.logger.Warnf("All requests should have a CF-RAY header. Please open a support ticket with Cloudflare. %s %s %s ", req.Method, req.URL, req.Proto)
+		logger.Warnf("All requests should have a CF-RAY header. Please open a support ticket with Cloudflare. %s %s %s ", req.Method, req.URL, req.Proto)
+	}
+	logger.Debugf("Request Headers %+v", req.Header)
+
+	if contentLen := req.ContentLength; contentLen == -1 {
+		logger.Debugf("Request Content length unknown")
+	} else {
+		logger.Debugf("Request content length %d", contentLen)
 	}
-	h.logger.Debugf("Request Headers %+v", req.Header)
 }
 
 func (h *TunnelHandler) logResponse(r *http.Response, cfRay string, lbProbe bool) {
+	logger := log.NewEntry(h.logger)
 	if cfRay != "" {
-		h.logger.WithField("CF-RAY", cfRay).Debugf("%s", r.Status)
+		logger = logger.WithField("CF-RAY", cfRay)
+		logger.Debugf("%s", r.Status)
 	} else if lbProbe {
-		h.logger.Debugf("Response to Load Balancer health check %s", r.Status)
+		logger.Debugf("Response to Load Balancer health check %s", r.Status)
 	} else {
-		h.logger.Infof("%s", r.Status)
+		logger.Infof("%s", r.Status)
+	}
+	logger.Debugf("Response Headers %+v", r.Header)
+
+	if contentLen := r.ContentLength; contentLen == -1 {
+		logger.Debugf("Response content length unknown")
+	} else {
+		logger.Debugf("Response content length %d", contentLen)
 	}
-	h.logger.Debugf("Response Headers %+v", r.Header)
 }
 
 func (h *TunnelHandler) UpdateMetrics(connectionID string) {