diff --git a/cmd/cloudflared/access/carrier.go b/cmd/cloudflared/access/carrier.go
index ead0dedf..f328ba84 100644
--- a/cmd/cloudflared/access/carrier.go
+++ b/cmd/cloudflared/access/carrier.go
@@ -3,6 +3,7 @@ package access
 import (
 	"crypto/tls"
 	"fmt"
+	"io"
 	"net/http"
 	"strings"
 
@@ -13,6 +14,7 @@ import (
 	"github.com/cloudflare/cloudflared/carrier"
 	"github.com/cloudflare/cloudflared/config"
 	"github.com/cloudflare/cloudflared/logger"
+	"github.com/cloudflare/cloudflared/stream"
 	"github.com/cloudflare/cloudflared/validation"
 )
 
@@ -38,6 +40,7 @@ func StartForwarder(forwarder config.Forwarder, shutdown <-chan struct{}, log *z
 	if forwarder.TokenSecret != "" {
 		headers.Set(cfAccessClientSecretHeader, forwarder.TokenSecret)
 	}
+	headers.Set("User-Agent", userAgent)
 
 	carrier.SetBastionDest(headers, forwarder.Destination)
 
@@ -58,7 +61,12 @@ func StartForwarder(forwarder config.Forwarder, shutdown <-chan struct{}, log *z
 // useful for proxying other protocols (like ssh) over websockets
 // (which you can put Access in front of)
 func ssh(c *cli.Context) error {
-	log := logger.CreateSSHLoggerFromContext(c, logger.EnableTerminalLog)
+	// If not running as a forwarder, disable terminal logs as it collides with the stdin/stdout of the parent process
+	outputTerminal := logger.DisableTerminalLog
+	if c.IsSet(sshURLFlag) {
+		outputTerminal = logger.EnableTerminalLog
+	}
+	log := logger.CreateSSHLoggerFromContext(c, outputTerminal)
 
 	// get the hostname from the cmdline and error out if its not provided
 	rawHostName := c.String(sshHostnameFlag)
@@ -76,6 +84,7 @@ func ssh(c *cli.Context) error {
 	if c.IsSet(sshTokenSecretFlag) {
 		headers.Set(cfAccessClientSecretHeader, c.String(sshTokenSecretFlag))
 	}
+	headers.Set("User-Agent", userAgent)
 
 	carrier.SetBastionDest(headers, c.String(sshDestinationFlag))
 
@@ -121,7 +130,19 @@ func ssh(c *cli.Context) error {
 		return err
 	}
 
-	return carrier.StartClient(wsConn, &carrier.StdinoutStream{}, options)
+	var s io.ReadWriter
+	s = &carrier.StdinoutStream{}
+	if c.IsSet(sshDebugStream) {
+		maxMessages := c.Uint64(sshDebugStream)
+		if maxMessages == 0 {
+			// default to 10 if provided but unset
+			maxMessages = 10
+		}
+		logger := log.With().Str("host", hostname).Logger()
+		s = stream.NewDebugStream(s, &logger, maxMessages)
+	}
+	carrier.StartClient(wsConn, s, options)
+	return nil
 }
 
 func buildRequestHeaders(values []string) http.Header {
diff --git a/cmd/cloudflared/access/cmd.go b/cmd/cloudflared/access/cmd.go
index 07b6dc2f..9d81e375 100644
--- a/cmd/cloudflared/access/cmd.go
+++ b/cmd/cloudflared/access/cmd.go
@@ -34,6 +34,7 @@ const (
 	sshTokenSecretFlag = "service-token-secret"
 	sshGenCertFlag     = "short-lived-cert"
 	sshConnectTo       = "connect-to"
+	sshDebugStream     = "debug-stream"
 	sshConfigTemplate  = `
 Add to your {{.Home}}/.ssh/config:
 
@@ -151,9 +152,12 @@ func Commands() []*cli.Command {
 							EnvVars: []string{"TUNNEL_SERVICE_TOKEN_SECRET"},
 						},
 						&cli.StringFlag{
-							Name:    logger.LogSSHDirectoryFlag,
-							Aliases: []string{"logfile"}, //added to match the tunnel side
-							Usage:   "Save application log to this directory for reporting issues.",
+							Name:  logger.LogFileFlag,
+							Usage: "Save application log to this file for reporting issues.",
+						},
+						&cli.StringFlag{
+							Name:  logger.LogSSHDirectoryFlag,
+							Usage: "Save application log to this directory for reporting issues.",
 						},
 						&cli.StringFlag{
 							Name:    logger.LogSSHLevelFlag,
@@ -165,6 +169,11 @@ func Commands() []*cli.Command {
 							Hidden: true,
 							Usage:  "Connect to alternate location for testing, value is host, host:port, or sni:port:host",
 						},
+						&cli.Uint64Flag{
+							Name:   sshDebugStream,
+							Hidden: true,
+							Usage:  "Writes up-to the max provided stream payloads to the logger as debug statements.",
+						},
 					},
 				},
 				{
diff --git a/logger/create.go b/logger/create.go
index d7a987e1..83048e59 100644
--- a/logger/create.go
+++ b/logger/create.go
@@ -175,7 +175,7 @@ func createFromContext(
 
 	log := newZerolog(loggerConfig)
 	if incompatibleFlagsSet := logFile != "" && logDirectory != ""; incompatibleFlagsSet {
-		log.Error().Msgf("Your config includes values for both %s and %s, but they are incompatible. %s takes precedence.", LogFileFlag, logDirectoryFlagName, LogFileFlag)
+		log.Error().Msgf("Your config includes values for both %s (%s) and %s (%s), but they are incompatible. %s takes precedence.", LogFileFlag, logFile, logDirectoryFlagName, logDirectory, LogFileFlag)
 	}
 	return log
 }
diff --git a/stream/debug.go b/stream/debug.go
new file mode 100644
index 00000000..0c175e4f
--- /dev/null
+++ b/stream/debug.go
@@ -0,0 +1,64 @@
+package stream
+
+import (
+	"io"
+	"sync/atomic"
+
+	"github.com/rs/zerolog"
+)
+
+// DebugStream will tee each read and write to the output logger as a debug message
+type DebugStream struct {
+	reader io.Reader
+	writer io.Writer
+	log    *zerolog.Logger
+	max    uint64
+	count  atomic.Uint64
+}
+
+func NewDebugStream(stream io.ReadWriter, logger *zerolog.Logger, max uint64) *DebugStream {
+	return &DebugStream{
+		reader: stream,
+		writer: stream,
+		log:    logger,
+		max:    max,
+	}
+}
+
+func (d *DebugStream) Read(p []byte) (n int, err error) {
+	n, err = d.reader.Read(p)
+	if n > 0 && d.max > d.count.Load() {
+		d.count.Add(1)
+		if err != nil {
+			d.log.Err(err).
+				Str("dir", "r").
+				Int("count", n).
+				Msgf("%+q", p[:n])
+		} else {
+			d.log.Debug().
+				Str("dir", "r").
+				Int("count", n).
+				Msgf("%+q", p[:n])
+		}
+	}
+	return
+}
+
+func (d *DebugStream) Write(p []byte) (n int, err error) {
+	n, err = d.writer.Write(p)
+	if n > 0 && d.max > d.count.Load() {
+		d.count.Add(1)
+		if err != nil {
+			d.log.Err(err).
+				Str("dir", "w").
+				Int("count", n).
+				Msgf("%+q", p[:n])
+		} else {
+			d.log.Debug().
+				Str("dir", "w").
+				Int("count", n).
+				Msgf("%+q", p[:n])
+		}
+	}
+	return
+}