diff --git a/ssh/tailssh/tailssh.go b/ssh/tailssh/tailssh.go
index 3865a50ba..37e73e140 100644
--- a/ssh/tailssh/tailssh.go
+++ b/ssh/tailssh/tailssh.go
@@ -1519,8 +1519,9 @@ func (ss *sshSession) startNewRecording() (_ *recording, err error) {
 
 	now := time.Now()
 	rec := &recording{
-		ss:    ss,
-		start: now,
+		ss:       ss,
+		start:    now,
+		failOpen: onFailure == nil || onFailure.TerminateSessionWithMessage == "",
 	}
 
 	// We want to use a background context for uploading and not ss.ctx.
@@ -1611,6 +1612,10 @@ type recording struct {
 	ss    *sshSession
 	start time.Time
 
+	// failOpen specifies whether the session should be allowed to
+	// continue if writing to the recording fails.
+	failOpen bool
+
 	mu  sync.Mutex // guards writes to, close of out
 	out io.WriteCloser
 }
@@ -1642,7 +1647,7 @@ func (r *recording) writer(dir string, w io.Writer) io.Writer {
 		// passwords.
 		return w
 	}
-	return &loggingWriter{r, dir, w}
+	return &loggingWriter{r: r, dir: dir, w: w}
 }
 
 // loggingWriter is an io.Writer wrapper that writes first an
@@ -1651,20 +1656,30 @@ type loggingWriter struct {
 	r   *recording
 	dir string    // "i" or "o" (input or output)
 	w   io.Writer // underlying Writer, after writing to r.out
+
+	// recordingFailedOpen specifies whether we've failed to write to
+	// r.out and should stop trying. It is set to true if we fail to write
+	// to r.out and r.failOpen is set.
+	recordingFailedOpen bool
 }
 
-func (w loggingWriter) Write(p []byte) (n int, err error) {
-	j, err := json.Marshal([]any{
-		time.Since(w.r.start).Seconds(),
-		w.dir,
-		string(p),
-	})
-	if err != nil {
-		return 0, err
-	}
-	j = append(j, '\n')
-	if err := w.writeCastLine(j); err != nil {
-		return 0, err
+func (w *loggingWriter) Write(p []byte) (n int, err error) {
+	if !w.recordingFailedOpen {
+		j, err := json.Marshal([]any{
+			time.Since(w.r.start).Seconds(),
+			w.dir,
+			string(p),
+		})
+		if err != nil {
+			return 0, err
+		}
+		j = append(j, '\n')
+		if err := w.writeCastLine(j); err != nil {
+			if !w.r.failOpen {
+				return 0, err
+			}
+			w.recordingFailedOpen = true
+		}
 	}
 	return w.w.Write(p)
 }