diff --git a/ssh/tailssh/tailssh.go b/ssh/tailssh/tailssh.go
index 18a2f5a7a..0f6f1b783 100644
--- a/ssh/tailssh/tailssh.go
+++ b/ssh/tailssh/tailssh.go
@@ -1607,7 +1607,11 @@ func (ss *sshSession) startNewRecording() (_ *recording, err error) {
 		rec.out, attempts, errChan, err = ss.connectToRecorder(ctx, recorders)
 		if err != nil {
 			if onFailure != nil && onFailure.NotifyURL != "" && len(attempts) > 0 {
-				ss.notifyControl(ctx, nodeKey, tailcfg.SSHSessionRecordingRejected, attempts, onFailure.NotifyURL)
+				eventType := tailcfg.SSHSessionRecordingFailed
+				if onFailure.RejectSessionWithMessage != "" {
+					eventType = tailcfg.SSHSessionRecordingRejected
+				}
+				ss.notifyControl(ctx, nodeKey, eventType, attempts, onFailure.NotifyURL)
 			}
 
 			if onFailure != nil && onFailure.RejectSessionWithMessage != "" {
@@ -1630,7 +1634,12 @@ func (ss *sshSession) startNewRecording() (_ *recording, err error) {
 				lastAttempt := attempts[len(attempts)-1]
 				lastAttempt.FailureMessage = err.Error()
 
-				ss.notifyControl(ctx, nodeKey, tailcfg.SSHSessionRecordingTerminated, attempts, onFailure.NotifyURL)
+				eventType := tailcfg.SSHSessionRecordingFailed
+				if onFailure.TerminateSessionWithMessage != "" {
+					eventType = tailcfg.SSHSessionRecordingTerminated
+				}
+
+				ss.notifyControl(ctx, nodeKey, eventType, attempts, onFailure.NotifyURL)
 			}
 			if onFailure != nil && onFailure.TerminateSessionWithMessage != "" {
 				ss.logf("recording: error uploading recording (closing session): %v", err)
diff --git a/tailcfg/tailcfg.go b/tailcfg/tailcfg.go
index d9a38eda0..7787ba407 100644
--- a/tailcfg/tailcfg.go
+++ b/tailcfg/tailcfg.go
@@ -2110,9 +2110,23 @@ type SSHEventNotifyRequest struct {
 type SSHEventType int
 
 const (
-	UnspecifiedSSHEventType       SSHEventType = 0
-	SSHSessionRecordingRejected   SSHEventType = 1
+	UnspecifiedSSHEventType SSHEventType = 0
+	// SSHSessionRecordingRejected is the event that
+	// defines when a SSH session cannot be started
+	// because no recorder is available for session
+	// recording, and the SSHRecorderFailureAction
+	// RejectSessionWithMessage is not empty.
+	SSHSessionRecordingRejected SSHEventType = 1
+	// SSHSessionRecordingTerminated is the event that
+	// defines when session recording has failed
+	// during the session and the SSHRecorderFailureAction
+	// TerminateSessionWithMessage is not empty.
 	SSHSessionRecordingTerminated SSHEventType = 2
+	// SSHSessionRecordingFailed is the event that
+	// defines when session recording is unavailable and
+	// the SSHRecorderFailureAction RejectSessionWithMessage
+	// or TerminateSessionWithMessage is empty.
+	SSHSessionRecordingFailed SSHEventType = 3
 )
 
 // SSHRecordingAttempt is a single attempt to start a recording.