diff --git a/lib/internal/debugger/inspect_probe.js b/lib/internal/debugger/inspect_probe.js
index e7abc2e48cd365..6e3cf25cacef2b 100644
--- a/lib/internal/debugger/inspect_probe.js
+++ b/lib/internal/debugger/inspect_probe.js
@@ -707,7 +707,8 @@ class ProbeInspectorSession {
 
   async callCdp(method, params, probe = null) {
     if (this.finished) { throw kInspectorFailedSentinel; }
-    this.inFlight = { __proto__: null, method, probe };
+    const inFlight = { __proto__: null, method, probe };
+    this.inFlight = inFlight;
     debug('CDP -> %s%s', method, probe !== null ? `, probe=${probe.index}` : '');
     try {
       const result = await this.client.callMethod(method, params);
@@ -730,6 +731,7 @@ class ProbeInspectorSession {
           this.recordInspectorFailure({
             reason: 'Target process exited during probe evaluation',
             advice: kReviewProbeExprAdvice,
+            inFlight,
           });
         }
         throw kInspectorFailedSentinel;
@@ -741,41 +743,47 @@ class ProbeInspectorSession {
           reason: 'Probe mode failed before user code ran',
           advice: kStartupTeardownAdvice,
           cdpError: err,
+          inFlight,
         });
       } else if (method === 'Debugger.evaluateOnCallFrame') {
         this.recordInspectorFailure({
           reason: 'The inspector could not evaluate a probe expression',
           advice: `The rejection details are recorded on the probe hit. ${kReviewProbeExprAdvice}`,
           cdpError: err,
+          inFlight,
         });
       } else if (this.lastProbeIndex !== null) {
         this.recordInspectorFailure({
           reason: 'Probe session failed after a probe evaluation',
           advice: 'If the failure repeats, review the most-recently-evaluated probe expression.',
           cdpError: err,
+          inFlight,
         });
       } else {
         this.recordInspectorFailure({
           reason: 'Probe session failed during inspector activity',
           advice: 'This is likely a Node.js bug. Please file an issue.',
           cdpError: err,
+          inFlight,
         });
       }
       throw kInspectorFailedSentinel;
     } finally {
-      this.inFlight = null;
+      if (this.inFlight === inFlight) {
+        this.inFlight = null;
+      }
     }
   }
 
   // Records the first inspector-side terminal for the session, later callers are ignored.
-  recordInspectorFailure({ reason, advice, cdpError, internalError }) {
+  recordInspectorFailure({ reason, advice, cdpError, internalError, inFlight = this.inFlight }) {
     if (this.finished) { return; }
     debug('recordInspectorFailure "%s": inFlight=%j, lastProbeIndex=%s, cdpError=%j',
-          reason, this.inFlight, this.lastProbeIndex, cdpError);
+          reason, inFlight, this.lastProbeIndex, cdpError);
     const child = this.child;
     const exitedAbnormally = child !== null &&
       (child.signalCode !== null || (child.exitCode !== null && child.exitCode !== 0));
-    const inFlightProbe = this.inFlight === null ? null : this.inFlight.probe;
+    const inFlightProbe = inFlight === null ? null : inFlight.probe;
     // This normally emits `probe_failure`, but yields to `probe_target_exit` when the child
     // has already exited abnormally and there is no in-flight probe to attribute to.
     if (exitedAbnormally && inFlightProbe === null) {
@@ -783,7 +791,7 @@ class ProbeInspectorSession {
       return;
     }
 
-    const failedCdpMethod = this.inFlight === null ? null : this.inFlight.method;
+    const failedCdpMethod = inFlight === null ? null : inFlight.method;
     let protocolError = null;
     // // `ERR_DEBUGGER_ERROR` is a Node-internal code, not a CDP-level protocol code
     if (cdpError !== undefined && cdpError.code !== 'ERR_DEBUGGER_ERROR') {