diff --git a/src/conductor/runner/BasicEvaluator.ts b/src/conductor/runner/BasicEvaluator.ts
index aa88ac7..7d7ad28 100644
--- a/src/conductor/runner/BasicEvaluator.ts
+++ b/src/conductor/runner/BasicEvaluator.ts
@@ -1,16 +1,25 @@
 import { ConductorInternalError } from "../../common/errors";
+import { RunnerStatus } from "../types";
 import type { IEvaluator, IRunnerPlugin } from "./types";
 
 export abstract class BasicEvaluator implements IEvaluator {
     readonly conductor: IRunnerPlugin;
 
     async startEvaluator(entryPoint: string): Promise<void> {
-        const initialChunk = await this.conductor.requestFile(entryPoint);
-        if (!initialChunk) throw new ConductorInternalError("Cannot load entrypoint file");
-        this.conductor.sendResult(await this.evaluateFile(entryPoint, initialChunk));
-        while (true) {
-            const chunk = await this.conductor.requestChunk();
-            this.conductor.sendResult(await this.evaluateChunk(chunk));
+        try {
+            const initialChunk = await this.conductor.requestFile(entryPoint);
+            if (!initialChunk) throw new ConductorInternalError("Cannot load entrypoint file");
+            this.conductor.sendResult(await this.evaluateFile(entryPoint, initialChunk));
+            while (true) {
+                const chunk = await this.conductor.requestChunk();
+                this.conductor.sendResult(await this.evaluateChunk(chunk));
+            }
+            // The REPL loop only exits if the conduit is terminated externally.
+            this.conductor.updateStatus(RunnerStatus.STOPPED, true);
+        } catch (e) {
+            // Always notify the host so it can unblock its own REPL loop.
+            this.conductor.updateStatus(RunnerStatus.ERROR, true);
+            throw e;
         }
     }
 
diff --git a/src/conductor/runner/RunnerPlugin.ts b/src/conductor/runner/RunnerPlugin.ts
index 83f74ab..33a1c7a 100644
--- a/src/conductor/runner/RunnerPlugin.ts
+++ b/src/conductor/runner/RunnerPlugin.ts
@@ -39,8 +39,14 @@ export class RunnerPlugin implements IRunnerPlugin {
             console.error(`Host expects at least protocol version ${message.data.minVersion}, but we are on version ${Constant.PROTOCOL_VERSION}`);
             this.__conduit.terminate();
         }],
-        [ServiceMessageType.ENTRY, function entryServiceHandler(this: RunnerPlugin, message: EntryServiceMessage) {
-            this.__evaluator.startEvaluator(message.data);
+        [ServiceMessageType.ENTRY, async function entryServiceHandler(this: RunnerPlugin, message: EntryServiceMessage) {
+            try {
+                await this.__evaluator.startEvaluator(message.data);
+            } catch (_e) {
+                // BasicEvaluator already sends RunnerStatus.ERROR; this is a safety net for
+                // evaluator subclasses that override startEvaluator without the same guarantee.
+                this.updateStatus(RunnerStatus.ERROR, true);
+            }
         }]
     ]);