diff --git a/src/gdb/GdbSessionManager.ts b/src/gdb/GdbSessionManager.ts
index bba9c63fb9..2c49aa72ac 100644
--- a/src/gdb/GdbSessionManager.ts
+++ b/src/gdb/GdbSessionManager.ts
@@ -25,6 +25,7 @@ import type {
 import { DEBUGGER_CONTROL_REPLY_BYTES } from "../domain/analysisResourceLimits.js";
 import { currentAnalysisOperationSnapshot } from "../domain/analysisOperationSnapshot.js";
 import { err, ok, type Result } from "../domain/result.js";
+import { ConfigurationError } from "../domain/configurationErrors.js";
 import {
   ProviderProcessSupervisor,
   spawnOwnedProviderProcess,
@@ -1371,6 +1372,7 @@ export class GdbSessionManager {
             );
             return ok({ result, evidence });
           } catch (cause) {
+            if (cause instanceof ConfigurationError) return err(cause);
             if (cause instanceof AnalysisCancelledError) return err(cause);
             if (cause instanceof AnalysisCapabilityUnavailableError)
               return err(cause as AnalysisError);
diff --git a/tests/boundary/providers/GdbSessionManagers.test.ts b/tests/boundary/providers/GdbSessionManagers.test.ts
index b4fb056dd6..4af7d8668b 100644
--- a/tests/boundary/providers/GdbSessionManagers.test.ts
+++ b/tests/boundary/providers/GdbSessionManagers.test.ts
@@ -23,6 +23,12 @@ process.stdin.on("data", chunk => {
  }
 });`;
 
+const debuggerDeadlineOverride = {
+  setting: "debugger.command_deadline_ms",
+  action: "set",
+  value: 5000,
+} as const;
+
 describe("persistent debugger session managers", () => {
   let directory: string | undefined;
   const fixtureOwner = createGdbFixtureOwner();
@@ -93,7 +99,7 @@ process.stdin.on("data", (chunk) => {
       4096,
     ],
   ] as const)(
-    "honors a single override for invalid %s",
+    "restores a GDB session after resetting invalid %s",
     async (setting, environmentName, value) => {
       directory = await mkdtemp(join(tmpdir(), "rea-gdb-setting-"));
       const provider = join(directory, "fake-gdb.mjs");
@@ -108,6 +114,10 @@ process.stdin.on("data", (chunk) => {
       const set = () =>
         settings.update({ changes: [{ setting, action: "set", value }] });
       expect(set().ok).toBe(true);
+      if (setting === "debugger.max_command_output_bytes")
+        expect(
+          settings.update({ changes: [debuggerDeadlineOverride] }).ok,
+        ).toBe(true);
       const manager = new GdbSessionManager({
         spawnProcess: fixtureOwner.spawnProcess,
         platform: "linux",