diff --git a/tests/restart-chaos/observer.ts b/tests/restart-chaos/observer.ts
index 7ed6e1fe0b9..0b3a27c5abf 100644
--- a/tests/restart-chaos/observer.ts
+++ b/tests/restart-chaos/observer.ts
@@ -694,13 +694,24 @@ export class TaskObserver {
 
   private async remoteWorkspaceFile(issueId: string, relative: string): Promise<string | null> {
     const captured = this.record.remoteFiles?.[relative];
-    return typeof captured === "string" ? captured : await readRemoteWorkspaceFile(this.api, issueId, relative);
+    const text = typeof captured === "string" ? captured
+      : await readRemoteWorkspaceFile(this.api, issueId, relative, { onError: message => this.noteRemoteFileError(relative, message) });
+    if (text !== null) delete this.record.remoteFileErrors?.[relative];
+    return text;
   }
 
   private async captureRemoteFilesAtDone(sample: TaskSample): Promise<void> {
     const wanted = this.definition.collect.files(this.plan.nonce);
     if (!wanted.length || this.lab.environmentKind === "local" || sample.issueStatus !== "done" || !this.record.issueId) return;
-    await captureRemoteWorkspaceFiles(this.api, this.record.issueId, wanted, this.record.remoteFiles ??= {});
+    await captureRemoteWorkspaceFiles(this.api, this.record.issueId, wanted, this.record.remoteFiles ??= {},
+      (relative, message) => this.noteRemoteFileError(relative, message));
+  }
+
+  private noteRemoteFileError(relative: string, message: string): void {
+    const errors = this.record.remoteFileErrors ??= {};
+    if (errors[relative] === message) return;
+    errors[relative] = message;
+    this.timeline.add("remote_file_read_failed", { taskId: this.plan.taskId, path: relative, error: message });
   }
 
   async workspacePath(): Promise<string | null> {
diff --git a/tests/restart-chaos/remote-oracle.test.ts b/tests/restart-chaos/remote-oracle.test.ts
index ec544bbd581..6e9ac351d92 100644
--- a/tests/restart-chaos/remote-oracle.test.ts
+++ b/tests/restart-chaos/remote-oracle.test.ts
@@ -38,6 +38,7 @@ beforeAll(async () => {
   server = createServer((incoming, outgoing) => {
     const url = new URL(incoming.url ?? "/", "http://x");
     if (url.pathname === "/api/issues/i1/file-resources/content" && url.searchParams.get("download") === "true") {
+      if (url.searchParams.get("workspace") !== "execution") { outgoing.writeHead(422, { "content-type": "application/json" }).end(JSON.stringify({ code: "no_local_workspace" })); return; }
       if (incoming.headers.origin !== baseUrl) { outgoing.writeHead(403).end(); return; }
       if (unavailableReads > 0) { unavailableReads -= 1; outgoing.writeHead(422, { "content-type": "application/json" }).end(JSON.stringify({ code: "workspace_unavailable" })); return; }
       if (sandboxReleased) { outgoing.writeHead(422, { "content-type": "application/json" }).end(JSON.stringify({ code: "workspace_unavailable" })); return; }
@@ -144,5 +145,32 @@ describe("oracle for a remote workspace", () => {
     expect(Object.values(artifacts.files)).toEqual([null, null]);
     expect(Date.now() - started).toBeLessThan(10_000);
   }, 60_000);
+
+  it("records why a remote file could not be read", async () => {
+    const api = {
+      baseUrl,
+      async get(route: string) {
+        if (route.endsWith("/comments") || route.endsWith("/runs")) return [];
+        return { id: "i1", status: "done", currentExecutionWorkspace: { cwd: "/home/daytona/workspaces/not-on-this-host" } };
+      },
+      async post() { return { id: "i1", identifier: "CHA-1" }; },
+      getText: (route: string) => new ChaosApi(baseUrl).getText(route),
+    } as unknown as ChaosApi;
+    const timeline = new Timeline(null);
+    const observer = new TaskObserver(plan, api, lab, timeline, { serverReady: true, faultInProgress: false });
+    await observer.launch();
+    sandboxReleased = true;
+    try {
+      await observer.poll(observer.record.createdAt! + 1_000);
+      await observer.poll(observer.record.createdAt! + 5_000);
+    } finally { sandboxReleased = false; }
+    expect(observer.record.remoteFileErrors?.[modulePath]).toMatch(/422.*workspace_unavailable/);
+    expect(timeline.entries.filter(entry => entry.kind === "remote_file_read_failed" && entry.path === modulePath)).toHaveLength(1);
+    await observer.poll(observer.record.createdAt! + 9_000);
+    expect(observer.record.remoteFiles?.[modulePath]).toBe(remoteFiles[modulePath]);
+    const artifacts = await observer.collectArtifacts();
+    expect(artifacts.files[modulePath]).toBe(remoteFiles[modulePath]);
+    expect(observer.record.remoteFileErrors?.[modulePath]).toBeUndefined();
+  }, 60_000);
 });
 
diff --git a/tests/restart-chaos/remote-workspace-files.ts b/tests/restart-chaos/remote-workspace-files.ts
index 897090f1281..2b62c6acfec 100644
--- a/tests/restart-chaos/remote-workspace-files.ts
+++ b/tests/restart-chaos/remote-workspace-files.ts
@@ -4,16 +4,17 @@ export const REMOTE_FILE_WAIT_MS = 4 * 60_000;
 export const REMOTE_FILE_POLL_MS = 2_000;
 
 function contentRoute(issueId: string, relative: string): string {
-  return `/api/issues/${issueId}/file-resources/content?path=${encodeURIComponent(relative)}&download=true`;
+  return `/api/issues/${issueId}/file-resources/content?path=${encodeURIComponent(relative)}&workspace=execution&download=true`;
 }
 
 export async function readRemoteWorkspaceFile(api: Pick<ChaosApi, "getText">, issueId: string, relative: string,
-  options: { waitMs?: number; pollMs?: number } = {}): Promise<string | null> {
+  options: { waitMs?: number; pollMs?: number; onError?: (message: string) => void } = {}): Promise<string | null> {
   const deadline = Date.now() + (options.waitMs ?? REMOTE_FILE_WAIT_MS);
   for (;;) {
     let unavailable = false;
     const text = await api.getText(contentRoute(issueId, relative), 15_000).catch((error: unknown) => {
       unavailable = error instanceof ChaosApiError && error.status === 422;
+      options.onError?.((error instanceof Error ? error.message : String(error)).slice(0, 400));
       return null;
     });
     if (text !== null || !unavailable || Date.now() >= deadline) return text;
@@ -22,9 +23,9 @@ export async function readRemoteWorkspaceFile(api: Pick<ChaosApi, "getText">, is
 }
 
 export async function captureRemoteWorkspaceFiles(api: Pick<ChaosApi, "getText">, issueId: string, wanted: readonly string[],
-  captured: Record<string, string | null>): Promise<void> {
+  captured: Record<string, string | null>, onError?: (relative: string, message: string) => void): Promise<void> {
   for (const relative of wanted) {
     if (typeof captured[relative] === "string") continue;
-    captured[relative] = await readRemoteWorkspaceFile(api, issueId, relative, { waitMs: 0 });
+    captured[relative] = await readRemoteWorkspaceFile(api, issueId, relative, { waitMs: 0, ...(onError ? { onError: message => onError(relative, message) } : {}) });
   }
 }
diff --git a/tests/restart-chaos/types.ts b/tests/restart-chaos/types.ts
index 5e5def6b5c1..787bef559e5 100644
--- a/tests/restart-chaos/types.ts
+++ b/tests/restart-chaos/types.ts
@@ -326,6 +326,7 @@ export interface TaskRecord {
   preFaultSnapshotError?: string | null;
   remoteWorkspace?: boolean;
   remoteFiles?: Record<string, string | null>;
+  remoteFileErrors?: Record<string, string>;
   /** Pre-fault files missing at rest; null when not checked. */
   lostFiles: string[] | null;
   /** B5: distinct bench progress values the observer read during polling. */