diff --git a/src/config/sessions/session-history-eviction.test.ts b/src/config/sessions/session-history-eviction.test.ts
index f0a082933056..7f16c9d876cc 100644
--- a/src/config/sessions/session-history-eviction.test.ts
+++ b/src/config/sessions/session-history-eviction.test.ts
@@ -1,7 +1,23 @@
 import { randomBytes } from "node:crypto";
 import fs from "node:fs";
 import path from "node:path";
-import { afterEach, beforeEach, describe, expect, it } from "vitest";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+const evictionWarnSpy = vi.hoisted(() => vi.fn());
+vi.mock("../../logging/subsystem.js", async () => {
+  const actual = await vi.importActual<typeof import("../../logging/subsystem.js")>(
+    "../../logging/subsystem.js",
+  );
+  return {
+    ...actual,
+    createSubsystemLogger: (subsystem: string) => {
+      const logger = actual.createSubsystemLogger(subsystem);
+      return subsystem === "sessions/history-eviction"
+        ? { ...logger, warn: evictionWarnSpy }
+        : logger;
+    },
+  };
+});
 import { executeSqliteQuerySync } from "../../infra/kysely-sync.js";
 import { beginSessionWorkAdmission } from "../../sessions/session-lifecycle-admission.js";
 import {
@@ -25,6 +41,7 @@ import { getSessionKysely } from "./session-accessor.sqlite-scope.js";
 import {
   enforceSqliteSessionHistoryDiskBudget,
   inspectSqliteSessionHistoryDiskBudget,
+  kickSessionHistoryDiskBudgetMaintenance,
 } from "./session-history-eviction.js";
 import { resolveSqliteTargetFromSessionStorePath } from "./session-sqlite-target.js";
 
@@ -344,6 +361,33 @@ describe("SQLite historical session disk budget", () => {
     expect(sessionExists("stale-live")).toBe(true);
   });
 
+  it("warns when a fire-and-forget budget sweep fails instead of swallowing it", async () => {
+    evictionWarnSpy.mockClear();
+    // The kick gate reads maxDiskBytes twice synchronously; the queued sweep
+    // re-reads it asynchronously. Throwing on the later read rejects the
+    // fire-and-forget promise, exercising the catch path deterministically.
+    let maxDiskBytesReads = 0;
+    const maintenanceConfig = {
+      mode: "enforce",
+      highWaterBytes: 1,
+      get maxDiskBytes() {
+        maxDiskBytesReads += 1;
+        if (maxDiskBytesReads > 1) {
+          throw new Error("sweep exploded");
+        }
+        return 1;
+      },
+    } as never;
+
+    kickSessionHistoryDiskBudgetMaintenance({ storePath, force: true, maintenanceConfig });
+    await vi.waitFor(() => {
+      expect(evictionWarnSpy).toHaveBeenCalledWith(
+        expect.stringContaining("disk-budget sweep failed"),
+        expect.objectContaining({ storePath }),
+      );
+    });
+  });
+
   it("warn mode reports physical overage without extracting or deleting history", async () => {
     await createHistoricalTranscript({
       content: "warn history",
diff --git a/src/config/sessions/session-history-eviction.ts b/src/config/sessions/session-history-eviction.ts
index cfbdf0aefa76..6dc823af1d0a 100644
--- a/src/config/sessions/session-history-eviction.ts
+++ b/src/config/sessions/session-history-eviction.ts
@@ -1,6 +1,7 @@
 import fs from "node:fs";
 import path from "node:path";
 import { executeSqliteQuerySync } from "../../infra/kysely-sync.js";
+import { createSubsystemLogger } from "../../logging/subsystem.js";
 import {
   collectActiveSessionWorkAdmissionIdentities,
   runExclusiveSessionLifecycleMutation,
@@ -441,6 +442,8 @@ async function pruneAllSessionTranscriptArchivesToHighWater(params: {
   };
 }
 
+const log = createSubsystemLogger("sessions/history-eviction");
+
 const PHYSICAL_BUDGET_CHECK_INTERVAL_MS = 30 * 60 * 1000;
 // Single-slot per store: ordinary entry writes kick a throttled background
 // budget pass so an over-budget database self-heals without waiting for a
@@ -503,8 +506,14 @@ export function kickSessionHistoryDiskBudgetMaintenance(params: {
     mode: maintenance.mode,
     maintenance,
   })
-    .catch(() => {
-      // Best-effort: budget pressure is retried on the next throttled kick.
+    .catch((error: unknown) => {
+      // Best-effort: budget pressure is retried on the next throttled kick,
+      // but a persistently failing sweep must stay operator-visible — silent
+      // failure here means unbounded disk growth with no signal.
+      log.warn("session history disk-budget sweep failed; retrying on next kick", {
+        error,
+        storePath: params.storePath,
+      });
     })
     .finally(() => {
       state.running = false;