diff --git a/server/src/__tests__/instance-settings-routes.test.ts b/server/src/__tests__/instance-settings-routes.test.ts
index 61a3a5b3644..70da7c9f6bd 100644
--- a/server/src/__tests__/instance-settings-routes.test.ts
+++ b/server/src/__tests__/instance-settings-routes.test.ts
@@ -70,6 +70,24 @@ function defaultSelectChain() {
     }),
   };
 }
+// Read the literal string value a drizzle-orm `eq()`/`and()` condition
+// binds as a query parameter. A test that must prove which dedup key the
+// route actually queried with — not just whether a row came back — walks
+// the condition object for its bound `Param` values, since the mock
+// `where()` above normally ignores its argument.
+function collectBoundParamValues(node: unknown, found: string[]): void {
+  if (node === null || typeof node !== "object") return;
+  const record = node as Record<string, unknown>;
+  if (typeof record.value === "string") found.push(record.value);
+  if (Array.isArray(record.value)) {
+    for (const entry of record.value) {
+      if (typeof entry === "string") found.push(entry);
+    }
+  }
+  if (Array.isArray(record.queryChunks)) {
+    for (const chunk of record.queryChunks) collectBoundParamValues(chunk, found);
+  }
+}
 const mockDb = {
   transaction: vi.fn(defaultTransactionImplementation),
   select: vi.fn(defaultSelectChain),
@@ -1977,6 +1995,71 @@ describe("instance settings routes", () => {
         expect(mockInstanceSettingsService.listCompanyIds).not.toHaveBeenCalled();
       });
 
+      it("does_not_treat_a_pre_restart_activity_row_as_a_duplicate_of_a_same_numbered_generation", async () => {
+        vi.useFakeTimers();
+        vi.setSystemTime(new Date("2026-01-01T00:00:00.000Z"));
+        const terminateAt = new Date("2026-01-01T00:00:30.000Z");
+        mockHeartbeatService.computeTaskDrain.mockReturnValue({
+          startedAt: new Date("2026-01-01T00:00:00.000Z"),
+          expiresAt: new Date("2026-01-01T00:01:00.000Z"),
+          terminateActiveTasks: true,
+          terminateAt,
+        });
+        // The in-memory generation counter starts at 0 on every process
+        // boot, so a fresh process can hand out generation 1 again. Model
+        // that here: this run's own generation is 1, standing in for a
+        // process restart after an earlier, unrelated termination also
+        // held generation 1.
+        mockHeartbeatService.applyTaskDrain.mockReturnValue(1);
+        mockHeartbeatService.isTaskDrainGenerationLive.mockReturnValue(true);
+        mockHeartbeatService.terminateActiveRunsForTaskDrain.mockResolvedValue(
+          new Map([["company-1", { attemptedRunIds: ["run-1"], cancelledRunIds: ["run-1"], failedRunIds: [] }]]),
+        );
+
+        // A row already sits in the table under the dedup key a
+        // generation-only scheme would have used for generation 1. It
+        // belongs to that earlier, unrelated termination — a real
+        // termination from before the restart — not to this run.
+        const preRestartEntityId = "task-drain-termination:1";
+        let queriedEntityId: string | null = null;
+        mockDb.select.mockImplementation(() => ({
+          from: () => ({
+            where: (condition: unknown) => ({
+              limit: () => {
+                const boundValues: string[] = [];
+                collectBoundParamValues(condition, boundValues);
+                queriedEntityId =
+                  boundValues.find((value) => value.startsWith("task-drain-termination:")) ?? null;
+                const matchesPreRestartRow = queriedEntityId === preRestartEntityId;
+                return Promise.resolve(
+                  matchesPreRestartRow ? [{ id: "activity-from-before-restart" }] : [],
+                );
+              },
+            }),
+          }),
+        }));
+
+        const app = await createApp(adminActor);
+        await request(app).post("/api/instance/task-drain").send({ ttlMs: 60_000, terminateActiveTasks: true });
+        mockLogActivity.mockClear();
+        mockDb.transaction.mockClear();
+
+        await vi.advanceTimersByTimeAsync(30_000);
+
+        // The dedup key this run queried with must not be the plain
+        // generation number, and it must not match the pre-restart row —
+        // otherwise this run's own outcome audit would be silently
+        // skipped as an apparent duplicate of a termination it never ran.
+        expect(queriedEntityId).not.toBeNull();
+        expect(queriedEntityId).not.toBe(preRestartEntityId);
+        expect(mockDb.transaction).toHaveBeenCalledTimes(1);
+        expect(mockLogActivity).toHaveBeenCalledWith(
+          TX_SENTINEL,
+          expect.objectContaining({ action: "instance.task_drain.active_tasks_terminated" }),
+          expect.any(Array),
+        );
+      });
+
       it("logs_the_full_termination_outcome_when_the_audit_write_cannot_be_retried_into_success", async () => {
         vi.useFakeTimers();
         vi.setSystemTime(new Date("2026-01-01T00:00:00.000Z"));
diff --git a/server/src/routes/instance-settings.ts b/server/src/routes/instance-settings.ts
index b1d5a8b7d29..19092ef91a4 100644
--- a/server/src/routes/instance-settings.ts
+++ b/server/src/routes/instance-settings.ts
@@ -1,3 +1,4 @@
+import { randomUUID } from "node:crypto";
 import { Router, type Request } from "express";
 import { and, eq } from "drizzle-orm";
 import { activityLog, type Db } from "@paperclipai/db";
@@ -143,8 +144,19 @@ type TaskDrainActorSnapshot = {
 // will succeed. If a later step in that same request then fails, the
 // request re-arms the deadline from this snapshot, so a failed
 // replacement or a failed stop never leaves a live drain with no timer.
+//
+// `generation` and `terminationId` answer two different questions.
+// `generation` comes from the process-local counter in the heartbeat
+// service, resets to 0 on every restart, and only proves whether this
+// timer's callback still names the live in-memory drain. `terminationId`
+// is a UUID minted once, when this termination is armed, and stays
+// unique across process restarts, so the audit dedup key below can use
+// it safely: an old activity row from before a restart can carry the
+// same `generation` number as a new termination, but never the same
+// `terminationId`.
 type ArmedTaskDrainTermination = {
   generation: number;
+  terminationId: string;
   initiatingActor: TaskDrainActorSnapshot;
   terminateAt: Date;
 };
@@ -190,6 +202,7 @@ export function instanceSettingsRoutes(db: Db) {
   // obsolete after the event loop had already queued it).
   async function runTaskDrainTermination(
     generation: number,
+    terminationId: string,
     initiatingActor: TaskDrainActorSnapshot,
     terminateAt: Date,
   ) {
@@ -206,16 +219,20 @@ export function instanceSettingsRoutes(db: Db) {
       //
       // A dropped connection can happen after the server commits the
       // transaction but before the driver reports success. So a retry
-      // cannot assume the first attempt never landed. The termination
-      // generation names this exact execution and never repeats, so each
+      // cannot assume the first attempt never landed. `terminationId`
+      // names this exact execution and never repeats — not even across a
+      // process restart, unlike the in-memory generation number — so each
       // retry uses it as a key: it checks for an existing row first, and
       // writes only when that check finds none. This stops a retry after
-      // an ambiguous failure from duplicating the row or its publication.
+      // an ambiguous failure from duplicating the row or its publication,
+      // and it stops a termination after a restart from matching an old
+      // row left by an unrelated termination that reused the same
+      // generation number.
       //
       // If every retry still fails, log the full outcome. An operator can
       // then recover it from the application log even though the audit
       // table write did not land.
-      const terminationEntityId = `task-drain-termination:${generation}`;
+      const terminationEntityId = `task-drain-termination:${terminationId}`;
       try {
         await retryOnTransientDbConnectionError(async () => {
           const alreadyRecorded = await db
@@ -274,6 +291,7 @@ export function instanceSettingsRoutes(db: Db) {
           {
             err,
             generation,
+            terminationId,
             terminateAt,
             executedAt,
             initiatingActor,
@@ -304,7 +322,12 @@ export function instanceSettingsRoutes(db: Db) {
         taskDrainTerminationTimer = null;
         armedTaskDrainTermination = null;
       }
-      runTaskDrainTermination(armed.generation, armed.initiatingActor, armed.terminateAt).catch((err) => {
+      runTaskDrainTermination(
+        armed.generation,
+        armed.terminationId,
+        armed.initiatingActor,
+        armed.terminateAt,
+      ).catch((err) => {
         logger.error({ err }, "task drain termination failed");
       });
     }, delayMs);
@@ -555,7 +578,12 @@ export function instanceSettingsRoutes(db: Db) {
           publishActivitiesBestEffort(postCommitActivityPublications, "instance.task_drain.started");
           const terminateAt = computed.terminateAt;
           if (terminateAt) {
-            scheduleTaskDrainTermination({ generation, initiatingActor, terminateAt });
+            scheduleTaskDrainTermination({
+              generation,
+              terminationId: randomUUID(),
+              initiatingActor,
+              terminateAt,
+            });
           }
           return computed;
         } catch (err) {