fix(webapp): schedule run-ops mint-kind flips to avoid duplicate runs

apps/webapp/app/env.server.ts

@@ -1753,6 +1753,10 @@ const EnvironmentSchema = z
     RUN_OPS_MINT_ENABLED: BoolEnv.default(false),
     RUN_OPS_MINT_FLAG_CACHE_TTL_MS: z.coerce.number().int().default(30_000),
     RUN_OPS_MINT_FLAG_CACHE_MAX_ENTRIES: z.coerce.number().int().default(10_000),
+    // Deterministic wall-clock cutover after a runOpsMintKind flip. Must exceed the sum
+    // of RUN_OPS_MINT_FLAG_CACHE_TTL_MS and the control-plane cache TTL so every process
+    // (stale or fresh) resolves to the same kind for the whole window. See mintFlipGrace.ts.
+    RUN_OPS_MINT_FLIP_GRACE_MS: z.coerce.number().int().default(90_000),
 
     // Session replication (Postgres → ClickHouse sessions_v1). Shares Redis
     // with the runs replicator for leader locking but has its own slot and

apps/webapp/app/routes/admin.api.v1.orgs.$organizationId.feature-flags.ts

@@ -1,9 +1,12 @@
 import type { ActionFunctionArgs, LoaderFunctionArgs } from "@remix-run/server-runtime";
 import { json } from "@remix-run/server-runtime";
+import type { Prisma } from "@trigger.dev/database";
 import { z } from "zod";
+import { env } from "~/env.server";
 import { prisma } from "~/db.server";
 import { requireAdminApiRequest } from "~/services/personalAccessToken.server";
 import { controlPlaneResolver } from "~/v3/runOpsMigration/controlPlaneResolver.server";
+import { stampMintKindFlip } from "~/v3/runOpsMigration/mintFlipGrace";
 import { validatePartialFeatureFlags } from "~/v3/featureFlags";
 
 const ParamsSchema = z.object({
@@ -82,18 +85,23 @@ export async function action({ request, params }: ActionFunctionArgs) {
       ? validatePartialFeatureFlags(organization.featureFlags as Record<string, unknown>)
       : { success: false as const };
 
-    const mergedFlags = {
-      ...(existingFlags.success ? existingFlags.data : {}),
-      ...validationResult.data,
-    };
+    const mergedFlags = stampMintKindFlip(
+      existingFlags.success ? existingFlags.data : {},
+      {
+        ...(existingFlags.success ? existingFlags.data : {}),
+        ...validationResult.data,
+      },
+      Date.now(),
+      env.RUN_OPS_MINT_FLIP_GRACE_MS
+    );
 
     // Update the organization's feature flags
     const updatedOrganization = await prisma.organization.update({
       where: {
         id: organizationId,
       },
       data: {
-        featureFlags: mergedFlags,
+        featureFlags: mergedFlags as Prisma.InputJsonValue,
       },
       select: {
         id: true,

apps/webapp/app/routes/admin.api.v2.orgs.$organizationId.feature-flags.ts

@@ -2,9 +2,11 @@ import type { ActionFunctionArgs, LoaderFunctionArgs } from "@remix-run/server-r
 import { json } from "@remix-run/server-runtime";
 import { Prisma } from "@trigger.dev/database";
 import { z } from "zod";
+import { env } from "~/env.server";
 import { prisma } from "~/db.server";
 import { requireUser } from "~/services/session.server";
 import { controlPlaneResolver } from "~/v3/runOpsMigration/controlPlaneResolver.server";
+import { stampMintKindFlip } from "~/v3/runOpsMigration/mintFlipGrace";
 import { flags as getGlobalFlags } from "~/v3/featureFlags.server";
 import {
   FEATURE_FLAG,
@@ -119,6 +121,17 @@ export async function action({ request, params }: ActionFunctionArgs) {
       );
     }
     featureFlags = validationResult.data;
+
+    const existingOrg = await prisma.organization.findFirst({
+      where: { id: organizationId },
+      select: { featureFlags: true },
+    });
+    featureFlags = stampMintKindFlip(
+      existingOrg?.featureFlags as Record<string, unknown> | null | undefined,
+      featureFlags,
+      Date.now(),
+      env.RUN_OPS_MINT_FLIP_GRACE_MS
+    );
   }
 
   try {

apps/webapp/app/v3/featureFlags.ts

@@ -19,6 +19,9 @@ export const FEATURE_FLAG = {
   computeMigrationRequireTemplate: "computeMigrationRequireTemplate",
   devBranchesEnabled: "devBranchesEnabled",
   runOpsMintKind: "runOpsMintKind",
+  // Grace-linger stamp carried alongside runOpsMintKind on flip. See mintFlipGrace.ts.
+  runOpsMintKindPrev: "runOpsMintKindPrev",
+  runOpsMintKindFlippedAt: "runOpsMintKindFlippedAt",
 } as const;
 
 export const FeatureFlagCatalog = {
@@ -54,6 +57,10 @@ export const FeatureFlagCatalog = {
   // Per-org run-ops-id mint cutover. Defaults to "cuid"; only honored when
   // RUN_OPS_MINT_ENABLED is on AND isSplitEnabled() is true.
   [FEATURE_FLAG.runOpsMintKind]: z.enum(["cuid", "runOpsId"]),
+  // Grace-linger stamp: the previously-effective kind and the flip timestamp, written
+  // by stampMintKindFlip on a genuine flip. Display-only (see ORG_LOCKED_FLAGS).
+  [FEATURE_FLAG.runOpsMintKindPrev]: z.enum(["cuid", "runOpsId"]),
+  [FEATURE_FLAG.runOpsMintKindFlippedAt]: z.string().datetime(),
 };
 
 export type FeatureFlagKey = keyof typeof FeatureFlagCatalog;
@@ -70,6 +77,8 @@ export const GLOBAL_LOCKED_FLAGS: FeatureFlagKey[] = [
 export const ORG_LOCKED_FLAGS: FeatureFlagKey[] = [
   FEATURE_FLAG.defaultWorkerInstanceGroupId,
   FEATURE_FLAG.taskEventRepository,
+  FEATURE_FLAG.runOpsMintKindPrev,
+  FEATURE_FLAG.runOpsMintKindFlippedAt,
 ];
 
 // Create a Zod schema from the existing catalog

apps/webapp/app/v3/runOpsMigration/mintFlipGrace.test.ts

@@ -0,0 +1,159 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import { effectiveMintKind, stampMintKindFlip, type MintFlagResolution } from "./mintFlipGrace";
+
+// GRACE-LINGER: during [flippedAt, flippedAt + GRACE) every process — stale or fresh —
+// must resolve to the SAME (old) kind; at/after the cutover every process resolves to
+// the SAME (new) kind. This collapses the cross-process divergence window.
+const GRACE_MS = 90_000;
+const T = 1_000_000;
+
+describe("effectiveMintKind", () => {
+  beforeEach(() => vi.useFakeTimers());
+  afterEach(() => vi.useRealTimers());
+
+  it("returns r.kind directly when prev is missing", () => {
+    const r: MintFlagResolution = { kind: "cuid" };
+    expect(effectiveMintKind(r, T, GRACE_MS)).toBe("cuid");
+  });
+
+  it("returns r.kind directly when flippedAtMs is missing", () => {
+    const r: MintFlagResolution = { kind: "runOpsId", prev: "cuid" };
+    expect(effectiveMintKind(r, T, GRACE_MS)).toBe("runOpsId");
+  });
+
+  it("CORE: stale and fresh resolutions agree at every instant during grace, then both flip to the new kind at cutover", () => {
+    const stale: MintFlagResolution = { kind: "cuid" };
+    const fresh: MintFlagResolution = { kind: "runOpsId", prev: "cuid", flippedAtMs: T };
+
+    for (const now of [T, T + 1, T + 1_000, T + 45_000, T + GRACE_MS - 1]) {
+      const staleResolved = effectiveMintKind(stale, now, GRACE_MS);
+      const freshResolved = effectiveMintKind(fresh, now, GRACE_MS);
+      expect(staleResolved).toBe("cuid");
+      expect(freshResolved).toBe("cuid");
+    }
+
+    for (const now of [T + GRACE_MS, T + GRACE_MS + 1, T + GRACE_MS + 60_000]) {
+      expect(effectiveMintKind(fresh, now, GRACE_MS)).toBe("runOpsId");
+    }
+  });
+
+  it("boundary: exactly at flippedAt + GRACE resolves to the NEW kind", () => {
+    const fresh: MintFlagResolution = { kind: "runOpsId", prev: "cuid", flippedAtMs: T };
+    expect(effectiveMintKind(fresh, T + GRACE_MS - 1, GRACE_MS)).toBe("cuid");
+    expect(effectiveMintKind(fresh, T + GRACE_MS, GRACE_MS)).toBe("runOpsId");
+  });
+});
+
+describe("stampMintKindFlip", () => {
+  beforeEach(() => vi.useFakeTimers());
+  afterEach(() => vi.useRealTimers());
+
+  it("a genuine flip (cuid -> runOpsId) stamps prev and flippedAt", () => {
+    const existing = { runOpsMintKind: "cuid" };
+    const outgoing = { runOpsMintKind: "runOpsId" };
+    const result = stampMintKindFlip(existing, outgoing, T, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("runOpsId");
+    expect(result.runOpsMintKindPrev).toBe("cuid");
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(T).toISOString());
+  });
+
+  it("defaults the existing effective kind to cuid when existing flags are null", () => {
+    const outgoing = { runOpsMintKind: "runOpsId" };
+    const result = stampMintKindFlip(null, outgoing, T, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("runOpsId");
+    expect(result.runOpsMintKindPrev).toBe("cuid");
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(T).toISOString());
+  });
+
+  it("resubmitting the same target kind mid-grace carries the stamp forward untouched (does not reset the cutover clock)", () => {
+    const existing = {
+      runOpsMintKind: "runOpsId",
+      runOpsMintKindPrev: "cuid",
+      runOpsMintKindFlippedAt: new Date(T).toISOString(),
+    };
+    const now = T + 10_000;
+    const outgoing = { runOpsMintKind: "runOpsId", someOtherFlag: true };
+    const result = stampMintKindFlip(existing, outgoing, now, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("runOpsId");
+    expect(result.runOpsMintKindPrev).toBe("cuid");
+    // Unrelated re-save: the cutover time must NOT slide forward.
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(T).toISOString());
+    expect(result.someOtherFlag).toBe(true);
+  });
+
+  it("an unchanged save after grace has elapsed carries the settled stamp forward and preserves unrelated flags", () => {
+    const existing = {
+      runOpsMintKind: "runOpsId",
+      runOpsMintKindPrev: "cuid",
+      runOpsMintKindFlippedAt: new Date(T).toISOString(),
+    };
+    const outgoing = { runOpsMintKind: "runOpsId", someOtherFlag: true };
+    const result = stampMintKindFlip(existing, outgoing, T + GRACE_MS + 5_000, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("runOpsId");
+    expect(result.someOtherFlag).toBe(true);
+    expect(result.runOpsMintKindPrev).toBe("cuid");
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(T).toISOString());
+  });
+
+  it("a flip-back requested after the original grace has elapsed stamps prev := the new settled (now-effective) kind, timestamped now", () => {
+    const existing = {
+      runOpsMintKind: "runOpsId",
+      runOpsMintKindPrev: "cuid",
+      runOpsMintKindFlippedAt: new Date(T).toISOString(),
+    };
+    const now = T + GRACE_MS + 1_000;
+    const outgoing = { runOpsMintKind: "cuid" };
+    const result = stampMintKindFlip(existing, outgoing, now, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("cuid");
+    expect(result.runOpsMintKindPrev).toBe("runOpsId");
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(now).toISOString());
+  });
+
+  it("a flip-back mid-grace re-stamps prev to the still-effective old kind, so it keeps serving that kind (no divergence)", () => {
+    const existing = {
+      runOpsMintKind: "runOpsId",
+      runOpsMintKindPrev: "cuid",
+      runOpsMintKindFlippedAt: new Date(T).toISOString(),
+    };
+    const now = T + 20_000;
+    const outgoing = { runOpsMintKind: "cuid" };
+    const result = stampMintKindFlip(existing, outgoing, now, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("cuid");
+    expect(result.runOpsMintKindPrev).toBe("cuid");
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(now).toISOString());
+  });
+
+  it("defaults outgoing kind to 'cuid' when runOpsMintKind is absent", () => {
+    const existing = { runOpsMintKind: "runOpsId" };
+    const outgoing: Record<string, unknown> = {};
+    const result = stampMintKindFlip(existing, outgoing, T, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("cuid");
+    expect(result.runOpsMintKindPrev).toBe("runOpsId");
+    expect(result.runOpsMintKindFlippedAt).toBe(new Date(T).toISOString());
+  });
+
+  it("treats a malformed existing flippedAt as no stamp", () => {
+    const existing = {
+      runOpsMintKind: "runOpsId",
+      runOpsMintKindPrev: "cuid",
+      runOpsMintKindFlippedAt: "not-a-date",
+    };
+    const outgoing = { runOpsMintKind: "runOpsId" };
+    const result = stampMintKindFlip(existing, outgoing, T, GRACE_MS);
+
+    expect(result.runOpsMintKind).toBe("runOpsId");
+    // The malformed flippedAt is carried forward verbatim, but an unparseable timestamp is
+    // inert when resolved (Date.parse -> NaN -> effectiveMintKind returns the target kind).
+    expect(result.runOpsMintKindFlippedAt).toBe("not-a-date");
+    expect(
+      effectiveMintKind({ kind: "runOpsId", prev: "cuid", flippedAtMs: NaN }, T, GRACE_MS)
+    ).toBe("runOpsId");
+  });
+});

apps/webapp/app/v3/runOpsMigration/mintFlipGrace.ts

@@ -0,0 +1,77 @@
+import type { RunIdMintKind } from "./runOpsMintKind.server";
+
+export type { RunIdMintKind };
+
+export type MintFlagResolution = {
+  kind: RunIdMintKind;
+  prev?: RunIdMintKind;
+  flippedAtMs?: number;
+};
+
+const DEFAULT_MINT_KIND: RunIdMintKind = "cuid";
+
+// Deterministic wall-clock cutover: during [flippedAt, flippedAt + graceMs) every
+// process — stale (hasn't re-read the flag) or fresh (has the new stamp) — resolves to
+// the OLD kind. At/after the cutover, every process resolves to the NEW kind.
+export function effectiveMintKind(
+  r: MintFlagResolution,
+  nowMs: number,
+  graceMs: number
+): RunIdMintKind {
+  if (r.prev === undefined || r.flippedAtMs === undefined) {
+    return r.kind;
+  }
+  return nowMs < r.flippedAtMs + graceMs ? r.prev : r.kind;
+}
+
+function readMintKind(flags: Record<string, unknown>, key: string): RunIdMintKind | undefined {
+  const value = flags[key];
+  return value === "cuid" || value === "runOpsId" ? value : undefined;
+}
+
+function resolveEffectiveFromFlags(
+  flags: Record<string, unknown> | null | undefined,
+  nowMs: number,
+  graceMs: number
+): RunIdMintKind {
+  const source = flags ?? {};
+  const kind = readMintKind(source, "runOpsMintKind") ?? DEFAULT_MINT_KIND;
+  const prev = readMintKind(source, "runOpsMintKindPrev");
+  const flippedAtRaw = source.runOpsMintKindFlippedAt;
+  const parsed = typeof flippedAtRaw === "string" ? Date.parse(flippedAtRaw) : NaN;
+  const flippedAtMs = Number.isNaN(parsed) ? undefined : parsed;
+
+  return effectiveMintKind({ kind, prev, flippedAtMs }, nowMs, graceMs);
+}
+
+// Stamps a grace window only when the outgoing TARGET kind differs from the stored one (a
+// genuine flip); prev := the currently-effective kind. A save that leaves the target kind
+// unchanged carries any in-flight stamp forward, so it can't reset the cutover clock.
+export function stampMintKindFlip(
+  existingFlags: Record<string, unknown> | null | undefined,
+  outgoingFlags: Record<string, unknown>,
+  nowMs: number,
+  graceMs: number
+): Record<string, unknown> {
+  const storedKind = readMintKind(existingFlags ?? {}, "runOpsMintKind") ?? DEFAULT_MINT_KIND;
+  const outgoingKind = readMintKind(outgoingFlags, "runOpsMintKind") ?? DEFAULT_MINT_KIND;
+  outgoingFlags.runOpsMintKind = outgoingKind;
+
+  if (outgoingKind !== storedKind) {
+    // Genuine target change: serve the currently-effective kind through the new grace window.
+    outgoingFlags.runOpsMintKindPrev = resolveEffectiveFromFlags(existingFlags, nowMs, graceMs);
+    outgoingFlags.runOpsMintKindFlippedAt = new Date(nowMs).toISOString();
+    return outgoingFlags;
+  }
+
+  const existing = existingFlags ?? {};
+  const existingPrev = existing.runOpsMintKindPrev;
+  const existingFlippedAt = existing.runOpsMintKindFlippedAt;
+  if (existingPrev !== undefined) {
+    outgoingFlags.runOpsMintKindPrev = existingPrev;
+  }
+  if (existingFlippedAt !== undefined) {
+    outgoingFlags.runOpsMintKindFlippedAt = existingFlippedAt;
+  }
+  return outgoingFlags;
+}

apps/webapp/app/v3/runOpsMigration/runOpsMintKind.flipLatency.test.ts

@@ -2,15 +2,15 @@ import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import { BoundedTtlCache } from "~/services/realtime/boundedTtlCache";
 import { computeRunIdMintKind, type RunIdMintKind } from "./runOpsMintKind.server";
 
-// LOCK of the CURRENT (intentional) flip-latency behavior, NOT a change request.
-// resolveRunIdMintKind caches the per-org mint kind in a process-singleton
-// BoundedTtlCache (TTL RUN_OPS_MINT_FLAG_CACHE_TTL_MS, 30000ms default) with get/set
-// and NO invalidation hook (runOpsMintKind.server.ts:38-45,56-81). So after a flag
-// flip a process keeps minting the stale kind until its cached entry expires; in
-// multi-instance prod each process expires independently. This suite reconstructs the
-// same flag fn over a real cache and pins both edges of that window.
+// LOCK of the raw per-process cache's flip-latency behavior in isolation, NOT a change
+// request. Production resolveRunIdMintKind now wraps this same staleness in a deterministic
+// wall-clock grace window (mintFlipGrace.ts) so every process resolves to the SAME effective
+// kind for the whole window, then all cross together. This raw staleness is now an
+// intentional, safe input to that resolution. computeRunIdMintKind is unaffected, so this
+// suite's assertions stand as-is.
 
-// Mirror of resolveRunIdMintKind's flag fn (runOpsMintKind.server.ts:56-81).
+// Bare cached-flag closure — deliberately NOT the production flag fn, which now layers
+// grace resolution on top (see runOpsMintKind.server.ts).
 function makeCachedFlag(
   cache: BoundedTtlCache<RunIdMintKind>,
   liveFlag: () => RunIdMintKind