app/models/draft-utils.ts

@@ -10,6 +10,7 @@ import { getSeasonSportsSimple } from "./season-sport";
 import { calculateDraftEligibility } from "~/lib/draft-eligibility";
 import { sendOnTheClockEmail } from "~/services/draft-email.server";
 import { notifyPickMadeOnDiscord } from "~/services/draft-discord.server";
+import { enqueuePickNotification } from "~/services/discord";
 import { getSocketIO, scheduleDraftRoomClosure } from "../../server/socket";
 import { runBracktHarvilleForFantasySeason } from "~/services/brackt.server";
 
@@ -833,21 +834,23 @@ export async function executeAutoPick(params: {
     if (!pickedSlot) {
       logger.warn(`[AutoPick] Skipping Discord pick announcement: no draft slot found for team ${teamId}`);
     } else {
-      notifyPickMadeOnDiscord({
-        seasonId,
-        leagueId: season.leagueId,
-        pickedTeamName: pickedSlot.team.name,
-        participantName: participantToPick.name,
-        sportName: participantToPick.sportsSeason.sport.name,
-        pickNumber,
-        nextPickNumber,
-        round: currentRound,
-        rawPickInRound,
-        isDraftComplete,
-        totalTeams,
-        draftSlots: draftSlots.map((s) => ({ teamId: s.teamId, draftOrder: s.draftOrder })),
-        db,
-      }).catch((err) => logger.error("[AutoPick] Discord pick announcement failed:", err));
+      enqueuePickNotification(season.leagueId, () =>
+        notifyPickMadeOnDiscord({
+          seasonId,
+          leagueId: season.leagueId,
+          pickedTeamName: pickedSlot.team.name,
+          participantName: participantToPick.name,
+          sportName: participantToPick.sportsSeason.sport.name,
+          pickNumber,
+          nextPickNumber,
+          round: currentRound,
+          rawPickInRound,
+          isDraftComplete,
+          totalTeams,
+          draftSlots: draftSlots.map((s) => ({ teamId: s.teamId, draftOrder: s.draftOrder })),
+          db,
+        }).catch((err) => logger.error("[AutoPick] Discord pick announcement failed:", err))
+      );
     }
 
     // Check if next team has autodraft enabled and trigger immediately

app/routes/api/draft.make-pick.ts

@@ -13,6 +13,7 @@ import { logger } from "~/lib/logger";
 import { runBracktHarvilleForFantasySeason } from "~/services/brackt.server";
 import { sendOnTheClockEmail } from "~/services/draft-email.server";
 import { notifyPickMadeOnDiscord } from "~/services/draft-discord.server";
+import { enqueuePickNotification } from "~/services/discord";
 
 import type { ActionFunctionArgs } from "react-router";
 export async function action(args: ActionFunctionArgs) {
@@ -305,21 +306,23 @@ export async function action(args: ActionFunctionArgs) {
 
   // Announce before triggering the chain so Discord messages arrive in pick-number
   // order. If the chain ran first, chained picks would announce before this one.
-  notifyPickMadeOnDiscord({
-    seasonId,
-    leagueId: season.leagueId,
-    pickedTeamName: currentDraftSlot.team.name,
-    participantName: participant.name,
-    sportName: participant.sportsSeason.sport.name,
-    pickNumber: currentPickNumber,
-    nextPickNumber,
-    round: currentRound,
-    rawPickInRound,
-    isDraftComplete,
-    totalTeams,
-    draftSlots: draftSlots.map((s) => ({ teamId: s.teamId, draftOrder: s.draftOrder })),
-    db,
-  }).catch((err) => logger.error("Discord pick announcement failed:", err));
+  enqueuePickNotification(season.leagueId, () =>
+    notifyPickMadeOnDiscord({
+      seasonId,
+      leagueId: season.leagueId,
+      pickedTeamName: currentDraftSlot.team.name,
+      participantName: participant.name,
+      sportName: participant.sportsSeason.sport.name,
+      pickNumber: currentPickNumber,
+      nextPickNumber,
+      round: currentRound,
+      rawPickInRound,
+      isDraftComplete,
+      totalTeams,
+      draftSlots: draftSlots.map((s) => ({ teamId: s.teamId, draftOrder: s.draftOrder })),
+      db,
+    }).catch((err) => logger.error("Discord pick announcement failed:", err))
+  );
 
   // Check if next team has autodraft enabled and trigger immediately
   if (!isDraftComplete) {

app/services/discord.ts

@@ -14,38 +14,73 @@ interface DiscordWebhookPayload {
   allowed_mentions?: { parse: string[]; users: string[] };
 }
 
+// Per-league serial queue: serializes pick notifications within a league to
+// respect Discord's per-webhook rate limit (~5 req/2s) during autodraft chains.
+// Keyed by leagueId so concurrent drafts in different leagues don't block each other.
+const leagueQueues = new Map<string, Array<() => Promise<void>>>();
+const drainingLeagues = new Set<string>();
+
+async function drainLeagueQueue(leagueId: string) {
+  if (drainingLeagues.has(leagueId)) return;
+  drainingLeagues.add(leagueId);
+  try {
+    for (;;) {
+      const queue = leagueQueues.get(leagueId);
+      if (!queue || queue.length === 0) break;
+      const task = queue.shift();
+      if (!task) break;
+      try {
+        await task();
+      } catch {
+        // task already .catch()es its own errors; this is a safety net so one
+        // bad task doesn't prevent the rest of the queue from draining
+      }
+    }
+  } finally {
+    drainingLeagues.delete(leagueId);
+    leagueQueues.delete(leagueId);
+  }
+}
+
+export function enqueuePickNotification(leagueId: string, fn: () => Promise<void>): void {
+  let queue = leagueQueues.get(leagueId);
+  if (!queue) {
+    queue = [];
+    leagueQueues.set(leagueId, queue);
+  }
+  queue.push(fn);
+  drainLeagueQueue(leagueId).catch(() => {});
+}
+
 export async function sendDiscordWebhook(
   webhookUrl: string,
   payload: DiscordWebhookPayload
 ): Promise<void> {
-  const response = await fetch(webhookUrl, {
-    method: "POST",
-    headers: { "Content-Type": "application/json" },
-    body: JSON.stringify(payload),
-  });
+  const body = JSON.stringify(payload);
+  const headers = { "Content-Type": "application/json" };
 
-  if (response.status === 429) {
-    // Cap at 10 s so awaited callers (e.g. settings actions) are never hung for
-    // a full Discord global-rate-limit window. Use || 1 instead of ?? 1 so that
-    // NaN (non-numeric header) and 0 both fall back to a 1-second default.
-    const retryAfterSeconds = Math.min(Number(response.headers.get("Retry-After")) || 1, 10);
-    await new Promise((r) => setTimeout(r, retryAfterSeconds * 1000));
-    const retry = await fetch(webhookUrl, {
-      method: "POST",
-      headers: { "Content-Type": "application/json" },
-      body: JSON.stringify(payload),
-    });
-    if (!retry.ok) {
-      const text = await retry.text().catch(() => "");
-      throw new Error(`Discord webhook failed after retry: ${retry.status} ${text}`);
+  for (let attempt = 0; attempt < 3; attempt++) {
+    const res = await fetch(webhookUrl, { method: "POST", headers, body });
+
+    if (res.status === 429) {
+      // Cap the total wait at 10 s so awaited callers (e.g. settings actions) are
+      // never hung for a full Discord global-rate-limit window. Use || 1 instead of
+      // ?? 1 so NaN (non-numeric header) and 0 both fall back to a 1-second default.
+      // Multiply by (attempt + 1) for progressive backoff, then cap the product.
+      const wait = Math.min((Number(res.headers.get("Retry-After")) || 1) * (attempt + 1), 10);
+      await new Promise((r) => setTimeout(r, wait * 1000));
+      continue;
     }
+
+    if (!res.ok) {
+      const text = await res.text().catch(() => "");
+      throw new Error(`Discord webhook failed: ${res.status} ${text}`);
+    }
+
     return;
   }
 
-  if (!response.ok) {
-    const text = await response.text().catch(() => "");
-    throw new Error(`Discord webhook failed: ${response.status} ${text}`);
-  }
+  throw new Error("Discord webhook failed after 3 retries (rate limited)");
 }
 
 /** Escape characters that trigger Discord markdown formatting. */