diff --git a/app/models/draft-utils.ts b/app/models/draft-utils.ts
index d50a537..9707204 100644
--- a/app/models/draft-utils.ts
+++ b/app/models/draft-utils.ts
@@ -827,23 +827,8 @@ export async function executeAutoPick(params: {
       logger.error("[AutoPick] Error updating Brackt EVs after pick:", error);
     }
 
-    // Check if next team has autodraft enabled and trigger immediately
-    // Only run the chain from the top-level call to prevent recursion
-    if (!isDraftComplete && params.chainEnabled !== false) {
-      await checkAndTriggerNextAutodraft({
-        seasonId,
-        nextPickNumber,
-        totalTeams,
-        draftSlots,
-        db,
-      });
-
-      // Fire-and-forget: sendOnTheClockEmail fetches the current pick number from
-      // the DB itself, so it always sees the post-chain state without blocking here.
-      sendOnTheClockEmail({ seasonId, totalTeams, draftSlots, db })
-        .catch((err) => logger.error("[AutoPick] On-the-clock email failed:", err));
-    }
-
+    // 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.
     const pickedSlot = draftSlots.find((s) => s.teamId === teamId);
     if (!pickedSlot) {
       logger.warn(`[AutoPick] Skipping Discord pick announcement: no draft slot found for team ${teamId}`);
@@ -865,6 +850,23 @@ export async function executeAutoPick(params: {
       }).catch((err) => logger.error("[AutoPick] Discord pick announcement failed:", err));
     }
 
+    // Check if next team has autodraft enabled and trigger immediately
+    // Only run the chain from the top-level call to prevent recursion
+    if (!isDraftComplete && params.chainEnabled !== false) {
+      await checkAndTriggerNextAutodraft({
+        seasonId,
+        nextPickNumber,
+        totalTeams,
+        draftSlots,
+        db,
+      });
+
+      // Fire-and-forget: sendOnTheClockEmail fetches the current pick number from
+      // the DB itself, so it always sees the post-chain state without blocking here.
+      sendOnTheClockEmail({ seasonId, totalTeams, draftSlots, db })
+        .catch((err) => logger.error("[AutoPick] On-the-clock email failed:", err));
+    }
+
     return {
       success: true,
       pick: draftPick,
diff --git a/app/routes/api/draft.make-pick.ts b/app/routes/api/draft.make-pick.ts
index ed89589..813ce90 100644
--- a/app/routes/api/draft.make-pick.ts
+++ b/app/routes/api/draft.make-pick.ts
@@ -303,6 +303,24 @@ export async function action(args: ActionFunctionArgs) {
     logger.error("Socket.IO error:", error);
   }
 
+  // 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));
+
   // Check if next team has autodraft enabled and trigger immediately
   if (!isDraftComplete) {
     try {
@@ -331,22 +349,6 @@ export async function action(args: ActionFunctionArgs) {
       .catch((err) => logger.error("On-the-clock email failed:", err));
   }
 
-  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));
-
   return Response.json({
     success: true,
     pick: draftPick,
diff --git a/app/services/discord.ts b/app/services/discord.ts
index 25d9188..2ad9c28 100644
--- a/app/services/discord.ts
+++ b/app/services/discord.ts
@@ -24,6 +24,24 @@ export async function sendDiscordWebhook(
     body: JSON.stringify(payload),
   });
 
+  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}`);
+    }
+    return;
+  }
+
   if (!response.ok) {
     const text = await response.text().catch(() => "");
     throw new Error(`Discord webhook failed: ${response.status} ${text}`);