diff --git a/apps/api/prod.env b/apps/api/prod.env
index 5789456..049594d 100644
--- a/apps/api/prod.env
+++ b/apps/api/prod.env
@@ -5,4 +5,5 @@ JWT_SECRET="op://Environment Variables - Naomi/Elysium/jwt secret"
 DATABASE_URL="op://Environment Variables - Naomi/Elysium/mongo url"
 ANTI_CHEAT_SECRET="op://Environment Variables - Naomi/Elysium/anti cheat secret"
 PORT="op://Environment Variables - Naomi/Elysium/port"
-CORS_ORIGIN="op://Environment Variables - Naomi/Elysium/origin"
\ No newline at end of file
+CORS_ORIGIN="op://Environment Variables - Naomi/Elysium/origin"
+DISCORD_MILESTONE_WEBHOOK="op://Environment Variables - Naomi/Elysium/discord milestone webhook"
\ No newline at end of file
diff --git a/apps/api/src/routes/apotheosis.ts b/apps/api/src/routes/apotheosis.ts
index c666fe9..cf35886 100644
--- a/apps/api/src/routes/apotheosis.ts
+++ b/apps/api/src/routes/apotheosis.ts
@@ -7,6 +7,7 @@ import {
   buildPostApotheosisState,
   isEligibleForApotheosis,
 } from "../services/apotheosis.js";
+import { postMilestoneWebhook } from "../services/webhook.js";
 
 export const apotheosisRouter = new Hono<HonoEnv>();
 
@@ -61,5 +62,11 @@ apotheosisRouter.post("/", async (context) => {
     },
   });
 
+  void postMilestoneWebhook(discordId, "apotheosis", {
+    prestige: newState.prestige.count,
+    transcendence: newState.transcendence?.count ?? 0,
+    apotheosis: newApotheosisData.count,
+  });
+
   return context.json({ newApotheosisCount: newApotheosisData.count });
 });
diff --git a/apps/api/src/routes/prestige.ts b/apps/api/src/routes/prestige.ts
index 02c83e7..fded59d 100644
--- a/apps/api/src/routes/prestige.ts
+++ b/apps/api/src/routes/prestige.ts
@@ -10,6 +10,7 @@ import {
   computeRunestoneMultipliers,
   isEligibleForPrestige,
 } from "../services/prestige.js";
+import { postMilestoneWebhook } from "../services/webhook.js";
 
 export const prestigeRouter = new Hono<HonoEnv>();
 
@@ -87,6 +88,12 @@ prestigeRouter.post("/", async (context) => {
     },
   });
 
+  void postMilestoneWebhook(discordId, "prestige", {
+    prestige: newPrestigeData.count,
+    transcendence: newState.transcendence?.count ?? 0,
+    apotheosis: newState.apotheosis?.count ?? 0,
+  });
+
   return context.json({
     runestones: runestonesEarned,
     newPrestigeCount: newPrestigeData.count,
diff --git a/apps/api/src/routes/transcendence.ts b/apps/api/src/routes/transcendence.ts
index 0b00229..09861b4 100644
--- a/apps/api/src/routes/transcendence.ts
+++ b/apps/api/src/routes/transcendence.ts
@@ -9,6 +9,7 @@ import {
   computeTranscendenceMultipliers,
   isEligibleForTranscendence,
 } from "../services/transcendence.js";
+import { postMilestoneWebhook } from "../services/webhook.js";
 
 export const transcendenceRouter = new Hono<HonoEnv>();
 
@@ -66,6 +67,12 @@ transcendenceRouter.post("/", async (context) => {
     },
   });
 
+  void postMilestoneWebhook(discordId, "transcendence", {
+    prestige: newState.prestige.count,
+    transcendence: newTranscendenceData.count,
+    apotheosis: newState.apotheosis?.count ?? 0,
+  });
+
   return context.json({
     echoes: echoesEarned,
     newTranscendenceCount: newTranscendenceData.count,
diff --git a/apps/api/src/services/webhook.ts b/apps/api/src/services/webhook.ts
new file mode 100644
index 0000000..ac57aa0
--- /dev/null
+++ b/apps/api/src/services/webhook.ts
@@ -0,0 +1,37 @@
+type MilestoneType = "prestige" | "transcendence" | "apotheosis";
+
+interface MilestoneCounts {
+  prestige: number;
+  transcendence: number;
+  apotheosis: number;
+}
+
+const MILESTONE_VERBS: Record<MilestoneType, string> = {
+  prestige: "prestiged",
+  transcendence: "transcended",
+  apotheosis: "reached apotheosis",
+};
+
+export const postMilestoneWebhook = async (
+  discordId: string,
+  milestone: MilestoneType,
+  counts: MilestoneCounts,
+): Promise<void> => {
+  const webhookUrl = process.env["DISCORD_MILESTONE_WEBHOOK"];
+  if (!webhookUrl) {
+    return;
+  }
+
+  const verb = MILESTONE_VERBS[milestone];
+  const content = `<@${discordId}> has ${verb}~! They are now on Prestige ${counts.prestige}, Transcendence ${counts.transcendence}, Apotheosis ${counts.apotheosis}!`;
+
+  try {
+    await fetch(webhookUrl, {
+      method: "POST",
+      headers: { "Content-Type": "application/json" },
+      body: JSON.stringify({ content }),
+    });
+  } catch {
+    // Graceful degradation — webhook failure must not affect the game action
+  }
+};