diff --git a/listener/src/index.ts b/listener/src/index.ts
index 1c71017..38f13d9 100644
--- a/listener/src/index.ts
+++ b/listener/src/index.ts
@@ -41,6 +41,15 @@ async function main() {
   if (config.analytics?.enabled) {
     initNotificationAnalyticsAggregator(config.analytics);
   }
+  const retryCount = process.env.DISCORD_RETRY_COUNT
+    ? parseInt(process.env.DISCORD_RETRY_COUNT, 10)
+    : undefined;
+  const backoffBaseSeconds = process.env.DISCORD_BACKOFF_BASE_SECONDS
+    ? parseFloat(process.env.DISCORD_BACKOFF_BASE_SECONDS)
+    : undefined;
+
+  return { webhookUrl, webhookId, retryCount, backoffBaseSeconds };
+}
 
   try {
     logger.info('Initializing database');
diff --git a/listener/src/services/discord-notification.ts b/listener/src/services/discord-notification.ts
index 9fbae5f..6e9593d 100644
--- a/listener/src/services/discord-notification.ts
+++ b/listener/src/services/discord-notification.ts
@@ -75,13 +75,30 @@ export class DiscordNotificationService {
     logger.info('Sending Discord notification', logContext);
 
     const message = this.formatEventMessage(event, contractConfig);
-    const startTime = Date.now();
+    const maxRetries = this.config.retryCount ?? 5;
+    const backoffBaseSeconds = this.config.backoffBaseSeconds ?? 1;
 
-    try {
-      const response = await this.sendWebhook(message);
-      const durationMs = Date.now() - startTime;
+    let attempt = 0;
+    while (attempt <= maxRetries) {
+      const attemptStart = Date.now();
+      try {
+        const response = await this.sendWebhook(message);
+        const durationMs = Date.now() - attemptStart;
+
+        if (response.ok) {
+          this.deduplicator.markSent(fingerprint);
+          logger.info('Discord notification sent successfully', {
+            eventId: event.id,
+            contractAddress: contractConfig.address,
+          });
+          logger.info('Discord notification delivered', {
+            ...logContext,
+            durationMs,
+            attempt,
+          });
+          return true;
+        }
 
-      if (!response.ok) {
         const errorText = await response.text();
         this.analytics?.record({
           notificationType: NotificationType.DISCORD,
@@ -97,10 +114,24 @@ export class DiscordNotificationService {
           statusText: response.statusText,
           error: errorText,
           durationMs,
+          attempt,
+        });
+      } catch (error) {
+        const durationMs = Date.now() - attemptStart;
+        logger.error('Error sending Discord notification', {
+          ...logContext,
+          error,
+          durationMs,
+          attempt,
         });
-        return false;
       }
 
+      // If we've exhausted retries, break and return false
+      if (attempt >= maxRetries) break;
+
+      // Exponential backoff: base * 2^attempt (seconds)
+      const delayMs = Math.pow(2, attempt) * backoffBaseSeconds * 1000;
+      logger.warn('Retrying Discord webhook', {
       this.deduplicator.markSent(fingerprint);
       this.analytics?.record({
         notificationType: NotificationType.DISCORD,
@@ -127,11 +158,19 @@ export class DiscordNotificationService {
       });
       logger.error('Error sending Discord notification', {
         ...logContext,
-        error,
-        durationMs: Date.now() - startTime,
+        attempt: attempt + 1,
+        nextDelayMs: delayMs,
+        maxRetries,
       });
-      return false;
+      await this.delay(delayMs);
+      attempt++;
     }
+
+    logger.error('Exceeded max Discord retry attempts', {
+      ...logContext,
+      maxRetries,
+    });
+    return false;
   }
 
   getMetrics() {
@@ -186,6 +225,10 @@ export class DiscordNotificationService {
     }
   }
 
+  private delay(ms: number): Promise<void> {
+    return new Promise((resolve) => setTimeout(resolve, ms));
+  }
+
   private async sendWebhook(message: DiscordMessage): Promise<Response> {
     try {
       const response = await sendWebhook(this.config.webhookUrl, message, {
diff --git a/listener/src/types/index.ts b/listener/src/types/index.ts
index 824a6cb..ffc392a 100644
--- a/listener/src/types/index.ts
+++ b/listener/src/types/index.ts
@@ -8,6 +8,8 @@ export interface ContractConfig {
 export interface DiscordConfig {
   webhookUrl: string;
   webhookId: string;
+  retryCount?: number;
+  backoffBaseSeconds?: number;
   deduplicationWindowMs?: number;
   deduplicationMaxSize?: number;
   timeoutMs?: number;