diff --git a/packages/services/service-common/src/helpers.ts b/packages/services/service-common/src/helpers.ts
index 9f7e858d0f..6dafa739f9 100644
--- a/packages/services/service-common/src/helpers.ts
+++ b/packages/services/service-common/src/helpers.ts
@@ -32,3 +32,7 @@ export function invariant(
   const value: string = provided ? `${prefix}: ${provided}` : prefix;
   throw new Error(value);
 }
+
+export function maskToken(token: string) {
+  return token.substring(0, 3) + '*'.repeat(token.length - 6) + token.substring(token.length - 3);
+}
diff --git a/packages/services/service-common/src/sentry.ts b/packages/services/service-common/src/sentry.ts
index 83f0e38b24..10d7b9e9da 100644
--- a/packages/services/service-common/src/sentry.ts
+++ b/packages/services/service-common/src/sentry.ts
@@ -1,42 +1,46 @@
 import type { FastifyInstance, FastifyPluginAsync } from 'fastify';
 import fp from 'fastify-plugin';
 import * as Sentry from '@sentry/node';
-import { cleanRequestId } from './helpers';
+import { cleanRequestId, maskToken } from './helpers';
 
 const plugin: FastifyPluginAsync = async server => {
   server.decorateReply('sentry', null);
 
   server.setErrorHandler((err, req, reply) => {
     Sentry.withScope(scope => {
-      scope.setUser({
-        ip_address: req.ip,
-      });
-
+      scope.setUser({ ip_address: req.ip });
       const requestId = cleanRequestId(req.headers['x-request-id']);
-
+      const tokenHeader = req.headers['x-api-token'] || req.headers.authorization;
+      const maskedToken = typeof tokenHeader === 'string' ? maskToken(tokenHeader) : null;
       if (requestId) {
         scope.setTag('request_id', requestId);
       }
-
       const { referer } = req.headers;
-
       if (referer) {
         scope.setTag('referer', referer);
       }
-
       scope.setTag('path', req.raw.url);
       scope.setTag('method', req.raw.method);
+      if (maskedToken) {
+        scope.setTag('masked_token', maskedToken);
+      }
       req.log.error(err);
       Sentry.captureException(err);
 
-      req.log.warn('Replying with 500 Internal Server Error');
+      if (err.code === 'FST_ERR_CRT_BODY_TOO_LARGE') {
+        req.log.warn('Payload too large');
+        void reply.status(413).send({
+          error: 413,
+          message: 'Payload Too Large',
+        });
+        return;
+      }
 
-      void reply.status(500).send(
-        JSON.stringify({
-          error: 500,
-          message: 'Internal Server Error',
-        }),
-      );
+      req.log.warn('Replying with 500 Internal Server Error');
+      void reply.status(500).send({
+        error: 500,
+        message: 'Internal Server Error',
+      });
     });
   });
 };