diff --git a/functions/_common/reusableHandlers.ts b/functions/_common/reusableHandlers.ts
index 57305c860e1..10dbbaca9d2 100644
--- a/functions/_common/reusableHandlers.ts
+++ b/functions/_common/reusableHandlers.ts
@@ -10,6 +10,10 @@ export async function handleThumbnailRequest(
     ctx: EventContext<unknown, any, Record<string, unknown>>,
     extension: "png" | "svg"
 ) {
+    setTimeout(() => {
+        throw new Error("Testing Sentry from Cloudflare Functions")
+    })
+
     const url = new URL(env.url)
     const shouldCache = !url.searchParams.has("nocache")
 
diff --git a/functions/_middleware.ts b/functions/_middleware.ts
index 3128310729e..d6ff27669f7 100644
--- a/functions/_middleware.ts
+++ b/functions/_middleware.ts
@@ -3,9 +3,17 @@ import { Env } from "./_common/env.js"
 
 export const onRequest = [
     // Make sure Sentry is the first middleware.
-    Sentry.sentryPagesPlugin<Env>((context) => ({
-        dsn: context.env.SENTRY_DSN,
-        environment: context.env.ENV,
-        tracesSampleRate: 0.01,
-    })),
+    Sentry.sentryPagesPlugin<Env>((context) => {
+        console.log(context.env)
+        return {
+            debug: true,
+            beforeSend(event) {
+                console.log("Sending event to Sentry:", event)
+                return event
+            },
+            dsn: context.env.SENTRY_DSN,
+            environment: context.env.ENV,
+            tracesSampleRate: 0.01,
+        }
+    }),
 ]
diff --git a/functions/deleted/[slug].ts b/functions/deleted/[slug].ts
index 08d6199152f..a7b3740da14 100644
--- a/functions/deleted/[slug].ts
+++ b/functions/deleted/[slug].ts
@@ -2,6 +2,7 @@ import { Env } from "../_common/env.js"
 
 /** Return a 404 status for tombstones of deleted pages. */
 export const onRequestGet: PagesFunction<Env> = async ({ env, request }) => {
+    throw new Error("Testing Sentry from Cloudflare Functions")
     const response = await env.ASSETS.fetch(request)
     if (response.redirected || response.status !== 200) return response
     return new Response(response.body, {