diff --git a/src/core/server/http/lifecycle/on_pre_routing.ts b/src/core/server/http/lifecycle/on_pre_routing.ts
index bd783a9f2ecfd7..e553f113a7cf8d 100644
--- a/src/core/server/http/lifecycle/on_pre_routing.ts
+++ b/src/core/server/http/lifecycle/on_pre_routing.ts
@@ -116,7 +116,25 @@ export function adoptToHapiOnRequest(fn: OnPreRoutingHandler, log: Logger) {
           appState.rewrittenUrl ?? new URL(request.url.href!, request._core.info.uri);
 
         const { url } = result;
-        request.setUrl(url);
+
+        // TODO: Remove once we upgrade to Node.js 12!
+        //
+        // Warning: The following for-loop took 10 days to write, and is a hack
+        // to force V8 to make a copy of the string in memory.
+        //
+        // The reason why we need this is because of what appears to be a bug
+        // in V8 that caused some URL paths to not be routed correctly once
+        // `request.setUrl` was called with the path.
+        //
+        // The details can be seen in this discussion on Twitter:
+        // https://twitter.com/wa7son/status/1319992632366518277
+        let urlCopy = '';
+        for (let i = 0; i < url.length; i++) {
+          urlCopy += url[i];
+        }
+
+        request.setUrl(urlCopy);
+
         // We should update raw request as well since it can be proxied to the old platform
         request.raw.req.url = url;
         return responseToolkit.continue;