diff --git a/README.md b/README.md
index a68555daf..39d55d2c4 100644
--- a/README.md
+++ b/README.md
@@ -217,6 +217,16 @@ network interaction.
 - `HTTP_PROXY`, `HTTPS_PROXY`, and `NO_PROXY` are supported through
   [`node-proxy-agent`](https://github.com/TooTallNate/node-proxy-agent).
 
+## Troubleshooting
+
+### Networking
+
+There are a wide variety of networking issues that can occur while running `corepack` commands. Things to check:
+
+- Make sure your network connection is active.
+- Make sure the host for your request can be resolved by your DNS; try using `curl [URL]` from your shell.
+- Check your proxy settings (see [Environment Variables](#environment-variables)).
+
 ## Contributing
 
 See [`CONTRIBUTING.md`](./CONTRIBUTING.md).
diff --git a/sources/httpUtils.ts b/sources/httpUtils.ts
index e3a745c0f..97fec0d83 100644
--- a/sources/httpUtils.ts
+++ b/sources/httpUtils.ts
@@ -22,7 +22,7 @@ export async function fetchUrlStream(url: string, options: RequestOptions = {})
     });
 
     request.on(`error`, err => {
-      reject(new Error(`Error when performing the request`));
+      reject(new Error(`Error when performing the request to ${url}; for troubleshooting help, see https://github.com/nodejs/corepack#troubleshooting`));
     });
   });
 }