diff --git a/README.md b/README.md
index 862b13eb..8cb8fbd0 100644
--- a/README.md
+++ b/README.md
@@ -34,5 +34,8 @@ If you'd like to build and run the Relay Proxy on Windows see [Windows](./docs/w
 ## Endpoints
 For info on the external Harness SaaS endpoints the Relay Proxy communicates with see [Endpoints](./docs/endpoints.md).
 
+## Debugging
+For help on debugging your Relay Proxy install see [Debugging](./docs/debugging.md).
+
 ## Contributing
 See the [contribution guide](CONTRIBUTING.md).
\ No newline at end of file
diff --git a/docs/debugging.md b/docs/debugging.md
new file mode 100644
index 00000000..9023ecd5
--- /dev/null
+++ b/docs/debugging.md
@@ -0,0 +1,40 @@
+# Debugging
+
+### Outbound requests
+To learn more about what requests the Relay Proxy sends see [Endpoints](./endpoints.md).
+
+### Debug mode
+See [Configuration](./configuration.md) for instructions on enabling debug mode for more detailed logging on requests being sent and handled by the Relay Proxy.
+
+### Healthcheck endpoint
+The Relay Proxy has a `/health` endpoint that can be queried to check the health of all the Relay Proxies dependencies. This can be hit using a request like this: 
+
+`curl https://localhost:7000/health`
+
+The response will look something like this:
+
+`{"cache":"healthy","env-0000-0000-0000-0000-0000":"healthy", "env-0000-0000-0000-0000-0002":"healthy"}`
+
+If using a Redis cache the cache healthcheck will verify that we could successfully ping the Redis client.
+
+You will have a health entry for each environment you've configured the Relay Proxy with. This will display if your streaming connection for these environments is healthy. You can find which friendly environment identifier this UUID maps to by checking your proxy startup logs. 
+
+
+### Sample CURL Requests
+These requests are made by the Relay Proxy to Harness SaaS on startup. They are also made by connected sdks to the Relay Proxy when they startup. As such they can be used to help diagnose connection issues either outbound from the Relay Proxy or inbound to it.
+
+On startup SDKS make 4 requests, the Relay Proxy makes these 4 requests for each environment you have configured it to connect to:
+- /auth
+- /feature-configs
+- /target-segments
+- /stream
+
+You can find examples of how to send requests directly to these endpoints in our [Sample Requests](./sample_curl_requests.md).
+
+## Common Issues
+### The Relay Proxy has fetched flags but doesn't receive any updates made on SaaS
+This is usually due to firewall issues on your internal network. With more stringent rules what can happen is that the `/stream` request receives a 200 response but the firewall blocks any of the sse events from being sent down the open connection. This can be tested using some of the sample curl requests provided above.
+
+**Short term workaround:** The quickest solution is to disable streaming connections between the Relay Proxy and Harness SaaS. This can be done by setting the `FLAG_STREAM_ENABLED` config option to false. This will force the Relay Proxy to poll once every minute for updated flag/target group values instead of receiving changes through the stream.  
+
+**Long term fix:** The longest term fix is to diagnose and resolve whatever firewall rules are causing the sse events to be blocked before they can reach the Relay Proxy.
\ No newline at end of file
diff --git a/docs/sample_curl_requests.md b/docs/sample_curl_requests.md
new file mode 100644
index 00000000..75a9ef54
--- /dev/null
+++ b/docs/sample_curl_requests.md
@@ -0,0 +1,59 @@
+# Sample cURL Requests
+
+These can be useful to debug info coming from SaaS or from the Relay Proxy.
+
+## Startup Requests
+These requests are made by the Relay Proxy to Harness SaaS on startup. They are also made by connected sdks to the Relay Proxy when they startup. As such they can be used to help diagnose connection issues either outbound from the Relay Proxy or inbound to it.
+
+On startup SDKS make 4 requests, the Relay Proxy makes these 4 requests for each environment you have configured it to connect to:
+- /auth
+- /feature-configs
+- /target-segments
+- /stream
+
+We will show these examples making requests to Harness SaaS. If connecting to the proxy replace https://config.ff.harness.io/api/1.0 with your Relay Proxy's address. An example will be shown for the /auth request.
+
+### Auth request
+Fetches an authentication token that can be used for future requests:
+
+`curl -v 'https://config.ff.harness.io/api/1.0/client/auth'  -H 'content-type: application/json'  --data-raw '{"apiKey":"${API_KEY}"}'`
+
+If sending this request to a Relay Proxy instance running on localhost:7000 this would be:
+
+`curl -v 'http://localost:7000/client/auth'  -H 'content-type: application/json'  --data-raw '{"apiKey":"${API_KEY}"}'`
+
+This should return a 200 code and a body that includes an auth token that we’ll use for future requests e.g.
+
+`{"authToken":"eyJhbGciOiJIUzI1NiI11nR5cCI6IkpXVCJ9.eyJlbnZ2Mm9ubWVudCI6IjgzMDAxOWM2LTIzYTUtNDhkNC1hYjhjLTQ4ZmE3NjdmMWRlYiIsImVudmlyb25tZW50SWRlbnRpZmllciI62mRldiIsInByb2plY3QiOiIwZmQzZTdlNS04ZWYzLTRhYzQtYmMyOS03ZTBiODI2ODIxMmQiLCJwcm9qZWN0SQRlbnRpZmllciI6InRlc3Rwcm9qIiwiYWNjb3VudElEIjoiTWRpTmJzN3BRNld0SDNqYVRBVzRjQSIsIm9yZ2FuaXphdHlvbiI6IjE2YzI1MjhhLWNkOWMtNDVlZi05NTZjLTZhOGRkYzkwMjZlMiIsIm9yZ2FuaXphdGlvbklkZW50aWZpZXIiOiJkZWZhdWx0IiwiY2x1c3RlcklkZW50aWZpZXIiOiIyIiwia2V5X3R5cGUiOiJTZXV2ZXIifQ.X3Xo7ztCNFOwLWjweDp6kzlGQ7vr6A3D9Jyc5uqK9NA"}`
+
+### Feature configs request
+This will check that feature configs can be retrieved successfully.
+
+`curl -v 'https://config.ff.harness.io/api/1.0/client/env/${ENV_ID}/feature-configs?cluster=${CLUSTER}'  -H 'Authorization: Bearer ${AUTH_TOKEN}'`
+
+${AUTH_TOKEN} - replace with the token from the auth request above
+
+${ENV_ID} - replace with the environment id - this can be found by decoding the auth token at JWT.IO  and grabbing the environment value it shows from the token claims.
+
+${CLUSTER} - same as ENV_ID this can be found by checking the `clusterIdentifier` field in the decoded token claims.
+
+### Target segments request
+This will check that target segments can be retrieved successfully.
+
+`curl -v 'https://config.ff.harness.io/api/1.0/client/env/${ENV_ID}/target-segments?cluster=${CLUSTER}'  -H 'Authorization: Bearer ${AUTH_TOKEN}'`
+
+See ^ for setting the AUTH_TOKEN, ENV_ID and CLUSTER fields.
+
+### Stream request
+Here we want to see if stream events are making their way to your network. If this is not the case then the issue lies within your network infrastructure not allowing our sse events to come through. To demonstrate this you can run the following curl both inside and outside your network.
+
+Firstly kick off this long lived request in a terminal (after it dumps the initial request info it should just hang and remain open printing nothing for now):
+
+`curl -v -N 'https://config.ff.harness.io/api/1.0/stream?cluster=${CLUSTER}' -H 'API-Key: ${API_KEY}'  -H 'Authorization: Bearer ${AUTH_TOKEN}'`
+
+See ^ for setting the AUTH_TOKEN, ENV_ID and CLUSTER fields.
+
+Then on the UI toggle a flag and you should see output like this in the terminal:
+
+`event: *
+data: {"event":"patch","domain":"flag","identifier":"flag","version":7}`