diff --git a/cli/planoai/config_generator.py b/cli/planoai/config_generator.py
index 522968c9..fcbae0e4 100644
--- a/cli/planoai/config_generator.py
+++ b/cli/planoai/config_generator.py
@@ -466,6 +466,15 @@ def validate_and_render_schema():
         "upstream_tls_ca_path", "/etc/ssl/certs/ca-certificates.crt"
     )
 
+    upstream_timeout_ms = overrides.get("upstream_timeout_ms")
+    if upstream_timeout_ms is not None:
+        timeout_s = f"{int(upstream_timeout_ms) // 1000}s"
+        llm_gateway["timeout"] = timeout_s
+        prompt_gateway["timeout"] = timeout_s
+        for listener in listeners:
+            if listener.get("type") == "agent" and "timeout" not in listener:
+                listener["timeout"] = timeout_s
+
     data = {
         "prompt_gateway_listener": prompt_gateway,
         "llm_gateway_listener": llm_gateway,
diff --git a/config/envoy.template.yaml b/config/envoy.template.yaml
index a780c3f1..40980167 100644
--- a/config/envoy.template.yaml
+++ b/config/envoy.template.yaml
@@ -336,7 +336,7 @@ static_resources:
                             auto_host_rewrite: true
                             prefix_rewrite: "/agents/"
                             cluster: bright_staff
-                            timeout: {{ listener.timeout | default('30s') }}
+                            timeout: {{ listener.timeout | default('300s') }}
                 http_filters:
                   - name: envoy.filters.http.compressor
                     typed_config:
@@ -517,12 +517,12 @@ static_resources:
                           route:
                             auto_host_rewrite: true
                             cluster: {{ llm_cluster_name }}
-                            timeout: 300s
+                            timeout: {{ llm_gateway_listener.timeout }}
                             {% if llm_gateway_listener.max_retries %}
                             retry_policy:
                               retry_on: "5xx,connect-failure,refused-stream,reset,retriable-status-codes"
                               num_retries: {{ llm_gateway_listener.max_retries }}
-                              per_try_timeout: 30s
+                              per_try_timeout: {{ llm_gateway_listener.timeout }}
                               retriable_status_codes: [429, 500, 502, 503, 504]
                               retry_back_off:
                                 base_interval: 0.5s