diff --git a/dist/web_stubs.c b/dist/web_stubs.c
index a78c371..b1365a8 100644
--- a/dist/web_stubs.c
+++ b/dist/web_stubs.c
@@ -237,6 +237,55 @@ el_val_t supabase_admin_invite(el_val_t project_url, el_val_t service_key, el_va
     return http_post_with_headers(EL_STR(url), body_json, headers);
 }
 
+/*
+ * supabase_admin_update_user — PUT {project_url}/auth/v1/admin/users/{user_id}
+ * with the service-role key to overwrite a user's user_metadata (and any other
+ * top-level fields in body_json).  Unlike /auth/v1/invite, this always writes
+ * the supplied data even when the user already exists.
+ *
+ * body_json example:
+ *   {"user_metadata":{"plan":"founding","stripe_customer_id":"cus_xxx","name":"..."}}
+ *
+ * Returns the raw JSON response from Supabase (includes the updated user object).
+ * Returns "" on transport error.
+ *
+ * Used by the Stripe webhook after supabase_admin_invite to guarantee the
+ * plan is stamped correctly regardless of whether the account was created
+ * before or after payment.
+ */
+el_val_t supabase_admin_update_user(el_val_t project_url, el_val_t service_key,
+                                    el_val_t user_id, el_val_t body_json) {
+    CURL *c = curl_easy_init();
+    if (!c) return EL_STR("");
+    char url[1024];
+    snprintf(url, sizeof(url), "%s/auth/v1/admin/users/%s",
+             EL_CSTR(project_url), EL_CSTR(user_id));
+    char auth_hdr[2048];
+    snprintf(auth_hdr, sizeof(auth_hdr), "Authorization: Bearer %s", EL_CSTR(service_key));
+    char api_hdr[2048];
+    snprintf(api_hdr,  sizeof(api_hdr),  "apikey: %s", EL_CSTR(service_key));
+    struct curl_slist *hdrs = NULL;
+    hdrs = curl_slist_append(hdrs, auth_hdr);
+    hdrs = curl_slist_append(hdrs, api_hdr);
+    hdrs = curl_slist_append(hdrs, "Content-Type: application/json");
+    hdrs = curl_slist_append(hdrs, "Accept: application/json");
+    _stub_resp_t r = {0};
+    curl_easy_setopt(c, CURLOPT_URL, url);
+    curl_easy_setopt(c, CURLOPT_CUSTOMREQUEST, "PUT");
+    curl_easy_setopt(c, CURLOPT_POSTFIELDS, EL_CSTR(body_json));
+    curl_easy_setopt(c, CURLOPT_HTTPHEADER, hdrs);
+    curl_easy_setopt(c, CURLOPT_FOLLOWLOCATION, 1L);
+    curl_easy_setopt(c, CURLOPT_TIMEOUT, 60L);
+    curl_easy_setopt(c, CURLOPT_WRITEFUNCTION, _stub_write);
+    curl_easy_setopt(c, CURLOPT_WRITEDATA, &r);
+    CURLcode rc = curl_easy_perform(c);
+    curl_easy_cleanup(c);
+    curl_slist_free_all(hdrs);
+    if (rc != CURLE_OK) { free(r.buf); return EL_STR(""); }
+    if (!r.buf) return EL_STR("");
+    return EL_STR(r.buf);
+}
+
 /*
  * gcs_get_token — fetch an OAuth2 bearer token.
  *
diff --git a/src/main.el b/src/main.el
index b25bf4d..a9511a9 100644
--- a/src/main.el
+++ b/src/main.el
@@ -415,8 +415,10 @@ fn waitlist_upsert(email: String, name: String, plan: String, source: String, at
     let ua_safe: String = str_replace(str_replace(user_agent,  "\\", "\\\\"), "\"", "\\\"")
     let num_field: String = if member_num > 0 { ",\"member_number\":" + int_to_str(member_num) } else { "" }
     let row: String = "{\"email\":\"" + e_safe + "\",\"name\":\"" + n_safe + "\",\"plan\":\"" + plan + "\",\"source\":\"" + source + "\",\"attestation\":\"" + a_safe + "\",\"user_agent\":\"" + ua_safe + "\"" + num_field + "}"
-    let resp: String = supabase_insert(sb_url, sb_key, "waitlist", row)
-    println("[waitlist] supabase insert -> " + resp)
+    // Use on_conflict=email,plan so existing rows are updated (upsert)
+    // rather than silently failing on duplicate key.
+    let resp: String = supabase_insert(sb_url, sb_key, "waitlist?on_conflict=email,plan", row)
+    println("[waitlist] supabase upsert -> " + resp)
     return ""
 }
 
@@ -1620,6 +1622,19 @@ fn handle_request_inner(method: String, path: String, headers: Map, body: String
                         let _cust_resp: String  = http_post_form_auth(cust_url, cust_body, stripe_auth)
                     }
                 }
+                // Always stamp user_metadata directly via Admin API.
+                // supabase_admin_invite re-sends a magic link for existing users
+                // but does NOT update their user_metadata — so plan stays "free"
+                // for anyone who signed up (attestation, waitlist) before paying.
+                // This PUT is idempotent: safe for both new and returning users.
+                if !str_eq(new_user_id, "") {
+                    let meta_body: String = "{\"user_metadata\":{\"plan\":\"" + plan_safe + "\""
+                        + ",\"name\":\"" + name_safe + "\""
+                        + ",\"stripe_customer_id\":\"" + cid_safe2 + "\""
+                        + ",\"email_verified\":true}}"
+                    let _meta_resp: String = supabase_admin_update_user(wb_sb_url, wb_sb_key, new_user_id, meta_body)
+                    println("[webhook] supabase user_metadata update for " + new_user_id + ": " + _meta_resp)
+                }
             }
 
             // 4. Forward to license API for key provisioning