diff --git a/client/src/extension.ts b/client/src/extension.ts
index f425f4db..85f3c929 100644
--- a/client/src/extension.ts
+++ b/client/src/extension.ts
@@ -24,12 +24,17 @@ const LANGUAGES = [
 /** These are keys of settings that have a scope of window or machine. */
 const workspaceSettingsKeys: Array<keyof Settings> = [
   "cache",
+  "certificateStores",
   "codeLens",
   "config",
+  "enable",
   "importMap",
   "internalDebug",
   "lint",
+  "path",
   "suggest",
+  "tlsCertificate",
+  "unsafelyIgnoreCertificateErrors",
   "unstable",
 ];
 
diff --git a/client/src/shared_types.d.ts b/client/src/shared_types.d.ts
index 61caeb96..bd4b4bec 100644
--- a/client/src/shared_types.d.ts
+++ b/client/src/shared_types.d.ts
@@ -7,6 +7,10 @@ import type { ConfigurationScope } from "vscode";
 /** When `vscode.WorkspaceSettings` get serialized, they keys of the
  * configuration are available.  This interface should mirror the configuration
  * contributions made by the extension.
+ *
+ * **WARNING** please ensure that the `workspaceSettingsKeys` contains all the
+ * top level keys of this, as they need to be sent to the server on
+ * initialization.
  */
 export interface Settings {
   /** Specify an explicit path to the `deno` cache instead of using DENO_DIR