diff --git a/src/session.ts b/src/session.ts
index cd49cb13ab..a4288d328d 100644
--- a/src/session.ts
+++ b/src/session.ts
@@ -540,6 +540,11 @@ export class SessionManager implements Middleware {
                     configurationSection: [ utils.PowerShellLanguageId, "files", "search" ],
                     // fileEvents: vscode.workspace.createFileSystemWatcher('**/.eslintrc')
                 },
+                // NOTE: Some settings are only applicable on startup, so we send them during initialization.
+                initializationOptions: {
+                    EnableProfileLoading: this.sessionSettings.enableProfileLoading,
+                    InitialWorkingDirectory: this.sessionSettings.cwd,
+                },
                 errorHandler: {
                     // Override the default error handler to prevent it from
                     // closing the LanguageClient incorrectly when the socket
diff --git a/src/settings.ts b/src/settings.ts
index d1c648bff8..e8051ecf75 100644
--- a/src/settings.ts
+++ b/src/settings.ts
@@ -268,7 +268,7 @@ export function load(): ISettings {
             //   is the reason terminals on macOS typically run login shells by default which set up
             //   the environment. See http://unix.stackexchange.com/a/119675/115410"
             configuration.get<IStartAsLoginShellSettings>("startAsLoginShell", defaultStartAsLoginShellSettings),
-        cwd:
+        cwd: // TODO: Should we resolve this path and/or default to a workspace folder?
             configuration.get<string>("cwd", null),
     };
 }