You will find information about updates for Reply Assistant on the following website:

To check if an update is available please go to the Ribbon of Outlook and click on the Help button in the Reply Assistant group and then click on "Check for Updates".

Reply Assistant will then automatically check if a newer version is available.

Reply Assistant automatically checks if a new update is available when you start Outlook.

If you do not want this, you can disable it in the settings. In the Outlook Ribbon click on the Settings button in the Reply Assistant group, then click Miscellaneous and then uncheck "Automatically check for updates on startup".

When Reply Assistant checks for updates it will ask out server which the newest version of Reply Assistant is.

It will not send any data about you. For more details see Data Privacy.