Monitoring the email headers, you may be able to spot if a proxy server is used using the Received or X-Forwarded-For headers. Unfortunately, the only way to test this (without administrator access yourself) is to send and receive emails between a personal account and an account you suspect is monitored. This is set up when your account mailbox is added to Outlook which, for corporate devices, is likely configured for you automatically. It’s also possible that your Outlook mailbox settings are designed to route through an email server over a specific proxy.
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