I don't think there's any evidence that windows sends cleartext passwords. The whole reason why NTLM is a thing is to avoid sending cleartext passwords.

▲

lazide 4 hours ago | parent [-]

Outlook appears to be

▲

p_ing 4 hours ago | parent [-]

The 'https://' disagrees with your 'sending clear text passwords' statement.

	▲	lazide 16 minutes ago \| parent [-]
		It’s clear text to the receiving server, which is what we’re talking about, not one way hashed.