For many of my notifications on my site, the From email is different than the Reply-to. The From email is an admin email through Outlook. The Reply-to email is an alias email from my company. The alias email forwards to an actual inbox of one of my co-workers. Many times when the person who was sent the notificiation replies it goes to the admin email. This is not consistent, so it is hard to nail down why this happens. Any ideas?
Microsoft recently had bug in their API that prevented the reply-to from working. If you’re sending through their services, it could be you’re coming up against this. See this thread.
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