I want to use Mac Mail for my work email address, which containts multiple outbound options (i.e. hr@, me@ etc). Is there a way to set up Mac Mail to have an account with multiple outbound addresses rather than adding in multiple accounts?

I want to use Mac Mail for my work email address, which containts multiple outbound options (i.e. hr@, me@ etc). Is there a way to set up Mac Mail to have an account with multiple outbound addresses rather than adding in multiple accounts?

This sounds like the age old problem with keychain & Safari. I don't know of a way to solve it without using something like 1Password.
The iOS app has it's own built in browser, so it has more control over what gets autofilled. Safari on OS X has an 1Password extension that handles account selection & autofill etc.
Keychain is great in principle, but it quickly falls down when you need tight integration with many ID's & different use cases (work, home etc).
I'd suggest you submit feedback to Apple about your thoughts. I did so years ago about this issue & this is how far we have come (back to the point where me.com synced passwords) :^)
http://apple.com/feedback/macosx.html
Other tools like lastpass or keypassx may also help if you want to truly segregate password storage, but that doesn't fix autofill, the way around that issue is to dedicate one browser for work.

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