Syncing Up Mail systems

My e-mail is thru Cox Communications. Depending on the situation, my MAC will attempt to send e-mail thru the MAC Mail....and fail ("The certificate for this server is invalid"). Is there a means to sync up (?) my MAC e-mail so when it wants to send it via MAC it can and when it wants to send it via Cox it can also?
Thanks,
Bob

I would also like to sync with two systems: one *at home*, on my Mac, and another *at work*, with Outlook on a PC.
However *I just want to sync the calendars and the addresses*.
And this does not working properly. Each time I change from one computer to the other, it is like the computer discovers a new iPhone. I have to set again the parameters in iTune and I am always asked to either replace the data from the iPhone or to merge them. I select this later solution of course. Then I always find again the discarded appointments, double addresses ... I often also find two times the same address (or phone numbers, …) for one contact, maybe when I modified it either on the iPhone or on the computer.
I would also like two have to calendars: one private, synchronised between my iPhone and my home computer only and one professional one that synchronises with my iPhone and both my computers: the one at home and the one at work. This does also not work, because if I deselect manually one of this calendar in iTune in order not to synchronise it, iTune will discard it from the iPhone and not from the computer ...
Does somebody have found any work around?
Thank you for any support or idea!!!

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