I just want to share an approach that made my day.
My objective: I want to have my contacts available on iCloud and all attached Macs.
My issue: The primary source of information is my Exchange account so I have the data available on my iPhone but unfortunately not at home on my Macs.
My painpoint: A clear segragation (private/business) is not an option for me (BTW: This is true for the calendar as well; if I am out of the office for some private reasons it does not make any sense to have such appointments entered in a different calendar because this would not reflect availability in the office).
My approach: Look for a solution that allows copying data within Outlook locally. It seems that any "sync option" one is going to install within Outlook simply adds some new folders but actually there is nothing I would really call "syncing". So I did some research for tools that are capable of syncing Outlook folders within Outlook itself. Finally I found a company called CodeTwo (www.CodeTwo.com) offering an Outlook plug-in named "FolderSync" for free. I installed this tool and configured the tool to sync my (more or less) local contacts folder with my newly created iCloud contacts folder. And it seems to work!
However, there are some drawbacks:
- The sync has to be kicked-off manually (via an icon that installs into the ribbon).
- There is no option to select either one-way or two-way syncing (it is always two-way which is not really what I want, I'd prefer one-way Exchange->iCloud).
- You can configure different folders to be synced (will be done in sequence) but you cannot change this sequence afterwards (I started off with the Exchange -> iCloud sync and wanted to add some backup to another local folder upfront if data gets accidentally destroyed in iCloud).
- If the tool runs into a MAPI error (happened several times for some mailing lists or weird contacts) it shows the error and stops (instead of caring on doing whatever can be done; BUT the good news is that if you restart the tool it will continue where it left off so it might take a while but after 5 to 6 times I had all my contacts in iCloud apart those that had issues).
Anyhow you might check this out for calendars, too (I did this for a sample calendar but had really lots of MAPI errors that required a lot of restarts of the sync). Maybe this will work for Hotmail and other connectors supplied by Microsoft, too.
And - no - I am not affiliated to this company.