In the past, we used to use the Outlook / iOS combination and syncing worked fine via USB connection. We and many others have found that USB syncing stops working for many users. Apple, which is getting rid of USB syncing on the Macintosh, says
they don't support USB syncing with Outlook 2013, and iCloud is the sync method they recommend. The problem is that Outlook + iCloud syncing seems to be ridiculously kludgy.
The core problem is that iCloud can't sync the regular Outlook Contacts and Outlook Claendar. Instead, it creates separate iCloud Contacts and iCloud Calendar within Outlook and uses those. This is very kludgy for several reasons:
1. If a meeting request comes in via email, it goes into the Outlook calendar, not the iCloud calendar. This means that when you click on the meeting in the email you are only shown the context in the Outlook calendar, and you have no idea whether
you have a committment at that time. If you accept the meeting, it goes into the Outlook calendar and you need to move it manually from the Outlook calendar into the iCloud calendar, which results in "Copy .." being put at the beginning of
all such events. To move the meeting, you need to undo the Overlay setting to display iCloud Calendar and Outlook Calendar side by side, resulting in events being very narrow, particularly on a small screen on a Surface Pro.
2. When an email arrives moving a meeting, the old copy of the meeting event doesn't get removed since it is now in the iCloud calendar, not the Outlook calendar. This results in the calendar being loaded with ghost meetings unless you hunt down
all original meetings manually. For many users, this results in wasted time slots.
3. If you don't use an iCloud email address, "Invite attendees" on an iCloud event fails silently since the invitation won't use any of the Outlook email accounts. For many users, this results in invitees not knowing about meetings.
4. If you use routine features of Outlook such as creating a new contact or using the Quick Access Toolbar icon to search for contacts, these only work with the Outlook contacts, not with the iCloud contacts. One needs to manually move contacts
to the iCloud contacts.
Apple enthusiasts will suggest resolving this syncing issue by abandoning Outlook and moving to MacOs. Microsoft enthusiasts will suggest resolving this syncing issue by abandoning iOS and getting a Windows phone. But Outlook and iOS are each
major products in their categories, and there must be many people who are afflicted with the kludgy syncing problem.
My questions are:
1. Are there workarounds one can use better than the manual ones described here or abandoning Outlook or iOS? Moving all email to iCloud would reduce some of the problems, but some organizations don't want to move their email to Apple's servers.
2. Satya Nadella has enunciated a committment to cross-platform compatibility. Is there any indication that it extends to getting Outlook and iCloud working together properly?
