Entourage’s support of Sync Services keeps confusing many users: while the contacts in Entourage show up just fine in Address Book, a number of problems appear with Entourage’s calendar and iCal. A number of users have been creating their calendar entries in iCal and are surprised to discover that, even though they have enabled calendar syncing in Entourage’s preferences, nothing seems to be happening. However, this is not the case; Entourage’s calendar does sync to iCal, and vice-versa, but the user needs to understand how this complex mechanism works.
First of all, a crucial distinction needs to be made between the different ways in which Entourage and iCal handle calendars: iCal supports multiple calendars, Entourage does not (except for Exchange). And while Entourage supports categories, iCal makes use of the previously mentioned different calendars to categorise appointments and tasks. This difference is crucial to a proper understanding of why synching does not work the way most users would expect it to work. Categories and calendars are not identical, which is why it is not immediately possible to sync categories in Entourage with calendars in iCal. Instead, the following scenario applies to both Entourage 2004 and 2008:
When you enable Sync Services in Entourage’s preferences (see screenshot above), a new calendar called “Entourage” is created in iCal (see screen shot below). All the items that are in Entourage’s calendar are synched to that calendar; create a new item in Entourage, and it shows up in the “Entourage” calendar in iCal. Similarly, if you use iCal and want the new events that you create to show up in Entourage as well, you will have to make sure that any new item is part of the “Entourage” calendar.
WARNING! If you decide to delete the “Entourage” calendar in iCal, be very, very careful! You will not get any supplementary warnings other than the standard dialogue, and if you do not pay attention, you will have deleted all your Entourage calendar events and to do items in one fell swoop. Do not delete the “Entourage” calendar in iCal unless you are absolutely sure what you are doing!
There are a number of drawbacks to this implementation of Sync Services: Entourage’s categories allow the user to make organizational distinctions which simply disappear when these calendar events are viewed in iCal’s “Entourage” calendar. Similarly, you cannot have calendar events that belong to two calendars at once in iCal, which means that you have to choose between using iCal’s convenient, colorized multiple calendars or the restrictive, monolithic “Entourage” calendar. This restriction is quite noticeable when you sync your iCal calendars with a portable device, such as mobile phones, Palm pilots, iPods or iPhones: iSync and iTunes allow you choose which calendars to sync with your mobile device, but if you use Entourage, there’s only one iCal calendar to choose from, namely “Entourage”. In other words, you only have two choices: either sync all your calendar and to do items, or none at all.
This restriction makes using iCal and Entourage simultaneously rather uncomfortable; sure, it is very convenient to have a built-in feature in Entourage that allows the user to sync his or her calendar with mobile devices, but at the same time, the current implementation is quite rough around the edges and does not allow for any subtleties. An ideal solution, in my opinion, would be a preference in Entourage that would allow the user to associate categories with iCal calendars. In other words, if you categorise an item in Entourage as “Work”, it would show up in the “Work” calendar in iCal, and so on. Such an implementation of Sync Services does not seem to be impossible, but in order to get Microsoft to look into this solution, we will need to get as many users as possible to complain about the current implementation by clicking on “Send Feedback on Entourage” inside Entourage’s Help menu and suggesting alternatives, such as the one mentioned above.