|Just for the record: the last update to the 'Desktop Sync Helper App' was over a year ago; we stopped distributing the helper some time between Feb to April 2012 immediately after we concluded that we could no longer continue to support the service; we removed all mentioning of wifi sync from the App Store description roughly around the same time; and we officially announced back in June 2012 that the next upcoming update will remove this feature for good.
We apologize to those who constantly relied on this feature, especially when it supposedly worked just fine for them in v2.7. If you're still on v2.7, please don't update to v2.8 as you'll lose this functionality.
Perhaps it's not immediately clear why we did this. Outlook and iCal Wi-fi sync relied heavily on two things:
1. An active Wifi-Only connection (would not work with an ethernet connection)
2. Bonjour installed separately on Windows, and Sync Services on Mac
When 2Do came out a few years ago on the iPhone, there was no iCloud and there wasn't any other app that we knew of that synced 'Over the Air' with iCal (Mac OS X) or Outlook (Windows). So beginning with v1.0 we supported Wifi Only Sync with iCal and later added support for Outlook (Windows). This all worked great.
Starting with Snow Leopard (OS X 10.6), Apple abandoned Sync-Services in favor of Over the Air sync with Mobile Me. Since 2Do relied heavily on Sync-Services for Sync to work on the Mac, this suddenly became obsolete. There wasn't any point supporting something that wouldn't last for too long. So that was it for iCal Wifi-Only sync on the Mac.
Around the same time Apple also stopped supporting Bonjour on Windows (their last update to Bonjour was June 2010). There were bugs and issues with the current implementation, not to mention bonjour had proven to be unreliable on windows and several network routers blocked multicast packets out of the box. This soon turned into a support nightmare. Apple then added iCloud sync support for Outlook (over CalDAV) as they began to shutdown MobileMe. Everything started pointing towards 'Over the Air' (OTA) Cloud sync solutions. It was either Cloud Sync or nothing.
In 2011, 2Do became the first task management app on the App Store to support OTA CalDAV sync (thus, it support MobileMe, iCloud, Yahoo! and Lion based iCal Server out of the box). We went with the flow and started steering towards cloud solutions, instead of sticking with Wifi-Only sync which is pretty much dead. Any developer who's had the experience of working with Wifi-Only sync knows what we're talking about, and this is exactly why Apple abandoned Sync Services too. It was buggy, unreliable, slow and of course worked only if you were on the same network as the PC / Mac you wanted to connect to.
Of course Microsoft is here to stay and so is Outlook. If at a later date Microsoft comes out with a better Sync solution or an SDK that has little or no reliance on 3rd party libraries and utilities, we would gladly offer this feature once again.
If you're on Windows: we have heard that Outlook is able to sync with your iCloud account. If this is the case, you should be able to simply sync 2Do with iCloud; and you should then still be able to use Outlook with 2Do. We are aware that this isn't optimal and has its own set of problems unfortunately.
On the Mac, we now have 2Do available on the Mac App Store natively. We're sure you'll love how seamlessly 2Do on iPhone / iPad / iPod syncs with 2Do on Mac using a number of cloud-sync solutions: iCloud, Dropbox, Toodledo. Those who don't wish to purchase the Mac app can simply sync 2Do 2.8 with iCloud, and will be able to view their tasks in the iCal reminders sidebar (Lion) and the native Reminders app (Mountain Lion).