Syncing Outlook with Mobile and iPhone

How do you sync calendars, contacts and mail between MS Outlook (2003) and Mobile Me/ iPhone if Outlook is running within the virtual machine on my MacBook Pro? When I was using Entourage within the MacOS syncing worked but now that I have to use MS Outlook I'm not sure how to get the information synced with my iPhone.

 

I was able to do this by installing iTunes in the VM. iTunes in the VM will then connect to Outlook. Then, when you plug in the iPhone it will ask which OS to connect to. connect to the VM and it works fine. It will even open iTunes when it starts syncing.

The only downside is that iTunes is INCREDIBLY slow in Win7, and even slower in Win7 in a VM.

 

I'm dumping my PC and now have a MacPro with Parallels. Should I be using Entourage or Outlook?
I was thinking Entourage b/c I wanted to try to stay on the Mac side as much as possible, but I'm concerned about losing the features of Outlook 2007 and the hassle trying to get everything transferred from Outlook to Entourage.
Any advice?

 

I don't know if it's "advice", but some things to think about -

First up would be the specs of your computer. I'm running a MBP with Snow Leopard and Windows 7, but only 2GB RAM.
Because of this, running Outlook in a Win7 VM is hit and miss. Sometimes it works fine, others it just bogs and locks up forcing me to restart the program. Btw, this is Outlook 2010 beta. I think if I had the ability to add more RAM this would help fix that problem.

Second, you will lose some of the features with Entourage. I'm using the Entourage 2014 pre-release and find it almost unusable, especially when I still have Outlook to compare. Mail setup was (for me) more difficult, but once you get that set it's done. There's no To-Do bar for tasks, so you still have to switch back and forth between screens to see everything. On the plus side, using Entourage means it's native so less of resource hog, and no VM to deal with.

Third, transferring isn't really a problem. I found it very easy to replicate all of my Outlook info in both Entourage and Mail/Address book. Almost all of my email addresses are IMAP (Hotmail & Live accts are still in Outlook only) so everything replicated just fine, and I just emailed my Contacts as vCards from Outlook to myself, and opened them in Entourage and Mail and they asked if I wanted to save them.

The biggest factor for me is the view, and tasks - I like being able to see email, tasks, appts and a calendar on one screen. Using the Mac side means using a separate program for each one of those.

Hope this helps.

 

Trevor,
Thanks for the advice. I forgot to mention that I use MobileMe, so getting contacts over should be pretty easy.
My main concern is trying to export/import from Outlook to Entourage all of my emails in personal folders that are no longer on the server. Any advice there? Some of the other blogs have recommended purchasing O2M @ www.littlemachines.com It's only $10 bucks if it works. Based on your post, I think you've talked me into using Entourage.. I'm excited to read Microsoft actually doing an update to Entourage. It's sad that Office for Mac 2008 is more outdated than PC Office 2007.

 

CAKID,
Glad I could help.
I've never used O2M but I've heard it works. And $10 isn't a bad deal.

There are however 2 free ways to move your mail. I've used both going from OL to Mail. I would imagine that they will work with Entourage the same. I know the first one will.

The first - if you have an IMAP email account you can drag of copy your folders into it and they will replicate wherever you see that account. I have a few POP accounts and (this is in Outlook) I copied the messages into a folder I set up in one of my IMAP accounts. Then I opened Mail and that folder was there with all my messages and I just moved them to the folder I wanted outside the IMAP account.

The second is to use Thunderbird - you can import all your mail into Thunderbird from Outlook, then export it all as an LDIF file and import into Mail.