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UPDATE: 4/11/16: I have removed old content on this post that no longer worked and replaced it with options that work as of today.  I will do my best to keep this post updated as technology changes.  Thanks for visiting!

Note that this post refers to syncing Outlook for WINDOWS (all versions, as far as I can tell) with your iPhone.   Microsoft offers these (rather complicated) directions for syncing Outlook for Mac with iPhone.  I can not speak to how well it works.  These difficulties are a sample of the reason that I recommend AGAINST Outlook for Mac as a productivity solution.  For other suggestions of productivity tools for Mac users, see this post and this post.

I used Outlook to run my life for almost a decade, and the majority of the training I do is still using Outlook as the support tool.  I also show you in my book how to adapt to Outlook my Empowered Productivity System for managing the details of your life and work. I think it is a very powerful PIM (personal information manager) that can easily handle the complexity of your life.  The one shortcoming is if you need to share calendars or other information, it’s easiest if you are running an Exchange server and this doesn’t make sense for everyone.

A question I get a lot is how to sync Outlook Tasks with iPhone.  The technology has changed since I originally wrote this post more than five years ago, and I will attempt to keep it updated with the latest information.  Some of the comments below may deal with prior content that has since been removed.  Also, these are instructions for those NOT using a corporate Exchange server.  If you are using an Exchange server, your Outlook tasks should be appearing in the Reminders app on your iPhone.  If you don’t like how that works, check out IMExchange2, or  TaskTask.

To sync Outlook Tasks with iPhone without an Exchange server is much harder than it should be.  However, if you need to do this, I can offer you four suggestions:  Akruto Sync, CompanionLink/DejaOffice, hosted Exchange for individuals, or MilkSync/Remember the Milk .

The first option is Akruto Sync. It lets you automatically sync Outlook Tasks with iPhone via Wi-Fi or the Internet without storing your data in the cloud. Akruto tells me that you can establish a two-way sync no matter what version of Outlook you are using and what generation of iPhone or iPad you have. It works like your own Exchange server and provides syncing encrypted with SSL-certificate. AkrutoSync guides you step by step through the following one-time setup process:

  1. Install AkrutoSync on your PC.
  2. Choose the type of connection: WiFi or Internet.
  3. Install SSL certificate provided by AkrutoSync.
  4. Configure your iPhone to work with given settings. (All the steps will be illustrated in AkrutoSync interface. The process takes about 2 minutes and 10 clicks.)

After this one-time setup is done, you don’t have to press anything or connect any cables. Your data remains in sync. Any changes you do to your Outlook Tasks will sync immediately to your phone and vice versa.

Another choice is CompanionLink (on your PC) and DejaOffice (on your iPhone).  The instructions for this are as follows:
1. Install CompanionLink on your PC.
2. Install the free DejaOffice app on the iPhone.
3. Configure CompanionLink to use DejaCloud as the sync method.
4. Select “Microsoft Outlook” as the database.
5. Click the Sync button.

You can automate the sync on a timer, as often as every 15 minutes. It seems to have all the features I recommend in an app, and my suggestion is to try this one first.

A third option is that hosted Exchange for individuals is now available for a nominal fee, from Office365.com and also from other providers.  This means that for a small monthly subscription (usually around $4-$5/month), you will no longer use the “local” version of Outlook that is installed on your PC, but instead have your Outlook hosted “in the Cloud,” which then allows you to select “Microsoft Exchange” when setting up a new account in “Mail, Contacts, Calendars” on iPhone.  Your tasks should sync directly into the Reminders app on iPhone, but as I mentioned above, if you don’t like how that works, you can try a third-party app called IMExchange2 or TaskTask.

The last option is the Remember the Milk app for iPhone, together with MilkSync for syncing with Microsoft Office (note my reservations at the end of this paragraph.)  These provide a two-way sync but only works with the Pro version of RTM, which as of this writing is $25/year.  You can try MilkSync free for 15 days without a pro account.  There are two BIG problems with RTM in my opinion. The first is that it does not offer alerts natively on your phone. In other words, if you set an alert to remind you of a task, that alert does not show up in your notifications. You have to get it by text, email or instant messenger. Even more of a problem than that: you can’t customize alerts for each task. You have to set global alerts, so all of your tasks get alerts, or none of them do. This makes RTM a poor solution, but if those issues don’t bother you, the rest of the features should work fine for you.

Please note that I am not affiliated with any of these companies in any way, and this technology seems to be ever-changing.  If you try any of these options, I would love to hear about your results!  You can email me directly at maura(at)regainyourtime(dot)com.

Don’t forget, to learn a great system for managing your tasks, calendar, email, and all the details of your life and work, check out my training for individuals, groups, and companies, and also my book!

I hope you have found this helpful.  Good luck!

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