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How to sync your Outlook contacts and calendars to the BlackBerry PlayBook

Calendar, Contacts, and the PlayBook
By Joseph Holder on 21 Feb 2012 06:26 pm EST
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Okay, this may be a bit of a shocker, but Research In Motion released the BlackBerry PlayBook 2.0 OS today! We here at CrackBerry have spent of most of the day poking and prodding the new OS to learn of its secrets. It seems you have as well. One of the biggest questions we're seeing from you is how do you sync Microsoft Outlook contacts and calendar entries with the PlayBook?

Outlook is a very powerful email and scheduling client used by many companies and individuals. At the moment, it appears that those users who connect to a Microsoft Exchange server have no issues with syncing - though web access to that account might be required. Not everybody uses an Exchange server though.

For the many who use Outlook as an email reader - perhaps with accounts like siteowner@mywebsite.com, the PlayBook won't be able to retrieve your contacts without a little outside help. To do that, I'm going to suggest you sync your Outlook contacts and calendar with a GMail account. How-to's after the break.

Google Calendar

Syncing your Outlook Calendar to GMail is the easy part. Download and install Google Calendar Sync. Once it starts, select how you want your calendar entries to work. Done. I've used the program before, and it works well. Your calendar gets sent to the Google cloud. Add that same GMail account to your PlayBook, and your Outlook calendar is synced with your BlackBerry PlayBook.

Contacts Sync

Unfortunately, things are not quite so simple in syncing Outlook contacts. While Google does make a program for doing just that, it's only for those folks who already pay for Google Apps. If you're looking for less expensive option, CNET.com has put together a nice how-to on using the free utility Contacts Sync. You do have to authorize the application to access your gMail account, so you'll first have to sign in to Google before downloading the tool. Once your contacts have been uploaded to Google, they should soon appear on your PlayBook.

Getting your Outlook contacts and calendars to your PlayBook requires a little bit of work. But after that small amount of effort is done, your PlayBook and Outlook contacts and calendars will be in lockstep, with just a little help from GMail. And certainly, this is only a temporary measure. I doubt it will be too long before you're reading our guide about how BlackBerry Desktop Software will do all of this for you.

Reader comments

How to sync your Outlook contacts and calendars to the BlackBerry PlayBook

87 Comments

Um.. not sure but I kinda want to wait for the BlackBerry Desktop version of it.

The only reason I don't why Google Contact Sync is it makes dupes... everytime.

Exactly!!!! When I sync my Outlook to Google and then from Google to BB and or PB duplicate events happen all the time. Then when you have a meeting 3 or 4 notifications on the BB and now 3 or 4 on the PB happen.

Yeah. There needs to be an equivalent DM function for this like we do with our Berry's. A wi-fi sync solution would be nice between Berry and PB. Could that even be done via BIS and BlackBerry ID? Gotta be something there...

No way in hell am I synching all my Outlook data with Google. Forget that.

Agreed..... Like I want to give google access to my Outlook lol. I'm kinda shocked that this was the work around you guys found :/ Haven't had time to look at this yet, but I'm sure there is a solution that doesn't include google's prying eyes.

My problem was that I was using the Google Sync on the desktop AND Google Sync on the BlackBerry... that is what caused all my entries to repeat four times each. Once I deleted the sync on the mobile device, the desktop sync was perfect. Haven't looked back since.

How about syncing your Blackberry Contacts and Calendar to your Playbook?! Its like they remembered to hook up everybody else but their own!! I don't get it!

Desktop Manager should send your calendar data to RIM's servers, and you PB connects automatically through wifi to get the info, two ways. Voila.

in other words, DM should do a bit more.....

Between our Blackberry ID and Blackberry Protect which already backs up all this data from the phone it seems like an automatic cloud-sync between the two devices should be a no-brainer.

Amazing how the Playbook and OS 2.0 rely on Microsoft Activesync for email retrieval and Google Gmail to sync calendar and contacts.

Time for the RIMCloud to be born... or BBCloud? BerryCloud? BlackCloud? PINCloud? Bah. Whatever.

RIM Cloud Services would be good here. Very good.

Is that even on their radar?

THIS! Seriously needs to happen. Most elegant potential solution I've seen. I'm enjoying OS2.0 otherwise, but am getting limited use/no use out of native email or contacts - ridiculous that it can't be synched. I keep waiting to read that it's a mistake and we just don't know HOW or something. :P

I totally agree here. I had wondered why I don't have contacts or calendar since OS 2.0. Really cannot believe that DM doesn't just do this! ONe of the reasons I went with the newer DM is I thought that was preparing me for this kind of issue in OS 2.0. A real shame. I'm not setting up a Gmail account just for this. I like using my outlook for e-mail, calendars and contacts. Have no idea why this wasn't even on the radar of OS 2.0 designers. Really? I'm less than impressed right now. I so love my Playbook, but this makes me wonder just what the designers are thinking. All these months, and I no longer have contacts and calendar on my Playbook? And if I do, I have to go outside Blackberry to do it? Shameful.

How about phone to PlayBook sync?

I already keep Outlook as my "standard" and only sync one way to the phone, so couldn't yuo do the same between phone & PlayBook?

I'm totally annoyed with this.... I have a gizzilion contacts (years in the making) on my blackberry.... And I can't get them to my playbook..... Un-freaking-acceptable RIM!!! I tried DM.... I can backup my contacts from my phone, but can't 'restore' that backup to my playbook..... Unbelievable.... There is nooooo way I am going to slowly add my hundreds of contacts.... And do what? Sync with gmail..... No thanks.... I don't have a gmail account and am not interested in farting around trying to make this work.... I sure hope RIM sends us a quick fix for this.... Cause manually typing email addresses in the mail app is a royal pain.... I might as well go back to the bridge!

I wish it were easier too so I feel your pain, but...
I did it in less than 30 minutes for 368 contacts from my BB.
It's not that horrifying.

I agree, plus the lack of a native Notes/Memos is a real negative. I rely on that as much as contacts and calender plus I maintain some sensitive information there and the thought of Google being in the middle or some other "Cloud" does not sit well. Bad enough that Google has either hacked their way into Crackberry blogs or Crackberry is inserting their ads for revenue.

I exported my contacts to a cvs file from my outlook account. Then imported to my hotmail account that I also have setup on my playbook. It Worked great all 500+ contacts.

i was reading up on that on the gmail info how did you make the file i coulndt figure it out. PM me with instructions please.

The best is to use office365 Exchange only plan 1 (at least).
You will have a full exchange server with BES(X) for a few bucks a month.

It's totally worth it and it works like a charm. I tried to sync my calendar/contacts long with 3rd party tools but it did never work correctly.

Since Office365, everything works easy and brilliant.
I can totally reccomend this.

This is exactally what I was thinking Bity. What plan are you using for a couple bucks a month ? I was looking at P1, it's $7 a month in Canada, well worth it for me considering all the other benefits, but may not be cost effective for others.

A few bucks a month? How much was it for you? When I looked into 365, it seemed I'd be on the hook for no less than 30 bucks per month - too much for just wanting a way to synch my Calendars.

The power of the Contacts app is useless when you can't easily get your contacts into it. This is ridiculous RIM. Same goes for the Calendar app.

Just give bridge apps. The same flow than native ones. Then we'll manage our synchronisation with our phone as usual. The point is not to sync, it's about the UI and the flow ...

Check out a program called sync2..

very lightweight, one time cost.. flawlessly syncs outlook to gmail and back for both contacts and calendar with no dupes or problems. Then simply connect the playbook to gmail via active sync as normal.

I use it in a similar capacity for work, it does the job absolutely perfectly.

And what about Tasks and Memos? I live and die by Tasks.

DM does all these for phones. How could they miss them for the Playbook. They've had a year to get this done!

- R.

Hear hear. The solution should replicate what it does for phones. Calendar, Contacts, Memos, Tasks. I too make heavy use of all of those.

I don't like or use Gmail or Hotmail. I don't trust Google with my contacts. I waited this long for the playbook to catch up to all the other tablets. CRAP!

I could of had a 4G Android phone and an Android tablet a year ago to let Google hackers hack my info!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Why do I want my personal info floating around the net in a gmail calendar? RIM really should have included the ability to sync with whatever major calendar suites are out there. (what else is there besides Outlook? :) ) Ability to sync a BB phone to it should have been a no-brainer too. I was looking forward to the new features, but if I can't keep it updated with a sync to Outlook, I'm stuck still using just my phone. Please, please, someone fix this...

we have had shaw issues too. my husband got his up and running this afternoon and I am trying to copy his but it didn't work. So I will keep trying.

Looks like using Outlook is useless with the Playbook. No tasks or memo's? Come on RIM, lets get your act together. And even though I use Google, I don't want to sync with Google. Every time I do, they double my entries and really screw my calendars and addresses up.
I want to use Outlook and I want to sync with my BB device. Period!

I agree that the new "native" calendar, contacts, etc. should interact with those on our phones, but you all do know that you can still get this information on the Bridge version of these apps, don't you? I moved the new "BlackBerry Bridge" icon up into the top ribbon for easy access.

Yes, I know it's a pain to check two spots for the same kind of data, but I'm sure RIM will fix this soon.

What I do is I use a paid for program called GSyncIt which is very powerful!
I sync, contacts, calendars, tasks, notes, whatever really.

The Bold 9900 and Playbook do not support multiple google calendars and this tool syncs all of my calendars into the default calendar and vice versa, this means I can put items in my calendar on Outlook within the right category or in the right calendar.
Then when it syncs it will sync that into the default Google calendar.

If anyone wants me to make a post about it I will do.

This was one of the things that I first tried was to sync the phone contacts and calendar with my phone. I was surprised when I realized there wasn't any option to do that.

The other thing I noticed is that on the native email, when you delete, it deletes on the server as well. When you delete on the phone it gives you the option to delete from just the phone or the server. I think I'm better off just using the bridge for email.

Works fine for my exchange account. It took a few minutes to update but everything is working as it should. Sync contacts, calendar and email...ah and writing this with my 9930 key board is a joy!

I'm sure that RIM will add Outlook support to a later version. All I want is to be able to sync my work calender with my home PC and my Playbook and it all seems to be working :) (providing I am actually getting though the works firewall as the laptop is connected on a VPN ATM).

I'm a loyal fan - RIM and CB - but really, you guys need to call this like it is... FAIL! It's absolutely unacceptable that they could release this without some way to sync calendar and contacts from the handset - or at least with contacts allow a one-time import. I'm willing to cut RIM lots of slack to get their act together, but this is ridiculous.

Absolutely TOTALLY agree. Very disappointing. I was worried about this when all the hype went to having native email ages ago.

K its working brilliantly and I'm getting the calender info from the works laptop straight to google and then downloaded to both my home PC and my Playbook. :)

Although I've got my settings set to Leave Messages on Server, when I delete an email or calendar item on the PB it's deleting the entry in my email account also. I do most of my work from my laptop and use Outlook, the PB and BB is for "on the road" responses.

Do i have something set up wrong?

No, that's how it works. When you view your emails on the PlayBook, you're essentially viewing them from the server and therefore when you delete on the PlayBook, you're deleting on the server. There's no option for "delete on handheld" or "delete on mailbox and handheld." You're always managing the mailbox/server.

To me it looks like the end for Rim. Waited so long for this! Can't directly Sync with Outlook Email
and Calendar, What is Rim thinking!This is an embarrassment to all Playbook Owners and BB users as a whole.To hold on this long and get fooled into thinking OS/2 would be awesome and smooth.Does Rim really think the average user is going to go to all that trouble to get their contacts? Customers want to push a button and have the operation done. This reminds me of the days of the old Pentium units with one wrong stroke and you screwed your computer up and had to get someone to fix it.Most people won't get it right.
Ipad and Iphone users are just laughing right now.
Forget about syncing with a Windows PC but to not be able to Sync with a BB Phone is unbelievable.To have to depend on the likes of Google, forget it.Best Security not likely.
With no fit between my BB phone and Playbook other than Bridging, I see no reason to continue on spending the money on a Data plan. The only good thing is I didn't spend a lot of money on the Playbook, can you imagine paying the price of an Ipad or Galaxy? This would have been the biggest Hoax of the Decade.Rim should have given us syncing of our calendar , tasks and memos at least, with the update.

let them laugh, anyways they don't have security, lets wait till RIM is able to figure out how this will be done without security issue.

With all due respect to all of you that know a lot more than I do Tech Wise but Rim also have had a year to get it right.
I can understand why Contacts and your email account could not be imported because then there would be no need for Rim and a email data plan. The calendar, task and memo syncing is just good customer service.Has no conflict of interest between Data Plan versus Wi Fi.Maybe all the American bashing of Rim and the Playbook has some credence, Rim may be too late into the game.

@BB4Torch: Spot on my friend! I believe the same, just getting us to cloud everything makes it lucrative for data plan consumption and at the end makes their product more lucrative for telecom companies....BUT: WHEN I SPENT 5 times more the money on my pb last year than its current price on sale, I was sold a different fairytale, this is misleading your clients. Now I have very nice native apps, a torch and a playbook, about 2000usd less in my pocket and I am obliged to use bridge with worse UI... my opinion: these two aspects of OS2 are only there for expansion of client base to no bb phone users... so I for one feel I got bumped off...

The other indicative thing is they proclaim that there is data synch and presented the apps a seemingless integration so they have not been clear on that too. While Rim was getting bashed I used to defend until yesterday but all out of the sadden I feel used...not to mention that the additional languages are there in os2 but you cannot type in these langues in the keyboard... half done, that is what I call it, just half done on OS2... too long a wait and windows8 on mobile is on the coming... just makes me wonder if I should finally let go of the dream... I do not want to but hey... I am not taking up more beating from RIM... hope they sort things out SOON *soon being in about a weeks time and not in 10 months when tablets will all be on 4core processors for the same money....oh i will not be getting that new playbook if they get it out unless they refund me on a half working first eddition for a year and a triple ammount of sale on the beggining i had to pay for...now they give it away like candy because it did not stick...and I helped all I could so that it sticked because i believed in RIM... I feel so naive...

Thanks to CB for the get around tutorials and efforts but honestly clouding on google my clients sensitive data when I am not using a BES but am using BIS is not at all a solution. Sorry folks BUSTED and FAIL in that one...

You said: not to mention that the additional languages are there in os2 but you cannot type in these langues in the keyboard.

Probably a setting problem on your tablet.
On the keyboard setting and choose automatic (not QWERTY) and the languages seem to work well, at least a few that I tried. Even has dictionaries and show you predictions and suggestions

I hear ya! This is how brands go bust. In an attempt to flirt with new customers, they neglect their existing fan base. I invested in a BB phone and Playbook for 2 reasons: 1) To support a Canadian brand
2) BB's focus on the business-user
I wasn't interested in dropping 1000 bucks on an Ipad so that I could have access to 2000+ games and toy-apps. I wanted a device to replace my paper-organizer. BB seemed to promise that. Then, with latest OS update, I have 2 Calendars on the device, and neither seamlessly or dependably synch my Outlook Calendar and Contacts data. Thanks BB, for the dream, but what I though I was buying was a real solution.

I totally agree. RIM is done, stick a fork in. This is an embarassment to loyal RIM customers, not to mention a rip-off and an insult. I did pay the big price when it first came out last year. Too bad for me, but you can bet RIM won't EVER burn me again. As much as I have despised iPad and iPhone for YEARS, I have to admit I was wrong and move on. iPhone, iPad, here I come!

I'm an IT guy that manages a BES. Don't do this. Do not try to google sync your contacts/calendars then put them on your device. Beyond being a pain to troubleshoot, this has led to problems on outlook calendars such as dupe calendar events. Just wait until BlackBerry completes ActiveSync compatibility.

I'd like to remind everyone that it took Apple over a year to get ActiveSync working, and a long while for Google to get it working on Android (if you call the current implementation working)

Besides, as soon as Touchdown for Exchange gets moved from the Android market onto BlackBerry, you won't even care about native email.

Thanks for that brkdncr!
the only thing in "just waiting untill RIM completes ActiveSync compatibility" is that we lately are loosing faith on how long that "Until" will be and when it gets hesre IF it gets here how it would work, you see, we get more info from CB than from RIM itself in relation to these things...

Really, thanks for your insight on the clouding.

Hi Kevin

Please have a tutorial on How to Set-up Microsoft Exchange server email account,
step by step and solution to known issue that can be found in the forum, Please also have separate tutorial for yahoo mail set up in playbook.

thanks in advance

KEVIN GET A LAWYER BECAUSE YOU WILL NEED ONE SOON!

If this post is not retracted and reverse publicly and in private PMs IMMEDIATELY I will personally take this post and Crackberry.com to every public online law firm and privacy firm that I can find until I am satisfied that there is sufficient legal action taken against Crackberry.com, and Mobilenation.com to shut these sites and all online properties down.

The liability and risk that the "advice" in this post opens up knows no bounds!

1. First off the only thing you will get are names and email addresses. Which can be a good thing.

2. Outlook has multiple address, phone numbers, email addresses and web sites address and notes per contact, This would not be a true field to field sync. This alone makes it BAD ADVICE.

3. AS someone who has had their identity stolen via the US Veterans Administration and hacked online stores I should know about how weak any cloud database is in INSECURITY! I have had to have my all of my bank cards replaced up to three times in any given year because of these events and now I have to have a second secure PIN and my bank cards no longer reflect my original accounts, they are essentially dummy numbers embossed in my cards to protect my accounts.

4 Direct device synchronization is the only private and secure way to have the above data on multiple devices for a non enterprise user.

5. As a degreed Network Engineer with computer forensics this is BAD ADVICE to trust all of the addresses, phone numbers, birth dates, anniversaries, group activities, business contacts and transactions to any cloud such as Google - gMail, Apple Inc, - iTunes and Microsoft - HotMail. These are not trustworthy organizations to hold that data in.

6. Any information that my friends, family, associates, business partners and colleagues share with me I hold in trust for the sake of their privacy and security as if it were precious cargo residing on my devices.

7. Email addresses plus date of birth can constitute an online signature for the agreement of an online contact. The reckless dissemination of this data is a legal liability that I do not think that Kevin et. al. wishes to take on.

REMOVE AND REVERSE THIS POST IMMEDIATELY or face a Cease and Desist Order with liable suit!

Man...someone got out of bed the wrong side this morning....sheesh, it's only advice not federal law. Let the consumer decide what is best....

ROFLMAO, his post was off the wall hilarious! I can barely type I am tearing up. Holy over reaction and freakout!

HA HA HA HA HA Haaaaaaaaaaaaaaaa.

The thing i liked about my BB was that everything worked and setup easily. Now we get OS2 after months of waiting and you cannot transfer your contacts!. I've tried setting up Gmail, got it on my phone, synced my contacts, got it on the PB - nothing happens. And it appears you cannot delete it off the PB account settings now!. And as for the native e-mail it wont recognise any of my e-mail accounts - keeps telling me my details are wrong. I've given up now so lets hope they sort this on DM soon!!!

Hmmm. Pretty sure my Palm3 could sync with Outlook contacts back in the 1990's. RIM needs to get this fixed before BB10 phones are ready. I also think that like Kevin said in the last podcast that RIM needs to make it so you can plug in an Android phone or iOS phone into DM to make it simple for people switching back. The really sad things is that you can't get contacts from a BB phone to the Playbook with one click. Not everyone keeps their address bookbin facebook and linkedin.

I setup my Google account on my Playbook and seems to have saved properly, but no syncing has occurred. Been trying for two days - anyone else? What am I missing?

The way i synced is to use the Outlook at my work to sync with my contacts with my blackberry. I sync'd it with a cable since i don't normally update my contacts all that often so it's a decent solution. It beats using Google as i don't want it in the cloud. (better at work then at google imo) Now my contacts are sync'd. I then use Microsoft exchange to sync the contacts,email with my playbook and ipad.

Right now my blackberry only gets email sync'd OTA (one-way) and no calender/contacts through web exchange. (don't have BES data) Kind of sucks that my ipad/playbook can sync all 3 but my phone can only do 1.

I've updated to OS2 from the beta OS, and it's a nice update. I've got my emails on it now. Only problem is, the calendar sync tool I've been using on my Blackberry and on my computers is Funambol, and so far I cannot figure out how to get this to sync with the playbook. I have the Android app running on it, but it only syncs with the Android calendar and contacts, not with the native Playbook calendar and contacts. Is this something that RIM can add in with a patch or update? I really rely on this. I don't see that I'd be able to realistically use the Funambol calendar to update a Google calendar and then sync to the Playbook. Who would I contact at RIM to get this feature put in? It couldn't be a very difficult thing to add in, just ask for the URL to the cloud server, and the username and pass, and boom, done.

I use Outlook for email, contacts and address book. My provider has gone to Google email with incoming and outgoing mail servers. I set up my message account on Playbook 2.0 and I cannot get address book or contacts. I have to set up the email account under a Google account in Playbook (a must) and it cannot do what my Blackberry 9800 does - sync with Outlook.
I want to sync my Playbook with Outlook without using Bridge. Am I missing something?

I agree with just about all these comments. I am wary about the cloud and google's eyes. I was an early adopter - full price. I REALLY feel burnt! Stock is never gonna come back either barring a miracle.

For those of you looking (or needing) to manually sync your Yahoo! contacts, I was able to do so using the following steps:

1). Ensure your Yahoo! contacts are up to date (import file (.csv) from Outlook, etc.))
2). On BBP device, goto Accounts, Add New Account.
3). Select E-Mail, Calander and Contacts.
4). At the prompt, enter your Yahoo! E-Mail Address and password.
5). Select Advanced Setup.
6). Select the CardDAV option
7). Enter Description, and Yahoo! Account settings.
8). For Server Address enter: carddav.address.yahoo.com
9). Save.

It worked for me, so hopefully it will work for you. Good Luck!!

Can someone post instructions for syncing Outlook through Microsoft Office 365 for BIS? This seems like the most secure solution. Also, with SharePlus on the PlayBook, and Office 365 offering online Office 2010 apps for creating and editing docs, and being able to download and edit docs on the PlayBook with Docs to Go, the email piece might be what finally gets me to commit to Office 365. I've been kind of considering a PlayBook/Office 365 environment for a few months and I've been playing with an Office 365 account that I set up, but putting all the pieces together has been daunting.

Sincere thanks for this info, Joseph.

The fact it is necessary is beyond ridiculous, though. As is the fact that we still have to use the Bridge to access *BlackBerry* e-mail on a *BlackBerry* devioce (yes, OS difference noted).

It's BS, that RIM did not think about an option to sync it via BT/Bridge.

When I bought Playbook in 04/2011 I connected it via bridge, and all my settings were automatically sync'd to PB.

RIM guys here you failed, really!!.

Let us just connect via bridge and all the Emails, contacts, calender, and tasks should be sync'd automatic. We can then switch bridge off (virtually).

There is no Rocket science behind it.

I don't use outlook, I do however have a Mac. I don't keep contacts up to date on iCalendar but would consider it if anyone's got suggestion on using with PB calendar...not that I'm dying to find the perfect solution as I'm not a business person.

One thing I wanted to point out though was that my BB curve contacts synced to my PB somehow. I have no idea how but maybe it was when I was tinkering with settings. Might be worth looking into, idunno. All I know is I didn't have to type them all in.

Great job so far RIM, keep the good updates coming and I will keep enjoying BB devices.

Most people using outlook are likely using exchange. (in which case, you use activesync and it works perfectly).

If you're using desktop manager to sync your calendar to your BB, why not just use Bridge? (and hide the native calendar altogether?)

so.. MS Exchange with ActiveSync is now working perfectly for me... but only AFTER a security wipe. This is also true with gmail... had it working then it stopped.

I know this shouldn't be the case... but after stuggling for days, and seeing this recommended, I can now say it worked for me.

Just thought I'd share for those still having issues that haven't tried this.

OK...I'm probably going to regret this (if all the paranoia about Google is even partly true), but I downloaded GoogleSync. Installed it and watched it sync over 500 calendar items. Went to Google Calendar and verified that they are in the cloud. I have this gmail account activated on my PB and calendar sync option is selected. Nothing appears on my PB calendar except everyone i know's birthday from Facebook. I only have one calendar in Google, so that should be automatically designated as the primary calendar, correct?

I set it up to sync every 60 minutes.

Your description sounded SOOOOO simple, yet it just never seems to be simple.

Any ideas would be VERY much appreciated!

Johnlindy

I did the same and it worked perfectly. It sync'ed contacts and all calendar entries. Make sure to ask the calendar to Refresh.

I prefer using the Bridge though.

After I tested with Goggle Calendar, I deleted all the entries since I subscribe to the paranoia.

For those not comfortable with Google and may be more comfortable with syncing through Windows Live....

I just sync'd my contacts and calendar using my hotmail account. Hopefully, this makes it easier for everyone until RIM updates their desktop software.

Here are the steps:

(1) If you don't already have one.. create a hotmail account.
(2) In outlook, export your contacts as an .csv file and save it. I have Outlook 2010 so I have to go into File, and then Options and then into Advance. There you'll see an Export button. Click on the export button and select "Export to a file". Next select "Comma Separated Values (DOS)". Next click on the Contact folder and then give it a name and ensure you remember the directory to put it in. I save the file to my Desktop.
(3) Also in outlook go into your calendar and go to File, then Save Calendar. Save the Calendar as an .ics file. I selected in options under range my whole calendar and "full calendar" instead of "availability"
(4) Next I logged into my hotmail account and went into Contacts. Selected "Manage" and "Import". Click on the Outlook icon. Then selected "From Outlook using csv" so you can import the file generated in (2). Click on Browse and then select your csv file. That's it for Contacts... it should now be updated in hotmail.
(5) Next I went into my Hotmail Calendar and clicked on Subscribe. Then click on Import from an ICS file and select your ICS file. That's it ... your calendar is updated in hotmail
(6) All your contacts and calendar entries should now have shown up in your blackberry playbook through your wifi.

Hopefully this works for you. I'm happy cause it literally only took me all of 3 mins to do.

-Lynxs

I don't even have to .csv to synchronize to my Hotmail account: The Outlook Connector takes care of that for me.
Getting the Outlook Connector to sync to the BB Desktop Manager was a bit tricky, though, as it doesn't want to create a linked data file on its own...

I was able to use Outlook connector to download all of my contact information to the Playbook just by dragging all of the contacts to the appropriate folder. The downside to this method is that if you remove a contact from your Hotmail account, it will remove it from the Playbook Contact List. I would like all of my contacts on my Playbook, but I do not want all of my contacts associated with my Hotmail account. Guess I will need to keep working on this...

Doesn't work for Win 7/Outlook 2010 users! Google synch doesn't support Outlook 2010. Nice to discover this now... Has anyone else discovered this? I wish Google, Windows, and Apple would all just play nice. Their focus should be on the end user experience.

I came here looking for a solution to synchronize my OUTLOOK to my PLAYBOOK.
I did not type Google Calendar anywhere in my search!
I tried the suggested fix (synchronize Outlook to Google Calendar - Google Calendar to PlayBook). What a freaking nightmare!!!!
I have had months of sales calls appointments wiped out, itineraries wiped out, doubled, tripled, even quadrupled appointments, cannot enter new appointments, cannot delete incorrect appointments and still cannot get anyone that seems to know how to correct the whole freaking mess!
Go to Google Calendar "known issues", like I did after this nightmare, and they have a little disclaimer stating that there are known issues with Google Calendar and synchronization with "third party' calendars (**please fill in"PlayBook OS2 calendar" here).
Has anyone figured out a patch or fix for this yet?
I now have to resort to hand writing my sales reports, type them into my Outlook appointment notes, back them up, e-mail them, print out paper copies of my daily sales calls and, basically, go backwards 10 years to do my job functions.
I don't even dare sync my phone for fear I'll wipe out all of the work I've had to enter manually into Outlook over the last few weeks.
Anyone?

I have Outlook 2010 and have been trying to figure this out for hours.... Then it just happened after I gave up trying... Download Outlook Connector and add your live account. Then make that live account your default account. If you sync your BB calendar with DM all your appointments will go right to your live calendar since it is the default account. Then hit send/receive and it will sync with your Live calendar on the net and your Playbook calendar.. I cant believe I got it working AFTER I stopped trying... Good luck!

I just realized Im in the wrong thread...
This is a way to sync your BB phone calendar with your Playbook native calendar and your windows live calendar. Sorry for any confusion. Could a moderator please put this in the right thread or delete it. Thanks!

calendar works, but does not get updated when Outlook calendar is updated. suggestions?
instructions for getting contacts to my Playbook did not work. got them to google contacts, but they have not showed up in the Playbook.