Sync Outlook 2011 > Iphone 5 > Win 7 Bootcamp

[Dal123]

I'm having real problems syncing these devices.

Outlook 2011 was syncing with Iphone 5 via iTunes and this was working both ways. The iPhone 5 would update calendar data to Outlook 2011 also. I spend the majority of my time in mac.

However I'm starting to spend more time in windows via Bootcamp in Win 7 and I need these 3 devices to sync in real-time. So I used iCloud thinking that was the answer. I could carry on as it was and then use the iPhone 5 to backup via iCloud.
Never usin iCloud before I must have changed something and the original Mac via Outlook 2011 is no longer syncing. Attached is my settings through iTunes. I do not know why it is no longer syncing. I've tried many different settings now. I've deleted my .plist files in home > preferences but no joy as yet.
Can anyone recommend what to do? I am reluctant to upgrade from Lion 10.7.5 as other software may not work with it.

Someone else must have experienced this predicament; any ideas on the best rout?

 

[campyguy]

You're missing one bit of input that would be helpful - which version of Outlook 2011 are you using...

MS removed local synching in an update that corresponded with Mountain Lion - the "iSync" conduit that synched devices locally was removed from MS Office and OS X.

Subsequent to that Office update - I don't recall which update it was as I've moved on - the ONLY means to sync between Outlook and iOS devices since that update came out (and all other newer versions of Outlook) for contacts, notes, and calendars is via an Exchange-based account (Exchange Server, Office 365, or Hosted Exchange) or specialized software (Mark/Space used to have capable software in this space but it was dependent upon iSync, which no longer is supported).

The only suggestion I have for you is to locate a not-updated version of Office 2011 Professional (which includes Outlook), and don't update it. I *think* the update that killed local synching on the Mac is 11.1.0. I use an Exchange Server and Office 365 and am on Yosemite - I can't help you beyond this advice.

 

[Dal123]

You're missing one bit of input that would be helpful - which version of Outlook 2011 are you using...

I *think* the update that killed local synching on the Mac is 11.1.0. I use an Exchange Server and Office 365 and am on Yosemite - I can't help you beyond this advice.

Thanks Campy, I'm using version 14.4.5. I don't think I updated, it was working fine on Monday and I do not have automatic updates selected.
It seems a bit of a coincidence since altering iCloud settings this enigma has presented itself.

I've done quite a lot of research on Microsoft Exchange Servers and sounds great. Though I went to purchase and I only see ones available for Office 365. It says that some features may not work in Outlook 2011.

 

[campyguy]

Thanks Campy, I'm using version 14.4.5. I don't think I updated, it was working fine on Monday and I do not have automatic updates selected.
It seems a bit of a coincidence since altering iCloud settings this enigma has presented itself.

I've done quite a lot of research on Microsoft Exchange Servers and sounds great. Though I went to purchase and I only see ones available for Office 365. It says that some features may not work in Outlook 2011.

One the back end of Apple's doings, I understand that they've been making changes from the "old" iCloud to the "new" iCloud with the issuance of 10.10.3 - that x.x.1 update was IMO a lot bigger than just the x.x.1 indicates, and the same goes for the update from 8.2 to 8.3. But, that's a side story.

On my end, I've decided to sell my MS Exchange Server license and move to Office 365 - the monthly fee has turned out to be much less costly for my small business (the Server Client Access License, or CAL) per employee isn't worth it to me anymore...

There's 3 "flavors", or plan types of Office 365 - Personal, Business, and Enterprise - and there's different versions of those plan types. Personal doesn't include email, some Business and some don't. Look here:
Personal:
https://products.office.com/en-us/buy/compare-microsoft-office-products
Business:
https://products.office.com/en-us/business/compare-office-365-for-business-plans

This is the plan I own, which includes 5 installs plus Hosted Exchange email:
http://www.amazon.com/Microsoft-Off...&keywords=office+365+business#customerReviews

One can find the Business Premium version online for 5 installs PC or Mac, managed by your Office 365 Portal. You get a "@onmicrosoft.com" email domain account for up to 5 users, plus all of the Office software for 5 installs and lots of storage (the plan says 1TB, but that's being upgraded to UL - one of my accounts shows 10TB...).

An Office 365 subscription gets you access to the PC and Mac beta versions of the new suite, the version I have allowed me to install 2011 on my Mac, 2013 on one my PCs and in my Win 8 VM that's on my Mac - the beta versions don't count against the 5 installs. I have two accounts set up for my junk and info, and I can dispose of or change them anytime.

The Amazon purchase linked to above is cheaper than buying the Personal Home version from a brick-and-mortar store or from MS directly, a no-brainer for me. If you go that route - opt for the 25-digit key card to get mailed to you, and you can sign up for a 1-month free trial while you wait for the card to show up then enter in the key card SN. AFAIK, you'd need to DL the Office 365 installer directly from MS as the installer for Office 365 has the "network validation connector" built in, so don't fall for buying an installer from an eBay reseller.

Office 2011 won't work with where MS is going on the back end, and the new version of the Mac Outlook is also missing some features that will be added in the future - so read the fine print carefully. MS has updated the new version of Outlook several times, and I'm happy with their work, so far.

 

[Dal123]

Thanks for that detailed review Campy; greatly appreciated. I can understand renting and subscribing to the exchange server. One thing I'm dead against though is renting my software. We've spent a fortune on software and I do not like where the industry is heading; ripping us all of with the subscriptions. Dead against that .

I think I will have to accept that I cannot get Outlook 2010 and 2011 to sync . Have to try to contact Microsoft or someone to get it working as it was working.

Thanks again for your detailed review; greatly appreciated!

 

[campyguy]

It's sad that so many users of older products are getting left behind, in a sense, when the "old stuff" works just fine for what it's needed for...

We do have one older Mac, on Lion, and I was trying to find some documentation on Apple's web site - every single link I clicked led to a web page that the page can't be found and referred me to Apple's Main Support Page.

I also had thought of a product created by a 3rd-party dev named Mark/Space (which I found in my Palm Treo days...), but they've discontinued all of their sync products as of 12/31/14, so the writing must be on the wall for the older sync conduits...

I didn't ask, and there's no reason to respond, but maybe an older version of iTunes on both platforms might turn the trick? The newer version of iTunes have the sync conduits removed - they don't "talk" to the "Sync Services" that no longer exist in 10.9/10.

As to the cost, I gave in and had to move on. I had to let my IT guy go (long story), then found a buyer for my Exchange Server (one less server now, tho'!), and found that by selling a few of my Office suites will pay for Office 365 for about 4 years for what we need (we also use iPads with SIM cards in them, which does not count against our install limit). Getting 5 installs for US$7 per month (US$12) - far cheaper than my CALs now. OK, so I'm getting soft! If I come up with a solution for our Lion box I'll pass it on to you. Cheers!

 

[Dal123]

Thanks for your time Campy; greatly appreciated. I'm all for investing in good software but a bit stubborn as I think renting the software is a rip off and it takes time to learn all the features in the software. I think it would be changing so quickly I would hardly be able to use the software.

My contacts are syncing but problems are happening with the calendar. It seems to hang and it's no longer syncing with iCal so I need to do a bit of digging there.

You're right, all the advanced troubleshooting via iTunes is no longer available where they are sneakily trying to push us towards Office 365 in secret partnership I think .

Thanks again .

 

[Dal123]

Managed to get the data from Outlook to transfer to the iPhone. Unfortunately

In a state of despair I dragged almost every .plist file you can think of from the Library > Caches. Anything relating to Microsoft or Apple Itunes went into the trash.
Restarted both and the data from Outlook is now transferring to my Iphone. Unfortunately the iPhone does not upload it's sync to Outlook though.

Hopefully this helps someone out and will save them 3 solid days; which is what it is has cost me! Thanks Apple and Microsoft !

 

[Dal123]

Nope actually only synced the one time; now corrupted again. New items are not showing up on the iPhone now!

 

[campyguy]

OK, three last bits - tax day here is tomorrow and my accountant is on her way...

For your Mac, if you haven't deleted it and tried again, use the Go>Library Menu Command, find the com.microsoft.Outlook.SyncServicesPreferences.plist file and delete it. Then Option-Click on the Sync Services charm icon in your Menu Bar, and select Reset, and do so. Reboot your Mac. Try Outlook sync services again...

You might need to find an older version of iTunes as well (as described above).

In Outlook 2010, ensure the iTunes add-in for Outlook "ItunesOutlookAddin" is enabled - if the add-in is not present, IMO only an older version of iTunes can re-install it.

Last, you didn't indicate which version of iOS is on your iPhone. Two of my iPhones are are iOS 8.3, and it seems as though Apple's changed the sandboxing somewhat - two of my file synching apps aren't working, and I read this on the MR home page: https://www.macrumors.com/2015/04/13/ios-8-3-ifunbox-itools-sandbox-app-access/ - if you think about the following logically, Outlook is synching files with iOS. If you've updated your iPhone to 8.3, that could be the source of your headaches...

Good luck, and cheers!

 

[Dal123]

Last, you didn't indicate which version of iOS is on your iPhone. Two of my iPhones are are iOS 8.3, and it seems as though Apple's changed the sandboxing somewhat - two of my file synching apps aren't working, and I read this on the MR home page: https://www.macrumors.com/2015/04/13/ios-8-3-ifunbox-itools-sandbox-app-access/ - if you think about the following logically, Outlook is synching files with iOS. If you've updated your iPhone to 8.3, that could be the source of your headaches...

Good luck, and cheers!

Thanks Campy, I've deleted iTunes and installed an older version. I'm using iOS 7 on the iPhone.

Just deleting Office now and going to install and old one. One thing regarding Office; If I revert from an old backup will the corrupted settings ruin my sync?
I have massive amounts of data via Calendar and categorized emails, calenders etc. Terrified of having to reconfigure my old email and loosing all the calendar entries.

Thanks again .

 

[campyguy]

Thanks Campy, I've deleted iTunes and installed an older version. I'm using iOS 7 on the iPhone.

Just deleting Office now and going to install and old one. One thing regarding Office; If I revert from an old backup will the corrupted settings ruin my sync?
I have massive amounts of data via Calendar and categorized emails, calenders etc. Terrified of having to reconfigure my old email and loosing all the calendar entries.

Thanks again .

I had to dig a bit, but, I did find an older link on MS's website - it's pretty detailed about how to use Apple's Sync Services, including backing up the key data folder - your Identity! The key to the link below is that it contains Service Pack 1, which I believe is the final update before the Sync Services engine was severed. I don't recall which version of iTunes was the final one before Sync Services was no longer used (relative to the engine that 3rd parties, including MS, used).

https://support.microsoft.com/en-us/kb/2452489

Also, review the content of this MS Support web page - I rebuilt my Outlook database every 2 months without fail, just to prevent issues.

https://support.microsoft.com/en-us/kb/2360509

Restoring is a PITA. Sorry for that. The source of your frustration seems to me to be your install of a newer version of iTunes. I don't have an archived copy of the older versions, having moved on to the dark side. Sticking to the applications that have the conduits you need should get you back up and running. If you work from a duplicated and rebuilt Identity - there's your backup.

Keep in mind that Outlook 2011 can import a Win Outlook PST file, so, there's that peace of mind - and you can give Apple a piece of your mind...
I'll be on the road for business for a few days but will be checking in from time to time. Good luck, and Cheers!

 

[Dal123]

Thanks Campy and for the links. I went for it last night.

iTunes:
Deleted iTunes 11 and reverted to iTunes 10.7 via this guide.

However when connecting the iPhone 5 via 7.1.2 it says that iTunes is too old to work with the iPhone 5.
So I was thinking of downgrading to iOS 6 on the iPhone. However I should not need to do this as it was all working via iTunes 11 with iOS 7. It must be that once you upgrade it is aware that the older version is obsolete and implants a kind of virus if you like. Upgrading all the time is not the answer people; be cautious!

MS Office
I deleted via Terminal and trashed all the sync .plist files in library > preferences.
Upon reinstalling MS Office Word worked fine. When trying to load Outlook it said it was too old to work with 'this identity'. So I began upgrading Office to enable Outlook to wor, restarting after each update. Which began to finally work last night on one of the versions in the 14 range I think.
Upon starting this morning it now says that an older version of the Microsoft Database Daemon is running and I must delete the daemon from the Startup Items. I restarted Outlook while holding the option key and rebuilt the database, restarted the computer and Outlook was as I had prior to all of this nonsense.

Everything seemed to be fine, just had a cup of tea and revisted the computer to see I had no emails in one of my inboxes (my primary email account of course). The option to Quit Outlook is greyed out and it is downloading my emails all over again. Thank god I still have emails on my computer (previously dragged here as I had too many emails on the server) and they are categorized. I notice as the inbox is redownloading the categories (and it is taking ages!) that I had previously assigned to them are now gone. Thank god I still have my calendar entries as this would be catastrophic!

I backed-up prior with Time Machine and tried restoring Outlook though this did not work. Seems the damage was deeper than Time Machine.
Where it took me a few attempts I lost my library on iTunes but this is still on the phone so not to worried and haven't tried reverting through Time Machine, doubtful it would do anything beneficial anyway as it didn't for Outlook; don't see why iTunes would be any different.

Quite an interesting advanced problem, and others please learn from my mistakes; don't upgrade unless it is absolutely essential! Most of the important compatibility firmware issues are not listed and they only have the silly pedantic details advertised prior to the upgrade so your previous brilliant software no longer does half of this stuff it used to do!

I'm going to take it to a professional Apple firm in London I've used before who really know their stuff and see how I can get this to work as it used to and hopefully sync in Bootcamp too.
Thanks for your help Campy; I'll post updates as to how to get this to work without upgrading to Office 365.

 

[Dal123]

What a nightmare! I tried restoring the Old Identity in Outlook. This did not work, I had to keep upgrading until I was finally able to bring in the backup. I spent all week working on this; a total of over 60 hours.
In the end I had to revert to the old backup by dragging my backup (prior to carrying out this operation) of Microsoft User Data.

Nothing has worked. I got iTunes back to 10.7 though I lost most of my library because it was a long time ago I upgraded to 11 and most of my songs were in iTunes 11 format.

I think my Calendar may be corrupted in Outlook 2011 from some of the research I have carried out.

Somebody managed to get over it by deleting Microsoft User Data and create a new Identity though this is not an option as previous emails are stored on my computer via Outlook 2011 as we are talking on approx 20GB of emails.

It's not iTunes because the sync between Outlook and iCal is not working properly. The problem is between Outlook and iCal with Outlook being the problem.
One cannot revert back to older versions once has upgraded Outlook as you cannot import the database which has been created on a newer identity. I've read a few articles on creating a new identity and copying the header rows of the new identity into the old backup - it didn't work.

 

[Dal123]

Update

Ok guys, any of you using IMAP do not try to rebuild your database; it can often make things worse as I'm experiencing.

Outlook will not even open now . I'm reluctantly going to try to create a New Identity. I don't think I'll be able to get my old emails back in as many of them were stored locally on my computer in Outlook 2011.
Don't think I can get these back now which is a catastrophic failure.
I'm going to try reverting to the old backup one last time and try to manually drag these emails somewhere. Then try dragging them back into the new identity.

If anyone does have any suggestions I would love to hear them.

 

[Dal123]

I found this app which works intermittently but is unsatisfactory as it's not using categories properly and is not up to par.

Wish I could get it back to iTunes and Outlook sync .