My iphone won't sync with Outlook contacts or calendar anymore. Any idea how to do this now?

Like you, I want nothing to do with any 'cloud' application since I find it to be unsecure (no matter WHAT I'm told about how secure it is.) I find it irritating when the 'answer' to problems is always to use a cloud ap. Anyway, I was running into a similar issue after updating my iPhone OS two days ago. It has to be the OS bug, since it was fine prior to that and nothing else changed on my system. Oddly enough, only one contact item wouldn't sync and kept defaulting to old info. I updated info on my phone, updated info in Outlook and still, somehow, the old info kept coming back.

I finally wiped both contacts (and the massive info in the notes section), put new in both the laptop and the iPhone, then followed your procedures. It worked!

Thank you so much.

I've suffered this problem intermittently (ie iTunes freezing when syncing iPad/iPods with Outlook on a PC) and it was bugging me badly! Then I stumbled on the answer - make sure you have Outlook open and running on your PC when you sync your device...

It seems that Outlook can act as a background data server *sometimes*, but the best way to ensure that iTunes doesn't *hang* is to have Outlook running. This is such a simple step that most people (including me) can overlook it when troubleshooting this problem.

Not sure if this will apply to users with Outlook on Macs, but give it a try and let us know how it works out... good luck.

you are a master, man

I ran into this problem a few weeks ago and couldn't figure out where the break-down was occurring. Today I figured it out, go to your Outlook Options, find a tab called Add-Ins, click on it. It will show you the Active, Inactive and Disabled Application Add-ins. Look for the Add-in that says iCloud Outlook Add-in. If it is located under the Inactive or Disabled, we need to Enable it again. You can go do to Manage: COM Add-in hit go, click on the iCloud file that may be listed as APLZOD32.dll, and enable it. Once you do that and save it, you will need to restart Outlook and this should fix the issue, at least it did for me.

I have been trying to solve this since I was upgraded to Yosemite. Calendar items added on my iPad or iPhone no longer show up on my Mac desktop. I tried the suggestions above but Outlook 2011 for Mac doesn't have an Options tab. From what I could find on a Google search the 2011 version does not support add-ins at all.

Thank you for this answer! It solved the problem I was having with the disabled cloud add-in. I've been sitting at my computer for HOURS trying to figure out why I couldn't enable it. Thank you, thank you, thank you!!

Their sync is horrible now, Jobs would not be impressed!!!

Notes to sync has been removed all together...Apple is really messing up and not sharing these updates, so when you need to have the accurate & updated information from your Notes you won't have them...and do you think you could find information online...NOT!.

Apple used to take pride in their support, once you are done you have no access or options, I cannot even post for some reason, this is supposed to be a "Community" correct where if you are past your 1 years support to be able to help each other...Steve Jobs would not be impressed...wife has a new iPhone 6 and hating it...time for change it seems as Apple is not the best option anymore!

They really are ******* me off.........

Yup, same here...Notes now missing, and you cannot find information on why...Job's would be so ****** to see how Apple has become!...Once the new Samsung comes out, making the move

I had the problem of all of a sudden NOT being able to sync my PC based Outlook 2010 contacts on Windows 7 (64 bit) via iTunes (v12.3) to my iPhone 6 (iOS 9).

I SUFFERED FOR 3 MONTHS trying to figure it out, and Apple Support and the self-proclaimed "Genius" Bar made matters worse by resetting all of my settings on my iPhone (without advising me to back it up first), WASTING HOURS OF MY TIME, and CAUSING ME MUCH GRIEF to rebuild my desired settings!!!

And NO, my dear friends at Apple, ditching Outlook and syncing instead with iCloud is NOT an acceptable solution.

Anyway, this solution worked for me:

In Control Panel (Windows 7), select Mail>Data Files and select the desired Outlook Data file to be the default and click "Set as Default". VOILA! ITunes suddenly was able to sync the desired PC based Outlook contacts list to my iPhone.

I assume the problem began when I added a new email account to Windows 7, and somehow the new account commandeered the mail settings and asserted itself as a default, knocking out my pre-existing default PC based contact list/Outlook data file, and causing the PC based default list’s contacts to disappear from my iPhone. NO ONE offered this solution that I figured out on my own, so hopefully it will help others too.

The worse part of this is that Apple support had no clue about this simple fix, and I stumbled on it before reading this post (this post would have saved me an hour of trying things and a wasted 45 min with Apple). Hopefully someone from Apple will read this and put it in their database.

Wanted to offer another option for people who prefer to sync directly with computers instead of the cloud. Try AkrutoSync (www.akruto.com). HTH.

Re: AkrutoSync.

Like all users, I am dismayed that we can no longer sync Microsoft Outlook notes to iPhone. I tried the AkrutoSync app on the 7 day trial and in 1 hour decided it had significant design limitations in syncing Contacts that I couldn't live with, so I returned to using iTunes.

AkrutoSync limitations:

1. Eliminates custom phone tags that you may create, and the "iPhone" tag. I deal with clients where a couple may each have their own cell, so I created tags called "Her Cell" and "His Cell" in addition to the canned "Home", "Work", etc. iPhone also has a tag called "iPhone" that I use as well for a contact. Akruto wiped them all out, and basically corrupted the contacts. Fortunately, I used best practice and had a fresh backup that I merely restored to the phone.

2. Cannot sync sub-folders in Contacts address book. For organization of my contacts, I use contacts folders to arrange contacts in logical groupings of client types or professions. So I have the Outlook default "Contacts", but also have other folders of contacts. Akruto setup only has a selectable radio button to pick ONE level or "folder". I emailed Akruto about this and received a prompt reply that, yes, it will only sync one level at a time. (I think they mean that I could sync several times, picking a different folder each time, but who wants to do that?!)

On the first one -- how did you do these custom tags? When I have an address book entry for a married couple and text both, I create a separate entry for one of them with their own mobile. There was no creative way to do it within a single entry and be able to know which one I was texting. Doing it this way -- I've never had a problem.

On the second one, I don't use more than one folder. So that's why it has not been a problem for me. Thanks for sharing your experience. Good to know this so I can let people know ahead of time. Still like to know how you're doing the first one to see if I can do things better.