Itunes and Outlook/iPhone calendar/contacts sync deprecated Rev 4 ?

Ok Ok... I know

I'm being stubborn old man, and will continue to get in trouble attempting to

depend on tools that are at end-of-life... But I was just trying to get one

last "sync" in between Classic Outlook 2024 and my iPhone 17 to catch

things up before I move to a new sync. solution

The contacts did sync, but there an internal field-mapping/sync. screw-up where

in about 1800 contacts out of 6500 total were duplicated in an odd way:

about 1800 Contacts that just have the field "company name" populated

with no data in the "full name" field.

got duplicated with the "full name" field populated with the data in

the "company name" field,

and SOME but NOT ALL of the other data from the original record was copied over

into the duplicate.

All the bad records seem to have:

1) data in "full name" field equal to the (original) "company name"

2) a modified date of yesterday (the day from ****): 09/08/26

I can’t come up with an easy way to fix this – BUT OF COURSE I am wide open to any ideas y’all

may have  😊

My next step will be to try using CompanionLink, it seems to be the most reliable option for my configuration

Here is the overview from another forum I follow:

Aside from CompanionLink and AkrutoSync, Sync2 (by 4Team Corporation) and CydiaImpactor/iTunes

alternatives like CopyTrans Contacts are worth considering, though

CompanionLink remains the most robust option for local USB and Wi-Fi syncing.

CompanionLink is generally favored for POP3 setups because of its granular

collision handling, allowing you to merge or overwrite directional data cleanly

without wiping existing iPhone contacts. The main drawback to CompanionLink is

that syncing through DejaOffice adds an extra step compared to direct

Exchange-emulation syncs, but it avoids the risk of data loss during initial

setup.

Ok ... I give up.

Very long story short it looks like the newer versions of iTunes do NOT install all of the components the older versions did, but even when I uninstall, clean-up,reboot, and install old x64 version 12.12.8.2 I can't get it to work.

Many hours wasted on something that "should be simple".

there are two 3rd-party sync options I have found: CompanionLink and AkrutoSync.

I may try and figure out which of those might be superior. CompanionLink seems to have the bigger marketshare.

sigh.............. where's my beer?

Jim

Well after keeping y’all waiting all this time

(sorry lots of issues on the personal front)

I am forced to report the first attempt to sync. On

the brand new Win11 Pro computer

With a clean install of iTunes 12.13.9.1 on my

brand new iPhone 17 pro which came w/ iOS 26.3

was a total failure. No sync. Of either the

contacts or calendar. 

Here’s a blow by blow:

I plugged the iphone in and the Microsoft phone

app. Wanted to get in on the game. I said NO.

Historically when I sync. I take my computer off-line

and have my iPhone in airplane mode just to keep the dust settled.

iTunes did not see the phone.

I think what happened next was that I turned wifi

back on and the phone was recognized.

I configured the settings in iTunes to sync

everything. I clicked sync and got his msg.

The information on the iPhone "xyz17" is

synced with another user account.

Do you want to sync this iPhone with the information

from this user account instead?

 "Merge Info" merges the information on

this iPhone with the information

from this user account.

"Replace Info" replaces the information

on this iPhone with the information from this user account.

After some research I concluded the correct answer

was to “merge”.

iTunes first backed up my iPHone which took a VERY

long time like 20 minutes ..

(I have s 265Gb phone w/ ~100Gb used)

Then it appeared to sync.  Spending some good amount of time on both

Contacts and Calendar

There were not prompts during the sync.

I was expecting to see some  “contact information is different between

devices how do you want to resolve…”

As I have not sync-ed since last year and have

added contacts to both devices, and edited some contacts.

But that didn’t happen

At the end, the iphone reported exactly the same

number of contacts as when it started.

That is not correct either.

I didn’t realize that in addition to regular

calendar there are two other calendars on the iphone:

Birthdays, and US holidays.  I turned both off, and with iphone still

plugged in re-sync-ed.

The sync was much quicker this time as iTunes did

not do another backup.

I looked for the backup file which on my Win10

computer was stored in: C:\Users\Me\Apple\MobileSync\Backup

but that folder does not exist on the new W11 laptop.

In short:  An abysmal failure.

Looking at task manager after the sync. there is a 32-bit process is

running in background:  com.apple.Outlook.client.exe

(I did install the 64-bit version of iTunes.)

My Outlook calendar seems OK,  BUT my contacts seem to be visually corrupted

when in “Business Card” view Which is my default view.

The Cards at the beginning of the alphabet are fine, but there is black band across the bottom of the cards

nearer the end of the alphabet that that increases in height and obscures the data at the bottom of the

card. THIS STINKS!

I have not had the courage to attempt the  “Reset View” option as yet.

I am considering going to a 3rd party sync. App. .....

Unless there is a miracle

Any suggestions WOULD BE SINCERELY appreciated

Jim

Ok ... I thought I had posted this here a bit ago, but I guess not...

My first attempt to get all the new gear working was ... a big fat zero:

Well after keeping y’all waiting all this time

(sorry lots of issues on the personal front)

I am forced to report the first attempt to sync. On

the brand new Win11 Pro computer

With a clean install of iTunes 12.13.9.1 on my

brand new iPhone 17 pro which came w/ iOS 26.3

was a total failure. No sync. Of either the

contacts or calendar. 

Here’s a blow by blow:

I plugged the iphone in and the Microsoft phone

app. Wanted to get in on the game. I said NO.

Historically when I sync. I take my computer off-line

and have my iPhone in airplane mode just to keep the dust settled.

iTunes did not see the phone.

I think what happened next was that I turned wifi

back on and the phone was recognized.

I configured the settings in iTunes to sync

everything. I clicked sync and got his msg.

The information on the iPhone "xyz17" is

synced with another user account.

Do you want to sync this iPhone with the information

from this user account instead?

 "Merge Info" merges the information on

this iPhone with the information

from this user account.

"Replace Info" replaces the information

on this iPhone with the information from this user account.

After some research I concluded the correct answer

was to “merge”.

iTunes first backed up my iPHone which took a VERY

long time like 20 minutes ..

(I have s 265Gb phone w/ ~100Gb used)

Then it appeared to sync.  Spending some good amount of time on both

Contacts and Calendar

There were not prompts during the sync.

I was expecting to see some  “contact information is different between

devices how do you want to resolve…”

As I have not sync-ed since last year and have

added contacts to both devices, and edited some contacts.

But that didn’t happen

At the end, the iphone reported exactly the same

number of contacts as when it started.

That is not correct either.

I didn’t realize that in addition to regular

calendar there are two other calendars on the iphone:

Birthdays, and US holidays.  I turned both off, and with iphone still

plugged in re-sync-ed.

The sync was much quicker this time as iTunes did

not do another backup.

I looked for the backup file which on my Win10

computer was stored in: C:\Users\Me\Apple\MobileSync\Backup

but that folder does not exist on the new W11 laptop.

In short:  An abysmal failure.

Looking at task manager after the sync. there is a 32-bit process is

running in background:  com.apple.Outlook.client.exe

(I did install the 64-bit version of iTunes.)

My Outlook calendar seems OK,  BUT my contacts seem to be visually corrupted

when in “Business Card” view Which is my default view.

The Cards at the beginning of the alphabet are fine, but there is black band across the bottom of the cards

nearer the end of the alphabet that that increases in height and obscures the data at the bottom of the

card. THIS STINKS!

I have not had the courage to attempt the  “Reset View” option as yet.

I am considering going to a 3rd party sync. App. .....

Unless there is a miracle

Any suggestions WOULD BE SINCERELY appreciated

Jim

Ok … I was plenty annoyed when my 1st attempt to get this going failed, so I ignored things for a little while.

Yesterday, doing a backup of the new machine I discovered a HUGE error on my part.

I had set iTunes to sync. Contacts to Outlool, but somehow it got flipped back to the “default” of 

“Windows Contacts”.

So a copy of all of my  contacts ended up in:   \<user name>\Contacts folder.  Hopefully easy to fix.

~~~~

Regarding Calendar sync:

I had a chant with ChatGPT last night.  I found that when I had installed iTunes  12.13.9.1 it

had NOT installed the COM Add-in that supports sync. 

The  “iTunes Outlook Add-In”  (I think that’s what it’s called) located at:

Outlook -> File -> Options -> Add-ins  (bottom of screen)  Manage COM add-ins ->  GO

Does not list the iTunes add-in, and if I try to add it, the folder that Outlook opens:

C:\Users\<user>\AppData\Roaming\Microsoft\AddIns  does NOT contain anything.

 ChatGPT claims that the required Add-in was removed from iTunes dropped after V12.12.x

Ring any bells?

MAYBE those of us (including me) that have had success with later versions of iTunes were able to use them as the Add-in was already installed by an earlier version?

Thoughts appreciated!!!

Thanks,

Jim

I could have SWORN ... (really sworn) that I posted an update a few days ago that went like this:

Ok … I was plenty annoyed when my 1st attempt to get this going failed, so I ignored things for a little while.

Yesterday, doing a backup of the new machine I

discovered a HUGE error on my part.

I had set iTunes to sync. Contacts to Outlool, but somehow it got flipped back to the “default” of “Windows Contacts”.

So a copy of all of my  contacts ended up in:   \<user name>\Contacts folder.  Hopefully easy to fix.

Regarding Calendar sync:

I had a chant with 

ChatGPT last night.  I found that

when I had installed iTunes  12.13.9.1 it

had NOT installed the COM Add-in that supports sync. 

The  “iTunes Outlook Add-In”  (I think that’s what it’s called)

Outlook -> File -> Options -> Add-ins  (bottom of screen)  Manage COM add-ins ->  GO

Does not list the iTunes add-in, and if I try to add it, the folder that Outlook opens:

C:\Users\<user>\AppData\Roaming\Microsoft\AddIns  does NOT contain anything.

ChatGPT claims that the required Add-in was removed from iTunes dropped after 

V12.12.x

Ring any bells?

MAYBE those that have had success with later versions of iTunes were able to use them as the  Add-in was already installed from a prior version?

Thoughts appreciated!!!

Thanks,

Jim

I understand completely ... this is WAY harder than it should be....

I found one thread that gave me a glimmer of hope:

iPhone 15 Pro not syncing with iTunes on … - Apple Community

This guy has W11 sync-ing w/ the MS STORE version of iTunes...

His "fix-it" comment was to disable power-saving mode on the usb-hub devices....

I did that ... hoping for the best, but no joy for me... :-(

Then I discovered that Bonjour was being blocked from internet access by the Windows Security Firewall...

I don't know that it NEED internet access but I allowed it ...

again, no joy for me... :-(

I had previously experimented with the non-store iTunes 12.12.1.1 getting no joy there either............

I might try ripping it out and installing the current MS-store version ...

after that ... I'm clueless and will likely try companionlink 3rd party offering............

As always, any tips will be graciously accepted ;-)

Jim

I re-discovered this article ... last updated in 2025:

https://www.thewindowsclub.com/using-itunes-app-microsoft-store-windows-10

Discussing the MS store version.

Interesting that it installs the older 32-bit version then does an overlay install on top of it...

I wonder if there is any love awaiting me there vs. the 64-bit EXE file version?

For giggles I just asked Grok...

I'm not sure it is telling the whole truth, but it does say iTunes/Outlook sync continues to work in V26

But it also says:

Ensure Outlook is open (I've always had mine closed and done a reboot before syncing.

It says iOS 26 supports this on iPhone 12 or later models

i.e. iTunes will transfer the data from your classic Outlook profile. This is a one-way sync from PC to iPhone (edits on iPhone won't push back to Outlook unless you sync again).

Ok ... I finally had a chance to get back to my sync. issue and am happy to report it appears to be RESOLVED.

The sync. takes so long that I was unable to try things one at a time ...

I was forced to condense the recovery efforts .......

• I ran ScanPST three times on my Outlook PST file
• Rebooted and launched iTunes
• Tried a regular sync. again and iTunes never reported that is sync-ed either contacts or calendar ... huh?
• Ok... I'm screwed ...
• hit the "reset warnings" button on the sync screen
• Checked all the sync settings/choices none were mis-configured
• Thought about it for a minute then ticked the boxes that said:
• "for the next sync. only replace contacts & Calendars on the iphone"

it worked ...

Maybe there were some neuanced changes to the data formats in iOS 26 which got reset

when I overlay-ed the data?

Anyway I'm running again...

It's hard for me to believe that so few iPhone owners seem to care about this situation...

but ... it is what it is..............

Thanks TT2 for hanging with me ;-)

Jim

I am successfully sync-ing with the following:

Windows 10 Pro

Outlook 2021

iOS 18.7

iTunes 12.13.1.3

I will shortly be upgrading to iOS 18.7.1

Am curious to know if anyone has made the big leap to iOS 26.x ???

Thanks,

Jim