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

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

Well... is this the end? :-(

I upgraded my iPhone 13 pro to iOS 26.0.1 as I bought a new Apple watch 11, and it required V26

Today I tried sync. to Outlook 2021 using the same technique I've used for years.

When I first plugged the phone in, iTunes took a long time to recognize it but did add it as a device.

When I asked for the sync there was some confusion on the "trust this computer" dialog,

and PIN/Trust dialog was required multiple times.

After that the sync appeared to go normally. iTunes reported that Contacts and calendar sync-ed.

via the progress thermometer, BUT the calendar did NOT sync.

I unplugged the phone and double-checked that outlook did not have any appts. that "repeat forever",

As that has been an issue for me in the past. Nope -- there were no repeat forever events...

Rebooted everything and tried again, but the calendar still did not sync.

I added a dummy appt. to the iPhone and tried again.

I never got the messages "sync-ing contacts" then "sync-ing calendar" progress thermometers.

and the appt. added to my iPhone did not appear in Outlook and still none of the appt. created in Outlook were on the iPhone.

Has anybody got any ideas?

Grok asserts that "Apple Devices" now handles contact/calendar sync to classic outlook directly via USB.

Has anybody given that a go?

Thanks,

Jim

Ahhhhhhhhhhhhhhhhh

Thank you TT2!

Any thoughts on either AkrutoSync  or  CompanionLink as a substitute?

Both sites are kinda vague about what they do,

AkrutoSync very briefly mentions setting up an exchange account?

Cloud-stuff is a non-starter for me ...

I travel to remote areas where there is no internet, or if it exists they are very proud to have a 5mb connction.

Then there's HIPPA compliance, but I won't even start that rant ;-)

Jim

Thank you tt2!

I've set a reminder for my self to "ping" this thread once a week to try and make sure it doesn't get closed due to inactivity.

;-)

Jim

Well ... here we are ...

In fairly rapid succession we have gone from iOS 18.6 to 18.6.1 to 18.6.2

I am still at 18.5

Has anybody tried iTunes sync at 18.6.x yet?

Thanks,

Jim

now ... 18.6.2 to fix CVE-2025-43300... which sounds pretty serious :-(

Well this morning Apple offered me both iOS 18.7 and iOS 26 ....

Y'all let me know your results if you give either of them a go!

Thanks,

Jim

Well ... "without thinking" I just bought an Apple Watch 11 ...

Which requires iOS 26.x

Has anybody tried a sync w/ 26 ?

Thanks,

Jim

Well.... dang..........

The forum won't let me edit my post above, but ...

While contacts appear to have sync-ed...

The calendar did NOT sync. (or did not sync completely) :-(