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Contacts on iPhone not syncing with Outlook (not using iCloud)

On 17 Feb 2024

I had issues using iTunes (12.13.1.3)

to sync my iPhone SE2 (iOS 17.3.1)

with Outlook 2019 (Version 2401 Build 16.0.17231.20236 32-bit )

running on Windows 10 Pro (version 22H2 OS build 19045.4046 Experience Pack 1000.19053.1000.0).  


Note:  This is a sync with my local computer (Not iCloud).  If I read correctly, others have had problems like mine. 


Also note throughout this you need to be sure iTunes stays focused on "This Computer", and not "iCloud" (See iTunes, Summary, Backups section). For some reason iTunes frequently seems to change to iCloud.


I hope the following is helpful.


Short review of issue:


  • Calendar sync with Outlook on PC went ok


  • Had about 510 contacts on phone.  About 10/510 were new contacts. 
  • 2/10 new contacts updated to Outlook with just names (no phone numbers or other info). 
  • The other 8/10 stayed on the phone.
  • Tried syncing again and found only the remaining 8 new contacts that didn’t sync with Outlook on my phone (other 502 were gone. Ouch.). 


  • Backed up Outlook contacts immediately.

  • Tried to restore iPhone with iTunes.  iTunes rejected my password (iTunes awhile back forced encryption and passwords with local backups).
  • Recalled about 1 month ago I had to patch/reinstall Office 2019 (errors with Outlook forced this).  Not sure if this was part of the problem, as I’ve synced since then.

  • Tried switching default Outlook accounts (I have Outlook connected with 2 “.live” e-mail accounts).  Another person posted switching default accounts helped them. After another sync, this led to about 612 “contacts” added to my phone.   About 12 looked like they might be “real contacts” and the rest looked like partial e-mails and hyperlinks.


  • Deleted all contacts on iPhone as they were now all "junk" (use 2 fingers to select, drag down, release, press with 1 finger for “long press”, and select delete.

  • Tried changing various settings in iTunes and changing between default Outlook accounts. No luck.
  • Also tried changing settings in “iTunes, info” section to sync contacts with “Windows Contacts” rather than “Outlook” and back (another person found this helpful).  Also tried changing “info, Advanced” setting to “Replace information on this iPhone, Contacts checkbox”.  No luck.  iTunes would not sync Outlook back to my iPhone.


Final solution to get contacts back on phone (found I could sync iPhone with “Windows Contacts” rather than “Outlook” so here is how I did this):


1) Make source file with contacts from Outlook:  Went in Outlook to “File, Open & Export, Import/Export, Export to a file”, then selected my contacts to export as .csv to local drive. Note the export tool caused issues.  I needed to clean up in the .csv.  It added ”~A” characters to some of the phone numbers.  It also added odd ASCII to the header label “First Name”.  In addition, it left the “First Name” column empty.  I cleaned this up in the .csv file with Excel as it seemed easier than on the phone.  Your mileage may vary.  ;-)

  • Cleaned up the Header name “First Name” (removed odd ASCII).
  • Cleaned up the “~A” with replace function (Ctrl H) in Excel (impacted about 20% of the phone numbers).
  • I found the last and first names in the “Name” column and filtered them with: =IF(D2<>"",RIGHT(D2,LEN(D2)-SEARCH("",D2)),"") to get the first names in the column.
  • Save final file in .csv format.


2) Backed up what was in “C:\Users\yourusername\Contacts” (copied folder and renamed).   Then selected all contacts in the “Contacts” folder and deleted them (there are tools at the top of the window to help).

3)  Used tools at top of Window-Folder “C:\Users\yourusername\Contacts” to import my .csv file with

all contacts from Outlook. 

4) Went back to iTunes and:

  • Go to "Summary" in iTunes (on the left side of window). Be sure you are working from "This Computer" and not "iCloud" (look in "Backups section).
  • Changed setting in “iTunes, info” section to sync contacts “Windows Contacts” rather than “Outlook” (look near the top of the window).
  • Changed iTunes “info, Advanced” setting to “Replace information on this iPhone, Contacts checkbox” (Look near the bottom of the window.  You might need to try with and without the box checked.  I had some odd iTunes behavior at this point.). Press "Apply" and wait/watch near the top of the window (it might sync contacts). Might have to also press Sync. Ran sync and now have contacts back on phone. 

iPhone SE

Posted on Feb 19, 2024 4:20 PM

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Posted on Feb 19, 2024 5:34 PM

The easy option is to sync both your computer and iPad to the Outlook server. Go to Settings/Mail/Accounts, tap on the Outlook account, and turn on the switch for Contacts. On Windows also make sure contacts sync to the Outlook server. This will keep your contacts in sync in real time through the Outlook mail server. You will never have to manually sync again.


You can do the same for Calendars, Notes and Reminders.

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Feb 19, 2024 5:34 PM in response to bob-zero

The easy option is to sync both your computer and iPad to the Outlook server. Go to Settings/Mail/Accounts, tap on the Outlook account, and turn on the switch for Contacts. On Windows also make sure contacts sync to the Outlook server. This will keep your contacts in sync in real time through the Outlook mail server. You will never have to manually sync again.


You can do the same for Calendars, Notes and Reminders.

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Mar 13, 2024 8:25 PM in response to Lawrence Finch

Thank you for sharing your thoughts. In the end, this was part of the solution (syncing Outlook and iPhone to Outlook Server on web).


I downloaded a .csv from Outlook of the best remaining contacts and cleaned them up in Excel. I considered putting them back on the iPhone with iCloud, but iClould does not seem to accept .csv format. This lead to syncing the iPhone with Outlook on the Web (as you and many others seem to find works). I tried .vcf format to import them to iCloud, but it did not like the .vcf from Microsoft.


Sadly I have a few reliability issues. I will have to keep watch with Outlook/iPhone:


1) Some Outlook/iPhone calendar events do not transfer well. Had one that stayed on Outlook 2019 correctly, disappeared from Outlook/web version, and shifted about 23 hours back in time on the iPhone/Outlook calendar. I suspect this was due to it being a reoccurring event. I opened it on Outlook 2019, made no changes, and hit save-close. It now shows up on Outlook Web. After about 30 minutes, it is still not updated correctly on the iPhone. I'm thinking the 23 hour change might have something to do with daylight savings time (like to just stay on Standard time like Arizona and Hawaii). ;-)


I think simple calendar entries are ok, but if you have reoccurring items (or use other less common features) your odds of having an incorrect event time/date go up (Outlook 2019, Outlook Web, and iPhone don't seem to exchange these accurately).


2) If you use the custom phone names on iPhone be careful. I have many that were moved/altered or completely lost. I don't think Outlook handles these well when it receives them from iPhone. Your milage may vary. ;-)


Hope this is helpful, and thanks for sharing.

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Contacts on iPhone not syncing with Outlook (not using iCloud)

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