Can no longer sync Outlook with iPhone calendar after iPhone update to 17.1.1

Post number 5 has been selected as the best answer.


Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
I have an iPhone 12 with a gmail email account. I don't sync my calendar with iCloud, it's sync'd with Microsoft Outlook. At first, search was not working, so I went to iPhone Calendar Search not working iOS 17… - Apple Community
The solution there didn't work. It had me delete my gmail account (not sure if it should have been iCloud account instead). I lost all my emails. I added them back in by creating the account again. However, ALL my calendars are completely blank (iPhone calendar, Awesome Calendar (1 & 2).

When I try to sync iPhone with Outlook, it won't sync (it says "preparing to sync" & then nothing). I really screwed up my calendars.

How can I sync my iPhone calendar with Outlook?

Thank you in advance.
Hi, you may wish to look at using gSyncit Fieldston Software
It can handle sync'ing of calendars and contacts from many providers.
Thank you for your reply. I will note that solution for the future. After a quick look at the description, I notice that it doesn't say it sync's Outlook with an iPhone (& I don't use iCloud calendars, as I find they cause duplicate entries). However, I deleted my 2 "Awesome calendars (1 & 2), downloaded them again, & now everything works.

Thank you again.
My iPhone stopped syncing with Outlook again. I can't use the above suggestion because I use iTunes, not iCloud to backup & to sync the phone with Outlook. I plug my iPhone into the computer (Windows 10) & open Outlook 2016. Outlook recognizes my iPhone because the icon shows up & it also allows me to backup my phone. However, when I try to sync the iPhone, it says copying diagnostic information, then preparing to synchronize, then synchronizing calendars. It will eventually stop (the swirling motion near the upper left corner of Outlook), but the calendars aren't sync'd.

I even tried downloading Outlook from the app store & creating an account (it seemed to require both email & calendar). I set Outlook as my default calendar, but it still wouldn't sync with my iPhone 12. This only started happening a couple days ago & I've made no changes to Outlook or my iPhone immediately before this happened. Does anyone know how to solve this?

Thank you.
Hi again, I use an iPhone 15 with Outlook mobile. Here's how I use gSyncit.
First of all, I use Google Calendar and Google Contacts to store my calendar and contacts data.
On my computer, I use Office 365 with Outlook calendar and contacts.
If I add/change/delete a calendar or contact, then gSyncit updates the Outlook data, as well as Google data.
This ensures my iPhone and Outlook data remain up-to-date.
If you have any questions, please get in touch.
Attached below is a schematic of the gSyncit process.

gSyncit Outline.jpg
Sorry it's taken so long to respond. Thank you for all the information. I really appreciate your expertise & time. What I'm actually trying to do is NOT have a calendar online, just on my desktop Outlook & my iPhone. Nevertheless, I really appreciate your reply. Hope you have a wonderful holiday season!
Hi phrab ... you are welcome.
If you had Googled your issue you would see there are many affected due to the 17.1.1 update.
In some cases it is suggested it's a Microsoft Exchange problem.
In any event, that's why I prefer to use Google calendar/contacts as the primary database.
gSyncit then handles the Outlook<->Google synchronization flawlessly.
I can't use the above suggestion because I use iTunes, not iCloud to backup & to sync the phone with Outlook.

AFAIK, iTunes is heavily depreciated on Windows 64-bit now-days.

For this purpose, you should be using iCloud (like most of us trying to do similar). We have been using current-version of iCloud for Windows here since days of Office-2010,

This works for us for two-different sets of users, Windows-desktops, iPhones, etc.

Microsoft Office 2021 Pro (with Outlook 2021) 64-bit
iCloud for Windows v 14.2 (for Microsoft App-Store)
Apple iPhones (recent SE-2 & SE-3 models)

We have Contacts, Calendars, Photos, iCloud-Drive, etc ... all syncing between desktops, phones, and of course ... .
Similar threads
Thread starter Title Forum Replies Date
P Email address auto-completes work fine on laptop, but no longer on desktop Using Outlook 3
D Outlook 2019 is no longer asking for password ... Using Outlook 5
V Outlook macros no longer run until VB editor is opened Outlook VBA and Custom Forms 0
BartH VBA no longer working in Outlook Outlook VBA and Custom Forms 1
T Outlook 2010 recipient no longer shows in 'Send To' Using Outlook 0
P Outlook 2013 search no longer works Using Outlook 2
P Posts in Folder No Longer Group by Conversation Column After Search Using Outlook 0
K Embedded photos no longer open with Photos or Photo Viewer Using Outlook 7
A Manually Building DisplayName <emailaddr> No Longer Works Using Outlook 0
U Keyboard Remapper no longer works in Outlook Using Outlook 1
J Copy to calendar function no longer working in outlook 365 Using Outlook 5
J Is it no longer possible to suppress Outlook 2019 Invalid Certificate name mismatch security alert via Registry? Using Outlook 1
W Outlook Calendar does not save view any longer! Using Outlook 3
J How to restore field no longer visible in field chooser? Using Outlook 1
T Office 2013 no longer updating automatically Using Outlook 2
RBLampert Outlook 2010 no longer (?) shrinks large images Using Outlook 4
J Calendar data can be viewed on, but no longer syncs to Outlook 2013 Using accounts in Outlook 3
J Cached mode no longer works with NTLM authentication Exchange Server Administration 0
K Outlook 2013 Outlook 2013 no longer syncing 1 of 5 IMAP accounts Using accounts in Outlook 0
Fabio Quintal Reply All no longer working Using Outlook 9
B calendar no longer syncing with Blackberry Using accounts in Outlook 5
P Country name no longer shows in Phone number popup? Using Outlook 5
Maybear Sudden change in Outlook, no image display, email no longer offers suggestions for address Using Outlook 8
T Messages no longer move to quote folder on shared mailbox after user adds -D to folder name Outlook VBA and Custom Forms 1
B Display of Sending Account in Outlook 2007 no longer works Using Outlook 2
B Right click-drag no longer creates hyperlinks Using Outlook 2
S Outlook no longer works with Yahoo Mail Using Outlook 9
C My BCM Database is no longer available to be shared with the Database Tool BCM (Business Contact Manager) 3
C Forwards and Replies from folders no longer going to Sent folder Using Outlook 2
P Outlook contact form no longer requiring Category selection to add new Using Outlook 1
E Double clicking on from email address does no longer open corresponding contact in Outlook 2007 Using Outlook 7
R Outlook 2010 No Longer Deletes Mail From Server Using Outlook 7
M Help - VB Macro no longer work Outlook VBA and Custom Forms 5
M Files in "Attach File" popup menu no longer alphabetical Using Outlook 3
J BCM no longer loads SQLServer BCM (Business Contact Manager) 2
R BCM 2007 no longer showing up within Outlook 2007 BCM (Business Contact Manager) 3
C After Office 2007 SP2 install - Outlook 2007 macro no longer worki Outlook VBA and Custom Forms 11
J BCM no longer loads sqlserver after SP2 upgrade BCM (Business Contact Manager) 2
Z Command button no longer firing after sending custom form over ema Outlook VBA and Custom Forms 1
O Any 3rd party tool that sync (mirror) from Outlook Contacts to Google Contacts? Using Outlook 4
O Any 3rd party tool that sync (mirror) from Outlook Calendar to Google Calendar? Using Outlook 5
B Sync Outlook Public Folders to Contacts Using Outlook 2
C reminders not synced by CodeTwo Sync for iCloud Using Outlook 2
O How to sync (one way) contacts between two Outlook (exchange) accounts? Using Outlook 0
P How to clear out all contacts in iCloud, so I can use iCloud-based sync program Using Outlook 1
S Sync Outlook (2021) tasks with Microsoft To Do Using Outlook 1
F Outlook 2019 Outlook 2019 Add and Sync to New computer Comcast server Using Outlook 2
KeithJB iCloud calendar sync only works one way! Using Outlook 3
Commodore iTunes sync on a new computer - any issues to be expected? Using Outlook 9
J VBA for outlook to compare and sync between calendar Outlook VBA and Custom Forms 1

Similar threads