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modern-authentication-troubleshooting2016
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  • Latanya Connal
  • modern-authentication-troubleshooting2016
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Opened Nov 24, 2025 by Latanya Connal@latanyaconnal6
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My accounts in Mail app stopped to sync p Apple Community

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I am aware of the difference between Gmail's labels vs. Outlook's folders, but I would expect that Gmail does what is necessary to make the folders appear correct over the IMAP connection to Outlook. For example, if I drag a message from Outlook's All Mail folder to Trash, I see that message disappear from the Inbox folder after a short delay. Hence, the trashing of messages is registering on Gmail. It's just that the contents seem completely disconnected from what I see using webmail.

Why IMAP Folder is Not Properly Syncing?

Meanwhile, the "connecting" or "Checking for mail..." just stays on the bottom status bar of the mail app. I deleted the Apple Mail Troubleshoot Office 365 Sync and Login Issues app from the phone, reinstalled from the App Store. So only wait when some "smarties" from apple IT solve problem in app ... Apple programmers use no CD/CI - simple sometimes update by "sales-manager requests", and without any critical-bug-checks ... Full cleanup of ALL accounts is not a solution(and re-add even helps not).

Chosen Solution

I work in a small company and for the past 2 weeks we've been having issues with customer support Outlook account. The account is used as IMAP in all customer support clients, every time you set up the mail in anyones computer rebuild Outlook data file quickly it just sync 30-50GB ost files... And because of the size, this is making the mail simply stop working after one day of normal use, forcing the users to end outlook process to make the mail sync again properly... But only when you close/open the mail again.

IMAP folder sync issue in the new Outlook (moved emails not syncing to webmail)

When you synchronize mail using IMAP between Gmail and a desktop mail client such as Outlook, there is a necessary delay between changes made independently at both ends being synchronized in both directions. When you are accessing Gmail via the web application everything is hosted on Google's cloud servers. So it must be something in IMAP protocol handling on the old server that makes the iOS Mail app go out of sync or crash the syncing mechanism on the iOS device. Maybe some encoding behavior or just a different linefeed or something that has changed over the years... Otherwise why even have the ability to auto-sync? If I need to click on each folder to force the sync/download from server then auto sync serves no purpose.

These are the common reasons why the IMAP folder is not syncing.With the help of this, you can also ensure that the server settings are properly configured or not.I have half dozen mail accounts a few microsoft a gamil and some other ones and there is no difference they are all acting the same.I use both webmail and Outlook desktop client to access my Gmail.If the server is down and you are experiencing issues, the problem IMAP folder is not syncing occurs.So, properly follow the above steps and backup your data from IMAP folders.So it must be something in IMAP protocol handling on the old server that makes the iOS Mail app go out of sync or crash the syncing mechanism on the iOS device.

My accounts in Mail app stopped to sync post update

When you are dealing with any problem, it is important to understand the reasons behind the issues. Below are some causes that contribute to the problem. There are various variables at play here however, generally speaking, Outlook performs best when operating as a front end for Microsoft Exchange and Gmail when accessed via a web browser. I’ve never heard of setting a path before for email, so apologies if this is a simple solution to those who come across this in the future. If disable faulty add-ins in Outlook you can, turn off IMAP, require 2FA, and use the native outlook client. Hate to be a Debbie Downer, but why are you using IMAP?

J.D. Power 2024 Certified Assisted Technical Program, developed in conjunction with TSIA. Based on successful completion of an audit and exceeding a customer satisfaction benchmark for assisted support operations. For faster and more reliable delivery, add to your trusted senders list in your email software. EDIT - the folder check add-on is for older versions of TB. We will never ask you to call or text a phone number or share personal information.

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Reference: latanyaconnal6/modern-authentication-troubleshooting2016#3