Aug 31, 2020

Emails not syncing past a specific date on all iOS devices

My Gmail account is not syncing emails past a specific date (Aug 24) to third party email clients on my two iOS devices. This is the case in both the Mail, and Outlook email clients. The Gmail app is working fine.

Steps taken to try and resolve include: Resetting the account in Outlook; removing and re-adding Google account to both Outlook and iOS Accounts; deleting and re-installing the Outlook and Mail apps; restarting devices between re-installs and adding accounts. 

Results: In all of the above cases, emails re-synced up until Aug 24th. No new emails are being downloaded, and the Outlook app appears to hang on 'Updating...' when trying to force a re-sync after all prior emails have been downloaded.

Only thing that hasn't been done is a full device reset - however, given that the same issue exists between iPad and iPhone, it seems more like an Account issue. My only other thought is potentially doing a password change, but it that doesn't jive with the fact that the account can authenticate and sync emails to a specific date.

Any thoughts or advice welcome. Thank you!
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Recommended Answer
Oct 27, 2020
Marking response provided by Craig S 1374 as solution, but should clarify that it was actually a comment in their linked issue that has the resolution, specifically this thread: https://support.google.com/mail/thread/71739044?hl=en&msgid=71739044

Suspected Root Cause:
In summary, Google considers that emails encrypted using S/MIME in Gmail is compatible only with GSuite accounts, not free Gmail accounts. So basically, if someone sends you an encrypted email in this format, then it creates a block when trying to sync messages using IMAP to third-party email apps/clients (e.g. Outlook or Apple Mail).

Recommended Fix:
For those with a similar issue, I recommend going through all the emails received on the day that messages stopped sync'ing to Outlook/Apple Mail and figure out which message might be encrypted and thus blocking all other messages. Locate the message in Gmail (web or mobile version) and either delete it or move it to a folder that you aren't sync'ing through IMAP. If you can, delete/archive all messages received on that date - see if that solves this issue.

In my case, the offending email  was an encrypted bank statement. Once deleted, emails started sync'ing to the current date in Outlook on iOS devices.
Original Poster David Barkhausen marked this as an answer
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Recommended Answer
Oct 23, 2020
I faced the same problem, but managed to track down the cause in my case.  See https://support.google.com/mail/thread/70918295?hl=en to see if it helps any of you

Google definitely has a bug on there end, but continues to ignore it.  They clearly don't care about their users.

If you haven't already, I also recommend opening a support case with Apple.  I've provided all the details to them as well and been told that they won't implement better error handling in their mail application unless they get enough reports of a problem.
Original Poster David Barkhausen marked this as an answer
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All Replies (18)
Sep 14, 2020
My wife's phone has the exact same issue, gmail through the built in iOS mail has stopped syncing as of a few days ago. Sent items are still syncing as are drafts. 

I deleted the account, rebooted the phone, and then re-added it to force a complete refresh. The inbox is now stuck at the exact same mail again.
Sep 29, 2020
I have the same problem. My iPhone Mail stopped syncing 12 September. Now my Macbook Mail app doing the same. I tried deleting the accounts and adding again. Did not work!
Update - now receiving mails on my Macbook but only mails dated after I did the account delete and added again. All my old mails on gmail server still not syncing to my Mail app.

Update: all mails synced on Macbook - seems the problem corrected itself. 
Now the iPhone must just do the same!
Last edited Sep 29, 2020
Oct 1, 2020
I have exactly the same problem from 21 August 2020! I have several gmail accounts on iPhone with the Apple App and only the account stopped importing mails into the inbox! All iPhone software up to date and took all steps mentioned by others to this thread. This is getting rediculous and Google seems to ignore our request for assistance!
Oct 10, 2020
Me also. Stopped syncing to iOS outlook. All other clients/platforms work ok. Also trying to send new email on iOS outlook generates failed to send error.
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