I’m having two different domains with the same sort of problems with emails. Their sites are live and well and have been for a while. One client started new emails, the other had their emails transferred from Gmail (these emails are months old). The problem we’re running into is a sync issue - their “Sent” inboxes either don’t show up, or they don’t sync up between different devices. So their phone shows they sent an email and their computer doesn’t. All the devices in question are Apple, and all the emails are being accessed on the Outlook app.
I’m wondering if anyone else has run into this issue? I also have apple and outlook app for my emails and do have problems with receiving emails on my phone in general, but I don’t have any sort of disconnect between seeing my sent inbox.
I also have clients on outlook and apple who do not have this issue so I’m really lost on where it’s coming from.
I neither use Apple, Apple Mail, nor Outlook. It could be a sync problem with the tool or IMAP.
But, the first steps I would take are:
Check the DNS settings for the mailboxes in question
Check if the email features work at all with the webmailer
Then check this with one tool and be thorough about the setup. If any device is set up as POP3, that device will download mail locally and cause major sync issues.
Sometimes, the Outlook app itself has a setting that needs adjustment:
Clear the Cache/Reset Account: In the Outlook mobile app, try going into the account settings for the affected mailbox and selecting an option like “Reset Account” or “Clear Cache” to force a fresh sync.
Re-add the Account: The most reliable fix for mobile sync issues is often to delete the email account from the Outlook app on the phone and then re-add it. This forces the app to pull the latest configuration from the server.
One troubleshoot for Apple I found while searching was:
Check the Underlying iOS/macOS Mailbox Behavior This is often the culprit for Apple devices, as the mail client (even when using Outlook) sometimes defers to the iOS/macOS system settings for folder mapping:
On the iPhone/iPad:
Go to Settings > Mail > Accounts.
Select the affected email account.
Tap the account (IMAP) to get to the details.
Select Advanced.
Under MAILBOX BEHAVIORS, tap Sent Mailbox.
Crucially: Ensure that the folder checked is the one ON THE SERVER (usually just called “Sent”) and that it is the same folder on all devices. Sometimes, Apple Mail defaults to an “On My Phone” or local folder.
If any client is configured to save sent messages locally, it breaks the sync. The setting to “Store sent messages on the server” is necessary.
Hi, @Andre — super helpful breakdown!
Just to add one thing that often ends up being the actual culprit in these “Sent not syncing” issues:
Check which Sent folder the server is using in webmail
If you log in to the mailbox through webmail (Outlook Web, Roundcube, cPanel webmail, etc.) you’ll see the real Sent folder the server uses.
All devices (iPhone, Mac Mail, Outlook app) should map to that exact folder.
If one device saves sent emails to a different folder (like “Sent Messages” or “On My iPhone”), the devices won’t match even if IMAP is set up correctly.
After that, resetting the Outlook app or re-adding the account usually forces it to sync to the right folder.
Oh yeah, I got a headache reading through the different folder set ups and deliberately not mention those before being sure everything works fine on the technical site
and deliberately not mention those before being sure everything works fine on the technical site