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If this does not resolve the issue, further investigation will be required to identify why Microsoft Outlook has not synchronized with Office 365.
I am facing an odd issue with Outlook 2011 for Mac.
This is when some work is left unsaved to the Exchange mailbox from the OST files.
In that case, use a trusted professional application which can recover the complete mailbox from the OST file. It retrieves even unsaved work from the old OST file.
Method 1: Moreover, users have to follow the below preventive measures to fix the issue regarding Mac Outlook 2011 not syncing with the Exchange Server: In case, only one folder is not syncing, but other folders are synced properly. This implies that you can re-sync the folder with the Exchange Server by following these steps: The data items from the Exchange Server are saved in the Outlook cache.
If this cache is corrupted or damaged, synchronization issues can occur with the Exchange Server Solution: Empty the cache in Outlook.
OST files, or if particular add-ins are installed in Microsoft Outlook.
Initially, you can confirm if the Sent Items Update has updated the sent item, or if Microsoft Outlook is displaying old data, by logging into the user’s mailbox using Outlook Web Access.
Generally, Mac Outlook users face an issue regarding connectivity of the Exchange Server. The post explains multiple workaround solutions to fix Mac Outlook 2016 not syncing with the Exchange Server.
When the Cached Exchange Mode option is enabled in Microsoft Outlook, no signature is visible for sent messages.
However, if the same messages are viewed with Outlook Web Access (OWA) - or if Cached Exchange Mode is disabled, the signature is visible.
How To Use The Inbox Repair Tool (scanpst.exe) If after repairing Outlook profile and restarting it the issue still persists, the Outlook profile should be recreated: Guide: How Do I Connect A Mail Client To My Mailbox?
You have enabled the Sent Items Update feature in Exclaimer Cloud - Signatures for Office 365, so signatures are visible when a sender views email messages in their Sent Items folder.