Hi Belle Fine,
Welcome to Microsoft Q&A.
Since a full uninstall/reinstall didn’t change anything, this is usually caused by sync or folder mapping, a filter/view hiding items, or the account being set up to save sent mail to a different folder (common with IMAP, Gmail, or custom domains). Reinstalling Outlook doesn’t reset those server or sync settings.
New Outlook for Mac
1) Reset the folder view (Saved Views can get corrupted)
- Go to View > Reset View (or Current View > Reset) to force the folder to redraw and reveal items that may be hidden.
2) Confirm where the sent mail actually is
- Check Sent Items and Outbox.
- If this is Gmail, your sent message may show in Sent Mail or All Mail (Gmail often doesn’t duplicate it into the Inbox, this can be expected behavior).
3) Compare with webmail
Sign in in a browser (Outlook on the web / Gmail web):
- Shows on the web but not on Mac = Mac sync/view issue
- Not on the web either = send/connectivity or account-side behavior
4) Check Sync Frequency
Make sure the account is allowed to sync frequently enough (a very long sync interval can make Sent items appear “missing” until the next sync cycle).
5) IMAP accounts: confirm Folder Subscriptions (Sent may not be subscribed)
On some IMAP setups the Sent folder won’t sync unless it’s subscribed. In Classic/Legacy Outlook for Mac, you can check this under: Tools > IMAP Folders > ensure Sent (and any provider-specific Sent folder) is checked/subscribed.
6) Rule out VPN/Proxy/network interference
If you’re on a VPN/proxy/corporate network, test sending while connected to a different network to rule out interrupted outbound connections affecting sync.
7) Check the “Sync Issues” folder
If available, check the Sync Issues folder, look for Sync Issues for logs that explain why items aren’t syncing.
8) If still not fixed
Remove and re-add the account (this resets sync + folder mapping more effectively than reinstalling Outlook).
If you share your account type (Outlook.com / Gmail / custom IMAP) and whether Sent items appear in webmail, I can point you to the most likely exact fix.
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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