Hi Keith Hummel,
Welcome to Microsoft Q&A forum.
I understand you no longer see sent messages in Classic Outlook and the Sent folder under your Gmail (IMAP) account appears empty. That can be very concerning when you rely on Sent items for record keeping.
I reviewed the Q&A Assist answer on the thread. The checks it suggests are generally appropriate for this scenario. Have you had a chance to try the Q&A Assist steps already, and did anything change afterward?
To add a bit more helpful context, there is one Gmail IMAP detail that often explains why Sent looks “missing” in Outlook:
1, Confirm the Gmail “Sent Mail” folder is actually available to IMAP and subscribed in Outlook
In Classic Outlook, IMAP accounts only sync folders that are subscribed. Microsoft documents how to query and subscribe to IMAP folders in Outlook. Reference: Choose which IMAP account folders appear in Outlook.
For Gmail specifically, Microsoft also notes that Outlook needs access to Gmail folders and recommends ensuring “Show in IMAP” is enabled for Sent Mail so it can appear and sync. Reference: Fix problems connecting your Google account to the Microsoft Cloud.
2, If sent items are not being saved locally, confirm the “save sent items” option is enabled
If the “Save copies of messages in the Sent Items folder” option is disabled, sent mail will not be saved in Sent Items. Reference: Emails aren't saved to Sent Items - Outlook | Microsoft Learn
3, About IMAP limitation
Microsoft also notes that for IMAP accounts you cannot change where sent items are stored, although Outlook can be configured to stop saving sent items locally if needed. Reference: Change where sent email messages are saved.
One quick question so the next step can be targeted: do you see the sent messages correctly in Gmail on the web under Sent Mail?
I hope this helps clarify what is most likely happening, and I will be glad to continue once you share what you observe.
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