Based on recent reports from multiple users, this behavior appears to be related to a change in newer Outlook for Microsoft 365 builds, rather than a local cache issue or client‑specific misconfiguration.
Microsoft has announced the retirement of the Contact Masking feature, which allowed users to hide suggested recipients by clicking the“X” next to a name in the To/Cc/Bcc suggestion list. This change is rolling out across Outlook Desktop, Web, and Mobile and reaches end of support on March 31, 2026. As part of this retirement, previously hidden suggestions may reappear, and the“X” delete icon may no longer be available or behave consistently in newer builds (including Version 2604, Build 19929.20086).
As a result, AutoSuggest entries in classic Outlook may no longer be reliably removable using the usual deletion methods. Entries that appear to be removed can reappear, which may look like looping or inconsistent AutoComplete behavior.
A related discussion Outlook 365 Classic Autocomplete gone strange describes similar, though not identical, symptoms. While that thread doesn’t describe the exact same looping behavior, it reinforces that AutoComplete removal and persistence has become inconsistent in recent versions of classic Outlook, which may explain why the usual deletion methods no longer work reliably.