Dear @David Free,
Thank you for posting your question in the Microsoft Q&A forum.
I completely understand how frustrating this feels, especially if this workflow worked well for you in the classic version of Outlook.
In Classic (Old) Outlook, this experience felt seamless because contacts and calendars were handled locally, which allowed more flexibility when working with multiple accounts. In New Outlook, however, the architecture has changed. Each account (Microsoft, IMAP, Google, Yahoo, etc.) now maintains its own separate contacts and calendars, and at this time there is no built‑in cross‑account sync capability. Changes made in one account will not automatically sync to others, which is why exporting and importing contacts is currently the only supported workaround. This behavior is by design in New Outlook, which aligns closely with Outlook on the web and uses a cloud‑based model where contacts are stored and synced per account only.
In this case, I recommend you continue using Classic Outlook, which still supports more advanced multi‑account contact workflows and remains fully supported.
Note: Please be reassured that if there is any update from Microsoft, I will update to you as soon as possible
Moreover, I totally agree with you that automatic contact and calendar syncing across accounts is an important feature, especially for users managing multiple providers and devices. To ensure your feedback reaches the right teams, I highly recommend submitting your feedback directly to Microsoft Ideas · Community, where our product development team can know your requirements and ideas for product improvements. If enough users raise ticket for the same idea, Microsoft may consider adding this feature in the future.
Note: As Microsoft Community moderators, please note that we are not involved in product design decisions and do not have direct access to the development roadmap, we want to assure you that your feedback has been acknowledged and is valued.
I hope this information is helpful. If you have any other questions please feel free to reach out
Thank you for your patience and understanding. I'm looking forward for your reply.
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