Managing personal Outlook.com account settings, security, and privacy
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Hi, Jeremy Willuhn
Thanks for explaining what you’ve already tried. Your tests point toward a service-side sending problem rather than Apple Mail or your signature; the IP-based Sender Support route is intended for problems sending to Outlook.com, not sending from your Hotmail account.
Here are some suggestions you can try:
Open Contact Microsoft Support using another personal Microsoft account, since sign-in on the support page failed with the affected account. Enter “Outlook.com sending blocked,” select Get Help, then Ask our Support Assistant and request for a live chat support session if offered, and choose the available chat option. Using another account to reach support is an established alternative, although chat availability varies.
Ask the agent to help route this to Outlook.com support for an outbound sending restriction review. Provide both existing request numbers, the full bounce reports, and the October 10 start date. Also explain that replies to their support address fail with 5.7.64, so email follow-up is currently unusable.
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