Why does Outlook keep asking for my password?

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Short answer

Almost always because the saved password is out of date or the outgoing server is missing its authentication setting. Confirm the password works by signing in to webmail first — that tells you whether the problem is the password or the configuration.

If webmail accepts it, remove the saved password in Windows Credential Manager and let Outlook ask again. Repeated prompts with a correct password almost always trace back to a stale stored credential rather than to the mail server.

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