Using New Outlook on Windows for personal email, calendar, and contact management
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Hi CULLEN Denise,
Welcome to Microsoft Q&A.
Thanks for sharing the error details. The JSON with a SessionId and INTERACTIONREQUIRED is typical of a Modern Authentication (Microsoft sign-in) prompt that can’t complete, which can happen when Outlook attempts a Modern Authentication flow that can’t complete for some non‑Microsoft mail providers. With BigPond/Telstra, you’ll usually get the best results by adding it strictly as IMAP, not as an Outlook.com/Google-type account.
Important: Add it as IMAP (don’t pick Outlook.com / Google)
When adding the account, choose IMAP (or “Advanced setup” > IMAP) and enter Telstra’s server details.
Telstra IMAP settings
- Incoming (IMAP):
imap.telstra.com— Port 993 — SSL - Outgoing (SMTP):
smtp.telstra.com— Port 465 (SSL/TLS) or 587 (STARTTLS) - Username: your full BigPond/Telstra email address
- Ensure SMTP authentication is ON (Outgoing server requires authentication)
If you want to avoid lockouts
Before retrying, remove the account from Outlook so it stops repeatedly attempting sign-in (repeated failures can trigger temporary blocks).
If you have 2-step verification (or Outlook still won’t sign in): use an App-Specific Password
Some Telstra mailboxes require an app-specific password for Outlook/IMAP even when your normal password works in webmail.
To generate it:
- Sign in to Telstra Webmail
- Settings > Accounts
- Under App-specific password, select Generate Password
- Use that generated password in Outlook (instead of your normal password)
Note: The exact menu names may vary slightly depending on your Telstra account type.
New Outlook vs Classic Outlook
If you’re using New Outlook, and it keeps looping with INTERACTIONREQUIRED, try adding the mailbox in Classic Outlook using manual IMAP as this is often more reliable for IMAP providers.
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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