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OAUTH2 with O365/Exchange MFA has been tested successfully on Alpine 2.25.
It does not work with Alpine 2.22 since needed menu items are missing.
This was documented against Alpine 2.25 on Ubuntu 20.04. (built from source)
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Learn how to configure applications and devices for email sending at Dartmouth. Basic Authentication for SMTP ends in September 2025—all setups must switch to OAuth. IP relay requests require security approval, and misuse may result in suspension.
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Want to have someone view your calendar, accept meeting invitations for you, or send email on your behalf? Read about email & calendar delegation and sharing.
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This KBA discusses email options for Linux users accessing our Microsoft 365 mailboxes.
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Dartmouth is retiring SMTP Basic Auth in September 2025; this guide shows how to send-only via smtp.office365.com using OAuth2, preferring delegated permissions (SMTP.Send) for security. App-only (SMTP.SendAsApp) is allowed only when scoped to specific mailboxes via an Exchange service principal, and the article outlines roles (App/Dev vs Email Team), key settings, and quick troubleshooting.
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Microsoft will retire Basic Authentication for SMTP Auth in Exchange Online, requiring all email-sending applications, devices, and legacy email clients to transition to Modern Authentication (OAuth). This change enhances security, reduces phishing risks, and aligns with Dartmouth’s security strategy. Application administrators and users must take action to update configurations before the deadline.
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Changing your personal email through Darthub
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- Microsoft and o365
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Simple guide to accessing Outlook email on an Apple iOS or iPadOS device
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- Microsoft and o365
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Instructions for formatting text in email messages when composing email in Outlook on the Web (BWA)
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- Microsoft and o365
- Outlook
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- Computer, AV, Device, and Printing
- Email & Calendar (outdated)
- Outlook - Email and Calendar
- Knowledge Base
- Computer, AV, Device, and Printing
- Email & Calendar (outdated)
Email security is primarily supported through the Microsoft Office 365 Email service. All email is filtered and sanitized by this service before delivering to users and other services including O365 mailboxes, Gmail, and other forwarding services. User experience and functionality may be slightly different depending on where your mailbox is maintained and this document is intended on providing a high-level overview only.
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These are the steps required to embed a link to your name pronunciation in your Gmail email signature