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Odysseus brings your email and calendar together with an AI triage layer built in. The inbox isn’t just a message list — it automatically scores urgency, tags categories, summarizes threads, drafts replies, and filters spam. The calendar is local-first with CalDAV sync, so your events live on your machine and optionally stay in sync with Radicale, Nextcloud, Apple Calendar, or Fastmail. Together, email and calendar are also fully accessible to the agent, so you can ask Odysseus to draft a reply, schedule a meeting, or remind you of an event — all from the chat window.

Email features

Odysseus connects to any standard IMAP/SMTP email provider. Each account is configured independently and can have different triage settings.

AI triage

When new messages arrive, Odysseus can automatically:
FeatureDescription
Urgency scoringAssigns a priority level (low / normal / high / urgent) based on sender, subject, and content
Auto-taggingApplies category labels (work, personal, bills, newsletters, etc.)
Auto-summaryGenerates a one-paragraph thread summary for long email chains
Reply draftsSuggests a draft reply, which appears as a document you can edit before sending
Spam detectionFlags likely spam and optionally moves it to the Spam folder

Per-account routing

Each email account can have its own triage configuration. For example, a work account can use a more aggressive urgency model while a personal account keeps auto-tagging but skips auto-reply drafts.

Adding an email account

1

Open Email Settings

Navigate to Settings → Email and click Add Account.
2

Enter IMAP details

Fill in the IMAP host, port, username, and password. Common settings:
ProviderIMAP hostPortSecurity
Gmailimap.gmail.com993SSL/TLS
Fastmailimap.fastmail.com993SSL/TLS
iCloudimap.mail.me.com993SSL/TLS
Self-hostedyour domain993SSL/TLS
3

Enter SMTP details

Fill in the SMTP host, port, username, and password for outbound sending.
4

Save and test

Click Save. Odysseus connects and syncs the inbox. Initial sync may take a moment for large mailboxes.

CalDAV calendar

The calendar is local-first: all events are stored in Odysseus’s local database and work offline. CalDAV sync pushes and pulls events to and from a remote calendar server.

Supported CalDAV providers

ProviderCalDAV URL format
Radicale (self-hosted)http://localhost:5232/<username>/
Nextcloudhttps://<server>/remote.php/dav/calendars/<username>/
Apple Calendar / iCloudhttps://caldav.icloud.com/
Fastmailhttps://caldav.fastmail.com/dav/

Adding a CalDAV account

1

Open Calendar Settings

Navigate to Settings → Calendar and click Add CalDAV Account.
2

Enter the CalDAV URL

Paste the CalDAV URL for your provider (see table above), along with your username and password (or app password).
3

Sync

Click Save. Odysseus performs an initial sync and imports existing events. Going forward, changes sync bidirectionally.
You can also import calendar data via .ics file — drag and drop an ICS export from any calendar app.

Notification channels

Reminders for notes, tasks, and calendar events are delivered through configurable channels:

Browser push

Native browser Notification API. Works on desktop and mobile (requires notification permission).

ntfy

Push notifications via ntfy. The bundled Docker Compose stack includes ntfy on port 8091. For an external ntfy server, set NTFY_BASE_URL in .env.

Email

Reminder sent via the configured SMTP account.
Configure your preferred channel in Settings → Reminders. See Notes & Tasks for task-level notification setup.

Outlook / Office 365 limitation

Odysseus email uses IMAP/SMTP with username and password authentication. Microsoft has disabled IMAP basic auth for Outlook.com and Office 365 accounts — normal Microsoft mailbox passwords will not work. OAuth 2.0 support is not yet implemented.Workarounds:
  • Use a non-Microsoft email provider (Gmail with an App Password, Fastmail, iCloud Mail, etc.)
  • For Exchange on-premises, ask your admin whether basic IMAP auth is still enabled
  • Watch the Odysseus roadmap for OAuth progress
See docs/email-outlook.md in the repository for the current limitation detail and planned direction.

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