10.2 Outlook Rules

Policy → Rules → Outlook Rules controls what happens when users send email and meeting requests: whether a label is mandatory, how attachments influence the email’s label, and which recipient domains label a message automatically. Content rules from 10.1 also run at Send; this page holds only the Outlook-specific settings.

The page has two cards:

Which Outlook does what

Email enforcement

What happens when a user clicks Send (classic Outlook)

Ada’s Outlook COM add-in runs these steps in order. The first step that cancels the send ends the sequence; the user sees the reason.

1. Masking — Mask rules (section 10.1) on subject + body; confirmation; Cancel stops the send.
2. Warnings — Warn rules; Confirm-mode Cancel stops the send.
3. Already labeled?
   • Content is classified again (the latest content counts, not the content at the time the label was chosen).
   • An Enforce rule requiring a higher label → the label is raised (Label raised to meet policy); requiring a different label of equal/higher rank → blocked (requires exactly).
   • Attachment gates (below), then the body marking is refreshed. Done.
4. Not labeled — recipient-based auto label — if a mail rule covers every recipient, its label is applied (see below), the attachment gates run, done.
5. Not labeled — Enforce rule — the required label is applied silently (Label applied (auto-rule)), attachment gates run, done.
6. Require a label off — no window; attachment gates still run; the message leaves unlabeled.
7. Require a label on — the classifier opens (pre-selected: highest of recommendation, top attachment label, default label). Cancel → Send blocked — no label. A label below an Enforce requirement → requires at least. Then the attachment gates, then the label is applied (Label applied (on send)).

Attachment gates (same order everywhere): the item’s own No-send label → unclassified attachment → attachment with a No-send label → attachment above the item’s label (raise or block).

In Outlook on the web, new Outlook and Outlook for Mac the sequence is the same with these differences: masking is automatic; a labeled message whose content requires another label is blocked (no silent raise); the default label is not used at Send; and when the content suggests a higher label than a mail rule (below), the user gets a Smart Alert instead of the classifier window. If the policy cannot be verified at Send, the web add-in blocks the send (“Classification could not be verified, so sending was blocked.”); if no policy was ever received on the device, sending is allowed.

Meetings and calendar items

In classic Outlook, meeting requests and appointments with attendees go through the same send checks as email: content classification, Enforce, attachment gates (on the attachments of the outgoing request), recipient-based auto label and the label-on-send classifier. The final label is also written to the outgoing meeting request. Masking, Warn rules and recipient exceptions are applied to email messages only.

Organizer handling (classic Outlook). When a meeting is sent, Outlook includes the organizer in the attendee list (sometimes as a Required attendee, e.g. from the Scheduling Assistant). Ada removes the organizer — identified by SMTP and Exchange address — before checking mail rules, so a rule for contoso.com still applies to a meeting sent by a fabrikam.com organizer to contoso.com attendees only.

Recipient-based auto label

What it does. A mail rule labels an outgoing unlabeled message silently when every recipient (To, Cc, Bcc) belongs to one of its domains. No classifier window appears.

List columns

The mail rule drawer (title = rule name or New mail rule, subtitle “Edit recipient-based auto label”)

The Enabled switch and group exclusions are set in the list, not in the drawer. A new mail rule is enabled.

Matching rules

Creating a mail rule

1. Policy → Rules → Outlook Rules. Choose Scope (Default or a group).
2. Click + Add Default mail rule (or + Add mail rule to Group).
3. Enter Policy name, choose Label, tick Groups if needed, and enter Recipient domains.
4. Click Save, then Publish & Sign.
5. Test: from a client, send an unlabeled message to an address in the domain — it should leave with the label and no window; add an outside recipient — the normal flow (classifier or block) should run.

Recipient lists compared

Three features use recipient lists; they look alike but do different things.

Worked examples

Example A — Any external recipient → require a label

Goal: internal mail flows without prompts; anything leaving the organisation must be labeled consciously.

1. Email enforcement: tick Require a label before sending email, Save.
2. Add a mail rule Internal mail: Label Internal, Recipient domains contoso.com, contoso.com.tr, contoso-group.com.
3. Publish.

Result: a message to colleagues only is labeled Internal silently. As soon as one external address is in To, Cc or Bcc, the rule no longer covers all recipients and the sender must choose a label (or an Enforce rule labels it).

Example B — Subsidiary mail labeled “Group Internal”

Mail rule Subsidiaries, Label Group Internal, domains fabrikam.com, fabrikam.de, Groups: Finance only. Finance users’ mail to subsidiaries is labeled automatically; other groups are unaffected.

Example C — Never email Strictly Confidential documents outside

Chapter 8: mark Strictly Confidential as a No-send label with send exception contoso.com. Here: Attachment label check on, Label from attachments on. Attaching such a document raises the email to Strictly Confidential; sending to an outside recipient is blocked with the list of recipients that are not allowed.

Audit events written by Outlook rules

Troubleshooting