Check ID: exchange_organization_mailtips_enabled
Provider: Microsoft 365
Service: exchange
Severity: MEDIUM
Categories: email-security, e3
Resource type: NotDefined

What this check verifies

Microsoft 365 Exchange Online organization has MailTips fully configured: MailTipsAllTipsEnabled, MailTipsExternalRecipientsTipsEnabled, MailTipsGroupMetricsEnabled, and MailTipsLargeAudienceThreshold 25.

Risk

Absent or lax MailTips reduces user cues, increasing unintended external sends and large-audience blasts, harming confidentiality. Missing group metrics or high thresholds hide risky recipient counts; no OOF/full-mailbox tips cause misdelivery that enables phishing loops and data exfiltration.

Recommendation

Apply defense in depth with consistent MailTips:
  • Enable external-recipient and group-metrics tips
  • Keep MailTipsLargeAudienceThreshold conservative (25)
  • Train users to heed tips before sending Pair with DLP and restricted forwarding to prevent accidental disclosure.

Remediation

Set-OrganizationConfig -MailTipsAllTipsEnabled true−MailTipsExternalRecipientsTipsEnabledtrue -MailTipsExternalRecipientsTipsEnabled true -MailTipsGroupMetricsEnabled $true -MailTipsLargeAudienceThreshold 25

References

Where this check fires

This check runs on every scheduled scan against your Microsoft 365 account. Findings appear at Cloud Security → Findings filterable by Check ID = exchange_organization_mailtips_enabled. To re-evaluate after a fix, hit Run now on the account’s schedule under Cloud Security → Schedules — the next scan re-checks this control and marks the finding fixed or keeps it persistent.
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