O365 Email Send and Hard Delete Exfiltration Behavior

name: O365 Email Send and Hard Delete Exfiltration Behavior
id: dd7798cf-c4f5-4114-ad0f-beacd9a33708
version: 6
creation_date: '2025-01-23'
modification_date: '2026-05-13'
author: Steven Dick
status: production
type: Anomaly
description: The following analytic identifies when an O365 email account sends and then hard deletes an email to an external recipient within a short period (within 1 hour). This behavior may indicate a compromised account where the threat actor is attempting to remove forensic artifacts or evidence of exfiltration activity. This behavior is often seen when threat actors want to reduce the probability of detection by the compromised account owner.
data_source:
    - Office 365 Universal Audit Log
    - Office 365 Reporting Message Trace
search: |-
    `o365_messagetrace` Status=Delivered
    | eval mailtime = _time
    | bin _time span=1hr
    | eval user = lower(SenderAddress), recipient = lower(RecipientAddress)
    | eval InternetMessageId = lower(MessageId)
    | join InternetMessageId, user, max=0
      [
      | search `o365_management_activity` Workload=Exchange (Operation IN ("Send*")) OR (Operation IN ("HardDelete") AND Folder.Path IN ("\\Sent Items","\\Recoverable Items\\Deletions"))
      | eval user = lower(UserId), sender = lower(CASE(isnotnull(SendAsUserSmtp),SendAsUserSmtp,isnotnull(SendOnBehalfOfUserSmtp),SendOnBehalfOfUserSmtp,true(),MailboxOwnerUPN)), subject = trim(CASE(Operation IN ("Send","SendAs","SendOnBehalf"),'Item.Subject',Operation IN ("SoftDelete","HardDelete"),'AffectedItems{}.Subject')), -time = _time,file_name = CASE(Operation IN ("Send","SendAs","SendOnBehalf"),split('Item.Attachments',"; "),Operation IN ("SoftDelete","HardDelete"),split('AffectedItems{}.Attachments',"; ")), file_size = CASE(Operation IN ("Send","SendAs","SendOnBehalf"),round(tonumber('Item.SizeInBytes')/1024/1024,2),true(),round(tonumber(replace(file_name, "(.+)\s\((\d+)(b\)$)", "\2"))/1024/1024,2)), InternetMessageId = lower('Item.InternetMessageId')
      | eval sendtime = CASE(Operation IN ("Send","SendAs","SendOnBehalf"),_time)
      | eval deltime = CASE(Operation IN ("SoftDelete","HardDelete"),_time)
      | bin _time span=1hr
      | stats values(sender) as sender, values(ClientInfoString) as http_user_agent, values(InternetMessageId) as InternetMessageId, values(file_name) as file_name, sum(file_size) as file_size, values(sendtime) as firstTime, values(deltime) as lastTime values(Operation) as signature, dc(Operation) as opcount, count by _time,subject,user
      | where opcount > 1 AND firstTime < lastTime
      ]
    | stats values(sender) as sender, values(http_user_agent) as http_user_agent, values(signature) as signature, values(file_name) as file_name, sum(file_size) as file_size, min(firstTime) as firstTime, max(lastTime) as lastTime  count by subject,user,recipient,Organization
    | eval externalRecipient = if(match(lower(recipient),mvindex(split(lower(Organization),"."),0)),0,1)
    | where externalRecipient = 1
    | `security_content_ctime(firstTime)`
    | `security_content_ctime(lastTime)`
    | `o365_email_send_and_hard_delete_exfiltration_behavior_filter`
how_to_implement: You must install the Splunk Microsoft Office 365 Add-on and ingest Office 365 management activity events AND Message Trace events.
known_false_positives: Users that habitually/proactively cleaning the recoverable items folder may trigger this alert.
references:
    - https://attack.mitre.org/techniques/T1114/
    - https://www.hhs.gov/sites/default/files/help-desk-social-engineering-sector-alert-tlpclear.pdf
    - https://intelligence.abnormalsecurity.com/attack-library/threat-actor-convincingly-impersonates-employee-requesting-direct-deposit-update-in-likely-ai-generated-attack
drilldown_searches:
    - name: View the detection results for - "$user$"
      search: '%original_detection_search% | search user = "$user$"'
      earliest_offset: $info_min_time$
      latest_offset: $info_max_time$
    - name: View risk events for the last 7 days for - "$user$"
      search: '| from datamodel Risk.All_Risk | search normalized_risk_object IN ("$user$") | stats count min(_time) as firstTime max(_time) as lastTime values(search_name) as "Search Name" values(risk_message) as "Risk Message" values(analyticstories) as "Analytic Stories" values(annotations._all) as "Annotations" values(annotations.mitre_attack.mitre_tactic) as "ATT&CK Tactics" by normalized_risk_object | `security_content_ctime(firstTime)` | `security_content_ctime(lastTime)`'
      earliest_offset: 7d
      latest_offset: "0"
    - name: Investigate Email for $user$
      search: '`o365_management_activity` Workload=Exchange (Operation IN ("Send")) OR (Operation IN ("HardDelete") AND Folder.Path IN ("\\Sent Items","\\Recoverable Items\\Deletions")) AND UserId = "$user$"'
      earliest_offset: $info_min_time$
      latest_offset: $info_max_time$
intermediate_findings:
    entities:
        - field: user
          type: user
          score: 20
          message: The user $user$ sent and hard deleted an email to an external recipient [$recipient$] within a short timeframe
        - field: recipient
          type: user
          score: 20
          message: The user $user$ sent and hard deleted an email to an external recipient [$recipient$] within a short timeframe
threat_objects:
    - field: subject
      type: email_subject
analytic_story:
    - Office 365 Account Takeover
    - Office 365 Collection Techniques
    - Suspicious Emails
    - Data Destruction
asset_type: O365 Tenant
mitre_attack_id:
    - T1114.001
    - T1070.008
    - T1485
product:
    - Splunk Enterprise
    - Splunk Enterprise Security
    - Splunk Cloud
category: cloud
security_domain: threat
tests:
    - name: True Positive Test
      attack_data:
        - data: https://media.githubusercontent.com/media/splunk/attack_data/master/datasets/attack_techniques/T1114/o365_suspect_email_actions/o365_exchange_suspect_events.log
          source: o365
          sourcetype: o365:management:activity
        - data: https://media.githubusercontent.com/media/splunk/attack_data/master/datasets/attack_techniques/T1114/o365_suspect_email_actions/o365_messagetrace_suspect_events.log
          source: o365_messagetrace
          sourcetype: o365:reporting:messagetrace
      test_type: unit