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Zimbra Webmail RCE: Archive Exploit to Mailbox Theft operation cover
IntermediateSIEMFirewallEmailPRO

Zimbra Webmail RCE: Archive Exploit to Mailbox Theft

A law firm Zimbra Collaboration server was compromised through a path traversal flaw in the cpio helper invoked during inbound email scanning (CVE-2022-41352). A crafted archive delivered over SMTP caused cpio to drop a JSP webshell directly into the Zimbra web root, giving the actor persistent server-side execution. They then used Zimbra's own CLI tooling to export targeted attorney mailboxes and exfiltrate the data. Reconstruct the chain from the mail delivery through the webshell activity to the data leaving the network.

45m
7 tasks
50 points
Pro

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Investigation Tasks

Complete each task by investigating alerts and submitting your findings.

1

Find the delivery vector

30

The Zimbra mail server began behaving unusually during the early morning window. Something arrived that should not have, and the impact traces back to the moment it was accepted. Determine exactly what the initial delivery looked like.

Hint available
2

Trace the exploit path

35

The archive was not simply stored safely; it triggered something during content scanning. Locate the evidence that shows what was written to disk and where, and identify the full path of the file that ended up in the Zimbra web root.

Hint available
3

Confirm the webshell operator

30

A file sitting in the web root does nothing until someone connects to it. Identify the external IP address that first interacted with the newly planted file over HTTPS.

Hint available
4

Name the data collection technique

25

The actor used the webshell to run Zimbra's own administrative tooling against specific mailboxes. Map the mailbox export activity to its MITRE ATT&CK technique identifier.

Hint available
5

Identify the exfiltration destination

30

After the mailbox exports ran, a large volume of data left the mail server. Determine the external IP address that received it.

Hint available
6

Classify the initial access technique

25

The entire intrusion hinged on a single vulnerability in the way the mail server processed an inbound archive. Map that exploitation step to its MITRE ATT&CK technique.

Hint available
7

Identify the persistence mechanism

25

The actor did not rely on re-exploiting the flaw each time they needed access. They left something behind that gave them a re-entry point on demand. Name the type of artifact that provided that persistent access.

Hint available

7 tasks · 200 points total

Training Tools

Skills You'll Build

Investigate realistic security alerts
SIEM log analysis
Firewall log analysis
Email log analysis
MITRE ATT&CK® technique identification
Triage decisions: escalate, investigate, or close
Evidence collection and documentation
Job-ready incident response methodology
Intermediate

Requires foundational alert triage skills. Multiple data sources to correlate.

Prerequisites

  • Basic understanding of security alerts
  • Familiarity with SIEM concepts
  • Familiarity with Firewall concepts
  • Familiarity with Email concepts

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