
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.
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Investigation Tasks
Complete each task by investigating alerts and submitting your findings.
Find the delivery vector
30The 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.
Trace the exploit path
35The 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.
Confirm the webshell operator
30A 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.
Name the data collection technique
25The 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.
Identify the exfiltration destination
30After the mailbox exports ran, a large volume of data left the mail server. Determine the external IP address that received it.
Classify the initial access technique
25The 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.
Identify the persistence mechanism
25The 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.
7 tasks · 200 points total
Training Tools
Skills You'll Build
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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