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Security audit

Outlook To Gmail

Security checks for vulnerabilities and agentic risk

Overview

This Outlook-to-Gmail migration skill is mostly coherent, but it includes under-guarded live mail-routing changes and a template that may encourage emailing temporary passwords.

Review and revise the runbook before installation or use: require an authorized cutover window, DNS backups, validation and rollback steps before changing MX records, and remove any instruction to send temporary passwords by email. Prefer SSO, password reset, or a secure identity-verified credential delivery process.

Vulnerability Patterns
  • Insecure Skill Coding PracticesFinds exploitable flaws such as hardcoded secrets or command injection
  • Skill Instruction HijackingAlters the agent's session goals or safety constraints when the skill loads
  • Agent Memory PoisoningWrites attacker-controlled rules into memory that affect later sessions
  • Remote Payload Retrieval and ExecutionFetches external code whose behavior can change after review
  • Embedded Malicious CodeShips malicious scripts inside the skill and executes them locally
Findings (1)

T09 · Insecure Skill Coding Practices

Warning
Location
references/client-templates.md:42
Finding
Temporary Password Disclosed in Client Email Template## Vulnerability Details **File Location**: `references/client-templates.md`, lines 42–45 **Vulnerability Type**: Plaintext credential disclosure through email **Risk Level**: Medium ```text **What you need to do:** 1. Go to https://mail.google.com and sign in with your work email 2. Your password is: [temporary password / SSO instructions] 3. Check that your emails and calendar look correct ``` ### Technical Analysis The user-announcement template instructs migration operators to place a temporary account password directly in an email message. Email is not an appropriate secret-delivery channel because messages may be retained indefinitely, forwarded, synchronized to unmanaged devices, included in backups, exposed through mail logs, or accessed through the source mailbox during and after migration. Although the value shown is a placeholder rather than a hardcoded credential, the template encourages an insecure operational practice when populated with a real password. ### Attack Path 1. A migration operator replaces the placeholder with a user's active temporary password. 2. The operator sends the migration announcement by email. 3. A threat actor obtains the message through a compromised mailbox, forwarding rule, shared mailbox, archived copy, backup, mail log, or unmanaged synchronized device. 4. The actor extracts the temporary password. 5. Before the password expires or is changed, the actor authenticates to the user's Google Workspace account. 6. If MFA is absent or bypassable, the actor accesses migrated email and any additional Workspace resources available to that account. ### Impact Assessment Successful exploitation could provide the privileges of the affected Google Workspace user. The accessible scope may include migrated email, contacts, calendars, and other Workspace services authorized for that account. Impact could increase if the affected user has administrative privileges, if MFA is not enforced, or if the password is reused elsewhere. ...[truncated 176 chars]
Remediation
## Remediation Suggestions - Remove the password field from the email template. - Send only SSO instructions or an approved account-activation workflow in the announcement. - Deliver credentials through a secure, identity-verified channel, such as a short-lived single-use activation or password-reset link. - Ensure activation links expire quickly, cannot be reused, and are invalidated after successful use. - Require users to establish a new password during first login rather than sending an operator-selected password. - Enforce MFA for all users and phishing-resistant MFA for privileged accounts. - Avoid sending activation material to the mailbox whose security depends on the disclosed credential. - Document procedures for identity verification, credential expiration, delivery failure, and suspected disclosure. - Review sent announcements, mail archives, and templates to ensure no live credentials remain after migration.
Vulnerability Patterns
  • Prompt InjectionInstruction Override, Hidden Instructions, Exfiltration Commands
  • Data ExfiltrationExternal Transmission, Env Variable Harvesting, File System Enumeration
  • Privilege EscalationExcessive Permissions, Sudo/Root Execution, Credential Access
  • Supply ChainUnpinned Dependencies, External Script Fetching, Obfuscated Code
  • Excessive AgencyUnrestricted Tool Access, Autonomous Decision Making, Scope Creep
Findings (3)

Missing User Warnings

Medium
Confidence
92% confidence
Finding
The skill gives concrete MX, SPF, DKIM, and DMARC cutover instructions that can directly reroute an organization's email flow, but it does not prominently warn that premature or incorrect DNS changes can cause mail outage, misdelivery, or authentication failures. In a migration skill this action is expected, but the lack of explicit guardrails, sequencing checks, and rollback cautions makes accidental operational harm more likely.

Missing User Warnings

Medium
Confidence
95% confidence
Finding
The user announcement template explicitly includes a placeholder for communicating a temporary password to end users, but provides no warning or constraint that credentials must be delivered through a separate secure channel. In a migration context, admins may copy this verbatim and email passwords alongside login instructions, creating a realistic path for credential exposure through mailbox compromise, forwarding, or interception.

Missing User Warnings

Medium
Confidence
95% confidence
Finding
The instruction to remove all existing MX records is operationally destructive and is presented without safeguards, sequencing guidance, or an explicit warning that inbound mail delivery can be disrupted if the cutover is done prematurely or incorrectly. In a migration skill, users are likely to follow this literally, which can cause mail outage, misrouting, or loss of service during transition.