Attack ChainAIDerived
Hypothetical attack flow derived from CVE metadata – not a confirmed exploit chain
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AccessReach SmarterMail sharing endpoint (AV:N)
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DeliveryQuery attachment download as oracle
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ExploitBrute-force ~19,000 System.Random seeds
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ExecutionDerive DES key and IV
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PersistForge arbitrary sharing token
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ImpactDownload victim emails, attachments, files
Vulnerability Assessment
| Weakness |
CWE
OWASP Top 10:2025
A04:2025 - Cryptographic Failures
ASVS 5.0
V11 - Cryptography Cryptographic PRNG selection
|
| Exploitation Conditions | Exploitation requires that the SmarterMail file/email sharing feature be in use and that the attachment download endpoint be network-reachable by the attacker, since that endpoint is the oracle used to recover the System.Random seed; the target must be running a build prior to 9610. No authentication and no user interaction are needed (PR:N/UI:N), and no prior access to the targeted content is required. What limits exploitation: the AC:H attack complexity - the attacker must send many requests to brute-force the ~19,000-value seed space through the oracle, so it is not a single-shot exploit; impact is confined to reading content (no integrity or availability impact); and it is not automatable per CISA SSVC. Restricting or authenticating access to the sharing/download endpoints removes the oracle and blocks the attack. |
| Impact | Signals are internally consistent and point to a real but non-trivial-to-exploit confidentiality issue rather than a mass-exploitation emergency. The CVSS 4.0 vector (AV:N/AC:H/AT:N/PR:N/UI:N/VC:H) and score of 8.2 reflect network reach and unauthenticated access but explicitly high attack complexity, matching the multi-request oracle brute force over ~19,000 seeds. Impact is confidentiality-only (VC:H, VI:N/VA:N) - the attacker reads content but does not modify or deny service. EPSS is very low (0.03%, 7th percentile) and CISA SSVC records Exploitation: none, Automatable: no, Technical Impact: partial, and this is not in KEV. There is no evidence of active exploitation or public POC. The main risk driver is that no prior access to the targeted content is needed, so successful exploitation exposes any user's mail and files. Net: a legitimate high-severity data-disclosure bug worth prioritized patching for internet-exposed SmarterMail, but not a drop-everything, wormable threat. |
| Exploit ScenarioDerived | An attacker who knows a target SmarterMail hostname repeatedly queries the unauthenticated attachment download endpoint, using its responses as an oracle to identify which of the ~19,000 System.Random seeds is in use. With the seed recovered, they reconstruct the DES key and IV, forge a valid sharing token for any email, attachment, or stored file, and download the victim's content without ever having credentials or a legitimate share link. No public exploit code is identified at time of analysis, and the high-complexity oracle brute force limits this to a motivated, targeted attacker. |
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Alert meAnalysisAIv1 – Jul 24, 2026
Sharing-token forgery in SmarterTools SmarterMail builds before 9610 lets remote unauthenticated attackers decrypt and access arbitrary emails, attachments, and file-storage contents. The file/email sharing endpoints protect tokens with DES-CBC keys and IVs derived from System.Random seeded with only ~19,000 possible values, and the attachment download endpoint leaks enough information to act as an oracle for recovering the seed. No public exploit is identified at time of analysis, and EPSS is low (0.03%), consistent with the high-complexity, non-automatable oracle attack it requires.
RemediationAI
Vendor-released patch: build 9610 (version 100.0.9610) - upgrade every SmarterMail instance to build 9610 or later per the SmarterTools release notes (https://www.smartertools.com/smartermail/release-notes/current). Until the upgrade is applied, reduce exposure by restricting reachability of the file/email sharing and attachment download endpoints: place the server behind a VPN or IP allowlist, or use a reverse proxy/WAF to block or rate-limit unauthenticated access to the attachment download endpoint that serves as the oracle, which raises the cost of the seed brute force at the expense of legitimate anonymous share-link access. Disabling public file/email sharing where it is not required removes the vulnerable token path entirely but breaks external sharing workflows. These are compensating controls only; because the root cause is weak key/IV generation, patching to build 9610 is the sole complete fix. Refer to the VulnCheck advisory (https://www.vulncheck.com/advisories/smartertools-smartermail-build-9610-cryptographic-weakness-via-weak-rng) for details.
Affected VersionsENISA
Affected Packages
Source: OSV (Open Source Vulnerabilities)
Affects your stack
Affects 1 package in euvd
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Technical ContextAI · show details
SmarterMail is a Windows/.NET commercial mail server and collaboration platform. The flaw is a CWE-338 (use of a cryptographically weak PRNG) issue: sharing tokens are encrypted with DES - itself a deprecated 56-bit block cipher - in CBC mode, but the real weakness is that the symmetric key and initialization vector are generated from .NET's System.Random, a non-cryptographic linear PRNG. Because System.Random is seeded with insufficient entropy, the effective seed space collapses to roughly 19,000 candidates. Since the same seed determines both key and IV for every sharing token, recovering the seed reconstructs the full keystream material, and the unauthenticated attachment download endpoint returns behavior that distinguishes correct from incorrect seed guesses, functioning as a decryption/validation oracle. The single affected CPE is cpe:2.3:a:smartertools_inc.:smartermail:*.
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Severity by source
CVSS:4.0/AV:N/AC:H/AT:N/PR:N/UI:N/VC:H/VI:N/VA:N/SC:N/SI:N/SA:N
Network-reachable and unauthenticated (AV:N/PR:N), but AC:H for the multi-request seed brute force via the oracle; confidentiality-only (C:H, I:N/A:N) since content is read, not altered.
Primary rating from Vendor (VulnCheck).
CVSS VectorVendor: VulnCheck
Lifecycle Timeline
4DescriptionCVE.org
SmarterTools SmarterMail builds prior to 9610 contain a cryptographic weakness in the file and email sharing endpoints that use DES-CBC encryption with keys and initialization vectors derived from System.Random seeded with insufficient entropy, reducing the seed space to approximately 19,000 possible values. An unauthenticated attacker can use the attachment download endpoint as an oracle to determine the seed in use and derive encryption keys and initialization vectors to forge sharing tokens for arbitrary emails, attachments, or file storage contents without prior access to the targeted content.
Executive ViewAI
Organizations running SmarterMail versions before build 9610 face direct risk of email compromise and data theft through a vulnerability in the sharing-token mechanism (CVE-2026-40514). Remote attackers without authentication can access sensitive emails, attachments, and stored files. This risk warrants immediate vulnerability patching to prevent potential breaches and ensure compliance with data protection requirements.
Apply vendor patch.
Threat Intelligence Overview
How this decision was reached
The engine reads each signal below and applies a fixed list of rules from top to bottom. The first rule that matches sets the recommended action – like a statement, every line is shown.
What every action level means
SSVC AssessmentENISA
Priority Score
Attack Technique
Information disclosure occurs when an application unintentionally exposes sensitive data that aids attackers in reconnaissance or directly compromises security.
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EUVD-2026-25856
NVD
CVE.org
EPSS
Vulnrichment
VulDB
GitHub PoC
Exploit-DB