Neither Snow Nor Rain Nor MITM... An Empirical Analysis of Delivery Security
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1 Neither Snow Nor Rain Nor MITM... An Empirical Analysis of Delivery Security Zakir Durumeric, David Adrian, Ariana Mirian, James Kasten, Kurt Thomas, Vijay Eranti, Nicholas Lidzborski, Elie Bursztein, Michael Bailey, J. Alex Halderman University of Michigan, University of Illinois Urbana-Champaign, Google
2 Who am I? I am a Ph.D. Candidate at University of Michigan. My research focuses on measurement-driven security. Developing tools for researchers to better measure the Internet Using this perspective to understand how systems are deployed in practice
3 Security in Practice SMTP Submission (TCP/587) Alice smtp.umich.edu
4 Security in Practice SMTP Submission (TCP/587) Alice smtp.umich.edu MX? DNS Server
5 Security in Practice SMTP Submission (TCP/587) Alice SMTP Delivery (TCP/25) smtp.umich.edu MX? DNS Server smtp.gmail.com
6 Security in Practice SMTP Submission (TCP/587) Alice SMTP Delivery (TCP/25) smtp.umich.edu MX? DNS Server smtp.gmail.com POP3/IMAP pop3.gmail.com Bob
7 Security in Practice SMTP Submission (TCP/587) Alice SMTP Delivery (TCP/25) smtp.umich.edu MX? DNS Server smtp.gmail.com POP3/IMAP pop3.gmail.com Bob
8 Security in Practice Alice SMTP Submission (TCP/587) SMTP Delivery (TCP/25) smtp.umich.edu MX? Delivery (SMTP) has no built-in security We ve added SMTP extensions to: 1. Encrypt in transit smtp.gmail.com DNS Server 2. Authenticate on receipt POP3/IMAP Deployment is voluntary and invisible to end users pop3.gmail.com Bob
9 STARTTLS: TLS for SMTP Allow TLS session to be started during an SMTP connection Mail is transferred over the encrypted session Sender (Alice) Mail server (smtp.source.com) Mail server (smtp.destination.com) Recipient (Bob) Passive Eavesdropper
10 STARTTLS Protocol TCP handshake 220 Ready EHLO 250 STARTTLS Sender STARTTLS 220 GO HEAD TLS negotiation Encrypted Recipient
11 Opportunistic Encryption Only Unlike HTTPS, STARTTLS is used opportunistically Senders do not validate destination servers the alternative is cleartext Many servers do not support STARTTLS A publicly-referenced SMTP server MUST NOT require use of the STARTTLS extension in order to deliver mail locally. This rule prevents the STARTTLS extension from damaging the interoperability of the Internet's SMTP infrastructure. (RFC3207)
12 What name to validate? Unlike HTTPS, unclear what name should go on the certificate MX Server (e.g., smtp.gmail.com) - No real security added - MITM returns bad MX record Domain (e.g., gmail.com) - No clear solution for large cloud providers MX? mx.gmail.com smtp.umich.edu DNS Server (1) A mx.gmail.com DNS Server (2)
13 STARTTLS Usage as seen by Gmail
14 STARTTLS Usage as seen by Gmail Yahoo and Hotmail deploy STARTTLS
15 100 Inbound Outbound Percent of Gmail Connections Poodle Vulnerability 0 01/ / / / / / / /2015
16 Long Tail of Mail Operators These numbers are dominated by a few large providers. Of the Alexa Top 1M with Mail Servers: % support STARTTLS - 34% have certificates that match MX server - 0.6% have certificates that match domain (which would allow true authentication) Not currently feasible to require STARTTLS
17 Common Implementations on Ubuntu Software Top Million Market Share Public IPv4 Market Share Default Incoming Default Outgoing Exim 34% 24% Postfix 18% 21% qmail 6% 1% Sendmail 5% 4% MS Exchange 4% 12% Other/Unknown 33% 38%
18 What s the simplest way to eavesdrop on servers that use STARTTLS?
19 Attack 1: STARTTLS Stripping TCP handshake 220 Ready EHLO Sender 250 XXXXXXXX Cleartext 250 STARTTLS Recipient
20 STARTTLS Stripping in the Wild Country Tunisia 96.1% Iraq 25.6% Papua New Guinea 25.0% Nepal 24.3% Kenya 24.1% Uganda 23.3% Lesotho 20.3% Sierra Leone 13.4% New Caledonia 10.1% Zambia 10.0%
21 STARTTLS Stripping in the Wild Country Tunisia 96.1% Iraq 25.6% Papua New Guinea 25.0% Nepal 24.3% Kenya 24.1% Uganda 23.3% Lesotho 20.3% Sierra Leone 13.4% New Caledonia 10.1% Zambia 10.0% Country Reunion 9.3% Belize 7.7% Uzbekistan 6.9% Bosnia and Herzegovina 6.5% Togo 5.5% Barbados 5.3% Swaziland 4.6% Denmark 3.7% Nigeria 3.6% Serbia 3.1%
22 Not Necessarily Malicious Organization Type Corporation 43% ISP 18% Financial Institution 14% Academic Institution 8% Healthcare Provider 3% Unknown 3% Airport 2% Cisco advertises this feature to prevent attacks and catch spam It s unclear if operators know they re inadvertently putting users at risk Signal as to how vulnerable protocols currently are Hosting Provider 2% NGO 1%
23 Attack 2: Lying DNS Servers Rogue Mail server Sender (Alice) Source Mail server Forward MX? IP: Destination Mail Server Recipient (Bob) DNS server
24 Attack 2: Lying DNS Servers Country Slovakia 0.08% Romania 0.04% Bulgaria 0.02% India 0.01% Israel 0.01% Poland 0.01% Switzerland 0.01% Ukraine 0.01% Others 10.1%
25 Authenticating
26 Authenticating DomainKeys Identified Mail (DKIM) Sender signs messages with cryptographic key Sender Policy Framework (SPF) Sender publishes list of IPs authorized to send mail Domain Message Authentication, Reporting and Conformance (DMARC) Sender publishes policy in DNS that specifies what to do if DKIM or SPF validation fails
27 Authentication in Practice SPF 11% No Auth 6% DKIM 2% SPF & DKIM 81% Gmail Authentication
28 Authentication in Practice SPF 11% No Auth 6% DKIM 2% Technology Top 1M SFP Enabled 47% DMARC Policy 1% SPF & DKIM 81% DMARC Policy Top 1M Reject 20% Quarantine 8% Empty 72% Gmail Authentication Top Million Domains
29 Moving Forward Two IETF proposals to solve real world issues: SMTP Strict Transport Security Similar to HTTPS HSTS (key pinning) Authenticated Received Chain (ARC) DKIM replacement that handles mailing lists
30 Gmail STARTTLS Indication Insecure Received Insecure Sending
31 Inbound Gmail Protected by STARTTLS Google Deploys STARTTLS Indicator
32 Current State of Affairs Providers are continuing to roll out transport security and authentication protocols, but many organizations lag in deployment STARTTLS currently provides no protection against active adversaries Several proposals in discussion for bridging these gaps Mail is used to communicate sensitive data and despite being hidden from view, its security is equally important
33 Neither Snow Nor Rain Nor MITM... An Empirical Analysis of Delivery Security Zakir Durumeric University of Michigan
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