Neither Snow Nor Rain Nor MITM... Real World Delivery Security
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1 Neither Snow Nor Rain Nor MITM... Real World Delivery Security Zakir Durumeric University of Michigan
2 How is your everyday protected?
3 Neither Snow Nor Rain Nor MITM... An Empirical Analysis of Delivery Security Zakir Durumeric, David Adrian, Ariana Mirian, James Kasten, Michael Bailey, J. Alex Halderman University of Michigan, Illinois Kurt Thomas, Vijay Eranti, Nicholas Lidzborski, Elie Bursztein Google ACM Internet Measurement Conference (IMC 15)
4 Delivery SMTP Submission (TCP/587) Alice smtp.umich.edu
5 Delivery SMTP Submission (TCP/587) Alice smtp.umich.edu MX? DNS Server
6 Delivery SMTP Submission (TCP/587) Alice smtp.umich.edu SMTP Delivery (TCP/25) MX? DNS Server smtp.gmail.com
7 Delivery SMTP Submission (TCP/587) Alice smtp.umich.edu SMTP Delivery (TCP/25) MX? DNS Server smtp.gmail.com POP3/IMAP pop3.gmail.com Bob
8 Delivery SMTP Submission (TCP/587) Alice smtp.umich.edu SMTP Delivery (TCP/25) MX? DNS Server smtp.gmail.com POP3/IMAP pop3.gmail.com Bob
9 Delivery SMTP Submission SMTP has no built-in security (TCP/587) Alice smtp.umich.edu We ve added SMTP extensions to: SMTP Delivery (TCP/25) MX? Encrypt in transit 2. Authenticate on receipt DNS Server However deployment is voluntary smtp.gmail.com and invisible to end users POP3/IMAP pop3.gmail.com Bob
10 STARTTLS: TLS for SMTP Allow TLS session to be started during an SMTP connection Sender (Alice) Recipient (Bob) Mail is transferred over the encrypted session Mail server (smtp.source.com) Mail server (smtp.destination.com) Eavesdropper
11 STARTTLS Protocol TCP handshake 220 Ready EHLO 250 STARTTLS STARTTLS 220 GO HEAD TLS negotiation Encrypted
12 Opportunistic Encryption Only A publicly-referenced SMTP server MUST NOT require use Unlike HTTPS, STARTTLS is used opportunistically of the STARTTLS extension in order to deliver mail locally. This rule prevents the STARTTLS extension from Senders do not validate destination servers the alternative is cleartext damaging the interoperability of the Internet's SMTP infrastructure. (RFC3207) Many servers do not support STARTTLS
13 What name to validate? Unlike HTTPS, unclear what name MX? should go on the certificate mx.gmail.com smtp.umich.edu DNS Server (1) MX Server (e.g., smtp.gmail.com) A mx.gmail.com - No real security added - MITM returns bad MX record DNS Server (2) Domain (e.g., gmail.com) - No clear solution for large Two Step DNS Resolution cloud providers
14 What name to validate? Unlike HTTPS, unclear what name should go on the certificate Cloud Provider % Top 1Mil Gmail 16% GoDaddy 5% Yandex 2% QQ 1% OVH 1% 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
15 STARTTLS Usage as seen by Gmail
16 STARTTLS Usage as seen by Gmail Yahoo and Hotmail deploy STARTTLS
17 100 Inbound Outbound Percent of Gmail Connections Poodle Vulnerability 0 01/ / / / / / / /2015
18 Cipher Selection Provider Incoming Key Exchange Incoming Cipher Certificate Name Outgoing Key exchange Outgoing Cipher Gmail ECDHE AES128-GCM match ECDHE AES128-GCM Yahoo ECDHE AES128-GCM match ECDHE RC4-128 Microsoft ECDHE AES256-CBC match ECDHE AES256 Apple icloud ECDHE AES128-GCM match DHE AES128-GCM Facebook mail RSA AES128-CBC mismatch ECDHE AES128-CBC Comcast RSA RC4-128 match DHE AES128-CBC AT&T ECDHE AES128-GCM match ECDHE RC4-128
19 Long Tail of Mail Operators These numbers are dominated by a few large providers Of the Alexa Top 1M Domains with Mail Servers: % support STARTTLS - 34% have certificates that match MX server - 0.6% have certificates that match domain
20 Long Tail of Mail Operators These numbers are dominated by a few large providers Of the Alexa Top 1M Domains with Mail Servers: % support STARTTLS - 34% have certificates that match MX server - 0.6% have certificates that match domain Needed to verify valid destination!
21 Common Mail Software 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%
22 Common Mail Software 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%
23 Common Mail Software 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%
24 StartTLS protects against passive eavesdropping. Nothing else.
25 What s the simplest way to eavesdrop on servers that use StartTLS?
26 STARTTLS Stripping (1) TCP handshake I wish I supported XXXXXXXX :( 220 Ready EHLO 250 XXXXXXXX 250 STARTTLS Cleartext
27 STARTTLS Stripping (2) TCP handshake 220 Ready EHLO 250 XXXXXXXX STARTTLS XXXXXXXX WTF??? Cleartext
28 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%
29 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%
30 Not Necessarily Malicious Organization Type Corporation 43% ISP 18% Financial Institution 14% Cisco advertises this feature to prevent attacks and catch spam Unclear if operators know they re putting users at risk Academic Institution 8% Healthcare Provider 3% Unknown 3% Airport 2% Hosting Provider 2% NGO 1%
31 Lying DNS Servers Rogue Mail server Sender (Alice) Source Mail server MX? IP: Forward Malicious DNS server Destination Mail Server Recipient (Bob)
32 DNS Spoofing Seen by Gmail 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%
33 Authenticating
34 Authenticating Sender Policy Framework (SPF) Sender publishes list of IPs authorized to send mail DomainKeys Identified Mail (DKIM) Sender signs messages with cryptographic key Domain Message Authentication, Reporting and Conformance (DMARC) Sender publishes policy in DNS that specifies what to do if DKIM or SPF validation fails
35 Sender Policy Framework (SPF) 1. Sender publishes a DNS record that specifies what servers can send mail for the domain: _spf.example.com IN TXT "v=spf1 ip4: /20 ~all" 2. Recipient looks up sender s SPF policy and and checks if the message was sent from an allowed host
36 Domain Keys Identified Mail 1. Sender publishes a cryptographic public key in DNS record _domainkey.gmail.com. 300 IN TXT "k=rsa\; p=miibijan AQAB 2. Sender attaches cryptographic signature in a message s headers DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=gmail.com; s= ; h=from:date:...:subject:to; bh=rjhxzraob5/q4159go00ye=; b=yzmpde8kxvpfx anudyxvgc 3. Recipient looks up key and checks a message s signature
37 Domain Keys Identified Mail 1. Sender publishes a cryptographic public key in DNS record _domainkey.gmail.com. 300 IN TXT "k=rsa\; p=miibijan AQAB 2. Sender attaches cryptographic signature in a message s headers DKIM-Signature: Impossible to know if a domain v=1; uses DKIM a priori. a=rsa-sha256; c=relaxed/relaxed; d=gmail.com; s= ; h=from:date:...:subject:to; bh=rjhxzraob5/q4159go00ye=; b=yzmpde8kxvpfx anudyxvgc 3. Recipient looks up key and checks a message s signature
38 Domain Message Authentication, Reporting and Conformance (DMARC) 1. Sender publishes a mail policy in a DNS record: _dmarc.yahoo.com IN TXT v=dmarc1; p=reject; pct=100; rua=mailto:dmarc_y_rua@yahoo.com;" 2. Recipient checks for a sender s policy and if they should reject messages without signatures, and/or report them to the sender
39 Authentication from Gmail Perspective SPF 11% No Auth 6% DKIM 2% SPF & DKIM 81% Delivered Gmail Messages
40 Authentication from Gmail Perspective SPF 11% No Auth 6% DKIM 2% Technology Top 1M SPF Enabled 47% DMARC Policy 1% DMARC Policy Top 1M SPF & DKIM 81% Reject 20% Quarantine 8% None 72% Delivered Gmail Messages Top Million Domains
41 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
42 Tracking Progress Censys STARTTLS Report Google Transparency Report
43 Conclusion Mail community has started to deploy new security extensions, but progress is slow for many organizations Unfortunately, until near pervasive deployment, it is unlikely that operators will require encryption Clear that StartTLS is not a long-term solution attacks are pervasive in many regions Both researchers and mail operators have a lot of remaining work to do
44 Neither Snow Nor Rain Nor MITM... Real World Delivery Security Zakir
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