SMTP [in]security. Ian Foster Jon Larson
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1 SMTP [in]security Ian Foster Jon Larson
2 Goals 1. Does the global system currently provide security against passive adversary (eavesdropper)? 2. Against an active adversary (man in the middle)?
3 Brief History of SMTP Many standards used on ARPAnet in 1970s Combined into SMTP by RFC 821 in 1982 Support for extensions (ESMTP) added by RFC 1869 in 1995
4 SMTP Primer 1. Mail User Agent (MUA) sends message to Mail Submission Agent (MSA) using SMTP, HTTP, etc. 2. MSA sends to intra-domain Mail Transfer Agent (MTA) using SMTP 3. MTA queries DNS server to find MX records for destination user 4. MTA of one domain sends to MX server of another using SMTP 5. MX server passes message to Mail Delivery Agent (MDA) 6. User retrieves using POP3/IMAP If encryption happens, it is done per-link Source:
5 Alice and Barbara Source:
6 Security in SMTP Early versions had no built in security All s sent in plaintext RFC 3207 in 2002 added support for TLS Encrypts connection between SMTP servers Use of TLS is not required Only encrypts link between servers Violates end-to-end principle
7 NSA Red Team Alice Barbara Source: Anonymous Eve LRRR Ruler of the planet Omicron Persei 8
8 Methodology 1. Query DNS to determine IP addresses of domain s MX servers 2. Establish connection on port Issue EHLO command a. Valid response indicates server supports ESMTP 4. Issue STARTTLS command a. Valid response indicates server supports encryption 5. Start SSL connection and collect cipher information
9 Methodology $ host ucsd.edu ucsd.edu has address ucsd.edu mail is handled by 5 inbound.ucsd.edu. $ telnet inbound.ucsd.edu 25 Trying Connected to Escape character is '^]'. 220 iport-acv2-in.ucsd.edu ESMTP > EHLO ucsd.edu 250-iport-acv2-in.ucsd.edu 250-8BITMIME 250-SIZE STARTTLS > STARTTLS 220 Go ahead with TLS $ host hotmail.com hotmail.com has address hotmail.com has address hotmail.com mail is handled by 5 mx1.hotmail.com. hotmail.com mail is handled by 5 mx2.hotmail.com. $ telnet mx1.hotmail.com 25 Trying Connected to mx1.hotmail.com. 220 COL0-MC2-F22.Col0.hotmail.com Sending unsolicited commercial or bulk to Microsoft's computer network is prohibited. Other restrictions are found at... Wed, 19 Mar :13: > EHLO ucsd.edu 250-COL0-MC2-F22.Col0.hotmail.com ( ) Hello [ ] 250-SIZE PIPELINING 250-8bitmime 250-BINARYMIME 250-CHUNKING 250-AUTH LOGIN 250-AUTH=LOGIN 250 OK > STARTTLS 554 Unable to initialize security subsystem
10 Data Sources Alexa Top Domains Leaked lists of addresses Adobe (141M, Nov 13), Gawker (500K, Dec 10) Top 20 domains account for > 60% of users Gives us the distribution of users among providers
11
12
13 Determining Security gmx.de -> outlook.com gmx.de -> aol.com Return-Path: Received: from mout.gmx.net (mout.gmx.net [ ]) (using TLSv1 with cipher DHE-RSA-AES128-SHA (128/128 bits)) (No client certificate requested) by mtain-dk12.r1000.mx.aol.com (Internet Inbound) with ESMTPS id 264DF for Tue, 18 Mar :58: (EDT) Received: from [ ] by 3capp-gmx-bs51 with HTTP; Wed, 19 Mar :58: Secure! x-store-info:j++/jtczmobr++wnraa4pa4f5xd6uensydyekesgc2m= Authentication-Results: hotmail.com; spf=pass (sender IP is ) dkim=none header.d=gmx.de; x-hmca=pass X-SID-PRA: X-AUTH-Result: PASS X-SID-Result: PASS X-Message-Status: n:n X-Message-Delivery: Vj0xLjE7dXM9MDtsPTE7YT0xO0Q9MTtHRD0xO1NDTD0y X-Message-Info: NhFq/7gR1vRIVO7c89UihwXoLMcdpm5/xh6Uow5+... Received: from mout.gmx.net ([ ]) by BAY0-MC1-F41.Bay0.hotmail.com with Microsoft SMTPSVC( ); Tue, 18 Mar :56: Received: from [ ] by 3capp-gmx-bs51 with HTTP; Wed, 19 Mar :56: Not secure! (using public records and standard protocols)
14 TLS Support
15 TLS Support For Top Mail Providers
16 Certificate Status
17
18 Conclusion Does the global system currently provide security against and passive adversary (eavesdropper)? Yes, if both providers support STARTTLS and you trust each MTA
19 Conclusion Does the global system currently provide security against an active adversary (man in the middle)?
20 Conclusion SMTP is inherently insecure violates end-to-end principle Difficult to assess secure practices Most hosted by small set of providers these don t all follow secure practices Only takes one weak link to break security
21 Other Studies Facebook Study Google Study
22 Questions?
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