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Philadelphia, April 26-27 2018
13
Understanding DMARC
Gabriella Davis - IBM Lifetime Champion for Social Business
Technical Director
The Turtle Partnership
Gab Davis
• Admin of all things and especially quite complicated
things where the fun is
• Working with the design, deployment and security of
IBM technologies within global infrastructures
• working with the real world security and privacy
aspects of expanding data ecosystems
• Stubborn and relentless problem solver
• http://turtleblog.infohttps://
www.turtlepartnership.com
• IBM Lifetime Champion
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Social Connections 13 Philadelphia, April 26-27 2018
13
The Problem With Mail
Social Connections 13 Philadelphia, April 26-27 2018
Relaying
• Using Your Servers
• Routing mail through “good” servers that are owned by a company gives “bad”
mail validity
• Properly configured servers stop that happening
• It takes only a few poor configured servers to successfully route millions of emails
• This is an administrative not a user problem
• It doesn’t hurt your users who don’t receive the mail
• It does cause bottlenecks on your servers trying to send mail
• Receiving hosts are often designed to check that the claimed sending domain matches
the address header
• It can result in your servers being blacklisted and not being able to send mail
Social Connections 13 Philadelphia, April 26-27 2018
Blacklists
My	SMTP	host	listening	on	port	
25/465	for	any	mail	SMTP	mail	not	
just	for	my	domain:	turtleweb.com	
My	SMTP	host	listening	on	port	
25/465	for	any	mail	SMTP	mail	not	
just	for	my	domain:	turtleweb.com	
Spam	Generating	Server	
domain:	fakemail.com	
Scans	for	any	open	listening	host	which	
will	accept	mail	not	for	their	own	
domain
Domain	being	spammed	
domain:	rivers.com
Carries	the	return_path	in	the	message	header
Social Connections 13 Philadelphia, April 26-27 2018
Preventing and Protecting Relaying
• Lock down servers to only accept mail for your own domains
• Use an edge service to verify valid domains
• Use SPF records
• These define the identities of servers sending mail from your
domains
• Receiving servers can check if the domain in the message
header has an SPF record for the connecting server
• Many receiving domains and servers do not accept mail without SPF
validation now
• SPF records are no longer enough
Social Connections 13 Philadelphia, April 26-27 2018
SPF
gab@turtleweb.com	
creates	email		to	
tim@gmail.com
turtleweb.com	SMTP	Server	
ip:	mail.turtleinfo.net gmail.com	SMTP	listener
turtleweb.com	DNS	Record	
SPF	Entry	
turtleweb.com.		IN	TXT	"v=spf1	mx	a	ip4:79.99.66.142	
a:mail.turtleinfo.net”
gmail	checks	SPF	record	in	DNS	
to	verify	if	the	sending	server	is	approved
Social Connections 13 Philadelphia, April 26-27 2018
Phishing
• Phishing - collecting personal information voluntarily from the
user
• Phishing scams can use spoofing techniques in order to seem
more genuine to the user
• Over 30% of phishing emails are opened
• Phishing can often be combined with spoofing to give the
request more authenticity but the goal is to gather information
• the goal of spoofing is usually to deliver a malicious payload
• Preventing phishing should simply be a case of user awareness
Social Connections 13 Philadelphia, April 26-27 2018
Why Don’t These Techniques Work
• Technical solutions do work if deployed rigidly, however:
• Mail systems are often complex
• If I want a user to send mail via my SMTP server, I can’t relay
check
• The risk of rejecting valid mail is greater than the risk of accepting
fraudulent mail
• People I want to receive email from often haven’t set up their own
SPF records
Social Connections 13 Philadelphia, April 26-27 2018
User Training Isn’t Enough
• Phishing increasingly relies on sophisticated social
engineering designed to win trust
• Users are aware of risk so the mails have become more
sophisticated
• The iOS problem
• Verbal verification is not always possible
• We need better ways of validating the source of mail
before it reaches the user and becomes their responsibility
Social Connections 13 Philadelphia, April 26-27 2018
Content Filtering
• Edge services specifically designed to check content
• estimates put the % of spam to around 90% of
received mail
• Filtering has moved from checking for certain words
or phrases to checking message structure
• it didn’t take long for spammers to work out how
to fool word filters
Social Connections 13 Philadelphia, April 26-27 2018
13
Defining DMARC
Social Connections 13 Philadelphia, April 26-27 2018
DMARC
• Domain Message Authentication Reporting and Conformance
• created by Google, Paypal, Microsoft and Yahoo
• A combination of processes and policies that provide both
validation of messages and reporting of fraudulent attempts
• These include SPF, content scanning, and DKIM
• DMARC policies tell the receiver what to do with non-
validated messages, resulting in useful data returned to
the sender
Social Connections 13 Philadelphia, April 26-27 2018
SPF
gab@turtleweb.com	
creates	email		to	
tim@gmail.com
turtleweb.com	SMTP	Server	
ip:	mail.turtleinfo.net gmail.com	SMTP	listener
turtleweb.com	DNS	Record	
SPF	Entry	
turtleweb.com.		IN	TXT	"v=spf1	mx	a	ip4:79.99.66.142	
a:mail.turtleinfo.net”
gmail	checks	SPF	record	in	DNS	
to	verify	if	the	sending	server	is	approved
Social Connections 13 Philadelphia, April 26-27 2018
DKIM - DomainKeys Identified Mail (simplified)
• A public/private key pair used to process every sending message
• DKIM ensures the receiving server that the message is valid and has not
been tampered with
turtleweb.com	sending	server	
creates	a	hash	using	its	private	key	containing	
both	my	sending	address	and	the	subject	and	
attaches	it	to	the	message	header	before	sending
gmail.com	receiving	server	
decrypts	the	hash	using	the	public	key	to	verify	it	
is	both	correct	and	unchanged	before	delivering	
the	mail	to	tim
DNS	
turtleweb.com's	DNS	record	contains	the	public	key	used	by	
mail.turtleweb.com	to	encrypt	“sender	and	subject”
sends	an	email	
to	tim@gmail.com
Social Connections 13 Philadelphia, April 26-27 2018
DMARC Policies
• Faked mail appears and disappears often without the genuine domain owner
knowing
• most systems just bounce, delete or quarantine the messages
• without knowing the scale of faked mail or even that someone is
impersonating my company how can I stop it?
• DMARC configuration has two parts
• telling the receiving server what to do with non genuine mail
• telling the receiving server where to send summary reports of non genuine
mail
• DMARC deployed correctly allows us to both pre-emptively manage faked mail
and have visibility of its existence
Social Connections 13 Philadelphia, April 26-27 2018
13
Deploying DMARC
Social Connections 13 Philadelphia, April 26-27 2018
Constructing SPF Records
• Several sites help you construct your SPF records
including
• spfwizard.net and mxtoolbox.com
• If you are unsure of the syntax, use one of these sites
• Mail failing a SPF check is then tagged
• Fail - resulting in non delivery
• Softfail - increased likelihood of being tagged as spam
• Neutral - ignore failure
Social Connections 13 Philadelphia, April 26-27 2018
Deploying DKIM
• The sending mail server must support DKIM encryption
• If it doesn’t then you will either have to install a DKIM custom package or route
mail through a server that does support it
• http://dkim.org/deploy/index.html
• The inbound server must support DKIM decryption
• most edge mail services do
• Use OpenSSL or a site such as
• https://www.socketlabs.com/domainkey-dkim-generation-wizard
• https://www.port25.com/dkim-wizard
• Store the generated public key in a TXT record in your domain
• Configure the DKIM package or enabled server to use the private key
Social Connections 13 Philadelphia, April 26-27 2018
DMARC Planning
• Enabling DMARC takes a significant amount of planning and testing
• The point of DMARC is to tell receiving servers to reject, delete or
deliver your mail
• configured incorrectly it can result in all your sent mail disappearing
• Start with test domains!
• Start with reporting-only policies
• Ensure you have an email address / mailbox configured for the
DMARC reports
• These will tell you if someone is sending mail as your domain that
don’t meet your SPF and DKIM settings
Social Connections 13 Philadelphia, April 26-27 2018
DMARC Deployment
• Use a DMARC wizard such as https://mxtoolbox.com/
DMARCRecordGenerator.aspx or https://www.unlocktheinbox.com/
dmarcwizard/ to review your options and create the right syntax
• DMARC questions include:
• How do you want mail that fails DMARC to be treated by the recipient?
• Where do you want your aggregate reports sent to?
• Do you want forensic (individual) reports generated on specific failures
such as SPF or DKIM
• Zone file TXT entry
• "v=DMARC1; p=none; sp=none; rua=mailto:dmarcreport@turtleweb.com;
ruf=mailto:dmarcanalysis@turtleweb.com; rf=afrf; pct=100; ri=86400”
Social Connections 13 Philadelphia, April 26-27 2018
DMARC and Domino
• Domino doesn’t support
• SPF checking
• DKIM key encryption
• DKIM decryption
• It’s unlikely to do so
• Edge services do support both SPF checking and DKIM encryption
• For DKIM encryption outbound, Domino mail can be routed
through a SMTP relay with an installed DKIM package
• or someone could write a DKIM add in for Domino
Social Connections 13 Philadelphia, April 26-27 2018
Summary
• Email isn’t going away
• DMARC isn’t a single solution, it’s a combination of technical tools
and processes
• Many of the technical tools have been around for years including
SPF, Reverse DNS and DKIM
• but not deployed widely as being too complex
• We have to take more responsibility for protecting people from
sophisticated phishing attempts not just from content
• DMARC is increasingly being required by receiving servers wanting to
protect their customers
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An Introduction To The DMARC SMTP Validation Requirements

  • 1. Philadelphia, April 26-27 2018 13 Understanding DMARC Gabriella Davis - IBM Lifetime Champion for Social Business Technical Director The Turtle Partnership
  • 2. Gab Davis • Admin of all things and especially quite complicated things where the fun is • Working with the design, deployment and security of IBM technologies within global infrastructures • working with the real world security and privacy aspects of expanding data ecosystems • Stubborn and relentless problem solver • http://turtleblog.infohttps:// www.turtlepartnership.com • IBM Lifetime Champion
  • 4. Social Connections 13 Philadelphia, April 26-27 2018 13 The Problem With Mail
  • 5. Social Connections 13 Philadelphia, April 26-27 2018 Relaying • Using Your Servers • Routing mail through “good” servers that are owned by a company gives “bad” mail validity • Properly configured servers stop that happening • It takes only a few poor configured servers to successfully route millions of emails • This is an administrative not a user problem • It doesn’t hurt your users who don’t receive the mail • It does cause bottlenecks on your servers trying to send mail • Receiving hosts are often designed to check that the claimed sending domain matches the address header • It can result in your servers being blacklisted and not being able to send mail
  • 6. Social Connections 13 Philadelphia, April 26-27 2018 Blacklists My SMTP host listening on port 25/465 for any mail SMTP mail not just for my domain: turtleweb.com My SMTP host listening on port 25/465 for any mail SMTP mail not just for my domain: turtleweb.com Spam Generating Server domain: fakemail.com Scans for any open listening host which will accept mail not for their own domain Domain being spammed domain: rivers.com Carries the return_path in the message header
  • 7. Social Connections 13 Philadelphia, April 26-27 2018 Preventing and Protecting Relaying • Lock down servers to only accept mail for your own domains • Use an edge service to verify valid domains • Use SPF records • These define the identities of servers sending mail from your domains • Receiving servers can check if the domain in the message header has an SPF record for the connecting server • Many receiving domains and servers do not accept mail without SPF validation now • SPF records are no longer enough
  • 8. Social Connections 13 Philadelphia, April 26-27 2018 SPF gab@turtleweb.com creates email to tim@gmail.com turtleweb.com SMTP Server ip: mail.turtleinfo.net gmail.com SMTP listener turtleweb.com DNS Record SPF Entry turtleweb.com. IN TXT "v=spf1 mx a ip4:79.99.66.142 a:mail.turtleinfo.net” gmail checks SPF record in DNS to verify if the sending server is approved
  • 9. Social Connections 13 Philadelphia, April 26-27 2018 Phishing • Phishing - collecting personal information voluntarily from the user • Phishing scams can use spoofing techniques in order to seem more genuine to the user • Over 30% of phishing emails are opened • Phishing can often be combined with spoofing to give the request more authenticity but the goal is to gather information • the goal of spoofing is usually to deliver a malicious payload • Preventing phishing should simply be a case of user awareness
  • 10. Social Connections 13 Philadelphia, April 26-27 2018 Why Don’t These Techniques Work • Technical solutions do work if deployed rigidly, however: • Mail systems are often complex • If I want a user to send mail via my SMTP server, I can’t relay check • The risk of rejecting valid mail is greater than the risk of accepting fraudulent mail • People I want to receive email from often haven’t set up their own SPF records
  • 11. Social Connections 13 Philadelphia, April 26-27 2018 User Training Isn’t Enough • Phishing increasingly relies on sophisticated social engineering designed to win trust • Users are aware of risk so the mails have become more sophisticated • The iOS problem • Verbal verification is not always possible • We need better ways of validating the source of mail before it reaches the user and becomes their responsibility
  • 12. Social Connections 13 Philadelphia, April 26-27 2018 Content Filtering • Edge services specifically designed to check content • estimates put the % of spam to around 90% of received mail • Filtering has moved from checking for certain words or phrases to checking message structure • it didn’t take long for spammers to work out how to fool word filters
  • 13. Social Connections 13 Philadelphia, April 26-27 2018 13 Defining DMARC
  • 14. Social Connections 13 Philadelphia, April 26-27 2018 DMARC • Domain Message Authentication Reporting and Conformance • created by Google, Paypal, Microsoft and Yahoo • A combination of processes and policies that provide both validation of messages and reporting of fraudulent attempts • These include SPF, content scanning, and DKIM • DMARC policies tell the receiver what to do with non- validated messages, resulting in useful data returned to the sender
  • 15. Social Connections 13 Philadelphia, April 26-27 2018 SPF gab@turtleweb.com creates email to tim@gmail.com turtleweb.com SMTP Server ip: mail.turtleinfo.net gmail.com SMTP listener turtleweb.com DNS Record SPF Entry turtleweb.com. IN TXT "v=spf1 mx a ip4:79.99.66.142 a:mail.turtleinfo.net” gmail checks SPF record in DNS to verify if the sending server is approved
  • 16. Social Connections 13 Philadelphia, April 26-27 2018 DKIM - DomainKeys Identified Mail (simplified) • A public/private key pair used to process every sending message • DKIM ensures the receiving server that the message is valid and has not been tampered with turtleweb.com sending server creates a hash using its private key containing both my sending address and the subject and attaches it to the message header before sending gmail.com receiving server decrypts the hash using the public key to verify it is both correct and unchanged before delivering the mail to tim DNS turtleweb.com's DNS record contains the public key used by mail.turtleweb.com to encrypt “sender and subject” sends an email to tim@gmail.com
  • 17. Social Connections 13 Philadelphia, April 26-27 2018 DMARC Policies • Faked mail appears and disappears often without the genuine domain owner knowing • most systems just bounce, delete or quarantine the messages • without knowing the scale of faked mail or even that someone is impersonating my company how can I stop it? • DMARC configuration has two parts • telling the receiving server what to do with non genuine mail • telling the receiving server where to send summary reports of non genuine mail • DMARC deployed correctly allows us to both pre-emptively manage faked mail and have visibility of its existence
  • 18. Social Connections 13 Philadelphia, April 26-27 2018 13 Deploying DMARC
  • 19. Social Connections 13 Philadelphia, April 26-27 2018 Constructing SPF Records • Several sites help you construct your SPF records including • spfwizard.net and mxtoolbox.com • If you are unsure of the syntax, use one of these sites • Mail failing a SPF check is then tagged • Fail - resulting in non delivery • Softfail - increased likelihood of being tagged as spam • Neutral - ignore failure
  • 20. Social Connections 13 Philadelphia, April 26-27 2018 Deploying DKIM • The sending mail server must support DKIM encryption • If it doesn’t then you will either have to install a DKIM custom package or route mail through a server that does support it • http://dkim.org/deploy/index.html • The inbound server must support DKIM decryption • most edge mail services do • Use OpenSSL or a site such as • https://www.socketlabs.com/domainkey-dkim-generation-wizard • https://www.port25.com/dkim-wizard • Store the generated public key in a TXT record in your domain • Configure the DKIM package or enabled server to use the private key
  • 21. Social Connections 13 Philadelphia, April 26-27 2018 DMARC Planning • Enabling DMARC takes a significant amount of planning and testing • The point of DMARC is to tell receiving servers to reject, delete or deliver your mail • configured incorrectly it can result in all your sent mail disappearing • Start with test domains! • Start with reporting-only policies • Ensure you have an email address / mailbox configured for the DMARC reports • These will tell you if someone is sending mail as your domain that don’t meet your SPF and DKIM settings
  • 22. Social Connections 13 Philadelphia, April 26-27 2018 DMARC Deployment • Use a DMARC wizard such as https://mxtoolbox.com/ DMARCRecordGenerator.aspx or https://www.unlocktheinbox.com/ dmarcwizard/ to review your options and create the right syntax • DMARC questions include: • How do you want mail that fails DMARC to be treated by the recipient? • Where do you want your aggregate reports sent to? • Do you want forensic (individual) reports generated on specific failures such as SPF or DKIM • Zone file TXT entry • "v=DMARC1; p=none; sp=none; rua=mailto:dmarcreport@turtleweb.com; ruf=mailto:dmarcanalysis@turtleweb.com; rf=afrf; pct=100; ri=86400”
  • 23. Social Connections 13 Philadelphia, April 26-27 2018 DMARC and Domino • Domino doesn’t support • SPF checking • DKIM key encryption • DKIM decryption • It’s unlikely to do so • Edge services do support both SPF checking and DKIM encryption • For DKIM encryption outbound, Domino mail can be routed through a SMTP relay with an installed DKIM package • or someone could write a DKIM add in for Domino
  • 24. Social Connections 13 Philadelphia, April 26-27 2018 Summary • Email isn’t going away • DMARC isn’t a single solution, it’s a combination of technical tools and processes • Many of the technical tools have been around for years including SPF, Reverse DNS and DKIM • but not deployed widely as being too complex • We have to take more responsibility for protecting people from sophisticated phishing attempts not just from content • DMARC is increasingly being required by receiving servers wanting to protect their customers
  • 25.