Check DANE TLSA security of an email domain

Features

• Test the local resolver configuration by verifying the validity of the root zone DNSKEY and SOA RRSets.

• Test whether DNSSEC is enabled for a given TLD.

• Check whether an email domain is fully protected (across all of its MX hosts) by DANE TLSA records, and whether these match the actual certificate chains seen at each IP address of each MX host.

• Perform certificate chain verification at a time offset from the current time to ensure that that certificates are not about to expire too soon.

A non-zero exit status is returned if any DNS lookups fail or if the MX records or MX hosts are in an unsigned zone, or if for one of the MX hosts no associated secure TLSA records are found. A non-zero exit status is also returned if any of the SMTP connections fail to establish a TLS connection or yield a certificate chain that does not match the TLSA records.

Note that danecheck prefers ECDSA to RSA, and only makes one connection to each IP address, so for hosts that have both ECDSA and RSA certificates, only the ECDSA certificate will be checked. Such hosts are rare, and when their TLSA records are only correct for one of RSA and ECDSA, it is almost always RSA that is properly configured and ECDSA that is neglected. So, for now, testing ECDSA in preference to RSA is typically a feature, not a bug.

Synopsis

The danecheck command options are as below.

$ danecheck --help
danecheck - check for and validate SMTP TLSA records

Usage: danecheck [-N | (-n|--nameserver ADDRESS)] [-t|--timeout TIMEOUT] 
                 [-r|--tries NUMTRIES] [-u|--udpsize SIZE] [-H|--helo HELO] 
                 [-s|--smtptimeout TIMEOUT] [-l|--linelimit LENGTH] 
                 [-R|--reserved] [-D|--down HOSTNAME] [-U|--down-only] 
                 [-4|--noipv4] [-6|--noipv6] [-A|--all] [-d|--days DAYS] 
                 [-e|--eechecks] [DOMAIN]

Available options:
  -h,--help                Show this help text
  -N                       Use /etc/resolv.conf nameserver list
  -n,--nameserver ADDRESS  Use nameserver at ADDRESS (default: "127.0.0.1")
  -t,--timeout TIMEOUT     DNS request TIMEOUT (default: 3000 ms)
  -r,--tries NUMTRIES      at most NUMTRIES requests per lookup (default: 6)
  -u,--udpsize SIZE        set EDNS UDP buffer SIZE (default: 1216)
  -H,--helo HELO           send specified client HELO name
  -s,--smtptimeout TIMEOUT SMTP TIMEOUT (default: 30000 ms)
  -l,--linelimit LENGTH    Maximum server SMTP response LENGTH (default: 4096)
  -R,--reserved            connect to reserved IP addresses
  -D,--down HOSTNAME       Specify one or more HOSTNAMEs that are down
  -U,--down-only           Limit connections to just the '-D' option hosts
  -4,--noipv4              disable SMTP via IPv4
  -6,--noipv6              disable SMTP via IPv6
  -A,--all                 scan all MX hosts, not just those with TLSA RRs
  -d,--days DAYS           check validity at DAYS in the future
  -e,--eechecks            check end-entity (leaf) certificate dates and names
  DOMAIN                   check the specified DOMAIN (default: ".")

When scanning the root domain, what's checked is secure retrieval of the root DNSKEY and SOA RRSets. Similarly, when scanning a top-level domain, what's checked is secure retrieval of its DS, DNSKEY and SOA records. For all other domains, MX records, address records and TLSA records are retrieved and must be DNSSEC signed.

Each MX host is expected to have TLSA records, an SMTP connection is made to each address of each such MX host (with the '-A' option connections are made to all MX hosts). A TLS handshake is performed to retrieve the hosts's certificate chain which is verified against the DNS TLSA RRs If anything is unavailable, insecure or wrong, a non-zero exit code is returned.

The '-D' option can be used multiple times to skip SMTP connections to MX hosts that are expected to be down. The '-U' option inverts the action of the '-D' option, and connects to only those MX hosts that are specified via the '-D' option (none if no such hosts are specified).

Reserved addresses include the address blocks from the IANA IPv4 and IPv6 special purpose address registries:

• IPv4 Special-Purpose Address Registry
• IPv6 Special-Purpose Address Registry

these include, for example, the RFC1918 private IPv4 ranges, and should not appear among the addresses of MX hosts of internet-facing email domains. If you're testing a non-public domain on an internal network, you can use the -R option to enable connections to reserved addresses.

Building the software

Prerequisite: A working GHC + Stack toolchain.

Haskell and stack can be downloaded from the Haskell platform website, and are also available as packages for various operating systems.

• Older versions of stack can be used to install a more current version, which typically installs into ~/.local/bin.

  $ stack upgrade
  $ stack update
  

Development libraries and headers

Some of the Haskell packages required for danecheck depend on optional C-libraries that may require the installation of additional OS packages. Below is a partial list of known optional dependencies absent on some systems. There are likely more on some systems.

• libicu for Unicode to ASCII conversion of domain names

Clone the danecheck Git repository and submodules

The danecheck repository uses submodules for some of its dependencies, the --recursive option to git clone will automatically clone the submodules.

$ git clone --recursive https://github.com/vdukhovni/danecheck
$ cd danecheck

Compile and install danecheck

Using a sufficiently recent version of stack, in the top-level directory of the cloned project run

$ stack install

which will compile and install a copy of the danecheck executable in Stack's default installation directory (typically ~/.local/bin).

Getting Started

Choose a working DNSSEC-validating resolver

It is assumed by default that your system has a working DNSSEC-validating resolver (BIND 9, unbound or similar) running locally and listening on the loopback interface at UDP and TCP at 127.0.0.1:53.

By default the system's /etc/resolv.conf file is ignored and the default nameserver list consists of just "127.0.0.1". If you want to specify a different validating resolver, use the -n option to select an alternate IP address. The /etc/resol.conf nameserver list can be selected via the "-N" option.

Check that the software and resolver are working

Assuming the installation directory is ~/.local/bin:

$ PATH=$HOME/.local/bin:$PATH
$ danecheck || printf "ERROR: root zone record validation failed" >&2

This should output a validated copy of the root zone DNSKEY and SOA RRSets and not print the ERROR message. For example (key base64 data abbreviated):

$ danecheck
. IN DNSKEY 256 3 8 AwEAAbPwrxwt...I5QymeSkJJzc= ; AD=1 NoError
. IN DNSKEY 257 3 8 AwEAAaz/tAm8...NR1AkUTV74bU= ; AD=1 NoError
. IN SOA a.root-servers.net. [email protected]. 2019101700 1800 900 604800 86400 ; AD=1 NoError

The ; AD=1 NoError DNS comments appended to each output line indicates that the resolver obtained a DNSSEC validated result. The . between the first and second DNS labels of the SOA contact mailbox field is displayed as an @ sign, since some domains have literal . characters in the localpart (first label) of the address. However, at present, the trailing . is not presently stripped from the domain part of the address.

Check your TLD

If your domain's ancestor TLD is not DNSSEC signed (still the case for some ccTLD domains), then DNSSEC will not be used for your domain either, except from resolvers that have configured a custom trust-anchor for your domain or one if its ancestor domains. When checking the DNSSEC status of a TLD danecheck outputs its DS, DNSKEY and SOA RRsets. For example:

$ danecheck org
org. IN DS 9795 7 1 364dfab3daf254cab477b5675b10766ddaa24982 ; AD=1 NoError
org. IN DS 9795 7 2 3922b31b6f3a4ea92b19eb7b52120f031fd8e05ff0b03bafcf9f891bfe7ff8e5 ; AD=1 NoError
org. IN DNSKEY 256 3 7 AwEAAb7ojfnp...nL5k7Y/VeZRpR ; AD=1 NoError
org. IN DNSKEY 256 3 7 AwEAAdEExfqc...9U9q91zgJ9bkn ; AD=1 NoError
org. IN DNSKEY 257 3 7 AwEAAZTjbIO5...r8ti6MNoJEHU= ; AD=1 NoError
org. IN DNSKEY 257 3 7 AwEAAcMnWBKL...nwXCNDXk0kk0= ; AD=1 NoError
org. IN SOA a0.org.afilias-nst.info. [email protected]. 2013668330 1800 900 604800 86400 ; AD=1 NoError

Checking your own domain

With your resolver tested for working root zone security and DNSSEC working for your TLD, you can proceed to regularly test your own domain. Example:

$ domain=openssl.org
$ danecheck "$domain" || printf "ERROR: DANE security check failed for: %s\n" "$domain"
openssl.org. IN DS 44671 8 2 30abf6c1b7de947ddf1c1b01206c126685e5eda880bf9dc8815eae7c474f83f9 ; AD=1 NoError
openssl.org. IN DNSKEY 256 3 8 AwEAAaJsnu//...v0lJQkbhta8V7 ; AD=1 NoError
openssl.org. IN DNSKEY 257 3 8 AwEAAbxptd2o...XBUsIsxlbmYs= ; AD=1 NoError
openssl.org. IN MX 50 mta.openssl.org. ; AD=1 NoError
mta.openssl.org. IN A 194.97.150.230 ; AD=1 NoError
mta.openssl.org. IN AAAA 2001:608:c00:180::1:e6 ; AD=1 NoError
_25._tcp.mta.openssl.org. IN TLSA 3 1 1 6cf12d78fbf242909d01b96ab5590812954058dc32f8415f048fff064291921e ; AD=1 NoError
  mta.openssl.org[194.97.150.230]: pass: TLSA match: depth = 0, name = mta.openssl.org
    TLS = TLS12 with ECDHE-RSA-AES256GCM-SHA384,P256
    name = mta.openssl.org
    depth = 0
      Issuer CommonName = Let's Encrypt Authority X3
      Issuer Organization = Let's Encrypt
      notBefore = 2019-08-26T11:00:16Z
      notAfter = 2019-11-24T11:00:16Z
      Subject CommonName = mta.openssl.org
      pkey sha256 [matched] <- 3 1 1 6cf12d78fbf242909d01b96ab5590812954058dc32f8415f048fff064291921e
    depth = 1
      Issuer CommonName = DST Root CA X3
      Issuer Organization = Digital Signature Trust Co.
      notBefore = 2016-03-17T16:40:46Z
      notAfter = 2021-03-17T16:40:46Z
      Subject CommonName = Let's Encrypt Authority X3
      Subject Organization = Let's Encrypt
      pkey sha256 [nomatch] <- 2 1 1 60b87575447dcba2a36b7d11ac09fb24a9db406fee12d2cc90180517616e8a18
  mta.openssl.org[2001:608:c00:180::1:e6]: pass: TLSA match: depth = 0, name = mta.openssl.org
    TLS = TLS12 with ECDHE-RSA-AES256GCM-SHA384,P256
    name = mta.openssl.org
    depth = 0
      Issuer CommonName = Let's Encrypt Authority X3
      Issuer Organization = Let's Encrypt
      notBefore = 2019-08-26T11:00:16Z
      notAfter = 2019-11-24T11:00:16Z
      Subject CommonName = mta.openssl.org
      pkey sha256 [matched] <- 3 1 1 6cf12d78fbf242909d01b96ab5590812954058dc32f8415f048fff064291921e
    depth = 1
      Issuer CommonName = DST Root CA X3
      Issuer Organization = Digital Signature Trust Co.
      notBefore = 2016-03-17T16:40:46Z
      notAfter = 2021-03-17T16:40:46Z
      Subject CommonName = Let's Encrypt Authority X3
      Subject Organization = Let's Encrypt
      pkey sha256 [nomatch] <- 2 1 1 60b87575447dcba2a36b7d11ac09fb24a9db406fee12d2cc90180517616e8a18

If the exit code indicates failure you should check the output for:

• DNS Failures
  • Any failed DNS queries (not NoError or NODATA) or insecure answers (AD=0)
  • Non-existent MX hosts or TLSA records
• SMTP failures
  • Failures to connect to an MX host at one or more of its IP addresses
  • Rejected or timed-out SMTP commands
  • Lack of STARTTLS support
  • Failure to complete the TLS handshake
• Chain verification failures
  • Failure to find matching TLSA records
  • Name check failure with DANE-TA(2) TLSA records
  • Certificate expiration with DANE-TA(2) TLSA records

Skipping out-of-service MX hosts

If some of your MX hosts are down, and you want to verify the certificate chains of only the remaining hosts, you can specify the --down option one or more times to skip SMTP tests for those hosts, their DNS security (including presence of TLSA records) will still be tested and will be required for the overall check to succeed. In the example below, the host bh.nic.cz is down and is skipped, allowing the overall check to succeed.

$ danecheck --down bh.nic.cz cznic.cz; echo $?
cznic.cz. IN DS 61281 13 2 fac1a7f06c7c...c6d07e7d8ef7 ; AD=1 NoError
cznic.cz. IN DNSKEY 256 3 13 rs6oetkFuqOg...swO3BfKoLw== ; AD=1 NoError
cznic.cz. IN DNSKEY 257 3 13 LM4zvjUgZi2X...TrDzWmmHwQ== ; AD=1 NoError
cznic.cz. IN MX 10 mail.nic.cz. ; AD=1 NoError
cznic.cz. IN MX 15 mx.nic.cz. ; AD=1 NoError
cznic.cz. IN MX 20 bh.nic.cz. ; AD=1 NoError
mail.nic.cz. IN A 217.31.204.67 ; AD=1 NoError
mail.nic.cz. IN AAAA 2001:1488:800:400::400 ; AD=1 NoError
_25._tcp.mail.nic.cz. IN TLSA 3 1 1 4f9736249ab5...6194f5bb2e09 ; AD=1 NoError
  mail.nic.cz[217.31.204.67]: pass: TLSA match: depth = 0, name = mail.nic.cz
    TLS = TLS12 with ECDHE-RSA-AES256GCM-SHA384
    name = jabber.nic.cz
    name = lists.nic.cz
    name = mail.nic.cz
    name = nic.cz
    depth = 0
      Issuer CommonName = Let's Encrypt Authority X3
      Issuer Organization = Let's Encrypt
      notBefore = 2017-08-03T13:02:00Z
      notAfter = 2017-11-01T13:02:00Z
      Subject CommonName = mail.nic.cz
      pkey sha256 [matched] <- 3 1 1 4f9736249ab5...6194f5bb2e09
    depth = 1
      Issuer CommonName = DST Root CA X3
      Issuer Organization = Digital Signature Trust Co.
      notBefore = 2016-03-17T16:40:46Z
      notAfter = 2021-03-17T16:40:46Z
      Subject CommonName = Let's Encrypt Authority X3
      Subject Organization = Let's Encrypt
      pkey sha256 [nomatch] <- 2 1 1 60b87575447d...0517616e8a18
mx.nic.cz. IN A 217.31.58.56 ; AD=1 NoError
mx.nic.cz. IN AAAA 2001:1ab0:7e1e:c574:7a2b:cbff:fe33:7019 ; AD=1 NoError
_25._tcp.mx.nic.cz. IN TLSA 3 1 1 a9205f093637...b519bf47a523 ; AD=1 NoError
  mx.nic.cz[217.31.58.56]: pass: TLSA match: depth = 0, name = mx.nic.cz
    TLS = TLS12 with ECDHE-RSA-AES256GCM-SHA384
    name = mx.nic.cz
    depth = 0
      Issuer CommonName = CZ.NIC SHA2 Root Certification Authority
      Issuer Organization = CZ.NIC, z.s.p.o.
      notBefore = 2017-02-13T09:29:27Z
      notAfter = 2019-02-13T09:29:27Z
      Subject CommonName = mx.nic.cz
      Subject Organization = CZ.NIC
      pkey sha256 [matched] <- 3 1 1 a9205f093637...b519bf47a523
    depth = 1
      Issuer CommonName = CZ.NIC SHA2 Root Certification Authority
      Issuer Organization = CZ.NIC, z.s.p.o.
      notBefore = 2016-02-19T13:58:59Z
      notAfter = 2026-02-16T13:58:59Z
      Subject CommonName = CZ.NIC SHA2 Root Certification Authority
      Subject Organization = CZ.NIC, z.s.p.o.
      pkey sha256 [nomatch] <- 2 1 1 eac0fdbe097f...81ab000c2955
bh.nic.cz. IN A 217.31.204.252 ; AD=1 NoError
bh.nic.cz. IN AAAA ? ; AD=1 NODATA
_25._tcp.bh.nic.cz. IN TLSA 3 1 1 4f9736249ab5...6194f5bb2e09 ; AD=1 NoError
0

Examples

STARTTLS not offered

Here STARTTLS is not offered (to at least some SMTP clients), even though TLSA records are published:

$ danecheck rnrfunco.net
rnrfunco.net. IN MX 10 tusk.sgt.com. ; AD=1 NoError
tusk.sgt.com. IN A 204.107.130.104 ; AD=1 NoError
tusk.sgt.com. IN AAAA ? ; AD=1 NODATA
_25._tcp.tusk.sgt.com. IN TLSA 3 0 1 bd60df4cc8c2...50ac0045659f ; AD=1 NoError
  tusk.sgt.com[204.107.130.104]: STARTTLS not offered

No matching TLSA records

Here none of the TLSA record match the certificate chain:

$ danecheck dipietro.id.au
dipietro.id.au. IN MX 10 mail.dipietro.id.au. ; AD=1 NoError
mail.dipietro.id.au. IN A 14.203.171.177 ; AD=1 NoError
mail.dipietro.id.au. IN AAAA ? ; AD=1 NODATA
_25._tcp.mail.dipietro.id.au. IN TLSA 3 1 1 7bf7ea3b070b...34e1e0044e6d ; AD=1 NoError
  mail.dipietro.id.au[14.203.171.177]: fail: TLSA mismatch
    TLS = TLS12 with ECDHE-RSA-AES256GCM-SHA384
    name = cloud.dipietro.id.au
    name = dipietro.id.au
    name = mail.dipietro.id.au
    name = www.dipietro.id.au
    name = xmpp.dipietro.id.au
    depth = 0
      Issuer CommonName = Let's Encrypt Authority X3
      Issuer Organization = Let's Encrypt
      notBefore = 2017-07-27T01:31:00Z
      notAfter = 2017-10-25T01:31:00Z
      Subject CommonName = dipietro.id.au
      pkey sha256 [nomatch] <- 3 1 1 51955a5a7b2e...7b158b18db73
    depth = 1
      Issuer CommonName = DST Root CA X3
      Issuer Organization = Digital Signature Trust Co.
      notBefore = 2016-03-17T16:40:46Z
      notAfter = 2021-03-17T16:40:46Z
      Subject CommonName = Let's Encrypt Authority X3
      Subject Organization = Let's Encrypt
      pkey sha256 [nomatch] <- 2 1 1 60b87575447d...0517616e8a18

TLSA Lookups ServFail

Here TLSA record lookups ServFail due to a buggy nameserver:

$ danecheck truman.edu
truman.edu. IN DS 52166 5 1 fc1b03d050bf...a69d7ed8676d ; AD=1 NoError
truman.edu. IN DNSKEY 256 3 5 AwEAAdKNi1TB...RSK2WheyT8zF ; AD=1 NoError
truman.edu. IN DNSKEY 257 3 5 AwEAAZianXgr...ZXk7AnTMbHM= ; AD=1 NoError
truman.edu. IN MX 5 barracuda.truman.edu. ; AD=1 NoError
barracuda.truman.edu. IN A 150.243.160.93 ; AD=1 NoError
barracuda.truman.edu. IN AAAA ? ; AD=0 ServFail
_25._tcp.barracuda.truman.edu. IN TLSA ? ; AD=0 ServFail