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USING TELEPORT AS A
BASTION JUMP HOST
HOW WE FOUND A FIREWALL VENDOR BUG
https://faelix.link/uknof40 — 2Mb
" THE INTERNET
ISN'T WORKING! "
Calls to Exa Networks' support team
THE PROBLEM
IT GETS WORSE THE MORE YOU LOOK AT IT
THE TASK AT HAND
▸ Isn't affecting all customers
▸ Initial suspicion of leased-line backhaul congestion…
▸ …but we found some DSL customers with problems too
▸ Intermittent, but not quite a heisenbug
▸ Manifested as timeout loading web pages
▸ All affected customers use Exa's new filtering service
WE NEED MORE DATA
AIM TO TEST FROM CUSTOMERS' NETWORKS
▸ Put some probe devices in some customer networks
▸ …to be able to "ssh" into them, run measurements.
▸ Don't want customers to have to open ports on routers.
▸ Some sort of NAT-piercing required.
▸ Security is vital:
▸ Don't want probe to be an attack vector into customer.
▸ Team of staff need access.
IOT SECURITY
(NETMCR #11)
@kooky_uk Tim Bray
SHOUT OUT #1
SSH CERTIFICATES
(NETMCR #13)
@TimJDFletcher Tim Fletcher
SHOUT OUT #2
IOT SECURITY WITH PI.PE
(NETMCR #17)
@steely_glint Tim Panton
SHOUT OUT #3
RIPE ATLAS PROBE SECURITY
(AQL IOT ROUNDTABLE)
@kistel Robert Kisteleki
SHOUT OUT #4
STANDING ON THE SHOULDERS OF GIANTS
RIPE ATLAS
▸ Plug it in, gets address/DNS by DHCP
▸ Connects to RIPE bastion hosts using ssh (with provisioning)
▸ Creates tunnels to itself for telemetry, read all about it:
▸ https://www.uknof.org.uk/uknof18/Kisteleki-Atlas.pdf
▸ Security rep is pretty good, e.g.
▸ https://www.mdsec.co.uk/2015/09/an-introduction-to-
hardware-hacking-the-ripe-atlas-probe/
STANDING ON THE SHOULDERS OF GIANTS
SSH BASTION HOSTS, WITH SSH CA
▸ The big players are doing it:
▸ https://code.facebook.com/posts/365787980419535/
scalable-and-secure-access-with-ssh/
▸ https://github.com/Netflix/bless
▸ How to apply this pattern to our "IoT" probe project?
WHO NEEDS ANOTHER SSHD?
WHY BOTHER USING TELEPORT?
▸ ssh CA out of the box, compatible with OpenSSHd
▸ 2FA out of the box (TOTP or U2F), no google_authenticator.pam
▸ ssh through-the-web out of the box
▸ Compliance Officer's dream: session recording jumphost.
▸ …and with "session_recording: proxy" it can do this for
legacy sshd implementations too! [caveat: Security Officer]
▸ Free OSS < $aa$_startup_pricing_model < enterpri$$$e
▸ $paid_editions feature include RBAC, LDAP/SASL integration
IN A BREAK FROM TRADITION, OPS LOBS THE PROBLEM AT DEVS
THE SOLUTION
▸ Ansible script #1:
▸ Deploys Teleport on a VM for bastion host
▸ Ansible script #2:
▸ Installs Teleport on a Raspberry Pi
▸ Preconfigures Teleport (as trusting cluster of bastion host)
▸ Bunch of Raspberry Pi / case / SD card combos
▸ Ship to customers with instructions about placement
▸ Exa's software team can now run diagnostics
DEPLOYMENT
TELEPORT
you!
proxy
auth
node client

(tsh or https)
you!
proxy
auth
node client

(tsh or https)
all-in-one
you!
proxy
auth
node client

(tsh or https)
bastion
node(s)
you!
proxy
auth
node client

(tsh or https)
all

separated
you!
proxynode client

(tsh or https)
RBAC

("enterprise")
auth
LDAP

SAML

etc
you!
proxies
auth
node client

(tsh or https)
HA auth
etcd /

dynamodb
load bal
you!
auth + proxy

& trusted cluster
auth
node

trusting cluster
client

(tsh or https)
bastionanother node
you!
auth + proxy

& trusted cluster
auth
trusting cluster client

(tsh or https)
bastionnode
you!
auth + proxy

& trusted cluster
auth
trusting cluster client

(tsh or https)
bastionnode
tsh login

--proxy teleport.example.com
--user networkmoose
ssh-key -A
LOGGING IN
"TWITCH FOR TERMINALS"
CO-OPERATIVE MULTIPLAYER MODE!
"…AND YOU WON'T
BELIEVE WHAT
HAPPENED NEXT…"
e: marek@faelix.net
t: @maznu
https://faelix.link/uknof40

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How we found a firewall vendor bug using Teleport as a bastion jump host

  • 1. USING TELEPORT AS A BASTION JUMP HOST HOW WE FOUND A FIREWALL VENDOR BUG https://faelix.link/uknof40 — 2Mb
  • 2. " THE INTERNET ISN'T WORKING! " Calls to Exa Networks' support team THE PROBLEM
  • 3. IT GETS WORSE THE MORE YOU LOOK AT IT THE TASK AT HAND ▸ Isn't affecting all customers ▸ Initial suspicion of leased-line backhaul congestion… ▸ …but we found some DSL customers with problems too ▸ Intermittent, but not quite a heisenbug ▸ Manifested as timeout loading web pages ▸ All affected customers use Exa's new filtering service
  • 4. WE NEED MORE DATA AIM TO TEST FROM CUSTOMERS' NETWORKS ▸ Put some probe devices in some customer networks ▸ …to be able to "ssh" into them, run measurements. ▸ Don't want customers to have to open ports on routers. ▸ Some sort of NAT-piercing required. ▸ Security is vital: ▸ Don't want probe to be an attack vector into customer. ▸ Team of staff need access.
  • 5. IOT SECURITY (NETMCR #11) @kooky_uk Tim Bray SHOUT OUT #1
  • 7. IOT SECURITY WITH PI.PE (NETMCR #17) @steely_glint Tim Panton SHOUT OUT #3
  • 8. RIPE ATLAS PROBE SECURITY (AQL IOT ROUNDTABLE) @kistel Robert Kisteleki SHOUT OUT #4
  • 9. STANDING ON THE SHOULDERS OF GIANTS RIPE ATLAS ▸ Plug it in, gets address/DNS by DHCP ▸ Connects to RIPE bastion hosts using ssh (with provisioning) ▸ Creates tunnels to itself for telemetry, read all about it: ▸ https://www.uknof.org.uk/uknof18/Kisteleki-Atlas.pdf ▸ Security rep is pretty good, e.g. ▸ https://www.mdsec.co.uk/2015/09/an-introduction-to- hardware-hacking-the-ripe-atlas-probe/
  • 10. STANDING ON THE SHOULDERS OF GIANTS SSH BASTION HOSTS, WITH SSH CA ▸ The big players are doing it: ▸ https://code.facebook.com/posts/365787980419535/ scalable-and-secure-access-with-ssh/ ▸ https://github.com/Netflix/bless ▸ How to apply this pattern to our "IoT" probe project?
  • 11. WHO NEEDS ANOTHER SSHD? WHY BOTHER USING TELEPORT? ▸ ssh CA out of the box, compatible with OpenSSHd ▸ 2FA out of the box (TOTP or U2F), no google_authenticator.pam ▸ ssh through-the-web out of the box ▸ Compliance Officer's dream: session recording jumphost. ▸ …and with "session_recording: proxy" it can do this for legacy sshd implementations too! [caveat: Security Officer] ▸ Free OSS < $aa$_startup_pricing_model < enterpri$$$e ▸ $paid_editions feature include RBAC, LDAP/SASL integration
  • 12. IN A BREAK FROM TRADITION, OPS LOBS THE PROBLEM AT DEVS THE SOLUTION ▸ Ansible script #1: ▸ Deploys Teleport on a VM for bastion host ▸ Ansible script #2: ▸ Installs Teleport on a Raspberry Pi ▸ Preconfigures Teleport (as trusting cluster of bastion host) ▸ Bunch of Raspberry Pi / case / SD card combos ▸ Ship to customers with instructions about placement ▸ Exa's software team can now run diagnostics
  • 16. you! proxy auth node client
 (tsh or https) bastion node(s)
  • 17. you! proxy auth node client
 (tsh or https) all
 separated
  • 18. you! proxynode client
 (tsh or https) RBAC
 ("enterprise") auth LDAP
 SAML
 etc
  • 19. you! proxies auth node client
 (tsh or https) HA auth etcd /
 dynamodb load bal
  • 20. you! auth + proxy
 & trusted cluster auth node
 trusting cluster client
 (tsh or https) bastionanother node
  • 21. you! auth + proxy
 & trusted cluster auth trusting cluster client
 (tsh or https) bastionnode
  • 22. you! auth + proxy
 & trusted cluster auth trusting cluster client
 (tsh or https) bastionnode
  • 23. tsh login
 --proxy teleport.example.com --user networkmoose ssh-key -A LOGGING IN
  • 24.
  • 27. "…AND YOU WON'T BELIEVE WHAT HAPPENED NEXT…" e: marek@faelix.net t: @maznu https://faelix.link/uknof40