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SSL/TLS

M
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
T 
L 
S
Awesome
Sauce,
or...
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
H 

Exception
in
thread
"main"
javax.net.ssl.SSLHandshakeException:
sun.security.validator.ValidatorException:
PKIX
path
building
failed:
sun.security.p




at
sun.security.ssl.Alerts.getSSLException(Alerts.java:192)





at
sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1949)





at
sun.security.ssl.Handshaker.fatalSE(Handshaker.java:302)





at
sun.security.ssl.Handshaker.fatalSE(Handshaker.java:296)





at
sun.security.ssl.ClientHandshaker.serverCertif cate(ClientHandshaker.java:1506)





at
sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:216)





at
sun.security.ssl.Handshaker.processLoop(Handshaker.java:979)





at
sun.security.ssl.Handshaker.process_record(Handshaker.java:914)





at
sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:1062)





at
sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1375)





at
sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1403)





at
sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1387)





at
sun.net. .protocol.https.HttpsClient.afterConnect(HttpsClient.java:559)





at
sun.net. .protocol.https.AbstractDelegateHttpsURLConnection.connect(AbstractDelegateHttpsURLConnection.java:185)





at
sun.net. .protocol.http.HttpURLConnection.getInputStream0(HttpURLConnection.java:1512)





at
sun.net. .protocol.http.HttpURLConnection.getInputStream(HttpURLConnection.java:1440)





at
sun.net. .protocol.https.HttpsURLConnectionImpl.getInputStream(HttpsURLConnectionImpl.java:254)





at
it.mulders.maarten.Demo.main(Demo.java:13)

Caused
by:
sun.security.validator.ValidatorException:
PKIX
path
building
failed:
sun.security.provider.certpath.SunCertPathBuilderException:
unable





at
sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:387)





at
sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:292)





at
sun.security.validator.Validator.validate(Validator.java:260)





at
sun.security.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:324)





at
sun.security.ssl.X509TrustManagerImpl.checkTrusted(X509TrustManagerImpl.java:229)





at
sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:124)





at
sun.security.ssl.ClientHandshaker.serverCertif cate(ClientHandshaker.java:1488)





 
13
more

Caused
by:
sun.security.provider.certpath.SunCertPathBuilderException:
unable
to
f nd
valid
certif cation
path
to
requested
target





at
sun.security.provider.certpath.SunCertPathBuilder.build(SunCertPathBuilder.java:146)





at
sun.security.provider.certpath.SunCertPathBuilder.engineBuild(SunCertPathBuilder.java:131)





at
java.security.cert.CertPathBuilder.build(CertPathBuilder.java:280)

at sun security validator PKIXValidator doBuild(PKIXValidator java:382)
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
7
L 
 
OSI
M
data
unit layers
Data
Data
Data
Segments
Packets
Frames
Bits
Application

Network
Process
to
Application
Presentation

Data
Representation

and
Encryption
Session

Interhost
Communication
Transport

End­to­End
Connections

and
Reliability
Network

Path
Determination
and

Logical
Addressing
(IP)
Data
Link

Physical
Addressing

(MAC
and
LLC)
Physical

Media,
Signal
and

Binary
Transmission
Host
Layers
Media
Layers
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
H 
 
SSL
 
TLS
SSL
1.0 never
released
SSL
2.0 1995
-
2011
(POODLE)
SSL
3.0 1996
-
2014
(POODLE)
TLS
1.0 1999
-
2011
(BEAST)
TLS
1.1 2006
TLS
1.2 2008
TLS
1.3 2018
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
D 
 

What's
the
issue?!
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
H 
 

1.
public/private
key
encryption
2.
signed
certificates
3.
certificate
authorities
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
1 
P 
 
P
K 
E
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
M 

1.
Select
two
prime
numbers:

2.
Calculate
product:

3.
Select
random
number
<
product:

4.
Find
 ,
so
that

a.

b.

c.

d.


 
varies
with
 :
when
 .
p = 11, q = 17
p ∗ q = 187
e = 3
d (d ∗ e) − 1 mod (p − 1) ∗ (q − 1) = 0
(d ∗ 3) − 1 mod (10 ∗ 16) = 0
320 mod 160 = 0
(321 − 1) mod 160 = 0
(107 ∗ 3) = 321 ⇒d = 107
d e e = 75, d = 183
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
N ,
 
 
P
 
Q

1.

2.
Find
d,
so
that

Pretty
hard
without
knowing
 
and
 !

When
you
know
 ,
calculating
 
is
easy.
p ∗ q = 299, e = 5
(d ∗ e) − 1 mod (p − 1) ∗ (q − 1) = 0
p q
p = 13, q = 23 d = 317
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
For
big
enough
 
and
 ,
finding
those
factors
will
cost
an
eternity!
So
we
can
distribute
 
and
even
 !
p q
p ∗ q e
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
L 
 
"G"
p ∗ q = 187, e = 3, G ⇒ 7
= = 343
7
e
7
3
343 mod 187 = 156
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
L 
 
"156"
Since
we
know
 
and
 ,
we
can
calculate

p q d = 107
= ≈ 4.6 ∗
156
d
156
107
10
234
mod 187 = 7
156
107
7 ⇒ G
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
N 
 
 

Client Server
1 ClientHello →
2 ← ServerHello
3 ← Certificate
4 ← ServerKeyExchange
5 ← ServerHelloDone
6 ClientKeyExchange →
7 ChangeCipherSpec →
8 Finished →
9 ← ChangeCipherSpec
10 ← Finished
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
D 
 

No-one
is
eavesdropping!
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
2 
S
C
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
A
certificate
contains:
Serial
Number
Subject
Validity
Usage
Public
Key
Fingerprint
Algorithm
Fingerprint
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
But
wait...
anyone
could
create
a
certificate!
So
we
also
need
Signature
Algorithm
Signature
Issuer
...
and
a
way
to
sign
certificates.
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
A
signature
is
a
mathematical
relationship
between
a
message

,
a
private
key
 
and
a
public
key
 .
It
consists
of
two
functions:
1.
signing
function

2.
verifying
function

x sk pk
t = f (sk, x)
[accept, reject] = g(pk, t, x)
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
3 
C
A
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
An
entity
that
issues
digital
certificates,
certifying
the
ownership
of
a
public
key
by
the
subject
of
the
certificate.
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
I
John
?
Alice
So,
who
is
John,
anyway?
“I
can
trust
you,
because
I
trust
John,
and
John
trusts
Alice,
and
Alice
trusts
you.
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Top-notch
security
procedures,
including
"key
ceremonies"
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
/**
intentionally
left
blank
*/
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
W 
 

Google
blacklists
247
certificates
in
Chromium
Microsoft
removes
the
DigiNotar
root
certificate
from
all
supported
Windows-releases
*
Mozilla
revokes
trust
in
the
DigiNotar
root
certificate
in
all
supported
versions
Apple
issued
Security
Update
2011-005


Update
Certificate
Revocation
Lists
(although
these
are
self-
signed)
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
D 
 

Trust
(for
what
it's
worth)
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
T ,
T 
 
T
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Simple
HTTP
client
with
TLS
support:


curl
­v
­k
<address>
Troubleshoot
trust
issues
and
see
certificates
being
used:


openssl
s_client
­showcerts
­servername
<address>
­
connect
<address>:443
Troubleshoot
supported
protocols,
ciphers,
...:


nmap
­­script
ssl­enum­ciphers
­p
443
<address>
Trace
(or
even
decrypt)
TLS
traffic:


ssldump
­i
eth0
port
443
and
host
<address>
(add
­Ad
­k
<keyfile>
­p
<password>
for
decryption)
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
JVM
S
­Djavax.net.ssl.trustStore=<file>


Denotes
where
a
truststore
can
be
found:
a
file
that
contains
trusted
certs.


­Djavax.net.ssl.trustStorePassword=changeit


is
the
password
to
that
file.
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
JVM
S
­Djavax.net.ssl.keyStore=<file>


Denotes
where
a
keystore
can
be
found:
a
file
that
contains
public
and/or
private
keys.


­Djavax.net.ssl.keyStorePassword=changeit


is
the
password
to
that
file.
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
JVM
S
­Djavax.net.debug=ssl[:flag]


Include
debug
logging
for
TLS
handshake
and
connections.
Additional
flags:
record session sessioncache pluggability plaintext
handshake defaultctx keymanager data packet
keygen sslctx trustmanager verbose
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
P
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
P 
 
 -
1.
Don't
use
SSL!


Use
TLS
v1.2
or
v1.3.
2.
Be
careful
whom
you
trust!
3.
When
in
doubt,
open
your
toolbox:


openssl,
curl,
nmap,
ssldump
and
Portecle
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals
Q
















I 

Router
by

Public
Key
Krüpto
by
 ,
 ,
and
 
( )
Puss
In
Boots
by

IANA
Root
KSK
Ceremony
#36
@

Beverwijk
by
 
@

unknown
author
Sándor
P.
Fekete Sebastian
Morr Sebastian
Stiller @ideainstruction
kisspng
https://www.iana.org/dnssec/ceremonies/36
Gerard
Hogervorst Wikimedia
Commons
Maarten
Mulders
(@mthmulders)
  Devoxx
UK
 #tlsformortals

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