Let's go HTTPS

ROME 18-19 MARCH 2016

Let's Go ! HTTPSSimone Carle4

! HTTPS

! HTTPS

I About HTTPS

II Obtaining an SSL cer?ficate

III Deploying an SSL cer?ficate

IV Serving HTTPS

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Simone Carle4@weppos

About HTTPS

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What is HTTPS?

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HTTPS (also called HTTP over TLS, HTTP over SSL, and HTTP Secure) is a protocol for secure communica?on over a computer network which is widely used on the Internet. HTTPS consists of communica?on over Hypertext Transfer Protocol (HTTP) within a connec?on encrypted by Transport Layer Security or its predecessor, Secure Sockets Layer. hTps://en.wikipedia.org/wiki/HTTPS

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https://en.wikipedia.org/wiki/HTTPS

What is HTTPS?HTTPS is a secure HTTP connec?on.

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HTTPS is HTTP over an encrypted connec?on secured by TLS (previously SSL).

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HTTPS is how websites securely exchange informa?on.

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Secure Connec@on

Encryp@on The process of encoding messages or informa?on in such a way that only authorized par?es can read it.

Authen@ca@on The process of determining whether someone or something is, in fact, who or what it is declared to be.

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KEEP CALM AND

HTTP IS NOT ENCRYPTED

HTTP ResponseHTTP Request

! HTTPS RequestHTTP Request

Authen@ca@on

Authen@ca@on

Authen@ca@on

Authen@ca@on

SSL Cer@ficate

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Why HTTPS?

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Why HTTPS?

! Security

! Ranking factor

! HTTP/2

! HTML 5 features

! Chrome Geo loca?on

! Firefox form + HTTPSIV

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! Security

• Data integrity

• User sensible informa?on

• Unencrypted traffic can be:

• sniffed

• modified (e.g. adver?sement or script injec?on)

! Ranking factorhTps://webmasters.googleblog.com/2014/08/hTps-as-ranking-signal.html

https://webmasters.googleblog.com/2014/08/https-as-ranking-signal.html

! HTTP/2hTps://webmasters.googleblog.com/2014/08/hTps-as-ranking-signal.html

https://webmasters.googleblog.com/2014/08/https-as-ranking-signal.html

! HTML 5 powerful featureshTps://blog.mozilla.org/security/2015/04/30/depreca?ng-non-secure-hTp/

hTps://sites.google.com/a/chromium.org/dev/Home/chromium-security/depreca?ng-powerful-features-on-insecure-origins

https://blog.mozilla.org/security/2015/04/30/deprecating-non-secure-http/

https://sites.google.com/a/chromium.org/dev/Home/chromium-security/deprecating-powerful-features-on-insecure-origins

! Chrome Geo locationhTps://codereview.chromium.org/1530403002/

https://codereview.chromium.org/1530403002/

! Firefox form + HTTPShTps://www.fxsitecompat.com/en-CA/docs/2015/non-hTps-sites-containing-login-form-will-be-marked-insecure/

https://www.fxsitecompat.com/en-CA/docs/2015/non-https-sites-containing-login-form-will-be-marked-insecure/

" SSL Cer@ficateA cer?ficate is a digital document that contains a public key, some informa?on about the en?ty associated with it, and a digital signature from the cer?ficate issuer.

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x.509 SSL Cer@ficate

# Version $ Serial Number % Issuer & Validity ' Subject ( Public Key

"

) Extensions

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Cer@ficate Types! Single-name cer?ficate example.com

! Wildcard-name cer?ficate *.example.com

! SAN cer?ficate example.com, www.example.com, foobar.com, …

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http://example.com

http://example.com

http://example.com

http://example.com

Symmetric vs Asymmetric

*!(

encrypt

(

decrypt

Shared secret key(

+John

+Jane

*!

Jane public key

Jane private key

(

(

+John

+Jane

(

decrypt

(

encrypt

encryp@on

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Symmetric encryp@on

"hello world!" "puggy eyxgr!"

"hello world!""puggy eyxgr!"

[["a", "b"],

["b", "w"],

["c", "n"],

["d", "r"],

["e", "u"],

["f", "o"],

["g", "v"],

["h", "p"],

["i", "s"],

["j", "z"],

["k", "k"],

["l", "g"],

["m", "m"],

["n", "h"],

["o", "y"],

["p", "c"],

["q", "j"],

["r", "x"],

["s", "d"],

["t", "t"],

["u", "f"],

["v", "i"],

["w", "e"],

["x", "l"],

["y", "a"],

["z", "q"]]

John encrypts John sends to Jane

Jane receives from John Jane decrypts

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How does HTTPS work?

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It's not a one-click setup :(yet

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Handshake, -

DISCLAIMER: This schema is simplified on purpose.

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HandshakeSYN

, -


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HandshakeSYN SYN ACK

, -


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. Client Random

( Cipher suites

ClientHello

, -


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. Client Random

( Cipher suites

/ Server Random

( Cipher suite

" Cer?ficates

0 Session ID

1 Server key exchange data

ClientHello

ServerHello, Cer?ficate, ServerKeyExchange, ServerHelloDone

, -


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. Client Random

( Cipher suites

/ Server Random

( Cipher suite

" Cer?ficates

0 Session ID


ClientHello


1 Client key exchange dataClientKeyExchange

, -


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. Client Random

( Cipher suites

/ Server Random

( Cipher suite

" Cer?ficates

0 Session ID


ClientHello


1 Client key exchange dataClientKeyExchange

SYMMETRIC KEY IS GENERATED

, -


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. Client Random

( Cipher suites

/ Server Random

( Cipher suite

" Cer?ficates

0 Session ID


ClientHello


1 Client key exchange data

! Client switches to encryp?on

! MAC of handshake

ClientKeyExchange

ChangeCipherSpec, Finished


, -


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. Client Random

( Cipher suites

/ Server Random

( Cipher suite

" Cer?ficates

0 Session ID


ClientHello




! MAC of handshake

ClientKeyExchange


! Server switches to encryp?on

! MAC of handshake



, -


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. Client Random

( Cipher suites

/ Server Random

( Cipher suite

" Cer?ficates

0 Session ID


ClientHello




! MAC of handshake

ClientKeyExchange


! Server switches to encryp?on

! MAC of handshake



2 Applica?on data2 Applica?on data

, -


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Cipher Suites

A cipher suite is a selec?on of cryptographic primi?ves and other parameters that defines exactly how security will be implemented.

Bulletproof SSL and TLS

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Cryptographic primi@ves

At the lowest level, cryptography relies on various cryptographic primi0ves. Each primi?ve is designed with a par?cular useful func?onality in mind. The primi?ves alone are not very useful, but we can combine them into schemes and protocols to provide robust security. For example, we might use one primi?ve for hashing, one for encryp@on and another for integrity checking.

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Obtaining an SSL cer@ficate

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self signed vs trusted• Provides encryp?on

• Provides authen?ca?on

• Issued and signed by a publicly trusted Cer?fica?on Authority

• Suitable for produc?on environments as well for tes?ng

• Generally not free

• Provides encryp?on

• Doesn't provide authen?ca?on

• self-signed

• Generally used for tes?ng

• Free

Cer?ficate AuthorityA Cer?ficate Authority (CA) is a trusted, private en?ty that issues digital cer?ficates.

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Chain of trust

• Browsers and opera?ng systems include a list of trusted cer?ficates • These cer?ficates are called root cer'ficates, and they generally belong to trusted

par?es, such as cer?ficate authori?esIV

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Chain of trust

• When a cer?ficate authority issues a cer?ficate, they sign the cer?ficate with their root cer?ficate

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Chain of trust

• Truthfully, in most cases cer?fica?on authori?es use sub-cer?ficates to sign your cer?ficate

• These cer?ficates are called intermediate cer'ficates, and they are signed with a root cer?ficateIV

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Chain of trust

• When the browser connects to a site via HTTPS, the browser reads the site cer?ficate

• The cer?ficate doesn't match a trusted root cer?ficateIV

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Chain of trust

• The browser aTempts to download the cer?ficate that was used to sign the current cer?ficate

• The cer?ficate doesn't match a trusted root cer?ficateIV

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Chain of trust


• The cer?ficate matches a root cer?ficate • The original cer@ficate is trusted :) • The en?re cer@ficate chain is trusted

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Chain of trust


• The cer?ficate doesn't match a root cer?ficate, and there are no more cer?ficates • The original cer@ficate is untrusted :( • The en?re cer@ficate chain is untrusted

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Create a Cer@ficateGenerate a

Private/Public key pair$ openssl genrsa -des3 -out private.key 2048

... Enter pass phrase for private.key: Verifying - Enter pass phrase for private.key:

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Private/Public key pair

Generate a

Cer?ficate Signing Request (CSR)

$ openssl req -nodes -new -key private.key -out server.csr

... Country Name (2 letter code) [AU]:US Common Name (eg, YOUR name) []:www.example.com ...

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Generate a


for a self-signed cer?ficate

Sign the cer?ficate

$ openssl x509 -req -days 365 -in server.csr -signkey private.key -out certificate.pem

hTps://devcenter.heroku.com/ar?cles/ssl-cer?ficate-self

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Request a trusted Cer@ficateGenerate a


Generate a


for a trusted cer?ficate

Request the Cer?ficate (*)

Request generally means purchase.

You can purchase an SSL cer?ficate either from a CA, or a reseller.

Some providers offer visual tools that help you with the request process (e.g. by genera?ng the CSR)

(*)

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Request a trusted Cer@ficateGenerate a


Generate a


for a trusted cer?ficate

Request the Cer?ficate (*)

• Select the cer?ficate type

• Submit the CSR

• Validate the request

• Obtain the cer?ficate

(*)

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! (DV) Domain Validated asserts control of a domain

! (OV) Organiza?on Validated asserts control of a domain as well basic organiza?onal vepng

! (EV) Extended Valida?on asserts control of a domain as well extended organiza?onal vepng

Cer@ficate Types

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5 Now you should have

1. A CSR file

2. A cer?ficate file

3. A private key file

4. (op0onally) A list of

intermediate cer?ficate files

-----BEGIN CERTIFICATE----- MIIENjCCAx6gAwIBAgIBATANBgkqhkiG9w0BAQUFADBvMQswCQYDVQQGEwJTRTEU MBIGA1UEChMLQWRkVHJ1c3QgQUIxJjAkBgNVBAsTHUFkZFRydXN0IEV4dGVybmFs IFRUUCBOZXR3b3JrMSIwIAYDVQQDExlBZGRUcnVzdCBFeHRlcm5hbCBDQSBSb290 MB4XDTAwMDUzMDEwNDgzOFoXDTIwMDUzMDEwNDgzOFowbzELMAkGA1UEBhMCU0Ux FDASBgNVBAoTC0FkZFRydXN0IEFCMSYwJAYDVQQLEx1BZGRUcnVzdCBFeHRlcm5h bCBUVFAgTmV0d29yazEiMCAGA1UEAxMZQWRkVHJ1c3QgRXh0ZXJuYWwgQ0EgUm9v dDCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBALf3GjPm8gAELTngTlvt H7xsD821+iO2zt6bETOXpClMfZOfvUq8k+0DGuOPz+VtUFrWlymUWoCwSXrbLpX9 uMq/NzgtHj6RQa1wVsfwTz/oMp50ysiQVOnGXw94nZpAPA6sYapeFI+eh6FqUNzX mk6vBbOmcZSccbNQYArHE504B4YCqOmoaSYYkKtMsE8jqzpPhNjfzp/haW+710LX a0Tkx63ubUFfclpxCDezeWWkWaCUN/cALw3CknLa0Dhy2xSoRcRdKn23tNbE7qzN E0S3ySvdQwAl+mG5aWpYIxG3pzOPVnVZ9c0p10a3CitlttNCbxWyuHv77+ldU9U0 WicCAwEAAaOB3DCB2TAdBgNVHQ4EFgQUrb2YejS0Jvf6xCZU7wO94CTLVBowCwYD VR0PBAQDAgEGMA8GA1UdEwEB/wQFMAMBAf8wgZkGA1UdIwSBkTCBjoAUrb2YejS0 Jvf6xCZU7wO94CTLVBqhc6RxMG8xCzAJBgNVBAYTAlNFMRQwEgYDVQQKEwtBZGRU cnVzdCBBQjEmMCQGA1UECxMdQWRkVHJ1c3QgRXh0ZXJuYWwgVFRQIE5ldHdvcmsx IjAgBgNVBAMTGUFkZFRydXN0IEV4dGVybmFsIENBIFJvb3SCAQEwDQYJKoZIhvcN AQEFBQADggEBALCb4IUlwtYj4g+WBpKdQZic2YR5gdkeWxQHIzZlj7DYd7usQWxH YINRsPkyPef89iYTx4AWpb9a/IfPeHmJIZriTAcKhjW88t5RxNKWt9x+Tu5w/Rw5 6wwCURQtjr0W4MHfRnXnJK3s9EK0hZNwEGe6nQY1ShjTK3rMUUKhemPR5ruhxSvC Nr4TDea9Y355e6cJDUCrat2PisP29owaQgVR1EX1n6diIWgVIEM8med8vSTYqZEX c4g/VhsxOBi0cQ+azcgOno4uG+GMmIPLHzHxREzGBHNJdmAPx/i9F4BrLunMTA5a mnkPIAou1Z5jJh5VkpTYghdae9C8x49OhgQ= -----END CERTIFICATE-----IV

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Deploying an SSL cer@ficate

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Install the cer@ficate on the server along with the private key, and intermediate cer?ficate chain.

Configure HTTPS configure protocol version, cypher suite and cypher sepngs.

To deploy HTTPS you need to:

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History of secure protocolsSSL 1 Never released

SSL 2 1996 A number of security flaws

SSL 3 1995 Broken. Vulnerable to POODLE aTack

TLS 1.0 1999

TLS 1.1 2006

TLS 1.2 2008IV

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Example configserver { listen 443 ssl http2; listen [::]:443 ssl http2;

# ssl certificate config ssl_certificate /path/to/certificate_and_intermediates; ssl_certificate_key /path/to/private_key;

# ssl session config ssl_session_timeout 1d; ssl_session_cache shared:SSL:50m; ssl_session_tickets off;

# protocol and cipher config ssl_protocols TLSv1 TLSv1.1 TLSv1.2; ssl_ciphers "EECDH+AESGCM:EDH+AESGCM:AES256+EECDH:AES256+EDH"; ssl_prefer_server_ciphers on; }

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hTps://mozilla.github.io/server-side-tls/ssl-config-generator/hTps://cipherli.st/

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https://mozilla.github.io/server-side-tls/ssl-config-generator/

https://cipherli.st/

Heroku$ heroku addons:create ssl:endpoint Adding ssl:endpoint on example... done, v1 ($20/mo)

$ heroku certs:add server.crt server.key Adding SSL Endpoint to example... done example now served by example-2121.herokussl.com. Certificate details: Expires At: 2012-10-31 21:53:18 GMT Issuer: C=US; ST=CA; L=SF; O=Heroku; CN=www.example.com Starts At: 2011-11-01 21:53:18 GMT

hTps://devcenter.heroku.com/ar?cles/ssl-endpoint

hTps://devcenter.heroku.com/ar?cles/ssl-cer?ficate-dnsimpleIV

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https://devcenter.heroku.com/articles/ssl-endpoint

https://devcenter.heroku.com/articles/ssl-certificate-dnsimple

Caddy server

hTps://caddyserver.com/

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https://caddyserver.com/

Caddy server

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Caddy server

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hTps://www.ssllabs.com/ssltest/

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https://www.ssllabs.com/ssltest/

Lifecycle of a Cer@ficate

6 Requested

! Issued

& Expired

4 Revoked

7 Rekeyed

Serving HTTPS

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Cookie security$ curl -I https://dnsimple.com

HTTP/1.1 200 OK Server: nginx Date: Tue, 15 Mar 2016 15:52:08 GMT Content-Type: text/html; charset=utf-8 Connection: keep-alive ETag: W/"f2d21600cdff911b9ee6a44dabcda234" Cache-Control: max-age=0, private, must-revalidate Set-Cookie: _session=eccefb19761929d668000056d1b2; path=/; HttpOnly; secure X-Request-Id: 9d77f4c5-ab6b-443e-91bd-76a0383d8ab5 X-Runtime: 0.016254 Strict-Transport-Security: max-age=31536000

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Cookie security$ curl -I https://dnsimple.com


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Mixed Content security error

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Chrome security debugger

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HSTS Header$ curl -I https://dnsimple.com


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HSTS Header

The first ?me your site is accessed using HTTPS and it returns the Strict-Transport-Security header, the browser records this informa?on, so that future aTempts to load the site using HTTP will automa?cally use HTTPS instead.

When the expira?on ?me specified by the Strict-Transport-Security header elapses, the next aTempt to load the site via HTTP will proceed as normal instead of automa?cally using HTTPS.

Strict-Transport-Security: max-age=31536000 Strict-Transport-Security: max-age=31536000; includeSubDomains Strict-Transport-Security: max-age=31536000; includeSubDomains; preload

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HSTS Header

The first ?me your site is accessed using HTTPS and it returns the Strict-Transport-Security header, the browser records this informa?on, so that future aTempts to load the site using HTTP will automa?cally use HTTPS instead.

When the expira?on ?me specified by the Strict-Transport-Security header elapses, the next aTempt to load the site via HTTP will proceed as normal instead of automa?cally using HTTPS.

Strict-Transport-Security: max-age=31536000 Strict-Transport-Security: max-age=31536000; includeSubDomains Strict-Transport-Security: max-age=31536000; includeSubDomains; preload

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HSTS HeaderStrict-Transport-Security: max-age=31536000 Strict-Transport-Security: max-age=31536000; includeSubDomains Strict-Transport-Security: max-age=31536000; includeSubDomains; preload

hTps://developer.mozilla.org/en-US/docs/Web/Security/HTTP_strict_transport_security

hTps://hstspreload.appspot.com/

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https://developer.mozilla.org/en-US/docs/Web/Security/HTTP_strict_transport_security

https://hstspreload.appspot.com/

Public Key Pinning

hTps://developer.mozilla.org/en-US/docs/Web/Security/Public_Key_Pinning

Public-Key-Pins: pin-sha256="base64=="; max-age=expireTime [; includeSubdomains][; report-uri="reportURI"]

Public-Key-Pins: max-age=5184000; pin-sha256="r/mIkG3eEpVdm+u/ko/cwxzOMo1bk4TyHIlByibiA5E="; pin-sha256="WoiWRyIOVNa9ihaBciRSC7XHjliYS9VwUGOIud4PB18="; pin-sha256="JbQbUG5JMJUoI6brnx0x3vZF6jilxsapbXGVfjhN8Fg="

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https://developer.mozilla.org/en-US/docs/Web/Security/Public_Key_Pinning

SecurityHeaders.io

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http://securityheaders.io

Let's Encrypt

Bulletproof SSL and TLS

hTp://bit.ly/codemo?on2016-sslbook

⋆⋆⋆⋆⋆

http://bit.ly/codemotion2016-sslbook

Simone Carle4! hTps://simonecarlep.com

@weppos

Thanks!

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