Five Tips For Using Self Signed SSL Certificates With iOS - HttpWatch BlogHttpWatch Blog

Five Tips for Using Self Signed SSL Certificates with iOS | HttpWatch BlogHttpWatch Blog
15/03/16 22:33
Five Tips for Using Self Signed SSL Certificates with iOS
SSL certificates are relatively cheap to purchase, but sometimes it would be easier if
you could create your own. You might need to setup SSL on development and test
servers that have different host names or on systems that will only ever be accessed
on your local network.
Self-signed SSL certificates allow you to quickly create certificates for free, without
having to pay a Certificate Authority (CA) or comply with any auditing requirements.
The downside of using self-signed certificates is that browsers will not automatically
trust sites that use them. In Mobile Safari you would see an error like this:
The HttpWatch iOS app provides some more detail:
https://blog.httpwatch.com/2013/12/12/five-tips-for-using-self-signed-ssl-certificates-with-ios/
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The rest of this post provides tips on how to setup iOS to avoid these errors and how
to simplify the creation and management of self signed certificates.
Tip #1 Dont Accept your Self-Signed Certificate in Mobile Safari

Its tempting to just select Continue or Details->Accept when you first try using your
self-signed certificate in Safari:
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This would allow you to open the site in Safari, but there are two significant downsides:
1. Accepting the certificate in Safari just adds an SSL exception that prevents Safari
warning you about the site. It doesnt install the certificate as a trusted certificate
on iOS. Any other apps (e.g. Chrome, HttpWatch, etc) on the device will still fail
to connect to the site.
2. Once the SSL exception is added there doesnt seem to be a way to remove it in
iOS 7. In previous versions going to Settings->Safari and selecting Clear Cookies
and Data would delete it. This no longer seems to work in iOS 7 (please leave a
comment if you know how to do this).
Tip #2 Install Self-Signed Certificates as an iOS Configuration Profile

You can add an SSL certificate to the trusted list in iOS by simply emailing the file to
yourself as an attachment:
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Then select Install to add the certificate. Once youve done this you use the certificate
without warnings in Safari or other iOS apps that use the devices keychain..
Also unlike Safari SSL exceptions, you can access the certificate at any time in
Settings->General->Profiles and remove it if required:
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Apple provides an iPhone configuration utility for Mac and PC that can also install
certificates. This would be a better option where email is not available or you have a
larger number of iOS devices to manage.
Tip #3 Dont create Self-Signed Certificates within IIS

Creating self-signed certificates in IIS appears to be easy. You just select the Create
Self-Signed Certificate menu item:
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Unfortunately, IIS uses the computer name as the host name in the certificate:
It most cases the computer name will not match the intended host name and you end
up with a self-signed certificate that is never trusted even when it is added to iOS:
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Its possible to fix this problem by installing and running the SelfSSL tool from the IIS 6
Toolkit. However, its probably easier just to use OpenSSL as described in the next tip.
Tip #4 Creating Self-Signed Certificates with OpenSSL is Easy

One of the easiest ways of creating a self-signed certificate is to use the OpenSSL
command line tool that is available on most platforms and installed by default on Mac
OSX.
First create a private key file:
openssl genrsa -out myselfsigned.key 2048
Then create the self signed certificate:

openssl req -new -x509 -sha256 -key myselfsigned.key -out myselfsigned.cer -days 365
-subj /CN=www.mysite.com
You can use any filenames you like for the key and certificate (.cer) files. The /CN
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parameter needs to be set to the required hostname (e.g. for https://www.mysite.com

in the example above). The days parameter specifies the expiration date as days from
todays date.
Theres even a site to do this if you dont feel like downloading OpenSSL, but of course
its more secure to do it yourself.
On Apache servers the key and certificate file can be used directly in your SSL
configuration. With IIS you need a PFX file so that you can import the certificate into
the Server Certificates section of IIS. OpenSSL can create the PFX file for you as well:
openssl pkcs12 -export -out myselfsigned.pfx -inkey myselfsigned.key
-in myselfsigned.cer
Tip # 5: Consider Creating Your Own Certificate Authority (CA)

One problem with self-signed certificates is that youll need to set up trust
relationships for each certificate on each device. An alternative is to create your own
Certificate Authority (CA) root certificate and then create certificates based on it.
Instead of paying a commercial CA to create SSL certificates on your behalf, you are
acting as your own CA. The advantage is that your custom CA certificate only has to be
installed once on each device. The devices will then automatically trust any certificates
you issue based on your root CA certificate.
Creating the CA certificate is a simple two step process. First create a private key file
as before:
openssl genrsa -out myCA.key 2048
Then create the certificate:

openssl req -x509 -sha256 -new -key myCA.key -out myCA.cer -days 730
-subj /CN="My Custom CA"
The certificate file (myCA.cer) created above can be publicly shared and installed on
iOS or other OSs to act like a built in trusted root CA. Custom CA certificates on iOS
are also stored in General->Settings->Profile:
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The private key file (myCA.key) is only used when creating new SSL certificates.
You can create as many certificates as you like based on this CA certificate. Theres an
extra step involved because you have to create a CSR (Client Signing Request) as if
you were purchasing a commercial SSL certificate.
First you would create a private key:
openssl genrsa -out mycert1.key 2048
and then create the CSR:

openssl req -new -out mycert1.req -key mycert1.key -subj /CN=www2.mysite.com
Then use the CSR to create the certificate:

openssl x509 -req -sha256 -in mycert1.req -out mycert1.cer -CAkey myCA.key
-CA myCA.cer -days 365 -CAcreateserial -CAserial serial
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The certificate created (mycert.cer) can be installed on a web server and accessed
from any iOS device that already has the CA certificate installed.
UPDATED September 24th, 2015 The OpenSSL certificate creation commands now
include the -sha256 flag to avoid browser warnings about the use of SHA1. This tip
was provided in a comment by Giancarlo Gomez Thanks
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Five Tips for Using Self Signed SSL Certificates with iOS | HttpWatch BlogHttpWatch Blog

The HttpWatch iOS app provides some more detail:

Tip #1 Dont Accept your Self-Signed Certificate in Mobile Safari

Tip #2 Install Self-Signed Certificates as an iOS Configuration Profile

Tip #3 Dont create Self-Signed Certificates within IIS

Tip #4 Creating Self-Signed Certificates with OpenSSL is Easy

Then create the self signed certificate:

parameter needs to be set to the required hostname (e.g. for https://www.mysite.com

Tip # 5: Consider Creating Your Own Certificate Authority (CA)

Then create the certificate:

and then create the CSR:

Then use the CSR to create the certificate:

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