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How to create a secure (HTTPS) OS X webserver | 34 comments | Create New Account

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See, when my friends said to me, 'Why would you buy a Mac? You're already seriously guru-istic in both Windows AND Linux! Why bother?', I'd answer: 'Cause real geeks never stop learnin'!'
This is an excellently written article, and looks so much more complete and thorough than the Apache-SSL Howtos I've seen for Linux. They're so poorly written that I gave up trying to get SSL working on Apache fairly quickly. It wasn't something I REALLY needed, just something to play with. With your article, I saw three points where I made mistakes immediately.
Nicely done and thanks!
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Answering the age-old question: which is more painful, going to work or gouging your eye out with a spoon?
www.workorspoon.com

Thanks.
The biggest problem I had found with the Linux-based tutorials was that none of them were written with the OS X file hierarchy in mind. Sure, you can delve into the dark hidden corners of the /folder structure, but I wanted to put things in context with /Users/username as much as possible so that a year from now, you can go back and easily figure out what was done.
Out of curiosity, what points did you get wrong?
Cheers.

Um, offhand, the biggest problems were the creation of a cert authority and/or self-signing the cert. Also, the removal of the password from the cert. The howtos made this look a ton more complex than you did. I didn't feel like bothering with that much work for a minor pet project.
I'm going to use this tonight to see if I can get it working on my Linux box. I still use Apache, but primarily as a reverse-proxy to my internal network. I'm using SSL_Proxy to encrypt packets, but would prefer to just use Apache and be done with it. SSL_Proxy was setup in 5 minutes (including download and compile time), this makes it look like Apache should be as quick!
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Answering the age-old question: which is more painful, going to work or gouging your eye out with a spoon?
www.workorspoon.com

I tried to follow this hint and once I was done and I restarted apache via sudo apachectl graceful I got the following error:
configuration broken, ignoring restart
/usr/sbin/apachectl graceful: (run 'apachectl configtest' for details)
Running configtest gives the following:
Processing config directory: /private/etc/httpd/users/*.conf
Processing config file: /private/etc/httpd/users/laubennd.conf
Processing config file: /private/etc/httpd/users/neil.conf
Processing config file: /private/etc/httpd/users/neill2.conf
Processing config file: /private/etc/httpd/users/ssl.conf
Syntax error on line 15 of /private/etc/httpd/users/ssl.conf:
SSLCipherSuite takes one argument, Colon-delimited list of permitted SSL Ciphers (`XXX:..:XXX' - see manual)
which tells me t hat the SSLCipherSuite is incorrect . . . I've double checked that I copied/pasted it exactly as in the hint.
Any ideas why it isn't working right?

Good hint - nice & clear. In case anyone needs another set of insructions, the one I used when setting up ssl was this one :
http://developer.apple.com/internet/serverside/modssl.html
which was also pretty clear and easy to follow (although providing this alternative reminds me of the old adage, about someone who has 2 clocks never knowing the exact time.. :-)
cheers
m

Don't most browsers choke on self-signed certificates?

I can only speak for Safari on OS X and Internet Explorer on XP: they don't exactly 'choke' as much as 'hiccough'. On a per-session basis, I get prompted with a warning message about the certs, but once I accept this, I can load pages just fine.
Since I am pretty much the only surfer of my pages (I have mine secured with mod-auth, too), I don't mind the minor inconvenience. If others were surfing, I might go ahead and get a real domain name and use one of the cert authorities.
On a side note- I would prefer to use mod-digest instead, but IE really chokes on some of my PHP pages then. Since I am using SSL, am I correct that that covers my mod-auth also? In other words, eventhough the password is sent in the clear, it's sent in the clear THROUGH SLL, so it's encrypted, right?

Yes, it is sent over the encrypted link, so it isn't clear-text. Digest authentication is flawed, anyway, so you really need SSL even when you use it.

No. Most offer you the option of importing the cert into your personal store. With IE, simply choose 'View Certificate' when the warning pops up, there's an 'Install Certificate' option within there. For Mozilla, it'll ask if you always want to accept that certificate. IIRC, Safari works similarly. The only time you should ever have a problem again is when the cert changes, which should only be when you change it..or someone else.. ;-)
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Answering the age-old question: which is more painful, going to work or gouging your eye out with a spoon?
www.workorspoon.com

Indeed, very nicely done.
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--
Everything Mac - http://everythingmac.org

Since I work out of a home office a lot, I often put files for clients to access from the network at home. This added bit of security gives those skittish clients a little extra peace of mind.
Nice job!

This hint is great. It's just begging for a nice user-friendly GUI tool to wrap up the functionality, though! anyone?
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In /dev/null, no one can hear you scream

I was planning on writing one over break in cocoa.

Take a look at SimpleCA at http://users.skynet.be/ballet/joris/SimpleCA/. which uses Tcl/Tk and runs on Linux and Windows. You should be able to get it going on OSX if you install Tcl/Tk.
Being able to create client certificates is very handy and should be part of any similar app for OSX.
-m

The original hint had: I would suggest the following instead: This setting will disable SSL version 2 (which has seciruty problems) as well as weak ciphers (LOW, EXP).
Having +eNULL is particulary discouraged since NULL ciphers are ciphers offering no encryption! The setting in the original hint doesn't seem to enable NULL ciphers on a server I tested it on but looks dangerous to me.
Great hint BTW.
-m

Thanks for the tweak on the CipherSuite; I was pulling from a .conf file on a Linux box that I have access to and didn't fine-comb through all the details.
Again, the initial goal of writing this hint was to help folks get their teeth around on how to get SSL up and running on their own OS X boxes; fine tuning for performance, security, or other customized tweaks is left for the braver souls to learn and share!

Hi
Great info on SSL - i've also implemented the 'better' cipher,
Also I think that the info in this link: http://developer.apple.com/internet/serverside/modssl.html could be of interest to all.
Quote from above article:
'You'll be asked for some information when you start this. Most of it is pretty self explanatory, but one item, in particular, is not. Here's what you'll be asked for:
Country Name (2 letter code) [AU]: (enter your country code here)
State or Province Name (full name) [Some-State]: (Enter your state here)
Locality Name (eg, city) []: (enter your city here)
Organization Name (eg, company) [Internet Widgits Pty Ltd]: (enter something here)
Organizational Unit Name (eg, section) []: (enter something here)
Common Name (eg, YOUR name) []: (this is the important one)
Email Address []: (your e-mail address)
The entry for 'Common Name' is the one that seems like it should be one thing, but is, in fact, another. For this entry, you want to enter your 'Server Name' as it appears in your httpd.conf (which you'll be modifying soon). A

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