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Installing trusted SSL certificates on 10.5 Server -- anyone successful?

I've got a freshly-intalled 10.5 server directly connected to the internet. The ideal goal is to use it as a workgroup/collaboration server for a small group of distributed people who are scattered all over the place geographically.

My problem is that I can't use the GUI certificate manager to successfully import GoDaddy.com signed SSL certificates. I can create the self-signed cert, create the CSR request just fine. When the signed cert comes back from the vendor I try to bring it into the Certificate Manager and I just get nothing back -- no message, no error, no log entries. Just a certificate management interface that still lists my cert as unsigned and untrusted. Any attempts to use SSL protected services will verify that the cert being offered up is still self-signed.

I did get the webserver to secure itself properly by using command line OpenSSL commands to create the private key and CSR. Manually importing the key, cert and CA files will work and will create a good webserver. The problem with this method is that only the webserver is protected. Attempts to use the Certificate with iChat and iCal servers result in errors.

Has anyone been successful with this? It seems many people are using 10.5 server within a firewall where short non-fully-qualified hostnames and bonjour networking can be used. I need this 10.5 server connected to the internet and I need to protect OD, iChat, iCal and Apache via SSL. The workarounds I see posted for iCal and iChat problems all seem to involve either disabling SSL or using a shortname instead of a fully qualified hostname.

Mac OS X (10.5)

Posted on Nov 9, 2007 8:49 AM

Reply
24 replies

Nov 9, 2007 9:20 AM in response to chrisdag

chrisdag wrote:
I've found and used Keychain Access.app in Applications/Utilities but can't seem to find any program called "CA Assistant" in the 10.5 server installation.



Interesting. I don't have access to my 10.5 server install at the moment. The "CA Assistant" program is mentioned in the documentation on page 63:

Apple wrote:
... If you need these functions, you can use Apple's CA Assistant in /Applications/Utilities. It allows these functions, and others.

Nov 9, 2007 9:29 AM in response to Brentk

Appreciate the feedback and tips!

Just to rule out the possibility that my SSL vendor (GoDaddy) is providing signed certs that are causing problems on 10.5 I'll go back to the documentation links you provided and try to set everything up with certs signed by my own created CA. For a small user group it should not be that hard to distribute the necessary CA files to establish the trust chain.

I still can't find the "CA Assistant" mentioned in the docs:

sh-3.2# find / -name "CA Assistant*" -print
sh-3.2#

Interesting!

Given recent appleseed related activities I think that 10.5.1 Server will be available soon. Maybe I should just slow down and wait on either the seed or official 10.5.1 release.

Nov 9, 2007 11:38 AM in response to chrisdag

I think I have the same problem. I originally could not get the certificate files to import from GoDaddy. After finding that they "partially" imported into the Keychain, I deleted them from there and tried importing the certificate into server admin again. that time it worked. I had to make sure I imported the certificate, the private key file AND the chain file that I found here:

https://certificates.godaddy.com/MacOSX_alt.go

In keychain manager everything looks valid and says it's verified, BUT none of the other services seem to think that's it's verified. Hopefully this will bring some more ideas.

On a side note, I couldn't find Certificate Assistant either. I found mine here: Open Keychain Access, go to the "Keychain Access" menu and you will see it there.

Nov 16, 2007 5:18 PM in response to chrisdag

I am having the same issue. Leopard Server has a different procedure than Tiger Server. I have my Certificate file, Private Key file, and Certificate Authority file. The server admin is where you add the certs. But it just won't take.
I point to the files, and click import, I get a "Certificate Import Failed" error. "Make sure the values you entered are correct, and that the certificate files on the server are valid."

They are text files... Any ideas?

Nov 18, 2007 3:02 PM in response to Chris Born

Chris, I'm seeing the same error. I made an SSL cert and CA from Certificate Assistant and get the same error when attempting to input the cert into Server Admin. The console gives the following error.

servermgr_info: [6468] [CertificateManager importIdentity:] Error importing certificate: SecKeychainItemImport (err = -25299)

This seems to correspond to

errSecDuplicateItem –25299
An item with the same primary key attributes already exists.

But I've looked through the keychain and I don't think I have a duplicate.

I'm also looking forward to an answer. I'd like to secure my email.

Nov 20, 2007 12:03 AM in response to chrisdag

I was successful with 10.5.1.
I got the .pfx file from the authority (not godaddy.com) and decomposed it using openssl into the private key, the server cert and the ca chain file.
These I imported using the certificate section of server admin.

Problems I had:
1) no go under 10.5.0
2) after the first try there where leftovers of that experiment in /etc/certificates under the same name as the new certificates, cleaned them by hand.
3) keychain application: I removed all prior certificates with the machines name and also all private keys for that machine name, in all keychains.

After these cleaning works, server admin imported the certificate without problems and I can use it now for apache (and therefore the wiki) and iChat.

Nov 20, 2007 7:19 PM in response to Maximilian Reiss

Just to throw a wrinkle into the situation. I've created a CA and a Cert. I have the Cert imported into Server Admin and have it working with IMAP/POP and I think SMTP.

When checking from Mail.app I get a dialog saying the Cert is from an unknown certifying authority and do I want to trust it. Since it's me I check the box that says always trust. It seems to work as long as Mail.app stays open.

After a quit/restart of Mail.app I see the same dialog. I have imported the CA.crt into my X509Anchors keychain and everything.

Does Apple really allow you to create your own CA and certs and then not let you trust them always?

Installing trusted SSL certificates on 10.5 Server -- anyone successful?

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