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Re: [Fed-Talk] CAC and PKI
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Re: [Fed-Talk] CAC and PKI



There's a bug with 10.4.x where the process that controlls the reader crashes when the system goes to sleep, and can't be restarted properly afterward. It doesn't matter if the reader was detached prior to sleep or not. You need to reboot for the reader to be accessible again.

I've never had the PIN entry problem you describe.

Entourage doesn't use Keychain at all, if I remember correctly. Mail.app will see the smartcard (assuming the controlling process hasn't died on you) and use it properly. This is entirely a Microsoft issue.

FYI, there's also a bug in Safari (actually, I would assume it's WebCore) where it won't use the certs that are in the smartcard keychain if you hold *any* certificate and private key in your login keychain. This includes SSL client authentication where the server specifies the DoD PKI root correctly.

Not much help, I know, but just so you know you're not crazy.  ;)

The above bugs are already submitted to Apple. I wish I could comment more on them but I can't.

(FWIW, I support the AF PKI SPO, so I'm kinda keen on these issues.)

-- Tim

Dalton Hamilton wrote:
Hello -
My name is Dalton Hamilton and I work at Landstuhl Regional Medical Center (LRMC) in Germany.
I'm the Senior European Network Engineer working for Medical Health Systems (MHS).


We recently purchased some Macs for LRMC, some in Rota Spain, and in Naples. We need to be able to send and received Digitally Signed and Encrypted email from Entourage 2004 using our CAC cards.

I've worked (and am still working) with a couple Apple contacts whom have been extremely helpful but due to the timezone differences, I'm not making progress fast enough.

Here is where I'm at so far -- I'm running 10.4.2:

1. Upgraded the firmware on the CAC Reader to V5.18. This allowed my system to see the CAC Reader and read the card. When I connect the CAC Reader, the pcscd process starts.
2. I've also installed the Common Access Card Viewer (CACV) application off the 10.4 Install DVD.
3. I then started the Keychain Access application and did Edit- >Keychain List and clicked on the "Shared" checkbox for X509Certificates.
3. Next I inserted my CAC ID and started the Common Access Card Viewer and it said it was loading the CAC info and then prompted me for my Keychain Password. At that time, I didn't realize the CAC Card itself was treated as a KeyChain -- even though I had made the above modifications to the Keychain Access application and could see the card showup as as a keychain. I typed in my user password and it prompted me again for a password, I again typed my user password, and it prompted me again for a password and I realized it must be talking about the CAC ID PIN number. I then typed the PIN number. Still no luck. I had locked the card already. I drove over the the DEERS/ RAPIDS group and they unlocked by card and let me put in another PIN (which I chose the same PIN number).
4. Once I was back at my system, I put the CAC ID in the reader and no luck at all -- the system would not detect the ID. I unplugged the CAC reader and plugged it back in and the system wouldn't detect the reader. I restarted the system and then the system would see the reader. I started Keychain Access and inserted my card and could see it showup as a keychain. I then inserted my CAC ID and started the CAC Viewer. It prompted for a keychain password and I very carefully typed the correct numbers. No luck, it prompted again. This tells me that the CAC Viewer can't communicate with the CAC ID properly.
5. I then moved on to Entourage. I setup Entourages security settings for the Signing Certificate and Encryption Certificate. I then sent a digitally signed email to another user. He sent me a signed email. I added his certificate/public-key to the contact and then sent him a signed and encrypted email. He responded with an encrypted email which my Entourage application could not decrypt. The error is "There was an error trying to decrypt the message or locating your encryption certificate." The attachment folder has a smime.p7m file in it. I double-clicked the smime.p7m and it prompted me to add the embedded or enclosed (or something like that) certificate to a keychain and gave me a pulldown list of keychains to add it to. Hmm, it didn't make sense but I tried it anyway, more out of frustration than logical sense. I added it to the Login keychain and the CAC Card keychain. Still nothing.
5. At the current moment, when I try to send an Digitally Signed email, I get an Entourage error reading "Could not save this message. An unknown error (1) occurred." and all I can do is hit ok. I can see all the certificates and private keys on the CAC card from the keychain access application.
6. Then sometimes I insert my card and it does not show up in the Keychain Access list.



Since I didn't take chronological notes on all this, I'm sure some of the above is a bit twisted; however, the point is, I'm really looking to get this working. I need this to work as it is a requirement to send Digitally Signed and Encrypted email for certain information. I want these systems to be successful and if I don't get it working, nobody else is. If anyone is monitoring this thread that can help, I'd be glad to give you a call or work offline via my military email address..


Many thanks
Dalton Hamilton
TIMPO Europe Senior Network Engineer

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 >[Fed-Talk] CAC and PKI (From: Dalton Hamilton <email@hidden>)



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