Remote OS X Server administration

I was having the same issue. On a hunch I restarted my test server and connecting remotely via the Server.app worked.

Note: After the restart while connecting with Server.app, I was prompted to trust the server certificate.

Bryan Dulock

ACN

Houston, TX

Check Console.app and see if you get the same as me while trying to connect. I posted a question here (no responses yet): Server: CFNetwork SSLHandshake failed (-9806)

So if you are using a signed 3rd party certificate to avoid the self-signed certificate warning... It appears to be broken in 10.10. This is if you do a clean install or during an upgrade. If you have modified the com.apple.servermgrd identity preference in Keychain to use a valid 3rd party SSL cert, you will NOT be able to connect remotely using Server.app 4.0. Bug report submitted. I recommend submitting duplicates.

Still trying to determine if the process for enabling this has changed. But following procedure that worked in Mavericks does not produce same results in Yosemite.

Reid

Apple Consultants Network

Author "Mavericks Server – Foundation Services" :: Exclusively available in Apple's iBooks Store

Author "Mavericks Server – Control and Collaboration" :: Exclusively available in Apple's iBooks Store

That does indeed seem to be the case. I will also submit a bug report.

Any workaround? If I set the identity preference back to the old com.apple.servermgrd certificate (which is expired), I still can't connect from a remote machine (perhaps because the cert. is expired?) and I don't know of a way to force a new one to be generated (removing both the old cert and the identity preference didn't cause a new one to be generated - which was only possible to attempt using the command line since Keychain Access wanted to crash when attempting to delete them).

Workaround posted by kirdes on this other thread (https://discussions.apple.com/thread/6603021?answerId=26902374022#26902374022&ac_cid=tw123456) - the thing I was missing was rebooting the server (which I usually don't do as part of troubleshooting).

sudo security set-identity-preference -n -s com.apple.servermgrd /Library/Keychains/System.keychain

sudo security delete-certificate -c com.apple.servermgrd /Library/Keychains/System.keychain

+ reboot gets a non-expired self-signed certificate back and I can connect.

thanks for that suggestion. that worked for me for getting past this until its resolved.

So we're 9 months along now, is it resolved by apple?

unfortunately did not fix my problem. Filed a bug report with Apple.