Lion server erased self signed certificate

Help!!! I accidentally deleted the self signed certificate that had the right keys for my third party SSL. Now I cannot replace the self signed certificate with the new SSL. Now what????

I will begin my answer by making an emphasis that the best way to protect your data in-transit is using a 2048 bit certificate signed by a trusted certificate authority (CA) instead of relying on the self-signed certificate created by SQL Server.
Please remember that the self-signed certificate created by SQL Server usage for data in-transit protection was designed as a mitigation against passive traffic sniffers that could potentially obtain SQL Server credentials being transmitted
in cleartext, but nothing more. Think of it as a mitigation against a casual adversary.
The self-signed certificate usage was not intended to replace real data in-transit protection using a certificate signed by a trusted CA and encrypting the whole communication channel. Remember, if it is self-signed, it is trivial to spoof.
After making this clarification, the self-signed certificate generated by SQL Server uses a 1024 bit key, but that size may be subject to change in future versions of the product. Once again, I would like to strongly discourage relying on the self-signed
certificate created by SQL Server for data in transit transmission.
BTW. Azure SQL Database uses a 2048 certificate issued by a valid certificate authority.
I hope this information helps,
-Raul Garcia
SQL Server Security
This posting is provided "AS IS" with no warranties, and confers no rights.

Similar Messages

SQL Server 2008 self-signed certificate is 1024bit or 2048bit?

When there is no user defined certificate available, SQL Server will generate a self-signed certificate when service starts, We have a tool scans and finds that in SQL 2005 the self-signed certificate is 1024bit, does someone know the default self-signed
certificate is still 1024bit or is it 2048bit in SQL 2008? Thanks a lot!!!

I will begin my answer by making an emphasis that the best way to protect your data in-transit is using a 2048 bit certificate signed by a trusted certificate authority (CA) instead of relying on the self-signed certificate created by SQL Server.
Please remember that the self-signed certificate created by SQL Server usage for data in-transit protection was designed as a mitigation against passive traffic sniffers that could potentially obtain SQL Server credentials being transmitted
in cleartext, but nothing more. Think of it as a mitigation against a casual adversary.
The self-signed certificate usage was not intended to replace real data in-transit protection using a certificate signed by a trusted CA and encrypting the whole communication channel. Remember, if it is self-signed, it is trivial to spoof.
After making this clarification, the self-signed certificate generated by SQL Server uses a 1024 bit key, but that size may be subject to change in future versions of the product. Once again, I would like to strongly discourage relying on the self-signed
certificate created by SQL Server for data in transit transmission.
BTW. Azure SQL Database uses a 2048 certificate issued by a valid certificate authority.
I hope this information helps,
-Raul Garcia
SQL Server Security
This posting is provided "AS IS" with no warranties, and confers no rights.

Web Server 7 Admin Server and Self-Signed certificate

Is it possible to create and install a self-signed certificate for the administration server in Sun Web Server 7. The default installation comes with a self-signed certificate but we would like to install our own certificate and not the certificate issued by "admin-ca-cert"
Message was edited by:
aar

As far as I know its not a problem. You can install your own certificate. Make sure that the certificate nick name is changed accordingly in "server-cert-nickname" in server.xml section as shown below :
<http-listener>
<name>admin-ssl-port</name>
<port>2224</port>
<server-name>alamanac.india.sun.com</server-name>
<default-virtual-server-name>admin-server</default-virtual-server-name>
<ssl>
<server-cert-nickname>Admin-Server-Cert</server-cert-nickname>
</ssl>
</http-listener>

How to import the self-signed certificate in runtime

HI.
I work to connect between JSSE client and OpenSSL server with self-signed certificate.
But I met the SSLSocketException during handshaking.
Many Solutions registered in this page.
But their are all using keytool.
My application connect many site support the self-signed certificate.
So, I want to import the certificate in run time.
How Can I do??
Please, answer me..
Thanks,

did you figure this out??? I need to know how to accept a self-signed certificate, otherwise it's this exception...
D:\javatools\apis\jsse1.0.2\samples\urls>java -cp jcert.jar;jnet.jar;jsse.jar;. URLReader
Exception in thread "main" javax.net.ssl.SSLException: untrusted server cert chain
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.a([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.ssl.ClientHandshaker.a([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.ssl.ClientHandshaker.processMessage([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.ssl.Handshaker.process_record([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.a([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.a([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.ssl.AppOutputStream.write([DashoPro-V1.2-120198])
at java.io.OutputStream.write(OutputStream.java:61)
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.HttpsClient.doConnect([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.NetworkClient.openServer([DashoPro-V1.2-12019
8])
at com.sun.net.ssl.internal.www.protocol.https.HttpClient.l([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.HttpClient.<init>([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.HttpsClient.<init>([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.HttpsClient.a([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.HttpsClient.a([DashoPro-V1.2-120198])
at com.sun.net.ssl.internal.www.protocol.https.HttpsURLConnection.connect([DashoPro-V1.2-120
198])
at com.sun.net.ssl.internal.www.protocol.https.HttpsURLConnection.getInputStream([DashoPro-V
1.2-120198])
at java.net.URL.openStream(URL.java:798)
at URLReader.main(URLReader.java:46)

How to erase all self signed certificates and force Server to use Signed SSL

I have been using a poorly managed combination of self-signed SSL certificates and a free one. I have purchased a good SSL from Digicert and am trying to configure the server to use it across the board. All of the services seem to be using it, but when I try to manage the server remotely, I seeing a self-signed certificate instead.
I look under the system keychain in K-Access and there are several self signed certificates there (including the one that I am seeing when I try to remote manage).
Can I replace those self-signed certs with the new one some how?

Don't delete those. However, you are on the right track. Follow these steps to resolve.
1: Launch Keychain Access
2: Select the System Keychain
3: Find the com.apple.servermgrd IDENTITY PREFERENCE (looks like a contact card) and double click to open it
4: In the Preferred Certificate popup, change com.apple.servermgrd to your purchased certificate
5: Press Save Changes to save.
6: Reboot the server or kill the servermgrd process to restart the service.
That should resolve your issue.
R-
Apple Consultants Network
Apple Professional Services
Author "Mavericks Server – Foundation Services" :: Exclusively available on the iBooks store

How to register iOS device when using self signed certificate with apple Server?

Hi,
I have installed the server.app by Apple and used a slef signed certificate for my server. Now I want to register my different devices (iMac, iPhone etc.). I could register the iMac without problesm (I just had to add my self signed certificate to the trusted certificates)
Sadly, with the iPhone it is not that easy. I can install the "trust profile", but still after that I can not register my device. It seems like it does not accept my self signed certificate for device registration. When adding a registration profile, I get the error "www._mydomain_.tld/devicemanagement/api/device/auto_join_ota_service" is not valid.
Nethertheless, I can install a profile with setting, e.g. my imap settings, via the profile management without problems.
Does anyone have an idea how to get around the problem with the self signed certificate?
Best regards

Try deleting the Server.app and download it again from the App Store, restart.
My Server is also using self signed certificates and is working with iOS device (Trust Profile needed first).

Can you use a self signed certificate on an external Edge Server interface?

Hi,
I have a small lab deployment for evaluation purposes. The Lync FE server works great for internal users. I have now added an Edge server. For the internal interface, I have a self signed certificate from our internal CA. (no problem there) For the external
interface, I have a self signed certificate from our own external CA. I have installed the cert on the client machine of the external user and installed it for trusted operation. I have used the RUCT and digicert tools to prove that the external self signed
cert is valid (root and intermediate have been checked for validity).
At first, when logging in from the Lync 2013 client on the external users machine, I would get an error from Lync about the cert being untrusted. I have now fixed that error by adding it as trusted. At this point, there are no errors or warnings in the Event
Viewer (in the application or system logs) However, I receive the following error from the Lync client, "Were having trouble connecting to the server... blah, blah".
Here is my question. Does the Microsoft Lync 2013 client and/or the "testconnectivity.microsoft.com" tool specifically prevent or forbid the use of self signed certificates on the external interface of an Edge server? They seem too.
I can tell if the certificate is my problem or something else. Any ideas on how to trouble shoot this?
Thx

Drago,
Thanks for all your help. I got it working.
My problem with the Lync client error, "Were having trouble connecting to the server... blah, blah", was NOT a certificate error. It was a problem with my Lync Server Topology. (My sip default domain needed to match my user login domain.)
Let me update everyone about self-signed certificates:
YES, you can self-sign a certificate on your external edge server. It is a pain, but possible.
I have a self signed certificate from our own external CA. I have installed the cert on the client machine of the external user for trusted operation. I have used the RUCT and digicert tools to prove that the external self signed cert is valid (root and
intermediate have been checked for validity).
Here are my notes:
Create/enable your own external Certificate Authority (CA) running on a server with internet access.
On the Lync Edge Server, run the "Lync Server 2013 - Development Wizard".
Click "Install or Update Lync Server System". (Lync will automatically determine its deployment state)
You should have already completed: Step1 and Step 2.
Run or Run Again "Step 3: Request, Install or Assign Certificates".
Install the "Edge internal" certificate.
Click "Request" button to run the "Certificate Request" wizard.
You use can "Send the request immediately to an online certificate authority" option to connect to your internal CA, and create the certificate.
Once the certificate has been created, use "Import Certificate" to import it.
Once imported, on the Edge Server, go to: (Control Panel -> Administrative Tools -> Internet Information Services (ISS) Manager -> Server Certificates -> Complete Certificate Request...
In the Lync deployment wizard - Certificate Wizard, "Assign the newly imported "edge internal" certificate.
Install the "Edge External" certificate (public Internet).
Click the "Request" button to run the "Certificate Request" wizard.
Press "next"
Select "Prepare the request now, but send it later (offline certificate request).
Supply the "Certificate Request File" name and location. (You will need the file later. It should have the file extension ".req").
Click next on the "Specify Alternate Certificate Template". (which means you are using the default options)
Give it a Friendly Name. Bit Length = 2048. I selected "Mark the certificate's private key as exportable" option.
Fill in the organization info.
Fill in the Geographical Information.
The wizard should automatically fill-in the "Subject name:" and "subject alternative name:' fields.
Select your "Configured SIP domains"
"Configure Additional Subject Alternative Names" if you want. Otherwise, next.
Verify the "certificate Request Summary". Click next.
Run the wizard script to "Complete". The wizard will create a file containing the certificate request with the file extension ".req". (Let's assume the file name is "myCert.req")
Move your myCert.req file to your external CA. Have your CA issue the cert (based on myCert.req) and export the new cert to a file. I save it as a P7B certificate. (Let's call it "ExternalCert.p7b")
In the Lync Deployment wizard - Certificate Wizard, click on "Import Certificate" for ExternalCert.p7b.
Once imported, on the Edge Server, go to: (Control Panel -> Administrative Tools -> Internet Information Services (ISS) Manager -> Server Certificates -> Complete Certificate Request... (assign it a friendly name. Let's say "EXTERNAL-EDGE")
For the "External Edge certificate (public Internet), click "Assign".
The "Certificate Assignment" wizard will run.
Click next.
From the list, select your cert "EXTERNAL-EDGE".
Finish the wizard to "complete".
You are finished on the server.
Move the "ExternalCert.p7b" file to the machine running the lync client. Install the cert via the "Certificate Import Wizard".
When installing it to a particular Certificate Store, select the "Place all certificates in the following store" option.
Browse
Select "Trusted Root Certification Authorities"
Finish the wizard.

In Firefox 4.0 with a Server with a self signed certificate using IPv6 I can not add a "Security Exception" for this certificate.

In Firefox 4.0 I have a server ... it contains a self signed certificate. Using IPv6 I can not add a "Security Exception" for this certificate.
1. I log onto the server (using IPv6). I get the "Untrusted connection page" saying "This connection is Untrusted"
2. I click on "Add Exception.." under the "I understand the Risks" section.
3. The "Add Security Exception" dialog comes up. soon after the dialog comes up I get an additional "Alert" dialog saying
An exception occured during connection to xxxxxxxxx.
Peer's certificate issuer has been marked as not trusted by the User.
(Error code sec_error_untrusted_issuer).
Please note that this works in Firefox 3.6.16 (in IPv4 and IPv6). It also works in Firefox 4.0 in IPv4 only IPv6 has an issue. What's wrong?

Exactly the same problem, except I'm using FF v6 for Windows, not FF v4 as for the lead post. This is for a self-cert which IS trusted, although the error message says it isn't.

Why, when I successfully connect to Server 2012 Essentials R2 via Anywhere Access does the Remote Desktop Connection use the self signed certificate for RDP instead of the SSL certificate I installed when I set up access anywhere?

Scenario:
Windows Server 2012 R2 Essentials
I purchased an SSL Cert from GoDaddy and I managed (after some challenges) to set up Anywhere access to use that new SSL Cert. I to rebooted the server and I am able to login to Anywhere Access vis https (using the SSL certificate) from PC, Mac and iOS.
So far so good.
The problem I am having is that when I click to launch a remote desktop connection to the server RDP connection wants to use the self signed SSL certificate of the server rather than the SSL Certificate I installed into Anywhere Access. As a result, I get
a security warning like this: "The identity of the remote computer cannot be verified. Do you want to connect anyway?"
The name in the certificate appears as ACME-SERVER.ACMEDOMAIN.local instead of the SSL Certificate I installed, which is
remote.acmedomain.com
If I lick to accept, RDP does work fine, it;s just using a self signed certificate. I want it to use the trusted certificate that I purchased and installed.
My guess is that there must be an additional step to tell Anywhere Access that when it generates the RDP session that it should use the cert? OR, is this just how it works?

Because....
the server does not have a 'trusted' certificate assigned to it.
Only the RDP Gateway has the trusted certificate for the external name.
If you want to remove that error, you have to do one of the following:
Make sure your domain uses a public top level domaim, and get a public trusted certificate for your server.
So, something like,
server.domain.publicdomain.com
Or,
Install that certificate on your remote computer so it is trusted.
Robert Pearman SBS MVP
itauthority.co.uk |
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How to issue a self-signed certificate to match Remote Desktop Gateway server address requested

I have an RDG server named gw.domain.local with port 3389/tcp forwarded from
gw.example.com.
Using RDGM snap-in I created a self-signed SSL certigicate with FQDN gw.example.com.
But when I connect over RDP from outside the local network I'm getting an error:
Your computer can't connect to the computer because the Remote Desktop Gateway server address requested and the certificate name do not match
Because certificate subject name is gw.domain.local indeed.
So there question is: how to issue a certificate properly, or how to assign an existing one the name to match?

Hi,
Thanks for your post in Windows Server Forum.
The certificate error which you are facing seems like certificate mismatch error, something like the security certificate name presented by the TS Gateway server does not match the TS Gateway name. You can try reconnecting using the FQDN name of the TS Gateway
server. You can refer below article for more troubleshooting.
TS Gateway Certificates Part III: Connection Time Issues related to TS Gateway Certificates
And for creating a SSL certificate for RD gateway, you can refer beneath articles.
1. Create a Self-Signed Certificate for the Remote Desktop Gateway Server
2. Obtain a Certificate for the Remote Desktop Gateway Server
Hope it helps!
Thanks,
Dharmesh

Generating Self Signed Certificate for iPlanet Directory Server for testing

Hi Experts,
I am unable to find how to generate self signed certificate for iPlanet Directory Server for testing purpose. Actually what i mean is i want to connect to the iPlanet LDAP Server with LDAPS:// rather than LDAP:// for Secured LDAP Authentication. For this purpose How to create a Dummy Certificate to enable iPlanet Directory Server SSL. I searched in google but no help. Please provide me the solution how to test it.
Thanks in Advance,
Kalyan

Here's one I did earlier.
Refers to Solaris 10
SSL Security
add a new certificate that lasts for ten years (120 months).
stop the instance:
dsadm stop <instance>
Remove DS from smf control:
dsadm disable-service <instance>
Change Certificate Database Password:
dsadm set-flags <instance> cert-pwd-prompt=on
     Choose the new certificate database password:
     Confirm the new certificate database password:
Certificate database password successfully updated.
Restart the instance from the dscc:
DSCC -> start <instance>
Now add a new Certificate which lasts for ten years (120 months; -v 120):
`cd <instance_path>`
`certutil -S -d . -P slapd- -s "CN=<FQDN_server_name>" �n testcert �v 120 -t T,, -x`
     Enter Password or Pin for "NSS Certificate DB":
Stop the Instance.
On the DSCC Security -> Certificates tab:
     select option to "Do not Prompt for Password"
Restart the instance.
On the Security -> General tab, select the new certificate to use for ssl encryption
Restart the instance
Stop the instance
Put DS back into smf control:
dsadm enable-service <instance>
Check the smf:
svcs -a | grep ds
# svcs -a|grep ds
disabled Aug_16 svc:/application/sun/ds:default
online Aug_16 svc:/application/sun/ds:ds--var-opt-SUNWdsee-dscc6-dcc-ads
online 17:04:28 svc:/application/sun/ds:ds--var-opt-SUNWdsee-dsins1

Step by Step Instructions for Installing Self Signed Certificate using Certificate Modification Tool

I am looking for some step by step instructions for installing the self signed certificate from my Microsoft SBS 2003 server on a Treo 755p and 750p. In particular I need some help with the form of the actual certificate and how to use the Certificate Modification tool.
Some questions I have are as follows:
1. When I install the certificate on a Windows Mobile device I used an exported version of the certificate. This export is done using the DER x.509 format. Is that the same form I’ll need for the Palm? Do I need some other form? Can/should I just use sbscert.cer file that is generated when SBS is configured?
2. Does the self signed cert need to be installed on the computer being used to update the Palm or do we just need to be able to access the appropriate .CER file?
3. There are three things included in the PalmCertificatesTool.zip file:
                                Trusted CAs (folder)
                                Cert2pdb.exe
                                PalmCertificates.exe
   How do I use these tools?
4. It looks like the PalmCertificates.exe file opens an interface that will allow me to browse to the desired .CER file. Then I suppose I use the < Generate PDB > to create something that needs to then be uploaded to the Palm device? Not having any real experience with a Palm device how do I upload and install this file?
5. Once uploaded do I do something on the device to install it?
If there is some white paper that provides step by step instructions on doing this that would be great.
Thanks,
Walt Bell
Post relates to: Treo 755p (Verizon)
Post relates to: Treo 755p (Verizon)

Thanks for that.
I have one question after reading the article 43375:
The article has you "Turn of AutoSync" and then "Reset the device". It then indicates the device should be left idle.
The next step relates to running the PalmCertificates.exe, navigate to the certificate file and add it and then run the < Generate PDB > button. Should the device be connected to the computer during this process? If so, at what point after the reset do you connect it to the computer?
Thanks!
Post relates to: Treo 755p (Verizon)

Possible to select self-signed certificate for client validation when connecting to VPN with EAP-TLS

In windows 8.2, I have a VPN connection configured with PPTP as the outer protocol and EAP : "Smart card or other certificate ..." as the inner protocol. Under properties, in the "When connecting" section I've selected "Use a certificate
on this computer" and un-checked "Use simple certificate selection".
My preference would be to use separate self-signed certificates for all clients rather than having a common root certificate that signed all of the individual client certificates. I've tried creating the self-signed certificate both with and without the
client authentication EKU specified, and I've added the certificate to the trusted root certificate authority store on the client. But when I attempt to connect to the VPN I can not get the self signed certificate to appear on the "Choose a certificate"
drop down.
Are self signed certificates supported for this use in EAP-TLS? If it makes a difference, I'm working with makecert (not working with a certificate server).
TIA,
-Rick

Hi Rick,
Thank you for your patience.
According to your description, would you please let me know what command you were using to make a self-signed certificate by tool makecert? I would like to try to reproduce this issue. Also based on my experience, please let me
know if the certificate has private key associated and be present in the local machine store. Hence, please move the certificate from the trusted root certificate authority store to personal store.
Best regards,
Steven Song
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Failed to create machine self-signed certificate for site role [SMS_SQL_SERVER]

SCCM 2012 has been successfully installed on the server:
SRVSCCM.
The database is on SQL Server 2008 R2 SP1 CU6 Failover Cluster (CLS-SQL4\MSSQLSERVER04)
Cluster nodes: SQL01 and SQL01. On all nodes made necessary the Security Setup of SCCM. No errors and warning on SCCM Monitoring.
The cluster service is running on the account: sqlclusteruser
The account has the appropriate SPN are registered:
setspn -L domain\sqlclusteruser
Registered ServicePrincipalNames for CN=SQL Cluster,OU=SQL,OU=Users special,OU=MAIN,DC=domain,DC=local:
MSSQLSvc/CLS-SQL4
MSSQLSvc/CLS-SQL4.domain.local
MSSQLSvc/CLS-SQL4:11434
MSSQLSvc/CLS-SQL4.domain.local:11434
After some time on the cluster hosts every day started appearing new folders with files inside:
srvboot.exe
srvboot.ini
srvboot.log
srvboot.log contains the following information:
SMS_SERVER_BOOTSTRAP_SRVSCCM.domain.local_SMS_SQL_SERVER started.
Microsoft System Center 2012 Configuration Manager v5.00 (Build 7711)
Copyright (C) 2011 Microsoft Corp.
Command line: "SMS_SERVER_BOOTSTRAP_SRVSCCM.domain.local_SMS_SQL_SERVER CAS K:\SMS_SRVSCCM.domain.local_SMS_SQL_SERVER8 /importcertificate SOFTWARE\MicrosoftCertBootStrap\ SMS_SQL_SERVER".
Set current directory to K:\SMS_SRVSCCM.domain.local_SMS_SQL_SERVER8.
Site server: SRVSCCM.domain.local_SMS_SQL_SERVER.
Importing machine self-signed certificate for site role [SMS_SQL_SERVER] on Server [SQL01]...
Failed to retrieve SQL Server service account.
Bootstrap operation failed: Failed to create machine self-signed certificate for site role [SMS_SQL_SERVER].
Disconnecting from Site Server.
SMS_SERVER_BOOTSTRAP_SRVSCCM.domain.local_SMS_SQL_SERVER stopped.

The site server is trying to install the sms_backup agent on the SQL Server Cluster nodes.
Without successfull bootstrap the siteserver backup is not able to run successfully.
Try grant everyone the read permisson on
HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\SMS on the SQL server nodes.
This worked for me.
After that a Folder named "SMS_<SITESERVER-FQDN>" appeared on C: on the SQL Cluster nodes, and a "SMS_SITE_SQL_BACKUP_FQDN" Service should be installed.
After the new Folder is created and the new Service is installed, you can safely remove the bootstrap Service by opening a command prompt and enter:
sc delete "SMS_SERVER_BOOTSTRAP_FQDN-of-SiteServer_SMS_SQL_SERVER"

How to replace an expiring self-signed certificate?

Well, I've successfully (I THINK) replaced two of the three certificates that are expiring.
First off - 90% of what's in the Security manual concerning certificates is useless to this issue. I don't want to know how the watch is made - I just want to tell time! In fact there is a GLARING typo on Page 167 of the Snow Leopard Server Security Configuration Manual showing a screenshot of the Certificate Assistant in Server Admin that is just plain wrong!
It's clear there is no way to RENEW the certificate. You have to delete the old one and replace it with a new certificate.
The issue I have is that with all the services using the certificate, I don't know what the impact to the end-users is going to be when I delete that expiring certificate.
It appears that a certificate is created automatically when the OS is installed, although I installed the OS Server on a virtual machine and I didn't see where it got created, nor was I given any input during the creation (like extending the expiration date).
I don't know whether those certificates are critical to the running of the OS or not, but I went through the process of creating a new certificate in Server Admin. I deleted the expiring certificate. Because the two servers on which the expiring certificate was deleted does not have any services running that require a certificate (such as SSL on my mail server), nothing bad seems to have happened or been impacted negatively.
I did, however, name the new certificate the exact same thing as the old certificate and tried to make sure that the parameters of the new certificate were at least as extensive as the old certificate. You can look at the details of the old certficate to see what they were.
Here's the "critical" area of the certificate that was "auto-created" on my virtual server. (It's the same as the one on my "real" server.
http://screencast.com/t/zlVyR2Hsc
Note the "Public Key Info" for "Key Usage": Encrypt, Verify, Derive. Note the "Key Usage" Extension is marked CRITICAL and it's usage is "Digital Signature, Data Encipherment, Key Cert Sign". Extended Key Usage is also critical and it's purpose is Server Authentication.
Here's a screenshot of the default certificate that's created if you create a new self-signed certificate in Server Admin:
http://screencast.com/t/54c2BUJuXO2
Note the differences between the two certificates. It LOOKS to me like the second certificate would be more expansive than the default issued at OS Install? Although I don't really care about Apple iChat Encryption.
Be aware that creating certificates starts to populate your server Keychain.
http://screencast.com/t/JjLb4YkAM
It appears that when you start to delete certificates, it leaves behind private keys.
http://screencast.com/t/XD9zO3n16z
If you delete these keys you get a message warning you about the end of the world if you delete private keys. I'm sorry if your world melts around you, but I'm going to delete them from my Keychain.
OK, now I'm going to try to create a certificate that is similar to the one that is created at start-up.
In Server Admin, highlight your server on the sidebar and click the "Certificates" tab in the icon bar.
Click the "+" button under your existing certificate and select "Create a Certificate Identity". (This is how I created the default certificate we just got through looking at except I clicked through all the defaults.)
Bypass "Introduction".
In the "Create Your Certificate" window I set the "Name" as exactly the same as the name of the expiring certificate. I'm HOPING when I do this for my email server, I won't have to go into the services using the certificate and select the new one. On the other hand, naming it the same as the old one could screw things up - I guess I'll know when I do it later this week.
The "Certificate Type" defaults to "SSL Server" and I think this is OK since that's what I'll be using this certificate for.
You HAVE to check the "Let me override defaults" if you want to, for example, extend the expiry period. So that's what I want to do, so I checked it.
In the next window you set the Serial Number and Validity Period. Don't try typing "9999" (for an infinite certificate) in the "Validity Period" field. Won't work - but you CAN type in 1826 (5 years) - that works - Go Figure!??? You can type in a bigger number than that but I thought 5 years was good for me.
The next part (Key Usage Extension) is where it gets sticky. OF COURSE there is NO DOCUMENTATION on what these parameters mean of how to select what to choose.
(OK here's what one of the "explanations" says: "Select this when the certificate's public key is used for encrypting a key for any purpose. Key encipherment is used for key transport and key wrapping (or key management), blah, blah, blah, blah, blah blah!") I'm sure that's a clear as day to you rocket scientists out there, but for idiot teachers like me - it's meaningless.
Pant, pant...
The next window asks for an email address and location information - this appears to be optional.
Key Pair Information window is OK w/ 2048 bits and RSA Algorithm - that appears to be the same as the original certificate.
Key Usage Extension window
Here's where it gets interesting...
I brought up the screenshot of the OS Install created certificate to guide me through these next couple of windows.
Since the expiring cert had "Digital Signature, Data Encipherment, Key Cert Sign" I selected "Signature, Data Encipherment and Certificate Signing".
Extended Key Usage Extension...
Hoo Boy...Well, this is critical. But under "Capabilities" it lists ANY then more stuff. Wouldn't you THINK that "ANY" would include the other stuff? Apparently not..."Learn More"?
Sorry, folks, I just HAVE to show you the help for this window...
+*The Extended Key Usage Extension (EKU) is much like the Key Usage Extension (KUE), except that EKU values are defined in terms of "purpose" (for example, signing OCSP responses, identifying an SSL client, and so on.), and are easily extensible. EKU is defined with object identifiers called OIDs. If the EKU extension is omitted, all operations are potentially valid.*+
KILL ME NOW!!!
OK (holding my nose) here I go...Well, I need SSL Server Authentication (I THINK), I guess the other stuff that's checked is OK. So...click "Continue".
Basic Constraints Extension...
Well, there is no mention of that on the original certificate, so leave it unchecked.
Subject Alternate Name Extension...
Nothing about that in the original certificate, so I'm going to UNCHECK that box (is your world melting yet?)
DONE!!!! Let's see what the heck we got!
http://screencast.com/t/QgU86suCiQH
Well, I don't know about you but that looks pretty close for Jazz?
I got some extra crap in there but the stuff from the original cert is all there.
Think we're OK??
Out with the old certificate (delete).
Oh oh - extra private key - but which is the extra one? Well, I guess I'll just keep it.
http://screencast.com/t/bydMfhXcBFDH
Oh yeah...one more thing in KeyChain Access...
See the red "X" on the certificate? You can get rid of that by double clicking on the certificate and expanding the "Trust" link.
http://screencast.com/t/GdZfxBkHrea
Select "Always Trust".
I don't know if that does anything other than get rid of the Red "X", but it looks nice. There seem to be plenty of certificates in the Keychain which aren't trusted so maybe it's unnecessary.
I've done this on both my file server and my "test" server. So far...no problems. Thursday I'll go through this for my Mail server which uses SSL. I'm thinking I should keep the name the same and not replace the certificates in the iCal and Mail service which use it and see what happens. If worse comes to worse, I may need to recreate the certificate with a different name and select the new certificate in the two services that use it.
Look...I don't know if this helps anyone, but at least I'm trying to figure this idiocy out. At least if I screw up you can see where it was and, hopefully, avoid it yourself.
If you want to see my rant on Apple's worthless documentation, it's here.
http://discussions.apple.com/thread.jspa?threadID=2613095&tstart=0

to add to countryschool and john orban's experiences:
using the + Create a Certificate Identity button in Server Admin is the same thing as running KeyChain Access and selecting Certificate Assistant from the app menu, and choosing Create a Certificate. Note that you don't need to create a Certificate Authority first.
in the second "extended key usage extension" dialog box, i UN-checked Any, PKINIT Server Authentication, and iChat Encryption. this produced the closest match to the server's default self-installed certificate.
when updating trust settings in Keychain Access, the best match to the original cert are custom settings - set Always Trust for only SSL and X.509 Basic Policy.
supposedly you can use Replace With Signed or Renewed certificate button from Server Admin and avoid needing to re-assign to services. however i was unable to get this to work because my new cert didn't match the private key of the old. for those interested in going further, i did figure out the following which might be helpful:
you can't drag and drop a cert from Keychain Access or Cert Manager. you need the actual PEM file. supposedly you can hold down the option button while dragging, but this didn't work for me. however you can view the certificates directly in etc/certificates. but that folder is hidden by default. a useful shortcut is to use Finder / Go To Folder, and type in "/private/etc/certificates"
now, on my system the modification date was the same for old and new certificates. why? because it seems to be set by when you last viewed them. so how do you know which is which? answer: compare file name to SHA1 Fingerprint at bottom of certificate details.
after you delete the old certificate, it will disappear in Keychain Access from "System" keychains. however in "login" keychains the old one will still be there but the new one won't. it seems to make sense to delete the old one from here and add the new one. somebody tell me if this is a bad idea. the + button does not work easily for this, you need to drag and drop from the etc/certificates folder.
lastly, the "common name" field is the server/host name the client will try to match to. you can use wildcard for this, e.g. *.example.com. if you need to, you can use the Subject Alternate Name to provide an alternative name to match to, in which case the common name field will be ignored, which is why by default the dNSName alternate field defaults to the common name. more info here: http://www.digicert.com/subject-alternative-name-compatibility.htm.
maybe that's hopeful to somebody. but i stopped there since things seem to be working.
last note, which you probably know already - if you don't want to bother installing the certificate in your client computers and phones, you can select Details when the first trust warning pops up and select Always Trust.
now, we'll see how everything works once people start really using it...

Lion server erased self signed certificate

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