VPN Design using CA (certificate authority)

In the process or redisgning current VPN deployment. Currently we have 300+ ASAs and 100 remote users on Windows Domain (Both are growing). Would like to use Certificates instead of Preshared Keys. Have some questions about the CA.
1) What are the pros and cons between using Enterprise or Standalone CA?
1a) What is more secure and more reliable?
1b) If we already have a domain, does using enterprise help? Benefits or problems?
2) Is it better to use 3rd party CA or manage one ourselves?
3) Any configuration tips or suggestions?

Did you check metalink Note:178806.1 ?
How to get SSL Certificates from a Microsoft Certification Services CA
You have to change some registry keys in the Mircosoft CA so it will work with Oracle.
Steve

Similar Messages

  • UCS Manager and using Microsoft Certificate Authority

    Has anybody gone through the process of setting up UCS Manager with a certificate issued from a Microsoft Certificate Authority?  If so I would appreciate some assistance.  I was able to successfully create a request and have generated the certificate, but I see no way of being able to put the request and the certificate chain back into UCS Manager.

    First you have to create a trusted point (under the Admin Tab -> Key Management). In the new trusted point, paste the public cert in base64 format of your root certificate authority. If you have a subordinate CA that's issuing then add that CA's cert too. If you have a whole tree of CAs, then you need to create a trusted point with all the CAs in the chain from the issueing CA up to the root. Paste one cert after the other, in order, up the chain, all in the same trusted point. If they're not in the right order or if you're missing the root, then the TP won't accept the cert.
    Once you have a trusted point you can accept the certificate you generated. In the KeyRing you used to generate the request, choose the new Trusted Point, and paste the new certificate in Base64 format into the Certificate field.
    Once that's done, you can go to Communication Management -> Communication Services, and for the HTTPS protocol, choose the new Key Ring. It might not take effect immediately, but after a few minutes your UCSM web site should start responding with the new certificate.
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    Note: There's a bug in UCS currently issue number CSCth62582. If your fabric interconnects fail over, the SSL cert will revert to the default self signed cert. You have to go back into Communication services and set it to default, save, then set it back to the new Key Ring.  

  • Windows Server 2008 R2 Standard "Certificate Authority Service" / Exchange Server 2010 EMC not starting and no AD connectivity for authentication.

    Hello,
    I am a new IT Manager at this company and need assistance big time. Their environment looks as follows:
    Server 1. Domain Controller Server (Windows Server 2008 R2 Standard) running active directory.
    Server 2. Email Server (Windows Server 2008 R2 Standard) running Exchange Server 2010 .
    * Note. No back ups to work with aside from whats mentioned below.
    DC had a virus infection causing a lot of issues on the shared network drives 2 days ago locking up all the files with a crypto ransom virus. Running Avast suppressed the infection. Had to recover the file shares which luckily had a back up. 
    The issue is that the Exchange Server 2 post this lost connectivity with the AD Server 1. Exchange Server 2 when launching EMC could not launch the console stating the following:
    "No Exchange servers are available in any Active Directory sites. You can’t connect to remote
    Powershell on a computer that only has the Management Tools role installed."
    Shortly after I found that it is possible the EMC launcher was corrupt and needed to be reinstalled following another blog post. I deleted the exchange management console.msc  per instructions only to discover I couldnt relaunch it because there was
    no way how. So I copied another msc file that happened to be on the DC Server 1  back to Exchange Server 2 and got it to launch again. 
    Another post said that it might be an issue with the Domain Account for the Computer, so to delete it in the AD Server 1 only to find that rejoining it from Exchange Server 2 using Computer>Properties> Chage Settings > Change is greyed out because
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    "The Trust Relationship between this workstation and primary domain failed."
    I tried running the Power Shell tools on Exchange Server 2 to rejoing and to reset passwords for domain accounts as noted in some other blogs but no luck as the Server 2 could not make the connection with Server1 or other errors it kept spitting out.
    I also during the investigation found the DNS settings were all altered on both the Server 1 and Server 2 which I luckily was able to change back to original because of inventorying it in the beginning when I started. 
    I need help figuring out if I need to rejoin the Exchange Server 2 manually by disabling the Certificate Authority Service (or removing the CA as listed here:
    https://social.technet.microsoft.com/Forums/exchange/en-US/fb23deab-0a12-410d-946c-517d5aea7fae/windows-server-2008-r2-with-certificate-authority-service-to-rejoin-domain?forum=winserversecurity
    and getting exchange server to launch again. (Mind you I am relatively fresh to server managing) Please help E-Mail has been down for a whole day now!
    Marty

    I recommend that you open a ticket with Microsoft Support before you break things more.
    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

  • Mail and SMTP server settings of ASA Certificate Authority for cisco anyconnect VPN

                       Dear All,
    i have the folloing case :
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    i want to issue a new certificate every 72 hours for the users ,and i want to send the one time password via email to each user.
    so what the setting of the mail and smtp server should be ,
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    i sent the email manually ,hwo can automate sending the OTP to our VPN users automatically vi their emails?
    Best regards,

    Thanks Jennifer.
    I did manage to configure LDAP attribute map to the specific group policy.
    Nevertheless, I was thinking whether I can have fixed IP address tied to individual user.
    Using legacy Cisco VPN Client, I can do it using IPSEC(IKEv1) Connection profile, where I set Pre-Shared Key and Client Address Pools. Each Client Address Pools has only 1 fix IP address.
    Example: let say my username is LLH.
    Connection Profile for me is : LLH-Connection-Profile, my profile is protected by preshared key.
    Client Address Pool for me is : LLH-pool, and the IP is 172.16.1.11
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    Using AnyConnect, I have problem. User can use any connection profile because I cannot set preshared key for AnyConnect. In that case, I cannot control who can use my Connection Profile and pretend to be me.
    Example:
    AnyConnect Connection Profile for me is : LLH-Connection-Profile, without any password
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    Thanks in advance for all the help and comment given.

  • How to find/replace existing certificates before decommissioning certificate authority?

    We plan to decommission a multi-use server that also contains our internal certificate authority and replace it with new dedicated CA servers in a more secure design (offline root CA etc.).
    Before we decommission our existing CA servers, how do we find a list of all the issued certificates that are still valid?
    We would need replace all those old certificates with new certificates from our new CA so the applications that use them don't break when the old certificates are removed/revoked and before we remove the GPO setting that makes our current CA a trusted root
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    on CA server you can filter issued certificates by "Certificate Expiration Date" column. In the Certification Authority MMC snap-in, select Issued Certificates folder, then click View -> Filter. Add a filter that would filter certificates
    where "Certificate Expiration Date" is greater than current date.
    My weblog: en-us.sysadmins.lv
    PowerShell PKI Module: pspki.codeplex.com
    PowerShell Cmdlet Help Editor pscmdlethelpeditor.codeplex.com
    Check out new: SSL Certificate Verifier
    Check out new:
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  • Certificate Authority - Custom Temp not showing up. W2k8R2ent

    Hi Guys,
    Couldn't see a forum for CA so I had to post it here. Hopefully its the right place.
    (Server is test domain 1 single ad no replication. Running Win 2k8 r2 enterprise)
    So here's the issue I am trying to create and export certificate for other users (eobo).
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    I am very new to CA so I am sure i am missing something or doing something wrong.
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    Hi,
    I’d suggest if the steps below doesn’t help to remove the CA. Make sure you are using Enterprise Edition (no upgrade from 2K3 or 2K9 standart) of windows
    and install it again as Enterprise Root CA. Check and see if you still have the issue before tweaking the CA further:
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      - Authenticated users
     - Domain Users
     - Interactive
    Open ADSI Edit and navigate to
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    Check permissions on the CA:
    Open the [Certificate Authority] console and right click on [properties > Security] and add the fallowing permissions:
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    [V] Request Certificates
    [Domain Admins]
    [V] Read
    [V] Issue and Manager Certificates
    [V] Manage CA
    [V] Request Certificates
    [Enterprise Admins]
    [V] Issue and Manager Certificates
    [V] Manage CA
    [Administrators]
    [V] Issue and Manager Certificates
    [V] Manage CA
    [V] Request Certificates
    [Domain Controllers]
    [V] Read
    [V] Issue and Manager Certificates
    [V] Manage CA
    [V] Request Certificates
    [Domain Computers]
    [V] Read
    [V] Request Certificates
    Will appreciate if you give feedback if this has helped you. If yes please select “Mark
    as answer”.
    Best Regards,
    Spas Kaloferov
    MCITP: SA6 | EA6 | VA7 | EDA7 |DBA10 | DBD10 | BID10 | EMA14 | SPA14 
    NetShell Services & Solutions | “Design the future with simplicity and elegance”
    Visit me at:
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    |
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  • The affects of removing a certficate template from a Certificate Authority

    I have inherited what I am beginning to believe is a poorly designed PKI Infrastructure. I have 1 root CA and 2 Issuing CAs all 2008 R2. My root certificate authority is expiring in about 2 months so I am planning to renew it and the Subordinate CAs soon.
    I see that the root CA has issued a lot of certificates and that many templates are available. The root is not offline. (I know not best practice).
    I would like to remove these templates from the Root CA and allow the subordinates to do all the issuing. If I do this before I renew the Root CA then all the certs currently issued will expire in 2 months and not be renewed on the Root CA.
    My questions are:
    In the scenario above will the certificates originally issued by the Root CA be renewed on the Subordinate CAs?
    Most of these certs seem to be auto enrolled. Will Auto Enrollment know to go to the Subordinate CA from now on?
    Are there any other concerns with taking this action that I should be aware of?
    Most of the certificate templates on the Root CA are default templates and I believe are Auto Enrolled. (I haven’t manually issued certs for these templates)
    Basic EFS
    Computer (I know this one is auto enroll)
    Domain Controller

    First, you have to renew all CA certificates starting with root (down to hierarchy) before you proceed.
    > In the scenario above will the certificates originally issued by the Root CA be renewed on the Subordinate CAs?
    yes. Clients will use any enterprise CA that supports specified template.
    > Most of these certs seem to be auto enrolled. Will Auto Enrollment know to go to the Subordinate CA from now on?
    again, yes, see above.
    My weblog: http://en-us.sysadmins.lv
    PowerShell PKI Module: http://pspki.codeplex.com
    Check out new:
    PowerShell FCIV tool.

  • Certificate Authority w/ NDES-SCEP

    Hello,
    I am embarking on a project that I would like to get some feedback on.
    We are in the process of implementing iPhones into our network. The iPhone is going to run a VPN. Most likely, we will run the Anyconnect VPN client. I have this
    and it is working fine.
    However, we have to manually connect to the VPN, put in the domain password, and connect before we can check our email. This is cumbersome. So, I am trying to use
    certificate based authentication and the iPhones “connect on demand” feature.
    I have read about a number of people using a Windows Server and running Certificate Services & Network Device Enrollment Service. This uses a protocol called
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    certificate to the windows server and the windows server would tell the ASA if it’s good. If the windows server said it was good, the ASA would then allow the VPN to connect.
    I have the Certificate Authority (windows server 2008 R2) installed and running. However, I am encountering some trouble getting the iPhone to get the certificate
    from it.
    I have read a number of white papers and forum postings from Microsoft, Cisco, and Apple. Some indications are that it’s feasible, but I am crossing a lot of
    technologies that are new to me and I am not sure if I am working uphill or what.
    My questions are…
    1). Is this is known configuration? Have you seen this configuration before? Was it successful?
    2). Does this sound feasible? Is there a more feasible way to provide VPN connectivity? The goal is to open the VPN from the phone when they open the email application,
    without having any user interaction.
    3). Within the Microsoft Certificate Services server, am I going to be able to manage the certificates individually and identify jim’s certificate separate
    from sally’s certificate? Or, sally’s iphone certificate separately from sally’s ipad certificate? Also, what is made to prevent anyone from enrolling a device with the server?
    4). Do you know of any good documentation on this? I have read a number of articles and white papers. But, for some reason, there still seems to be something lacking.
    Seems like all the established documentation only addresses one aspect of this.
    At any rate, any comments or suggestions in regards to the above would be much appreciated. I appreciate that this is a Microsoft forum. So, I don't expect much commentary
    in regards to the Cisco / Apple side of this. But, whatever you can conribute from the windows server perspective would be great.

    Hello,
    it will be better to ask in Security Forums: http://social.technet.microsoft.com/Forums/fr-FR/winserversecurity/threads
    This
    posting is provided "AS IS" with no warranties or guarantees , and confers no rights.
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  • Certificate authority Server (Digitial Certificate)

    Hi Everyone ,
    We are planing to to buy a digital Certificate Manager, which we will be using to issue certificates to our all the cisco routers placed at ATM machines.
    so that they can be authenticated and then to be connected via VPN to main branch.
    I did some google and found many certificate authority issuing server , like , RSA , Digi-Cert , IBM and many more, i am just confused which one is best to implement here.
    Any suggestion will be highly appriciated.

    If this is internal and you only need it for devices you controll you can create your own Certificate Authority on Linux/Windows
    http://technet.microsoft.com/en-us/library/cc772393(v=ws.10).aspx (windows)
    http://www.g-loaded.eu/2005/11/10/be-your-own-ca/ (linux - fedora)

  • How do I use the Certificate Assistant to set up secure email for clients

    I was at first thrilled to find the Certificate Assistant, and now I'm frustrated. I need to have secure, encrypted email for my psychotherapy clients. I thought that if I created my own certificate authority and then issued certificates to my clients, I would be fine. But I can't get this to work. I set up my own authority, but when I try to get a certificate (using a different email account) I can't get it to work. For example, I go to the website created on mac.com and click the "download an invitation" button and then click the download, which opens the Assistant. I fill out the form, but I get an error saying I haven't configured an email account. How do I "configure" an email account? I mean, I use this account all the time; what more configuration does it need?
    Second question. Will anybody with a Windows machine be able to use that webpage? Seems like it's a mac only program, so what good is it in the real world?
    I know I could try to do this with Thawte or whatever, but asking my clients to get trusted so I can use encryption is unreasonable. If not having my own authority (if I could get THAT to work) is there any other way? Are there any good things to read about this? With the federal HIPAA privacy requirements, there are lots of doctors wrestling with this question.

    If you are referring to your "iCloud account", then simply tap "settings / iCloud" - delete the account you are currently logged in with, and add the correct one.
    iCloud Set up - http://www.apple.com/ca/icloud/setup/.

  • How do I set up my own certificate authority

    I tried google on the above question, and the most recent thing I found was 7 years old. replacing the phrase used generates a lot of hits with a very poor signal to noise ratio.
    I have OpenSSL (in the cygwin distribution), which is quite recent, but frankly its documentation leaves just about everything to be desired. I found pyca, but it has no documentation at all (and it is a couple years old).
    I tried the steps appended below, but invariably the attempt to sign the certificates fails with an obscure error message about OpenSSL not finding one thing or another.
    At this stage, I just don't care whether I do this using something in the J2SDK such as keytool or OpenSSL, as long as I can get it done. Or if there is some other opensource software tool I can use, terrific. This is primarily for the purpose of securing communications within an Intranet, and secondarily for signing applets and applications distributed through WebStart. If I am not mistaken, I'll need a certificate for each of my servers. Right?
    If you know of an URL where this is well explained and illustrated, great. Give that to me.
    Otherwise, a simple illustration (or a correction of what I've appended below) would be appreciated. I believe I understand what ought to be happening. It ought to be rather simple to do, but there are these irritating and frustrating minor details getting in the way. For example, the steps I show below seem simple, but everything appears to get messed up by some of the contents of openssl.cnf in 'usr/ssl', in the cygwin directory, and there is no explanation of how to set things up for the first time you use OpenSSL within Cygwin (or on unix for that matter).
    Any assistance would be appreciated.
    Thanks,
    Ted
    ========failed attempt=====================
    # Generation of Certificate Authority(CA)
    openssl req -new -x509 -keyout cakey.pem -out cacert.pem -config /usr/ssl/openssl.cnf
    # Create server request and key
    openssl req -new -keyout server-key.pem -out server-req.pem -days 36502 -config /usr/ssl/openssl.cnf
    # Remove the passphrase from the key
    openssl rsa -in server-key.pem -out server-key.pem
    # Sign server cert
    openssl ca -policy policy_anything -out server-cert.pem -infiles server-req.pem -config /usr/ssl/openssl.cnf
    # Create client request and key
    openssl req -new -keyout client-key.pem -out client-req.pem -days 36502 -config /usr/ssl/openssl.cnf
    # Remove a passphrase from the key
    openssl rsa -in client-key.pem -out client-key.pem
    # Sign client cert
    openssl ca -policy policy_anything -out client-cert.pem -infiles client-req.pem -config /usr/ssl/openssl.cnf

    The following works for me:
    NB: Some of the output has been removed in the interests of privacy (this will not affect the outcome)
    1. Create CA key and certificate
    1.1 Create a new file called "serial" containing the value "01".
    1.2 Create an empty file "index.txt"
    1.3 Create a subdirectory "newcerts"
    1.4 Execute.... create a key for your CA
    [ben@localhost ca]$ openssl genrsa -out ca.key 2048
    Generating RSA private key, 2048 bit long modulus
    .....................................+++
    ..........................................................+++
    e is 65537 (0x10001)
    1.5 Execute... create a certificate for your own CA
    [ben@localhost ca]$ openssl req -config ./openssl.cnf -new -x509 -key ca.key -out cacert.pem -days 365
    You are about to be asked to enter information that will be incorporated
    into your certificate request.
    What you are about to enter is what is called a Distinguished Name or a DN.
    There are quite a few fields but you can leave some blank
    For some fields there will be a default value,
    If you enter '.', the field will be left blank.
    Country Name (2 letter code) [GB]:
    County or State (full name) []:
    City or town (eg, Hitchin) []:
    Organization Name (eg, company) []:
    Organizational Unit Name (eg, section) []:
    Common Name (eg, your name or your server's hostname) []:
    Email Address []:
    2. Create PK key and .csr
    2.1 Execute...
    [ben@localhost ca]$ keytool -genkey -alias PK
    Enter keystore password: password
    What is your first and last name?
    [Unknown]:
    What is the name of your organizational unit?
    [Unknown]:
    What is the name of your organization?
    [Unknown]:
    What is the name of your City or Locality?
    [Unknown]:
    What is the name of your State or Province?
    [Unknown]:
    What is the two-letter country code for this unit?
    [Unknown]:
    Is CN=, OU=, O=, L=, ST=, C=GB correct?
    [no]: yes
    Enter key password for <PK>
    (RETURN if same as keystore password):
    2.2 Create .csr
    [ben@localhost ca]$ keytool -certreq -alias PK -file PK.csr
    Enter keystore password: password
    3. Sign PK with CA cert
    [ben@localhost ca]$ openssl ca -config ./openssl.cnf -in PK.csr -out PK.pem -keyfile ca.key -days 365
    Using configuration from ./openssl.cnf
    Check that the request matches the signature
    Signature ok
    Certificate Details:
    Serial Number: 0 (0x0)
    Validity
    Not Before: Jan 5 19:48:33 2006 GMT
    Not After : Jan 5 19:48:33 2007 GMT
    Subject:
    countryName = GB
    stateOrProvinceName =
    organizationName =
    organizationalUnitName =
    commonName =
    X509v3 extensions:
    X509v3 Basic Constraints:
    CA:FALSE
    Netscape Comment:
    OpenSSL Generated Certificate
    X509v3 Subject Key Identifier:
    D6:2D:7E:71:77:9E:1A:BB:54:69:98:63:6A:6A:E2:BA:12:C4:D7:DD
    X509v3 Authority Key Identifier:
    keyid:92:7C:33:7C:EC:1D:76:C5:B8:F0:30:6D:10:12:40:E5:E7:EA:24:31
    DirName:/C=GB/ST=/L=/O=/OU=/CN=/emailAddress=
    serial:F0:D1:38:36:65:6D:71:D5
    Certificate is to be certified until Jan 5 19:48:33 2007 GMT (365 days)
    Sign the certificate? [y/n]:y
    1 out of 1 certificate requests certified, commit? [y/n]y
    Write out database with 1 new entries
    Data Base Updated
    4. Convert PK certificate into DER format
    [ben@localhost ca]$ openssl x509 -in PK.pem -out PK.der -outform DER
    5. Import CA certificate into keystores
    [ben@localhost ca]$ keytool -import -alias ca -file cacert.pem
    Enter keystore password: password
    Owner: EMAILADDRESS=, CN=, OU=, O=, L=, ST=, C=GB
    Issuer: EMAILADDRESS=, CN=, OU=, O=, L=, ST=, C=GB
    Serial number: f0d13836656d71d5
    Valid from: Thu Jan 05 19:41:09 GMT 2006 until: Fri Jan 05 19:41:09 GMT 2007
    Certificate fingerprints:
    MD5: AF:3D:8E:25:12:24:04:1F:40:70:BC:A0:9E:0E:44:84
    SHA1: B8:E8:0B:A5:86:33:21:0C:B5:3C:6E:F2:DE:7B:31:0F:59:AE:21:E4
    Trust this certificate? [no]: yes
    Certificate was added to keystore
    6. Import signed PK into keystore
    [ben@localhost ca]$ keytool -import -alias pk -file PK.der
    Enter keystore password: password
    Certificate reply was installed in keystore
    REF:
    http://www.yorku.ca/dkha/docs/jsse_cert/jsse_cert.htm
    http://httpd.apache.org/docs/2.2/ssl/ssl_faq.html#ownca
    http://www.openssl.org/docs/apps/ca.html#
    openssl.cnf:#
    # OpenSSL example configuration file.
    # This is mostly being used for generation of certificate requests.
    # This definition stops the following lines choking if HOME isn't
    # defined.
    HOME               = .
    RANDFILE          = $ENV::HOME/.rnd
    # Extra OBJECT IDENTIFIER info:
    #oid_file          = $ENV::HOME/.oid
    oid_section          = new_oids
    # To use this configuration file with the "-extfile" option of the
    # "openssl x509" utility, name here the section containing the
    # X.509v3 extensions to use:
    # extensions          =
    # (Alternatively, use a configuration file that has only
    # X.509v3 extensions in its main [= default] section.)
    [ new_oids ]
    # We can add new OIDs in here for use by 'ca' and 'req'.
    # Add a simple OID like this:
    # testoid1=1.2.3.4
    # Or use config file substitution like this:
    # testoid2=${testoid1}.5.6
    [ ca ]
    default_ca     = CA_default          # The default ca section
    [ CA_default ]
    dir          = .               # Where everything is kept
    certs          = $dir/certs          # Where the issued certs are kept
    crl_dir          = $dir/crl          # Where the issued crl are kept
    database     = $dir/index.txt     # database index file.
    #unique_subject     = no               # Set to 'no' to allow creation of
                             # several ctificates with same subject.
    new_certs_dir     = $dir/newcerts          # default place for new certs.
    certificate     = $dir/cacert.pem      # The CA certificate
    serial          = $dir/serial           # The current serial number
    #crlnumber     = $dir/crlnumber     # the current crl number must be
                             # commented out to leave a V1 CRL
    crl          = $dir/crl.pem           # The current CRL
    private_key     = $dir/private/cakey.pem# The private key
    RANDFILE     = $dir/private/.rand     # private random number file
    x509_extensions     = usr_cert          # The extentions to add to the cert
    # Comment out the following two lines for the "traditional"
    # (and highly broken) format.
    name_opt      = ca_default          # Subject Name options
    cert_opt      = ca_default          # Certificate field options
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