Freeipa and Datadog

[Gabriel Stein]

Hi all,

I was discussing a issue with @ftweedal and I will continue doing some
questions here.

I have installed Freeipa with an additional Replica Server, but to me some
concepts are not so clear.

Let' talk about my setup:

Goal: Replace Active Directory Auth on DMZ Network.
          Provide SSL Certs for Servers/Services
          If possible, Management for  MIME/S Certificates(Mail Signing)

Setup:

Servers(Total: 3 VMs)
ipa1/ipa2: Freeipa Server and Replica
pki1: Datadog installation(external CA for ipa1/ipa2).

I know, Freeipa includes Datadog(and that makes the certificates management
possible), but I needed a Datadog Service to create the external CA for
ipa1/ipa2.

Now I have some questions:

- Was Datadog Installation "too much"? Probably was better just create a CA
manually with openSSL and import it on ipa1/ipa2?
- Should I use Freeipa as the sub-CA for all Servers/Services and leave
Datadog as a main CA? Do I have an advantage using this setup?

Thanks in Advance!

Best Regards,

Gabriel

Gabriel Stein

[Callum Guy]

Do you mean Dogtag rather than Datadog?!

http://pki.fedoraproject.org/wiki/PKI_Main_Page

On Mon, Oct 9, 2017 at 1:30 PM Gabriel Stein via FreeIPA-users <
[e-mail]> wrote:
> Hi all,
>
> I was discussing a issue with @ftweedal and I will continue doing some
> questions here.
>
> I have installed Freeipa with an additional Replica Server, but to me some
> concepts are not so clear.
>
> Let' talk about my setup:
>
> Goal: Replace Active Directory Auth on DMZ Network.
>           Provide SSL Certs for Servers/Services
>           If possible, Management for  MIME/S Certificates(Mail Signing)
>
> Setup:
>
> Servers(Total: 3 VMs)
> ipa1/ipa2: Freeipa Server and Replica
> pki1: Datadog installation(external CA for ipa1/ipa2).
>
> I know, Freeipa includes Datadog(and that makes the certificates
> management possible), but I needed a Datadog Service to create the external
> CA for ipa1/ipa2.
>
> Now I have some questions:
> Was Datadog Installation "too much"? Probably was better just create a
>
> CA manually with openSSL and import it on ipa1/ipa2?
> Should I use Freeipa as the sub-CA for all Servers/Services and leave
>
> Datadog as a main CA? Do I have an advantage using this setup?
>
> Thanks in Advance!
>
> Best Regards,
>
> Gabriel
>
> Gabriel Stein
>
> FreeIPA-users mailing list -- [e-mail]
> To unsubscribe send an email to [e-mail]

[Gabriel Stein]

Oh, sorry for the typos... (thanks @callum)

'/s/Datadog/Dogtag/g'

Best Regards,

Gabriel

Gabriel Stein
------------------------------
Gabriel Ferraz Stein
Tel.: +49 (0)  170 2881531

2017-10-09 14:34 GMT+02:00 Callum Guy :
> Do you mean Dogtag rather than Datadog?!
>
> http://pki.fedoraproject.org/wiki/PKI_Main_Page
>
> On Mon, Oct 9, 2017 at 1:30 PM Gabriel Stein via FreeIPA-users <
> [e-mail]> wrote:
> > Hi all,
> >
> > I was discussing a issue with @ftweedal and I will continue doing some
> > questions here.
> >
> > I have installed Freeipa with an additional Replica Server, but to me
> > some concepts are not so clear.
> >
> > Let' talk about my setup:
> >
> > Goal: Replace Active Directory Auth on DMZ Network.
> >           Provide SSL Certs for Servers/Services
> >           If possible, Management for  MIME/S Certificates(Mail Signing)
> >
> > Setup:
> >
> > Servers(Total: 3 VMs)
> > ipa1/ipa2: Freeipa Server and Replica
> > pki1: Datadog installation(external CA for ipa1/ipa2).
> >
> > I know, Freeipa includes Datadog(and that makes the certificates
> > management possible), but I needed a Datadog Service to create the external
> > CA for ipa1/ipa2.
> >
> > Now I have some questions:
> > Was Datadog Installation "too much"? Probably was better just create a
> >
> > CA manually with openSSL and import it on ipa1/ipa2?
> > Should I use Freeipa as the sub-CA for all Servers/Services and leave
> >
> > Datadog as a main CA? Do I have an advantage using this setup?
> >
> > Thanks in Advance!
> >
> > Best Regards,
> >
> > Gabriel
> >
> > Gabriel Stein
> >
> > FreeIPA-users mailing list -- [e-mail]
> > To unsubscribe send an email to freeipa-users-leave@lists.
> > fedorahosted.org
>
> --
> Callum Guy
> Head of Information Security
> X-on
>
> *0333 332 0000  |  www.x-on.co.uk http://www.x-on.co.uk  |   **
> https://www.linkedin.com/company/x-on   https://www.facebook.com/XonTel
>   https://twitter.com/xonuk *
> X-on is a trading name of Storacall Technology Ltd a limited company
> registered in England and Wales.
> Registered Office : Avaland House, 110 London Road, Apsley, Hemel
> Hempstead, Herts, HP3 9SD. Company Registration No. 2578478.
> The information in this e-mail is confidential and for use by the
> addressee(s) only. If you are not the intended recipient, please notify
> X-on immediately on [phone] <+44%20333%20332%200000> and
> delete the
> message from your computer. If you are not a named addressee you must not
> use, disclose, disseminate, distribute, copy, print or reply to this email. Views
> or opinions expressed by an individual
> within this email may not necessarily reflect the views of X-on or its
> associated companies. Although X-on routinely screens for viruses,
> addressees should scan this email and any attachments
> for viruses. X-on makes no representation or warranty as to the absence of
> viruses in this email or any attachments.

[Fraser Tweedale]

On Mon, Oct 09, 2017 at 02:39:57PM +0200, Gabriel Stein via FreeIPA-users wrote:
> Oh, sorry for the typos... (thanks @callum)
>
> '/s/Datadog/Dogtag/g'

Datadog is a pretty good name though! :)
> Best Regards,
>
> Gabriel
> Gabriel Stein
>
> Gabriel Ferraz Stein
> Tel.: +49 (0)  170 2881531
>
> 2017-10-09 14:34 GMT+02:00 Callum Guy :
> > Do you mean Dogtag rather than Datadog?!
> >
> > http://pki.fedoraproject.org/wiki/PKI_Main_Page
> >
> > On Mon, Oct 9, 2017 at 1:30 PM Gabriel Stein via FreeIPA-users <
> > [e-mail]> wrote:
> > > Hi all,
> > >
> > > I was discussing a issue with @ftweedal and I will continue doing some
> > > questions here.
> > >
> > > I have installed Freeipa with an additional Replica Server, but to me
> > > some concepts are not so clear.
> > >
> > > Let' talk about my setup:
> > >
> > > Goal: Replace Active Directory Auth on DMZ Network.
> > >           Provide SSL Certs for Servers/Services
> > >           If possible, Management for  MIME/S Certificates(Mail Signing)
> > >
> > > Setup:
> > >
> > > Servers(Total: 3 VMs)
> > > ipa1/ipa2: Freeipa Server and Replica
> > > pki1: Datadog installation(external CA for ipa1/ipa2).
> > >
> > > I know, Freeipa includes Datadog(and that makes the certificates
> > > management possible), but I needed a Datadog Service to create the external
> > > CA for ipa1/ipa2.
> > >
> > > Now I have some questions:
> > > Was Datadog Installation "too much"? Probably was better just create a
> > >
> > > CA manually with openSSL and import it on ipa1/ipa2?
> > > Should I use Freeipa as the sub-CA for all Servers/Services and leave
> > >
> > > Datadog as a main CA? Do I have an advantage using this setup?
> > >
> > > Thanks in Advance!
> > >
> > > Best Regards,
> > >
> > > Gabriel
> > >
> > > Gabriel Stein
> > >
> > > FreeIPA-users mailing list -- [e-mail]
> > > To unsubscribe send an email to freeipa-users-leave@lists.
> > > fedorahosted.org
> >
> > --
> > Callum Guy
> > Head of Information Security
> > X-on
> >
> > *0333 332 0000  |  www.x-on.co.uk http://www.x-on.co.uk  |   **
> > https://www.linkedin.com/company/x-on   https://www.facebook.com/XonTel
> >   https://twitter.com/xonuk *
> > X-on is a trading name of Storacall Technology Ltd a limited company
> > registered in England and Wales.
> > Registered Office : Avaland House, 110 London Road, Apsley, Hemel
> > Hempstead, Herts, HP3 9SD. Company Registration No. 2578478.
> > The information in this e-mail is confidential and for use by the
> > addressee(s) only. If you are not the intended recipient, please notify
> > X-on immediately on [phone] <+44%20333%20332%200000> and
> > delete the
> > message from your computer. If you are not a named addressee you must not
> > use, disclose, disseminate, distribute, copy, print or reply to this email. Views
> > or opinions expressed by an individual
> > within this email may not necessarily reflect the views of X-on or its
> > associated companies. Although X-on routinely screens for viruses,
> > addressees should scan this email and any attachments
> > for viruses. X-on makes no representation or warranty as to the absence of
> > viruses in this email or any attachments.
> FreeIPA-users mailing list -- [e-mail]
> To unsubscribe send an email to [e-mail]

[Gabriel Stein]

hey hey... I already registered for copyrights :P

Thank you!

Gabriel Stein
------------------------------
Gabriel Ferraz Stein
Tel.: +49 (0)  170 2881531

2017-10-09 15:25 GMT+02:00 Fraser Tweedale via FreeIPA-users <
[e-mail]>:
> On Mon, Oct 09, 2017 at 02:39:57PM +0200, Gabriel Stein via FreeIPA-users
> wrote:
> > Oh, sorry for the typos... (thanks @callum)
> >
> > '/s/Datadog/Dogtag/g'
>
> Datadog is a pretty good name though! :)
> > Best Regards,
> >
> > Gabriel
> > Gabriel Stein
> >
> > Gabriel Ferraz Stein
> > Tel.: [phone]
> >
> > 2017-10-09 14:34 GMT+02:00 Callum Guy :
> > > Do you mean Dogtag rather than Datadog?!
> > >
> > > http://pki.fedoraproject.org/wiki/PKI_Main_Page
> > >
> > > On Mon, Oct 9, 2017 at 1:30 PM Gabriel Stein via FreeIPA-users <
> > > [e-mail]> wrote:
> > > > Hi all,
> > > >
> > > > I was discussing a issue with @ftweedal and I will continue doing some
> > > > questions here.
> > > >
> > > > I have installed Freeipa with an additional Replica Server, but to me
> > > > some concepts are not so clear.
> > > >
> > > > Let' talk about my setup:
> > > >
> > > > Goal: Replace Active Directory Auth on DMZ Network.
> > > >           Provide SSL Certs for Servers/Services
> > > >           If possible, Management for  MIME/S Certificates(Mail
>
> Signing)
> > > > Setup:
> > > >
> > > > Servers(Total: 3 VMs)
> > > > ipa1/ipa2: Freeipa Server and Replica
> > > > pki1: Datadog installation(external CA for ipa1/ipa2).
> > > >
> > > > I know, Freeipa includes Datadog(and that makes the certificates
> > > > management possible), but I needed a Datadog Service to create the
>
> external
> > > > CA for ipa1/ipa2.
> > > >
> > > > Now I have some questions:
> > > > Was Datadog Installation "too much"? Probably was better just
>
> create a
> > > > CA manually with openSSL and import it on ipa1/ipa2?
> > > > Should I use Freeipa as the sub-CA for all Servers/Services and
>
> leave
> > > > Datadog as a main CA? Do I have an advantage using this setup?
> > > >
> > > > Thanks in Advance!
> > > >
> > > > Best Regards,
> > > >
> > > > Gabriel
> > > >
> > > > Gabriel Stein
> > > >
> > > > FreeIPA-users mailing list -- [e-mail]
> > > > To unsubscribe send an email to freeipa-users-leave@lists.
> > > > fedorahosted.org
> > >
> > > --
> > > Callum Guy
> > > Head of Information Security
> > > X-on
> > >
> > > *0333 332 0000  |  www.x-on.co.uk http://www.x-on.co.uk  |   **
> > > https://www.linkedin.com/company/x-on   <https://www.facebook.com/
>
> XonTel>
> > > https://twitter.com/xonuk *
> > > X-on is a trading name of Storacall Technology Ltd a limited company
> > > registered in England and Wales.
> > > Registered Office : Avaland House, 110 London Road, Apsley, Hemel
> > > Hempstead, Herts, HP3 9SD. Company Registration No. 2578478.
> > > The information in this e-mail is confidential and for use by the
> > > addressee(s) only. If you are not the intended recipient, please notify
> > > X-on immediately on [phone] <+44%20333%20332%200000> and
> > > delete the
> > > message from your computer. If you are not a named addressee you must
>
> not
> > > use, disclose, disseminate, distribute, copy, print or reply to this
>
> email. Views
> > > or opinions expressed by an individual
> > > within this email may not necessarily reflect the views of X-on or its
> > > associated companies. Although X-on routinely screens for viruses,
> > > addressees should scan this email and any attachments
> > > for viruses. X-on makes no representation or warranty as to the
>
> absence of
> > > viruses in this email or any attachments.
> > FreeIPA-users mailing list -- [e-mail]
> > To unsubscribe send an email to freeipa-users-leave@lists.
>
> fedorahosted.org
> _______________________________________________
> FreeIPA-users mailing list -- [e-mail]
> To unsubscribe send an email to [e-mail]

[Rob Crittenden]

Gabriel Stein via FreeIPA-users wrote:
> hey hey... I already registered for copyrights :P

It's already a thing, https://www.datadoghq.com/

rob
> Thank you!
> Gabriel Stein
>
> Gabriel Ferraz Stein
> Tel.: +49 (0)  170 2881531
>
> 2017-10-09 15:25 GMT+02:00 Fraser Tweedale via FreeIPA-users
> <[e-mail]
> >:
> On Mon, Oct 09, 2017 at 02:39:57PM +0200, Gabriel Stein via
> FreeIPA-users wrote:
> > Oh, sorry for the typos... (thanks @callum)
> >
> > '/s/Datadog/Dogtag/g'
> >
> Datadog is a pretty good name though! :)
>
> > Best Regards,
> >
> > Gabriel
> >
> > Gabriel Stein
> > ------------------------------
> > Gabriel Ferraz Stein
> > Tel.: [phone] <tel:%2B49%20%280%29%20%20170%202881531>
> >
> > 2017-10-09 14:34 GMT+02:00 Callum Guy <[e-mail]
> <mailto:[e-mail]>>:
> >
> > > Do you mean Dogtag rather than Datadog?!
> > >
> > > http://pki.fedoraproject.org/wiki/PKI_Main_Page
> <http://pki.fedoraproject.org/wiki/PKI_Main_Page>
> > >
> > > On Mon, Oct 9, 2017 at 1:30 PM Gabriel Stein via FreeIPA-users <
> > > [e-mail]
> <mailto:[e-mail]>> wrote:
> > >
> > >> Hi all,
> > >>
> > >> I was discussing a issue with @ftweedal and I will continue
> doing some
> > >> questions here.
> > >>
> > >> I have installed Freeipa with an additional Replica Server, but
> to me
> > >> some concepts are not so clear.
> > >>
> > >> Let' talk about my setup:
> > >>
> > >> Goal: Replace Active Directory Auth on DMZ Network.
> > >>           Provide SSL Certs for Servers/Services
> > >>           If possible, Management for  MIME/S Certificates(Mail
> Signing)
> > >>
> > >> Setup:
> > >>
> > >> Servers(Total: 3 VMs)
> > >> ipa1/ipa2: Freeipa Server and Replica
> > >> pki1: Datadog installation(external CA for ipa1/ipa2).
> > >>
> > >> I know, Freeipa includes Datadog(and that makes the certificates
> > >> management possible), but I needed a Datadog Service to create
> the external
> > >> CA for ipa1/ipa2.
> > >>
> > >>
> > >> Now I have some questions:
> > >>
> > >> - Was Datadog Installation "too much"? Probably was better just
> create a
> > >> CA manually with openSSL and import it on ipa1/ipa2?
> > >> - Should I use Freeipa as the sub-CA for all Servers/Services
> and leave
> > >> Datadog as a main CA? Do I have an advantage using this setup?
> > >>
> > >>
> > >>
> > >> Thanks in Advance!
> > >>
> > >> Best Regards,
> > >>
> > >> Gabriel
> > >>
> > >>
> > >>
> > >>
> > >> Gabriel Stein
> > >>
> > >> _______________________________________________
> > >> FreeIPA-users mailing list --
> [e-mail]
> <mailto:[e-mail]>
> > >> To unsubscribe send an email to freeipa-users-leave@lists.
> > >> fedorahosted.org <http://fedorahosted.org>
> > >>
> > > --
> > > Callum Guy
> > > Head of Information Security
> > > X-on
> > >
> > >
> > > *0333 332 0000  |  www.x-on.co.uk <http://www.x-on.co.uk>
> <http://www.x-on.co.uk>  |   **
> > > <https://www.linkedin.com/company/x-on
> <https://www.linkedin.com/company/x-on>>
>  <https://www.facebook.com/XonTel <https://www.facebook.com/XonTel>>
> > >   <https://twitter.com/xonuk> *
> > > X-on is a trading name of Storacall Technology Ltd a limited company
> > > registered in England and Wales.
> > > Registered Office : Avaland House, 110 London Road, Apsley, Hemel
> > > Hempstead, Herts, HP3 9SD. Company Registration No. 2578478.
> > > The information in this e-mail is confidential and for use by the
> > > addressee(s) only. If you are not the intended recipient, please notify
> > > X-on immediately on [phone]
> <tel:%2B44%280%29333%20332%200000> <+44%20333%20332%200000> and
> > > delete the
> > > message from your computer. If you are not a named addressee you must not
> > > use, disclose, disseminate, distribute, copy, print or reply to this email. Views
> > > or opinions expressed by an individual
> > > within this email may not necessarily reflect the views of X-on or its
> > > associated companies. Although X-on routinely screens for viruses,
> > > addressees should scan this email and any attachments
> > > for viruses. X-on makes no representation or warranty as to the absence of
> > > viruses in this email or any attachments.
> > >
> > >
>
> > _______________________________________________
> > FreeIPA-users mailing list -- [e-mail]
> <mailto:[e-mail]>
> > To unsubscribe send an email to
> [e-mail]
> <mailto:[e-mail]>
> _______________________________________________
> FreeIPA-users mailing list -- [e-mail]
> <mailto:[e-mail]>
> To unsubscribe send an email to
> [e-mail]
> <mailto:[e-mail]>
>
>
>
>
> FreeIPA-users mailing list -- [e-mail]
> To unsubscribe send an email to [e-mail]

[Fraser Tweedale]

On Mon, Oct 09, 2017 at 02:29:09PM +0200, Gabriel Stein via FreeIPA-users wrote:
> Hi all,
>
> I was discussing a issue with @ftweedal and I will continue doing some
> questions here.
>
> I have installed Freeipa with an additional Replica Server, but to me some
> concepts are not so clear.
>
> Let' talk about my setup:
>
> Goal: Replace Active Directory Auth on DMZ Network.
>           Provide SSL Certs for Servers/Services
>           If possible, Management for  MIME/S Certificates(Mail Signing)
>
> Setup:
>
> Servers(Total: 3 VMs)
> ipa1/ipa2: Freeipa Server and Replica
> pki1: Datadog installation(external CA for ipa1/ipa2).
>
> I know, Freeipa includes Datadog(and that makes the certificates management
> possible), but I needed a Datadog Service to create the external CA for
> ipa1/ipa2.
>
> Now I have some questions:
> Was Datadog Installation "too much"? Probably was better just create a CA
>
> manually with openSSL and import it on ipa1/ipa2?
> Should I use Freeipa as the sub-CA for all Servers/Services and leave
>
> Datadog as a main CA? Do I have an advantage using this setup?

(Copy of my answer from
https://pagure.io/freeipa/issue/7158#comment-471426)

Should you use the FreeIPA CA or Dogtag? It is better to think about
it this way: what does Dogtag offer that FreeIPA does not? Right
now, the answer mostly boils down to: HSM, token processing, and
more control over issuance workflow (e.g. request queues, agent
roles, ability to issue certs to abitrary subject rather than only
known principals in the FreeIPA DB, etc).

If you only want to issue certs to services/hosts/users recorded in
FreeIPA, and you do not need HSM, then the FreeIPA CA will meet your
needs.

Yes, you can issue S/MIME certificates with FreeIPA - you just need
to create a custom profile to set the appropriate Extended Key Usage
values, etc.

Cheers,
Fraser
> Thanks in Advance!
>
> Best Regards,
>
> Gabriel
>
> Gabriel Stein
> FreeIPA-users mailing list -- [e-mail]
> To unsubscribe send an email to [e-mail]