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Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere SSL Certificates for Mere Mortals VMworld 2017 Content: Not for publication or distribution

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Page 1: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Adam Eckerle, @eck79VCIX6-DCVSr. Technical Marketing Architect

SER2936BE

#VMworld #SER2936BE

vSphere SSL Certificates for Mere Mortals

VMworld 2017 Content: Not fo

r publication or distri

bution

Page 2: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

• This presentation may contain product features that are currently under development.

• This overview of new technology represents no commitment from VMware to deliver these features in any generally available product.

• Features are subject to change, and must not be included in contracts, purchase orders, or sales agreements of any kind.

• Technical feasibility and market demand will affect final delivery.

• Pricing and packaging for any new technologies or features discussed or presented have not been determined.

Disclaimer

#SER2936BE CONFIDENTIAL 2

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Page 3: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

3#SER2936BE CONFIDENTIAL

VMworld 2017 Content: Not fo

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Page 4: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Certificate Lifecycle Management

VMware Certificate Authority

VMCA

VMware Endpoint Certificate Store

VECS

Located on:Embedded Deployment and Platform Services Controller

Located on:Embedded Deployment andvCenter Server Node

4#SER2936BE CONFIDENTIAL

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Page 5: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

VECSVMCA

VMware Endpoint Certificate Store (VECS)

5

Signed

VMCACertificate

Machine SSLCertificate

#SER2936BE CONFIDENTIAL

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Page 6: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

VMware Endpoint Certificate Store (VECS)

▪ Repository for Certificates and Private Keys

▪ Mandatory Component

▪ Key Stores:

– Machine SSL Certificates

– Trusted Roots

– Solution Users Certificates

▪ Generally managed via Certificate Manager

▪ vecs-cli available for more advanced operations or automation

▪ Does Not Manage Single Sign-On Certificates

6#SER2936BE CONFIDENTIAL

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Page 7: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

VMware vSphere 6.x Certificate Types

▪ Machine SSL Certificate

▪ ESXi Certificates

▪ Solution User Certificates

▪ Single Sign-On Certificates

7#SER2936BE CONFIDENTIAL

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Page 8: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

ESXi Certificates

▪ Post-install, ESXi always has an auto-generated certificate

▪ VMCA will provision a signed certificate when host is joined to vCenter (default mode)

▪ Custom certificates can be use if desired (custom mode)

▪ ESXi certificates are stored locally on each host in the /etc/vmware/ssl

▪ VMCA issued certificates can be renewed via the vSphere Client or PowerCLI

#SER2936BE CONFIDENTIAL 8

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Page 9: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

ESXi Certificates

9

Example:

function refreshcerts {

process {

$hostid = Get-VMHost $vmhost | Get-View

$hostParam = New-Object VMware.Vim.ManagedObjectReference[] (1)

$hostParam[0] = New-Object VMware.Vim.ManagedObjectReference

$hostParam[0].value = $hostid.moref.value

$hostParam[0].type = 'HostSystem'

$_this = Get-View -Id 'CertificateManager-certificateManager'

$_this.CertMgrRefreshCertificates_Task($hostParam)

}

}

#SER2936BE CONFIDENTIAL

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Page 10: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Machine SSL Certificates

▪ Server verification and secure communicatione.g. HTTPS or LDAPS

▪ Each node has its own Machine SSL Certificate. i.e. Embedded Deployment; vCenter Server; or Platform Services Controller

▪ All services communicate through the reverse proxy

▪ Traffic does not go to the services themselvese.g. The vpxd service uses the MACHINE_SSL_CERT to expose its endpoint.

10#SER2936BE CONFIDENTIAL

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Page 11: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Certificate Replacement Options for vCenter

11

VMCA Default

• VMCA provides the Root certificate

• All vSphere certificates chain to VMCA

• Regenerate certificates on demand easily

• Recommended

VMCA Enterprise

• Replace VMCA CA cert with a subordinate CA certificate from the Enterprise PKI

• Upon removal of the old VMCA CA certificate, all old certificates will be regenerated

Custom

• Disable VMCA as CA

• Provision custom certificates for each solution user and endpoint

• More complicated

• For highly security conscious customers only

Hybrid

• Replacement of the Machine_SSL certs

• VMCA for Hosts and Solution Users

• Very popular with high security customers

• Recommended

#SER2936BE CONFIDENTIAL

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Page 12: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

VMware vSphere 6.x Certificate Manager

12

Appliance Deployment

/usr/lib/vmware-vmca/

bin/certificate-manager

Windows Deployment

<Drive>:\Program Files\VMware\

vCenter Server\vmcad\

certificate-manager

#SER2936BE CONFIDENTIAL

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Page 13: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Common Certificate Manager Use Cases

13

VMCAas Root CA

(Default or Option 4)

VMCA as Enterprise CA

Subordinate

(Option 2)

Custom CA

(Option 1 & 5)

Hybrid

(Option 1)

#SER2936BE CONFIDENTIAL

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Page 14: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Demo: VMCA as Root CA (Default)

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Page 15: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Full Custom (No VMCA)

▪ Essentially bypass VMCA

▪ Generate a CSR & Certificate for each:

▪ Machine SSL

▪ Solution User

▪ ESX Host

▪ Manual installation and renewal

▪ Most secure (highly regulated / secure environments)

▪ Most amount of work

15#SER2936BE CONFIDENTIAL

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Page 16: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

VMCA as Enterprise CA Subordinate

▪ Does NOT support wildcard cards or SubjectAltName

▪ You CANNOT create subsidiary CAs of VMCA

▪ No explicit limit to the length of the certificate chain

▪ Synchronize time for all nodes in environment

16

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Page 17: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Custom certificates for the Web Client

VMCA for everything else (User Solutions, ESX hosts)

Hybrid Approach Concepts

17

OperationsSecurity

#SER2936BE CONFIDENTIAL

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Page 18: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Hybrid Mode: 3rd Party Cert for Client access

18

What many security concerned companies are using for their vSphere environments

3rd Party Certificate Authority

DC1.lab.local

VCSA

vCenter Serverhttps://vcsa.lab.local

https://esxi-a.lab.local

SSL Certificate issued by DC1.lab.local Certificate Authority

SSL Certificate issued by vcsa.lab.local VMCA

#SER2936BE CONFIDENTIAL

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Page 19: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Implementing Hybrid Mode (High Level)

19

1. Use Option 1 to:• Replace Machine_SSL cert on all

PSCs in SSO Domain

• Replace Machine_SSL cert on all vCenter Servers in SSO domain

2. Use vSphere Client / PowerCLI to replace certs on ESX hosts

#SER2936BE CONFIDENTIAL

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Page 20: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Let’s Compare!

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Page 21: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

Example Environment

21

• 6 vCenter Servers• 2 Sites• 50 Hosts per vCenter Server

• 300 Hosts total

Approach SubCAs Machine SSL

Solution Users

ESXiHosts

Total Certificates

Subordinate CA 4 0 0 0 4

Full Custom N/A 10 28 300 338

Hybrid N/A 10 0 0 10

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Page 22: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

WalkthroughStep-by-step available at https://featurewalkthrough.vmware.com

Accompanying blog post at http://vmware.com/go/hybridvmca

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Page 23: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

#SER2936BE CONFIDENTIAL 23

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Page 24: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

© 2017 VMware Inc. All rights reserved.

vSphere Centralvspherecentral.vmware.com

• Curated repository of vSphere resources including blogs, KBs, videos, and walkthroughs

• Simple to access and a single URL to remember

• Conveniently export resources to PDF for offline viewing

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Page 25: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

© 2017 VMware Inc. All rights reserved.

vSphere 6.5 Topology & Upgrade Planning Toolvspherecentral.vmware.com/path-finder

• Guided walkthrough to assist in making critical topology and upgrade decisions

• Provides steps, diagram, and important resources for planning, execution, and post-upgrade

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Page 26: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

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Page 27: SER2936BE vSphere SSL Certificates for Mere Mortals or … · 2019-06-27 · Adam Eckerle, @eck79 VCIX6-DCV Sr. Technical Marketing Architect SER2936BE #VMworld #SER2936BE vSphere

#migrate2vcsa | @eck79 | @emad_younishttp://blogs.vmware.com/vsphere

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