This document provides guidance on planning and executing a successful upgrade of vCenter Server. It outlines the key steps in the upgrade process including awareness, assessment, planning, preparation, performing the upgrade, and post-upgrade steps. It also discusses considerations for different vCenter Server deployment types and topologies. The presentation aims to help users understand the upgrade process and mitigate issues that could occur.

1. Italy VMUG UserCon – 14 November 2017

3. Plan a successful vCenter
Server upgrade

4. Ivaylo Radev
• Staff, II
• VMware
• vCenter lifecycle management

5. Who am I?
• Master degree in computer science
• 13+ years of experience
• 7+ years within Vmware
• 5+ years in upgrade framework team

6. Runbook for vCenter Server upgrade
Awareness Assess Plan Prepare Upgrade Post-upgrade
Learn about new
vSphere version
Recognize a need to
upgrade vSphere
Identify gaps
Discover current
environment
Check Compatibility
Guide (HCL)
Check Interoperability
Matrixes
Decide to upgrade and
its scope
Respond to vCenter
requirements
Determine upgrade
sequence
Identify dependencies
and remediation
Budget a
maintenance window
Create a worksheet
Create rollback plan
Upgrade VMFS
Upgrade Hardware
Version
Upgrade VMware
Tools
Upgrade VDS
Reconfigure if needed
Address dependencies
and remediation
Collect information
and download
Validate requirements
Prepare licenses
Test rollback plan
Backup
Test upgrade
Take snapshot
Perform health check
Run Host Agent Pre-
upgrade Checker
Upgrade PSC
Upgrade vCenter(s)
Update vCenter
license(s)
Validate upgraded
vCenter

7. vCenter Server Components
vCenter Server
Platform Services
Controller
vCenter Server Server Appliance 6.5
Virtual Machine
Platform Services
Controller 6.5
Single Sign-On
Custom Roles
Licensing
Global Permissions
Certifi cate Authority
Tags
vCenter Server
6.5

8. vCenter Server – Embedded Deployment
• Both vCenter Server & PSC components
• No Enhanced Linked Mode
• vCenter High Availability Supported
• No Load Balancer required
• Supports all vCenter Server Maximums
Virtual Machine
Platform Services
Controller 6.5
vCenter Server
6.5

9. vCenter Server – External Deployment
• Separate Virtual Machines
• Enhanced Linked Mode
• vCenter High Availability Supported
• Load Balancer required for:
• Automatic PSC Failover
• vCenter HA
Virtual Machine
Platform Services
Controller 6.5
Virtual Machine
vCenter Server
6.5

10. vCenter Topologies
(A) vCenter with
Embedded PSC
(B) vCenter with
External PSC
(C) PSC in Replicated Configuration
OR OR
(D) vCenter Deployment across Sites (E) vCenter Server Deployment
Across Site w/ Load Balancer
OR

11. PSC HA and vCenter HA
vCSA (Passive)
Virtual Machine
or Physical Server
vCSA (Passive)
Platform Services Controller
Virtual Machine
or Physical Server
Platform Services Controller
vCSA (Active)
vCenter Server
vCSA (Active)
vCenter Server
Load Balancer
vCSA (Passive)
vCSA (Active)
vCenter Server
Platform Services Controller
Single Highly Available VC in Embedded Mode Multiple Highly Available VC in Enhanced Linked Mode

12. Upgrade and Topology
• Embedded and External deployments are supported
• Topology is not changed during upgrade
• Don’t stay in deprecated topology after upgrade
• Reconfigure from unsupported topology to supported topology
before upgrade
• Consolidation of vSphere SSO domain only available in vSphere
5.5

13. Upgrade vCenter with Embedded SSO
Architecture is unchanged
vSphere 5.5
vCenter Server
vCenter Server
Web Client
Inventory Service
SSO
vSphere 6.5
vCenter Server
vCenter Server
Web Client
Inventory Service
PSC

14. Upgrade vCenter With External
Components
1. Upgrade Single Sign-On
to PSC
2. Upgrade vCenter Server
SSO 5.x
vCenter Server
Inventory Service
Web Client
PSC 6.5
vCenter Server 6.5
vCenter Server
Web Client
Inventory Service

15. Upgrade vCenter With Replicated
External SSO
1. Upgrade one Single
Sign-On to PSC
2. Upgrade another Single
Sign-On to PSC
3. Upgrade first vCenter
Server
4. Upgrade second
vCenter
SSO 5.xPSC 6.5
vCenter Server 5.x
vCenter Server
Web Client
Inventory Service
SSO 5.x
vCenter Server 5.x
vCenter Server
Web Client
Inventory Service
PSC 6.5
vCenter Server 6.5
vCenter Server
Web Client
Inventory Service
vCenter Server 6.5
vCenter Server
Web Client
Inventory Service

16. Repoint Replicated Embedded PSC to
External PSC
1. Deploy an external SSO
replicating with
embedded SSO
2. Repoint vCenter to
external SSO
3. Uninstall embedded
SSO
4. Upgrade SSO to PSC
5. Upgrade vCenter to 6.0
SSO 5.x
vCenter Server
vCenter Server
Web Client
Inventory Service
vCenter Server 5.x
vCenter Server
Web Client
Inventory Service
SSO
vCenter Server
vCenter Server
Web Client
Inventory Service
vCenter Server 5.x
vCenter Server
Web Client
Inventory Service
SSO
vCenter Server
vCenter Server
Web Client
Inventory Service
vCenter Server 6.5
vCenter Server
Web Client
Inventory Service
vCenter Server
vCenter Server
Web Client
Inventory Service
vCenter Server 6.5
vCenter Server
Web Client
Inventory Service
PSC 6.5

17. Preserved data on upgrade
• The identity of upgraded vCenter/PSC is preserved (UUID, IP,
FQDN, Certs, etc)
• AD membership
• Inventory & Configuration is migrated by default
• Historical & Performance(SET) data migration is optional

18. Install/ Upgrade/ Migrate as a 2 Stage
Process
Stage 1
Deploy OVF
Stage 2
Configure Appliance
Make troubleshooting and fixing the environmental issues like
network, DNS, NTP etc. easier.
1. Deploy with a number of supported tools to deploy the vCSA.
2. Configure via Installer UI or Appliance Management UI.

19. vCSA Deploy/Upgrade/Migrate Orchestrators
Directly from VCSA ISO
vCenter Server Appliance CLI

20. Migrate VC IP Address
vCenter Server Appliance (Source)
vCenter
Server
Single Sign-
On
Client machine
Installer
vCenter Server Appliance (Target)
PSC
vCenter
Server
Deploy vCSA OVF
using temporary IP
Shutdown source vCenter Server Start migration processExport VC data and
configurations
Migrate data and
configurations to target vCSA over sshConfigure and start services
Data &
Configs
Data &
Configs
Temp IP Address
PostgreSQL
Connect to vSphere Web
Client using VC IP
Browser
VC IP Address
PostgreSQL

21. Windows vCenter Server News
Announced on Friday 8/25
http://vmwa.re/goodbyewinvc
vCenter Server
6.5

22. Migrate vCenter for Windows to vCenter
Server Appliance
• Windows vCenter upgrade and migrate to vCSA.
• Deployment type and configurations consideration
• External DBs to embedded DB consideration

23. Migration Process
Step 1: Migration Assistant
• vCenter Server pre-checks
• Data Transport Mechanism
• VMware Update Manager Included
Step 2: Migration Tool
• Stage 1: VCSA Deployment
• Stage 2: Configuration / Data Import

24. vCenter Server
(Source/Windows)
vCenter
Server
Single Sign-
On
Client machine
Installer
Migration
Assistant
vCenter Server Next
(Target/Appliance)
Single Sign-
On
vCenter
Server
Download and run
Migration Assistant
Deploy vCSA OVF
using temporary IP
Shutdown source vCenter Server Start migration processExport VC data and
configurations
Migrate data and
configurations to target vCSAConfigure and start services
External
Database
Data &
Configs
Data &
Configs
Temp IP Address
PostgreSQL
Migrate VC IP Address Connect to vSphere Web
Client using VC IP
Browser
VC IP Address

25. Migration for VUM on Windows to vCSA
• As of vCenter 6.0 U1, VUM fully integrated into vSphere web-
client
• Full VUM operations both remediate/scan available via the
vSphere Web Client
• VUM embedded within vCSA

26. vSphere Upgrade Process
Step 1: SSO (5.5) / PSC (6.0)
Step 2: vCenter
Step 3: Hypervisor (ESXi)
Step 4: Virtual Machines –
VM Tools / Compatibility
Step 5: Storage - VMFS

27. Budget a maintenance window
• How long does the migration process take?
• Estimating vCenter Server 5.5 to vCenter Server Appliance 6.0
migration time KB 2146420
• Estimating vCenter Server 5.5 or 6.0 to vCenter Server Appliance 6.5
migration time KB 2147711

28. System downtime during upgrade
• It is difficult to significantly decrease the amount of time it takes to
upgrade a single vCenter
• Skip migrating Historical & Performance(SET) data
• Deploy target vCSA up front maintenance window
• Avoid multi-hop upgrade, e.g. 55 60  65
• Many customers stagger their upgrades over multiple maintenance
windows
0
2
4
6
8
10
Sequential Upgrade Concurrent Upgrade
Total Duration
Upgrade Duration - Sequential
Upgrade Duration - Concurrent

29. The most frequently seen environment
errors
• Certificates management
• Networking misconfigurations
• AD permission issues
• The products on top of vCenter Server stop working after
vCenter Server upgrade – products compatibility
• Unsupported version compatibility, e.g. 60u3 -> 65GA

30. vSphere Interoperability Matrices
vSphere 5.1 & 5.0 end of life
http://www.vmware.com/go/interop
KB 2145103
Using the VMware Product
Interoperability Matrixes
KB 2006028

31. Limitations
• The certificates chain does not conform Vmware standards
Resolution: Re-generate SSL certificate with DNS name or static IP address
• Source Windows/vCSA machine has multiple IP addresses/NICs, only a single
address will be migrated to vCSA; the one matching the VC certificates
Resolution: Add back the rest of IP addresses after completing migration
• Source VC machine will get shutdown as part of upgrade process. You won’t be able
to access your 3rd party products
Resolution: Evacuate your 3rd party products before upgrading vCenter Server
• Local Windows OS users and groups are not migrated to the Photon OS of the
vCenter Server Appliance 6.5
Resolution: Re-create Local OS users and groups after upgrading vCenter Server

32. vCenter Upgrade – Best Practices
• Prepare the necessary resources – Temporary IP address, passwords,
AD permissions, regenerate certs, supported topologies, etc
• Use FQDN
• Select proper sizing – CPU/Mem/Disk
• Windows OS and DB compatibility
• Check Compatibility Matrix for VMware Solutions / 3rd Party Solutions
• VMware Compatibility Guide – Verify Hardware is Supported
• Stick to recommended topologies (KB 2147672)
• Backup DB and VM prior to upgrade
• …

33. vCenter Upgrade – Best Practices (2)
• …
• Have rollback plan
• Network
• Ensure proper forward and reverse DNS records for static IP
address configuration
• Ensure proper routing between VC/PSC or PSC/PSC when different
VLAN/Portgroups are used
• If using VDS, portgroup must be Ephemeral when using ESXi as a
deployment target
• Time synchronization
• Ensure proper time synchronization

34. vCenter Upgrade – Best Practices
Check after Upgrade
• Network settings are correctly migrated
• AD registration is correct
• Domain is correct
• Certificates are valid
• Login to vCenter to check data are migrated
• Inventory data
• Users, permissions, and roles
• Event history
• Performance charts

35. Important vSphere Documents
vSphere 6.5
Documentation
Compatibility
Guide
Product
Release
Notes
KB Articles

36. vSphere
Central vspherecentral.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

37. vSphere 6.5 Topology and
Upgrade Planning Tool
http://www.vmw.re/65upgradetool
• Online, browser-based tool – no
install necessary
• Walks you through key decisions
when planning and upgrade or new
deployment
• Provides upgrade/deployment steps
along with a diagram and links to key
documentation

38. Upgrade Resourceshttp://www.vmware.com/products/vsphere/upgrade-center/overview

39. vSphere 6.5 Upgrade Documents
Knowledge Base Articles
• Information before upgrading to vSphere 6.5 (2147548)
• VMware vSphere Upgrade Policies (2149713)
• Update Sequence for vSphere 6.5 and its compatible VMware products (2147289)
• Best Practices for upgrading to vCenter Server 6.5 (2147686)
• Revert a failed upgrade/migration (2146453)
• Supported and Deprecated Topologies for VMware vSphere 6.5 (2147672)
• vCenter Single Sign-on and Platform Services Controller High Availability Compatibility Matrix (2112736)
• Supported Upgrade paths for vSAN 6.6 (2149840)
• Migrating VMFS 5 datastore to VMFS 6 datastore (2147824)
Documentation
• VMware vSphere 6 Documentation
• Release Notes
• Compatibility and Configuration Limits
• Product documentation including vSphere Upgrade Guide
• Guest Operating System Installation Guide
• VMware Compatibility Guide

40.  Automate the upgrade preparation
 Make the upgrade process even more resilient
 Simplifying Install/Upgrade User Experience
 Decrease vCenter Server Downtime during upgrade
Future plans

41. Thank You!

42. Backup slides

43. Hypervisor Upgrades - ESXi
Support for
latest server
hardware
VM, Host,
and Cluster
scalability
boosts
vSAN
improvements
vMotion
Enhancements

44. VM Tools
Production Cluster
ESXi
ESXi
ESXi
App 1
Tools - Current
Tools – Out of Date
Tools – Out of Date
Tools – Out of Date
App 2
Tools - Current
App 3
App 4
App 5

45. VM Compatibility formerly vHardware
Production Cluster
HW v10
HW v10
HW v13
ESXi
ESXi
ESXi
Schedule available per VM
App 5
App 4
App 3
App 5
App 5
HW v10
HW v11

46. Storage – VMFS6
Feature / Function VMFS6 (v6.5) VMFS5 (v5.x)
Access for ESXi 6.5 hosts Yes Yes
Access for ESXi hosts version 6.0 and earlier No Yes
Datastores per host 512 512
Automatic space reclamation Yes No
Space reclamation form guest OS Yes Limited
MBR storage device partitioning No Yes
Block size 1 MB 1 MB
Default snapshots
VMFSsparse (virtual disks < 2 TB
SEsparse (virtual disks > 2 TB)
SEsparse