ESX upgrade and planning

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I have been asked to formulate a plan to upgrade vmware infrastructure at one our sites. It is realy outdated currently running esx 3.5 u2 and vcenter 2.5. I have looked in to the hardware compatibility and upgrade paths. Basically with our current hardware we can only go up to esx/esxi 4. We are due to get new hardware in 6 months where I plan to roll out esxi 5. What I plan on doing is going from 3.5 u2 to u5 and then updating to esx 4 u2. Then waiting 6 months and doing a fresh install of esxi 5.

Firstly what do you think about that, any suggestions on this, should i just wait 6 months. The last update of esx was 4 years ago so what would another 6 months harm?

Second question is, does anyone have any templates of a document that would be used to formulate such a plan. What sort of things should be in the document that you can think of. I have a rough idea but if anyone has any information on things to consider when writing such a plan that would help.
 
Is your vcenter server running as a VM or on a physical server?
Is it on a 64bit OS?.
Are you using Site Recovery Manager?

Support wise, you should really do the upgrade now.
However, I think i'd be inclined to leave it, it isn't going to save you any work in 6 months time anyway.

If you do have to upgrade now, then you'll need to upgrade vcenter first. vcenter 2.5 will not manage anything past ESX3.5.
You may be aware already - but you didn't specifically state this step in your post so thought I'd confirm.

The plan to upgrade is reasonably straight forward.
Upgrade vCenter to latest compatible version (4.1 and beyond require a 64bit OS)
Upgrade 1 ESX host to latest compatible version.
Check everything will migrate and work correctly on upgraded host - including any backups.
Upgrade other ESX hosts.
Done.

There are lots of vmware published document and blog posts on how to do it, but make sure you double check everything against the compatibility matrices and interoperability guides.
 
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The vcenter is a windows 2003 server running sql 2005 a physical server.

We have an enterprise license but i don't think we use or even have recovery manager installed.

We won't be able to install 4.1 because we can only go to Esx 4.0 u2 from 3.5 u5. I would probably update to vcenter 4.0 and use vsphere 4.0. Thought i should add that the esx hosts are dl385 g2 so only support up to esx 4.0 u3 and esxi 4.0 u2.

What I meant by the plan document was something more a long the lines of formatting and any other fancy words that can be put in to such documents to make seem like you did a good job. But I guess ill just put some dates and times next to each step and thanks for pointing out the steps. I didn't think of testing backups.

Why is it that vcenter has to be upgraded first ?

Could i not just install vsphere 4 on a client pc or server and then connect directly to the esx server that was just upgraded. Is there a specific reason?

Would you suggest then migrating all the active guests across to the upgraded host and starting them all up one by one to make sure that they all work ok. if so i guess this is why you suggest upgrading vcenter first. Then import some backups?
 
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Why is it that vcenter has to be upgraded first ?

vCenter will support previous versions of ESX/ESXi, it may allow you to add future ESX/ESXi hosts but the results can be strange and unpredictable.
(I can speak from experience on this - weird CPU spikes on the VM's, strange behaviour during vmotion - all went away after upgrading vcenter as I should have done had I read the documentation properly).

So whenever you're doing upgrades, always check the interoperability and compatibility guides, and always do the vcenter server first.

Could i not just install vsphere 4 on a client pc or server and then connect directly to the esx server that was just upgraded. Is there a specific reason?

You could, but definitely remove the ESX host from the existing cluster before upgrading it.

Would you suggest then migrating all the active guests across to the upgraded host and starting them all up one by one to make sure that they all work ok. if so i guess this is why you suggest upgrading vcenter first. Then import some backups?

If you upgrade vcenter first and a single host, you can switch off DRS, and vMotion selected test machines to the upgraded host.
You can then do all the tests you need before deciding to upgrade all the other hosts.

If you create a segregated vCenter with a single upgraded host, then you would need to shutdown each guest, unregister it, then register it on the new vCenter.
I hope you have a very understanding company who will let you do this during the day, or pay you overtime.


As an edit to my previous plan, I should add doing a backup of the vCenter DB befire an upgrade is essential.
 
Here is my plan so far:

Part 1: ESX 3.5 to ESX 3.5 update 5 and vCenter 2.5 to vCenter 2.5 u6b

1. Update vCenter to version 2.5 update 6b
2. Update one ESX host to 3.5 update 5
3. Test guests are ok after update and migrate guests from other hosts and test, test backups are working.
4. Upgrade other ESX hosts to 3.5 update 5

Part 2: ESX 3.5 u5 to ESX 4 u3 and vCenter 2.5 u6b to vCenter 4.0 u3

1. Update vCenter to version 4.0 u3
2. Update one ESX host to 4.0 u3
3. Test guests are ok after update and migrate guests from other hosts and test, test backups are working.
4. Upgrade other ESX hosts to 4.0 u3

esx host are dl385 g2 (yes g2) last software update was 2008. highest vmware version supported is 4.0 u3. Getting new hardware in 6 months+-
 
If you create a segregated vCenter with a single upgraded host, then you would need to shutdown each guest, unregister it, then register it on the new vCenter.
I hope you have a very understanding company who will let you do this during the day, or pay you overtime.


As an edit to my previous plan, I should add doing a backup of the vCenter DB befire an upgrade is essential.

I was under the impression that I would have to shut down all the guests on the esx hosts before applying the upgrade. But to be honest I have not looked in to that aspect yet. I will most likely come in on the weekend and get overtime for it and have a few hours down time.
 
Here is my plan so far:<Snip>
Plan looks good, you may be able to skip straight to part 2, but no idea if the upgrade path from such old versions is even published any more.
I'd go with how you have it planned - get to the latest version of VC2.5 ESX 3.5 and upgrade from there and you should be fine.

I was under the impression that I would have to shut down all the guests on the esx hosts before applying the upgrade. But to be honest I have not looked in to that aspect yet. I will most likely come in on the weekend and get overtime for it and have a few hours down time.

No need to shut anything down.
The VC upgrade can be done without affecting any guests. you just can't do anything that you'd need VC for (vMotion etc) while it's happening.

As for the ESX hosts, as long as everything is on shared storage you can just put one host into maintenance mode, let everything migrate to the remaining host(s), shut it down and do the upgrade.
 
Can't update to esx 4 from our current version because it is too old. I am not sure if vmotion is enabled, will have to check that. I will look in to maintenance mode and upgrade guides before i do anything. Thanks!


DRS is enabled. So Ill put one in to maintenance mode and wait for it to migrate and then do the update. Ill read the installation guide first though. :D

I do wonder if i could just go straight to vcenter 4.0 u3 instead of going to 2.5 update 6 first. Seeing at the vcenter are backwards compatible.
 
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I do wonder if i could just go straight to vcenter 4.0 u3 instead of going to 2.5 update 6 first. Seeing at the vcenter are backwards compatible.

You probably can, VC 4.0 was the first upgrade from 2.5 - so it'd make sense to be able to.
This is the page you need, and this is the main document.

You haven't said what the VC DB is running on - read through the doc as not all versions of SQL are supported.
Also in the doc - make sure you have all your vSphere licensing ready to go, ESX4 is licensed through VC now, so you'll need the V2.5 licensing module installed to continue licensing for your ESX 3.5 hosts.

Those are the bits I've picked up on from when I did it - but read through the doc it covers everything you need to know or have thought of.
 
We only have the root passwords for one of the three ESX boxes. I have created a new guest with 2008 r2 and vcenter 4.1. I am then going to migrate all the guests to the host with the password and then add that host to the vcenter 4 server. Then i am going to reinstall esxi 4 on to the host with no password. Then i am going to migrate the guests from esx 3.5 to esxi 4 hosts. Will that work? This guy was saying I might have problems with license server.
 
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Make sure you use 64bit OS for vcenter, just install it all in trial mode then upgrade and sort all the licences after the migration is complete
 
I used 2008 r2 which is 64bit. I have actually already used the vcenter 4 standard license. The vcenter 2.5 license server will still be active during the migration. SO i was thinking of just using the old license server option in the options. Do you think i should uninstall it and install it in evaluation mode.
 
1. Make note of network config on a current ESX host.
2. Put host in maintenance mode.
3. Install fresh copy of desired ESX variant.
4. Build new VC and create a new cluster.
5. Add old ESX hosts and migrate machines across to the new cluster.
6. Repeat 2 & 3 on other hosts.
7. Job done.

Bugger updating - just as quick to do a clean install.

Time frame - 1/2 a day depending on number of hosts and vm's.
 
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