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Exchange 2016 Upgrade to CU16 failing at Mailbox Role: Client Access step. Can't create IIS directory. Any solutions?

High Priority
30 Views
Last Modified: 2020-05-20
OS: Server 2016 Standard
Software: Exchange 2016

Attempting to upgrade Exchange to CU16. Have dealt with several issues that stopped the install so far, but now getting the following error when it's trying to upgrade the Client Access portion: "An IIS directory entry couldn't be created. The error message is The system cannot find the path specified."

I found things online saying that this indicated a corrupt IIS, so I uninstalled and reinstalled IIS, but that didn't change anything.

I've included the relevant portion of the Exchange Upgrade Error file in case anyone can glean anything from it,

There are extenuating circumstances that make this a significant issue at the moment, and I need to get mail working again quickly, so I hope there is someone out there with some insight right now. This is email for a 911 dispatch center, so it's highly mission critical.

Thank you for any help you can provide.

Stace Johnson
Exchange-Upgrade-Error.txt
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BrentDevOps

Commented:
Is the default website for IIS there ( folders and all )?

Author

Commented:
Yes, they are.


BrentDevOps

Commented:
Shoudnt be question marks next to them though...  Did you happen to take a snapshot of the machine before upgrading?

Author

Commented:
Update: Based on Brent's question above, I tried to go to http://localhost to see if the default website would come up, and it's not. I'm getting a 403 error, so maybe there's something wrong with IIS in general that's keeping the install from completing.

Author

Commented:
No, unfortunately, I didn't get a snapshot. I wasn't actually expecting to have to do this today, but we're behind the 8 ball.

I have already uninstalled and reinstalled IIS, but apparently the reinstall didn't go well.
BrentDevOps

Commented:
Sounds like a permissions issue.. did someone fiddle with those?  
BrentDevOps

Commented:
Sorry, permissions issue on the IIS directories or with the IIS account.
BrentDevOps

Commented:
could be someone put a redirect on the default site and thats going to a permission denied resource or directly to the non-functional OWA page.

Author

Commented:
I thought I had replied to this already about permissions, but I'm not aware of anyone having changed them.

I did find some weird bindings in IIS.

Author

Commented:
Current working theory is that if I can get IIS to display the default web page, then the installation should be able to create the IIS folder it's trying to create.

Anyone have any suggestions on repairing a default website that won't load?
DevOps
Commented:
At the risk of breaking things worse, you could uninstall IIS, delete all the directories in the folder, then reinstall IIS.  Verify the default sites loads, then retry CU16 ( which is basically a full install of exchange ).  You could save a backup of the IIS configuration and zip up the folder to save for later, but this is all real messy.

If you still have the previous CU, you could try to reinstall that as well.  I mean, i would take a snapshot ( if its a VM ) first.  really should have done that first.  again, super messy.

The  other better option is to stop right now, call MS support, open a ticket  for 500 bucks and see if they can walk you through the resolution ( assuming its a known issue they may not bill you ).  I have opened up 2 tickets with them, one for a CU that simply wouldnt install that they fixed pretty quickly with a bunch of registry changes(would have never fixed this myself).  The other ticket took months but was found to be a bug.  Unfortunately, it may be quick or it may take longer, no telling to you get them on the phone.  

Few things for the leadership:  If email is that critical, move to 365 (with e3 or higher), they offer all sorts of deals for government.  Or spin up a redundant server that mirrors the datastores.  Take snapshots before upgrades.  ( sorry for the soapbox but exchange (imo) is no longer a thing anyone should maintain locally ).

Been running exchange since 5.5 and the CU upgrades introduced a whole new level of borkery to exchange.  They basically made snapshots critical to success/uptime ( course now its best practice, i am getting old )

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Author

Commented:
Hi Brent,

That's exactly what I've been doing. I completed uninstalled and reinstalled IIS and deleted all the files in c:\inetpub and c:\windows\system32\inetsrv, then rebooted and reinstalled all the IIS files. Then the default website would load. I'm rerunning the install now. Fingers crossed.

No worries on the soapbox. There are some extenuating circumstances regarding just opening a ticket with Microsoft; this server is in Azure, and our MCP did not make us the customer of record. So we can't even open a ticket with Microsoft. When we try, we get the message that we are not the customer of record. Then the MCP proceeded to do a horrible job supporting us, including not setting up Azure backups at all. We're trying to work with Microsoft get out from under them right now, but the server decided to have problems before we could get that all resolved.

Looks like I'm going to have to re-setup all the prereqs now, too. But this feels like progress. Thank you for your suggestions, Brent. If this works, I'll mark your most recent post as the solution.

More later after I finish rebuilding things.

Author

Commented:
Unfortunately, after completely rebuilding IIS and confirming that the default website is now loading, I'm back to almost the beginning. Upgrade is failing on Mailbox Role: Client Access Services with the following error:

"Microsoft.Exchange.Management.Metabase.IISGeneralCOMException: An IIS directory entry couldn't be created. The error message is The system cannot find the path specified."

Sounds like a permissions thing, as Brent said above. At least IIS is running now, but I'm wiped and I'm going to go home. I've been working on this specific issue for over 12 hours.

I'll be back in the morning and check this thread in case anyone has any insights. Brent, thank you for your responses earlier. I appreciate you trying to help.

Stace
Warwick ReimanModern Workplace Consultant
CERTIFIED EXPERT

Commented:
I had this issue recently for a customer in a middle of a cross forest migration, Installing CU 16 even with Run as admin etc into an environment that already has Exchange 2016 running normally. IIS behaved and failed to start properly. Found going back to CU 15 and updating worked fine.

Possibly not much help, but I found this to be the quickest way round, and possibly wait for cu 17
AmitIT Architect
CERTIFIED EXPERT
Distinguished Expert 2017

Commented:
I saw, you did lot of troubleshooting already. I advise you to better open Microsoft case. Last option, you might need to reinstall Exchange with disaster recovery method.

Also note, never take Exchange snapshot, that would create more problem.

Author

Commented:
I've contact the MCP for the Azure environment where the server is located, and they are going to see what they can do. Continuing to troubleshoot the IIS directory problem. (Confirmed that Exchange Trusted Subsystem is a local admin, but still getting the issue.)

Stace

Author

Commented:
Everyone,

This is resolved. We brought in Microsoft support, and from their suggestions, we built a new VM and then they did a recovery to the new server.

Thanks for your insights and interest.

Stace
BrentDevOps

Commented:
Glad they got that fixed.  Rebuilding the whole thing is the nuclear option usually.  I have had to do it before and its not pretty, so i dont wish that on anyone.  Hopefully the leadership can agree on moving to 365 at some point.

Author

Commented:
Yep, that's the plan long-term. Thank you for your help, Brent.

Stace
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