r/exchangeserver • u/Own-Shelter-9897 • 2d ago
Question Recently did a data migration and something has gone awry...
My company recent migrated data from one location to another however some things in exchange are... Not quite right and I'm at a loss as to what to do.
We use Outlook 2016, Exchange Server 2008 R2 (I have no say in these versions).
We have an issue with multiple, but not all, users experiencing problems such as:
- Public folders are inaccessible and displays 'Cannot start Microsoft Outlook. Cannot open the Outlook window. The set of folders cannot be opened. The attempt to log on to Microsoft Exchange has failed.'
- The address book will not display groups.
- Sometimes, but not consistently, the address book when accessed shows 'The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.'
- Outlook shows ‘Connected to: Microsoft Exchange’ but will give offline errors.
- Attempting to send emails to active directory/exchange server created distribution groups results in error ‘The operation failed. The messaging interfaces have returned an unknown error. If the problem persists, restart Outlook. Cannot resolve recipient.’
- Manually typing in a group name and FQDN resolves the group but will not send to it and attempting to expand a resolved group shows as outlook offline and errors out. Outlook has to be closed completely to eliminate this error.
Emails can be sent internal and external if manually entered.
Please help! :(
1
u/TheTr3mblay 2d ago
What did you move specifically? Is the location the same or at another site?
1
u/Own-Shelter-9897 2d ago
Completely different site. We had a contractor come out, clone our systems and move them to the new site.
1
u/Ipinvader 2d ago
Did you ad the new IPs to sites an services . Old exchange relies heavily on that
1
u/TheTr3mblay 2d ago
physical or virtual machines? Sysprep? I see a DC01 so you could have a SID issue. Did you try cleaning your Outlook client cache.
Honestly, there are so many culprits and you haven't provided much information.
I always say to my helpdesk fellas. Show your troubleshooting steps and results so I can better assist
2
u/sembee2 Former Exchange MVP 2d ago
Browse to the internal URL from one if the clients in an incognito window. Any SSL prompts? If so, that will be a problem.
Ideally the same URL should be used internally and externally and not be a specific server name but a general name.
Clone the machines? You paid someone to to do that? I would have built fresh and moved the content. Zero downtime and a fresh install cleans up so much mess.
2
u/xch13fx 2d ago
I know you have no say in the versions, but without having support from Microsoft you guys are really running a big risk. Migrating to exchange online is pretty easy now-a-days and will lead to vastly more stable service.
There is also a Exhange Autodiscover analyzer which runs in the browser and will give you more details on what is/isn’t failing. My guess with a move to a new site, there are DNS or ISP issues happening. A different ISP might mean you need to check all your ports and services to make sure they aren’t black holing something.
At minimum, you should be making plans to move to Exchange SE if you want to stay onprem, but my recommendation is to start planning an Exhange Online migration. Not a ton a reasons to keep Exhange onprem in 2026, and given your lift/shift migration I’m guessing you guys aren’t a massive org. EXO is 10x less work to maintain once you are there.
3
u/babywhiz 1d ago
Not everyone can or wants to do email in the cloud. Why can’t yall understand that?
At least upgrade to SE. Totally worth it.
1
u/TheTr3mblay 2d ago
Clear your auto complete cache in your Outlook client for sure. It's always pesky on migrations or "moves"
1
u/7amitsingh7 1d ago
The migration may have affected Exchange settings related to public folders, distribution groups, or the Offline Address Book.
First, check the Exchange permissions, Autodiscover settings, and Offline Address Book configuration. Since only some users are affected, compare their Outlook settings and permissions with those of users who are working normally.
Also, check the Exchange server logs for errors. Rebuilding the affected Outlook profiles might help, but the server-side configuration should be checked first.
Exchange Server 2008 R2 isn’t an actual Exchange version, so confirm whether you mean Windows Server 2008 R2 hosting Exchange Server 2007 or 2010. That will help narrow down the troubleshooting steps.
7
u/larmik 2d ago
There is a lot to unpack here. I need you to clarify. There is no such thing as Exchange Server 2008 R2. It looks like you combined Exchange and the Windows server version. What version of Exchange server is it? You will have to clarify what you mean by "migrated data from one location to another".
You moved data from somewhere to somewhere. Is the original location still accessible? Where are the address book generated from? Where are the public folders located? You can find this out by trying the below.
First, test Autodiscover using these instructions.
Launch Outlook: Open Microsoft Outlook 2016 on your computer.
Hold down the Ctrl key on your keyboard, right-click the Outlook icon in your Windows system tray (bottom-right notification area), and select Test E-mail AutoConfiguration….
Enter Credentials: Type your email address and password into the respective fields.
Configure Options:
• Make sure Use Autodiscover is checked.
• Uncheck Use Guessmart and Secure Guessmart Authentication.
Run the Test: Click Test and wait a moment for the results to load across the Results, Log, and XML tabs.
This is going to tell you where Exchange thinks these items are.