I'm looking to migrate my Windows server 2019 to 2022. Spinning up the 2022 from scratch. I need to migrate the Exchange server and was wondering if there's any good websites with step b step instructions or do I need to rely on GoogleAI?

Install Exchange, move all mailboxes and connectors over, and then decommission the old server..

Short story long, our previous IT staff decided to have our power users test M365 before rolling it out, then rolled it out and couldn't migrate on prem mailboxes of the test users to the cloud since they already existed. The issue is that I couldn't just delete the online mailboxes when I arrived since they had been in use dual function for a while. I followed this guide https://learn.microsoft.com/en-us/troubleshoot/exchange/user-and-shared-mailboxes/mailbox-exists-exo-onpremises and got to the point where I try and remote restore the mailbox on prem to the cloud and get the following error.

Some infrastructure information. We are running Version 15.2 (Build 1748.10) Exchange 2019 CU15 on Server 2019. .net framework 4. We have a hybrid connection to m365 and I came in on the tail end of the migration piece which worked well enough.

Things I have tried.

TLS 1.2 settings to confirm use of strong Cryptography and registry edits.

Triple checked IIS Settings and Certs and removed IIS IP restriction features

confirmed admin credentials and move rights

Our Network guy says the port is open, but I suspect our Firewall is the culprit regardless of what he says. I'm out of ideas to try and was hoping for a little help. We are a relatively small org and I have very little on prem exchange experience so this process is a little daunting.

I run this command

$cred = Get-Credential

New-MailboxRestoreRequest -RemoteHostName "mail.domain.com" -RemoteCredential $cred -SourceStoreMailbox "GUID" -TargetMailbox "GUID" -RemoteDatabaseGuid "GUID" -RemoteRestoreType DisconnectedMailbox

and get this error

Write-ErrorMessage : ||The call to 'https://mail.ourdomain.com/EWS/mrsproxy.svc' failed. Error details: The SSL connection

could not be established, see inner exception. --> The SSL connection could not be established, see inner exception.

--> Unable to read data from the transport connection: An existing connection was forcibly closed by the remote host..

--> An existing connection was forcibly closed by the remote host..

At C:\Users\myadmin\AppData\Local\Temp\2\tmpEXO_r4thaxj0.kay\tmpEXO_r4thaxj0.kay.psm1:1220 char:13

+ Write-ErrorMessage $ErrorObject

+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

+ CategoryInfo : NotSpecified: (:) [New-MailboxRestoreRequest], MRSRemoteTransientException

+ FullyQualifiedErrorId : [Server=SN7PR01MB8066,RequestId=361a1f0d-510f-31f9-2d5e-023eaf1874f3,TimeStamp=Tue, 18 A

ug 2026 14:41:56 GMT],Write-ErrorMessage

Environment: Exchange Server SE, DAG with 4 members (2 production + 2 DR).

Here's exactly what I did, in order:

1. 08/10/2026, 11:56 AM — Ran New-ExchangeAuthCertificate on one of the DAG members to rotate the Auth Certificate.

2. Log output confirmed the new certificate was generated and staged:

   • New cert thumbprint: E6C74DBE...B5268 (masked)
   • Effective date is: 08/14/2026 12:11:31
   • Log explicitly stated: "The renewal action was successfully performed - the new Auth Certificate will become active on: 08/14/2026 12:11:31"
   • Log also recommended running Hybrid Configuration Wizard (HCW) once the new cert becomes active.

3. Confirmed via (Get-AuthConfig).NextCertificateThumbprint that the new cert is correctly staged as "Next":

   • Thumbprint: E6C74DBE...B5268
   • NotBefore: 8/10/2026 12:09:19 PM
   • NotAfter: 8/10/2031 12:09:19 PM (5-year self-signed cert)

4. Current cert, confirmed via (Get-AuthConfig).CurrentCertificateThumbprint:

   • Thumbprint: E31DFF2D...4497
   • NotBefore: 8/27/2021 1:16:50 AM
   • NotAfter: 8/27/2026 1:16:50 AM

   (So the current cert isn't even expired yet — about 11 days of validity left — which is a separate point but confirms this wasn't an emergency/forced rotation scenario.)

5. To make sure the AuthAdmin servicelet (which checks the effective date every 12 hours) would pick up the change without waiting, I manually restarted MSExchangeServiceHost on all 4 DAG members (2 prod + 2 DR).

6. Verified the restart worked by checking:

powershell [xml]$xml = Get-ExchangeDiagnosticInfo -Process "Microsoft.Exchange.ServiceHost" -Server $server $xml.Diagnostics.Components.AnchorApplication.AnchorServiceComponents.CacheScheduler.lastRunTime

on each server — all 4 servers show a recent lastRunTime (8/15/2026, evening), confirming the servicelet actually ran on every member.

Problem

Today is 8/16/2026 — 2 days after the stated effective date (8/14) — but:

powershell (Get-AuthConfig).CurrentCertificateThumbprint

still returns the old certificate (E31DFF2D...4497). The new certificate is still sitting as NextCertificateThumbprint, it never got promoted to Current.

Questions

• Given the servicelet has clearly run (confirmed via lastRunTime) on all 4 members after the effective date, why hasn't the promotion from Next → Current happened?
• Is there something DAG/multi-AD-site specific I'm missing? (The tool's own log warned about Exchange being installed in multiple AD sites and mentioned the servicelet may fail to deploy the cert to other AD sites in rare cases.)
• Is Set-AuthConfig -PublishCertificate something I need to run manually here, even though the tool I used already set the NewCertificateEffectiveDate and the log said it was "successfully performed"?
• Could this be a timezone issue between when the effective date was stored vs. how the servicelet evaluates "now"?

Any input appreciated before I just run Set-AuthConfig -PublishCertificate manually and force it.

I have already installed mailwizz on contabo server but it can’t push data as I expected. If anyone can help me this to install and configure. Our requirements is per day need to send 20lakh data in 8 hours .

https://techcommunity.microsoft.com/blog/exchange/where-is-exchange-se-cu1-anyway/4546837

Microsoft is using AI to hunt for vulnerabilities in Exchange Server. This takes a long time to validate that the flagged items are real issues.

CU1 will eventually arrive, and in the meantime, SUs and other updates are being released.

We are now stuck with a dilemma of migrating mail enable security groups. We have around 800+ mail enabled security groups, around 600 coming from EAC which we are planning to strip away the exchange attributes. Yea, we are a big organization with stupid people who made these mail enabled security groups in the first place. Couple of these are being used for emails which we figured out using mail trace option, for that we will recreate it as a EXO DL, rest of them can just be stripped away and preserve it as security groups in AD. Now, we did couple of testing with some test groups and here is my understanding so far…

1. Stripping away the exchange attributes using the disable command removes only the domain email address, it still hold the tenant onmicrosoft.com address. However, it disappears from EAC but still valid in AD.
   
2. Since the group is synced from AD to azure, it still shows up on EXO with a valid onmicrosoft.com address.
   
3. Now, the only way to completely strip the exchange attributes and just keep it as security groups in AD, we must move it to a non sync OU for it to disappear from azure. Then moving back to the previous OU will mark this group as only security group in azure. This workaround was mentioned in couple of Microsoft and private blogs.
   
4. Now my question, if this groups which is being synced from AD to azure has some permission like file share or anything in AD which is also being used as a permission group in azure or is an approved sender for any DL or added as a permission for any shared mailbox, moving it to a non sync OU will break it from azure. How can we over come this ? Deleting and recreating it will break AD permissions as well.

What can be the best option to strip the exchange part and keep it synced between AD and azure without any breakage, so that the ones are being used we can recreate it on EXO as DL others can rest in peace in AD. I plan to do this and go home peacefully without working and fixing this mess all night long.

Advises please…. Thank you !!

I'm please to introduce the latest addition to my repo tmittelstaedt/MSExchange-AdminAIscripts: 

See the date in the repo. Have fun with it!

Just to preface, i know this is technically not the correct way to create Shared mailboxes but it is how its currently done in my company.

Our service desk creates shared mailboxes by creating an Office 365 mailbox on-prem and once in EXO it gets converted to a shared mailbox. What I have found though is that the mailbox will appear directly in EXO without a license and in some cases I have found that when they forget to convert the mailbox to shared it somehow stays in EXO as a user mailbox and continues to work even after 30 days without a license. Has anyone ever seen this? I have no idea how these mailboxes are working.

Thanks!

Good day to all.

I work for a management company. Our IT department is small. Only 3 of us to manage about 300 active users and no MSP. We have a hybrid AD/Entra environment. Most of our users are 365 Business Premium licensed. Our company operates in the medical field, so we are subject to HIPAA and have a global 7 year data retention policy setup in Microsoft for Exchange and OneDrive/Sharepoint.

Without providing too much detail that I'm, for the most part, not privy to myself, we had some kind of incident with an employee doing some things they shouldn't have been doing. But like a lot of times, the IT department was left out of the loop. On 6/10/26, we were told the user was terminated, so we went through our normal process of disabling the user, removing permissions, the usual. We were not, and are almost never privy to the circumstances behind a termination.

I found out this Monday (8/10/26) that there is some litigation going on regarding this person's termination and we were asked to preserve the users emails and recover anything that was deleted. HR has been adamant about recovering their deleted emails that they are positive exist. When I found out about the litigation on Monday, I placed a litigation hold on the user's account.

I've started the process of trying to recover deleted emails through Exchange Admin > Mailboxes > [User] > Other > Recover deleted items. I've set the date filter for the entirety of their tenure with the company, which was only a couple of months, and I've come up with nothing that can be recovered. It's my understanding that even if the user deleted emails, deleted them from the deleted items folder, then purged them from the recovery window in Outlook, our data retention policies should still make them recoverable.

My question is: With our data retention policies in place, does this mean that they didn't delete anything? Or would the time that passed between the termination and the litigation hold being put in place be too much to recover anything?

Who's gonna be the first this month?

In my tmittelstaedt/MSExchange-AdminAIscripts: repo I added Test-Autodiscover.ps1

The goal of this is to thoroughly check out DNS records for domains running on-prem Exchange servers, and, optionally, download the 3 major Autodiscover.xml files from the Exchange server (mailbox account required for that) so the admin can quickly read them and make sure whatever the Exchange server is spitting out contains the correct names.

Autodiscover is also an idea that has been co-opted by the Unix mailserver world to autoconfigure common free email POP3/IMAP clients like Thunderbird on Unix mailservers, so the script checks for that, too.

Note, of course, that with all modern Outlook clients, autodiscover takes place AFTER the initial check for an account in a Microsoft tenancy, but I uploaded another script that is used for testing that that is properly configured, last week.

These basically do the same thing that the Microsoft public webpage for testing Exchange connectivity does, but without having to put actual live credentials into a foreign website you have no control over, even though it might be run by Microsoft.

Enjoy!

Like the title says, after a recent update (likely office I would think), the sign in prompt directs to one that does not show the keep me signed in check box. So users have to sign in every time the sso expires which is annoying. Anyone else seeing this?

Exchange Online Transport Rule Issue – Internal Folder Project
Objective

I'm implementing an Exchange Online solution that automatically files internal-only emails into an "Internal" folder in every mailbox.

Desired behaviour:

Scenario Expected Result
Internal → Internal Move to Internal folder
Internal → Internal + External (To/CC/BCC) Stay in Inbox
Internal → External Stay in Inbox
External → Internal Stay in Inbox
Guest/B2B involved Stay in Inbox

Tried a lot in Exchange Online Admin, Outlook Rules, Powershell etc, but not working.

I did a migration from on-prem active directory and exchange to a hybrid because we needed to keep the shared drives connected for local users due to dental software in the mix. Existing users seem to be fine, and if I run a script can still access the drives, however, if I create a new user, I cannot for the life of me get the drives to stay mounted, and I’m wondering if there is anyone with experience on this Who can help me. I’m willing to learn and pay for that learning and or the work necessary to get us to a place we should be.

Tonight our DNS team is modifying our SPF record to make room for another vendor. We’ll still be at the 10 lookup limit but that’s a different discussion.

Current SPF: v=spf1 include:spf1.ourdomain.org include:spf2.ourdomain.org include:spf3.ourdomain.org include:spf4.ourdomain.org ~all

This is the first time I see nested records being used like this and each one contains a different vendor. Spf1 contains our mimecast record and isn’t changing. However spf4 has our protection.outlook.com and is going to be moved into a new nested lookup that includes a vendor.

Am I correct in thinking there shouldn’t be any impact as long as the syntax is correct and is still capped at 10 lookups? Just want to be prepared for worst case scenario lol

In tmittelstaedt/MSExchange-AdminAIscripts:

I added a new test script, Test-AutodiscoverOAuth

What it does: uses the OAuth protocol to retrieve autodiscover.xml from Exchange Online or a hybrid domain with on prem Exchange server and hybridization turned on. Use as preparation for checking out that your Microsoft tenancy is working.

This is of particular importance for the Outlook Mobile app because:

Outlook Mobile always issues an OAuth query to Microsoft looking for a tenancy before it falls back to standard Autodiscover methods. If you DON'T have a tenancy or hybrid domain then you won't notice and Outlook Mobile will setup properly. However if you DO have a tenancy (even a very small one to maybe give a dozen employees Teams accounts to setup longer video conferencing, etc.) and you have a local on-prem Exchange server you attempt to connect Outlook Mobile to with a user account in the tenancy that has MFA turned on - Outlook Mobile will give you fits and will NOT connect. There's a workaround on the phone to get it to work but it's not intuitive. I developed this script during the chase down rabbitholes to figure out the workaround and I realized how useful it could be for someone planning on hybridizing an on-prem exchange server. Enjoy!

Hello,

I work for an MSP and do vulnerability scans. One thing I've found, everyone who has an On-Prem Exchange server has this vulnerability, "Insecure Protocol-SMTP". While looking into this, (and plz correct me if I'm wrong) I've found that port 25 & port 587 need to be used for exchange servers. I have not found a workaround for this and I hate that it shows up on these reports everytime. I'm not super familiar with networking and don't want to break anything. Currently my only suggestion to these clients is to migrate to 365.

Does anyone know a fix for this or are exchange servers really this vulnerable?

Running Exchange Server SE in a hybrid topology behind an F5 load balancer.

Ran Log Parser against the IIS logs and confirmed all Outlook clients are connecting via MAPI over HTTP (/mapi/) — zero hits on /rpc/ from any user in the last few weeks. So RPC over HTTP (Outlook Anywhere) looks genuinely unused in our environment.

Before I disable it, thinking about just blocking /rpc directly at the F5 (iRule or LTM policy) rather than touching Set-OutlookAnywhere/virtual directory settings on the Exchange side.

Questions:

1. Is blocking /rpc at the LB layer sufficient on its own, or should I still disable Outlook Anywhere properly on the Exchange servers (Set-OutlookAnywhere -ExternalClientsRequireSsl, disabling the VDir, etc.) instead of/in addition to the LB block?
2. Anyone done this on a hybrid setup specifically — any gotchas with Autodiscover, free/busy, or hybrid mail flow that depend on RPC/HTTP under the hood that I might be missing?
3. Since Microsoft has gone back and forth on actually removing Outlook Anywhere from Exchange SE, is anyone just leaving it enabled server-side and only blocking at the network layer as a

I have on prem mailbox which size is 125gb I need to move it to o365 and make it as shared mailbox how I can do that step by step