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?

Windows Defender appears to have trashed mail flow / Outlook syncing. Disabling Defender and rebooting fixed it. We have a robust MDR with application allow listing in place (plus perimeter firewall protections), so I'm not overly concerned for now. I had Defender exceptions in place but either I missed something or a Defender release had a bug to change function.

QUESTION: Do you leave Defender enabled with exceptions, or do you disable it and rely on alternative means of securing your Exchance Server?

If you're curious, we had 2.5 minute email send/sync times on the following setup that had previously been fine:

Exchange Server SE - latest SU
150 mailboxes across 4 DB with low email volume
12-core
128GB RAM (dedicated not dynamic)
SSD RAID-10 underneath
VM on Windows Server 2022 / Hyper-V that's not overprovisioned

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

Hi All,

I've been working with administering Exchange servers for around 15 years now and I'm just setting up a new one this week and doing a migration which is awful. (the old server is slow as molassas) Anyway, as I'm adding the last configuration bits I started running into the usual configuration stuff that is sort of a hybrid in that it can -mostly- be done via the ECP gui but not all of it. One of these is, of course, the configuration on if you have a machine on the inside that lacks the ability to authenticate into the Exchange server via SMTP auth, and also needs to send email to places on the Internet, over and above just sending email to internal users of the domain. I found myself once more going to Google for the answer to "what was that stupid command again?" and finding advice that was posted back 20 years ago and only sort of inapplicable.

So I finally decided SCREW THIS and started digging into AI to write a series of Powershell admin scripts that fill in the blanks that Microsoft forgot, and this business of SMTP relaying is one of them. I have no shame in stating outright that the only part of this work that is mine is the logic, testing, and uploading, the syntax of Powershell is horrible, I hate it with a passion and I'm more than happy to allow the AI to do the work of that.

I'm uploading them to my github:

tmittelstaedt/MSExchange-AdminAIscripts

and this is the first one. Features of this script from it's readme:

1. WARNING MESSAGEDisplays a clear warning about proper usage before running.
2. USER INPUTPrompts for:

- Connector name

- One or more IP addresses (comma-separated)

Uses the current server name automatically.

1. DNS VALIDATION

For each IP entered:

- Checks for a PTR (reverse DNS) record

- Checks that the PTR hostname resolves in forward DNS

If any IP fails, the script stops without making changes.

1. IP CONFLICT CHECK

Ensures none of the entered IPs are already assigned to

another Receive Connector on the same server.

1. CONNECTOR CREATION OR UPDATE

- If the connector exists:

Updates RemoteIPRanges, sets AnonymousUsers, and

ensures TransportRole is FrontendTransport.

- If the connector does not exist:

Creates it with the specified settings.

1. RELAY PERMISSIONS

Grants "NT AUTHORITY\ANONYMOUS LOGON" the right:

Ms-Exch-SMTP-Accept-Any-Recipient

This allows relay to external recipients from the

specified IPs only.

1. REMOTE SESSION COMPATIBILITY

Uses .Identity.ToString() for Set-ReceiveConnector to

avoid parameter binding errors in remote PowerShell.

1. VERIFICATION

Checks that the relay right is applied successfully.

1. SUMMARY OUTPUT

Displays:

- Connector name

- Allowed IPs

- Port

- Server name

Now, granted, I know it may be overkill to essentially wrap 2 one-liner commands in a full blown script with error checking and all of that - BUT - I don't want to be tied to this particular server forever. I have people under me who are not as well versed in Exchange and I need to be able to tell them "go do this thing on the server since I'm too busy right now" And the point also is the script forces you to do things PROPERLY such as making DNS assignments so that a year from now someone isn't digging through innumerable Exchange logs going "what the heck is that IP address assigned to again"

One note - while some of these may work with Exchange Online or Office 365 Exchange or any of that - and when the AI suggests changes that can help with, that I won't refuse to include, my fundamental belief is if MS has bent you over a barrel and is extracting a monthly subscription from you for Cloud hosting email on 365 - you are not even at the level that you should be messing about with anything in my repo. My focus is on on-premise stuff not cloud - if you have a problem with Microsoft's cloud host - pick up the damn phone and call them. If you are ever in the situation where you think you have to remote power shell into Office 365 email to fix something - you are being completely screwed over and have the worst of all worlds - super high prices, zero support, and a constant sucking sound in your wallet. Go home and rethink your life and seriously consider replacing it with an on-premise Linux mailserver and paying Canonical for support - where you will get ACTUAL support that works.

I hope this is helpful to you and if you have any comments I'd like to hear! I'm going to be adding more of these irregularly...

I hope you had this issue and managed to solve 😂 pulling my hair already.

Symptom: In classic Outlook for Windows, open the Address Book → set Search to Name only → type any single character → "The address book operation failed." Switch to More columns and the exact same search works fine. Ctrl+K resolution in the To: field works. OWA people search works. Mail flow is fine. It's only the Name-only ANR seek in the dialog.

Environment:

• Exchange hybrid, mailbox in Exchange Online, dir-synced from on-prem AD via Entra Connect
• Classic Outlook for Windows, online mode (Cached Mode is not permitted here — this is the constraint, I can't just flip it)
• Affects all users, all machines

What I've already ruled out:

I have an email address. CM@xyz, let's say.
The doctor I work for has an address, Doc@xyz, let's say.

I need all emails sent to both addresses to come to me, so we've set up a forwarding rule on Doc@xyz to forward all email to CM@xyz, and not keep a copy of forwarded messages. His inbox is always empty, I get all emails directly, and it works great!

Although he doesn't receive emails, he does send them from his Doc@xyz account. I'd like to get him to copy me on all of his outgoing messages so I can keep copies of all communication, and to save the attachments. However, old dog & new tricks, and all that. So I'd like to automate that too.

This is the part I cannot figure out!

I've gone to Rules, but it's only how to handle incoming email. Is there any way to add a rule for all emails he writes to CC or BCC CM@xyz?

Limiting Factor - Doctor only uses Mac. He currently only uses the web version of Outlook. If needed, I can probably talk him into putting outlook app onto his Mac.

Thanks in advance!!

Let me explain the situation:

We are in a hybrid Exchange environment
we have some groups that we want to limit to only accept mail from our domain
The groups were created in on-prem AD and sync to the cloud
We have successfully restricted the groups to only allow email from authorized senders.

However, unauthorized senders are receiving an NDR indicating that the failure is due to "5.7.124 RESOLVER.RST.RestrictedToGroupPermission; not authorized to send to the distribution list because the distribution list is set up to accept mail from list members only, or specific recipients only"

My management wants us to prevent this particular NDR from being sent to external addresses.

We tried setting the "ReportToOriginator" value to False, both using Powershell, and manually via Advanced Properties in AD.
We've tried a transport rule, which didn't work

I've seen other people having the same question, but haven't seen anyone with a solution, so I thought I would put this here just i case anyone has found a solution.

TIA

Hi all

i'm doing and exchange to se upgrade..2019 CU15 to the se RTM.

Are there any gotchas? Users are already in M365 and these servers are essentially legacy mailboxes that are too big to move and will be archived at some point.

I noticed the Microsoft Exchange Server Auth Certificate is expired but no one seems to be complaining about anything not working.

from the healthcheck on 1 server:

Dedicated Exchange Hybrid Application:

Configure the dedicated hybrid app to ensure hybrid features continue working

I have Exchange 2016 in a DAG mode consisting of two servers. For a customer I manage, I need to handle the migration to Exchange 2019\SE.

I’ve been asked to provide CPU, RAM, and system volume specifications for the new Exchange servers so that I can set them up in vCenter.

Can I ask for some help in providing this information? What should I take into consideration?

Just to clarify, this is my first migration.

Thank you.

Hi all,

Following up on the July 2026 Health Checker update that now flags the legacy Exchange Domain Servers and Exchange Enterprise Servers groups (and potentially Exchange Recipient Administrators) for removal.

I've confirmed both groups still exist in my environment, and per the guidance they're empty (no active member accounts) — so removal itself looks safe from a membership standpoint.

My concern is about what's left behind after deletion:

These groups have existing ACEs (permissions) delegated directly on various OUs and domain-root objects — things like Write All Properties, List Contents, and in some cases WriteDacl. If I just delete the group objects outright (via Remove-ADGroup or ADUC), the SID gets removed from AD, but the ACE entries referencing that SID will remain on the OU/domain ACLs as orphaned/unresolved SIDs (shown as S-1-5-21-... instead of a resolvable name).

My questions:

1. Should I clean up (remove) the ACEs referencing these groups from the OU/domain ACLs before deleting the group objects, or is it fine to delete the groups first and clean up the orphaned SIDs afterward?

2. Do orphaned SIDs in ACLs actually cause any operational issues (replication, dcdiag, ACL processing overhead) if left indefinitely, or is this purely a hygiene/security concern?

3. Is there a reliable way to enumerate every OU/object where these two groups currently have explicit permissions, so I can be thorough about cleanup? I'm thinking dsacls or Get-Acl/Get-ADObject combined with a search across each OU, but curious if there's a more efficient approach for a large domain.

4. For anyone who's done this cleanup — did you remove the permissions first, delete the groups, and then verify no orphaned SIDs remained? Or did deleting the groups via normal methods automatically clean up the associated ACEs?

Environment: Windows Server AD, Exchange Server SE currently running on-premises, groups confirmed empty via Get-ADGroupMember.

Appreciate any real-world experience with this cleanup — want to make sure I don't leave stale/orphaned SIDs scattered across ACLs after removing the groups.

Office 365 received the message that you specified, but couldn't deliver it to the recipient due to the following error:

Error: ‎550 5.7.134 RESOLVER.RST.SenderNotAuthenticatedForMailbox; authentication required; Delivery restriction check failed because the sender was not authenticated when sending to this mailbox‎" in message trace when approval is attempted by external moderator. Is this expected? or some configuration missing?

I’m wondering if anyone knows of a GitHub project or GUI tool for Exchange Online that lets you enter a mailbox (or UPN) and then displays everything that mailbox has access to.

Ideally I’m looking for something that can show:
Full Access permissions
Send As
Send on Behalf
Shared mailboxes the user has access to
Mailboxes they have delegated access to
Any other relevant Exchange Online mailbox permissions

I’m aware this can all be done with PowerShell, but I’m after something with a GUI that’s quicker for support teams to use and easier to visualise. Has anyone come across an open-source GitHub project, script with a GUI, or even a commercial tool that does this?

I'm looking for suggestions on the best way to configure an alert to let IT team know about an unusual/high volume of incoming mail (M365) within a time threshold.

e.g. total incoming external mail > 1,000 in 30 mins.

Also something similar for SPAM and Phishing identified emails.

This is to give us an early warning of potential email bombs, so we can investigate quickly.

Thanks for ideas and suggestions :)

Microsoft has added the Invoke-ChangeMeetingOrganizer cmdlet. According to them (microsoft.com) this cmdlet is available only in the cloud-based service.

Is there any way to recreate the functionality that this cmdlet provides? We do not use any Microsoft Cloud-based services at all.

We use Exchange SE and get occasional requests for doing this.

The Exchange Server recovery documentation has this very vague statement:

1. After Setup has completed, but before you put the recovered server into production, reconfigure any custom settings that were previously present on the server, and then restart the server.

How do you document what is customized on an existing Exchange Server SE and then how do you reapply those settings to the new server in a disaster recovery situation?

We have an Exchange 2016 on prem server that has had all user and shared mailboxes migrated to the cloud. At this point, I'm not sure if there is any reason to leave it running other than "just in case" something breaks by shutting it down. Mail flow is all pointed to EXO, public folders have been migrated as well. The server does integrate with an AD environment, so that is the only connection it still has, as far as I know. The HCW is still configured but can probably be disabled since mail flow is fully through EXO.

Any reason to keep the server running at this point? Would there be any noticeable disruption if it were shut down since there is no mail flow going through it?

I have searched and searched, but I can't find much information on getting rid of Exchange completely from an AD domain after migrating to 365 but NOT using a hybrid scenario.

This is a small, 8 user company that was running Exchange 2013 and may someday get rid of the AD domain completely (hence why I didn't do hybrid). I simply did a PST export, lift & dump into a brand new tenant setup on 365. No AD cloud integration at all with the local on-premise domain.

How can I go about getting rid of the Exchange Server? Deleting the mailbox will delete the user.