EWS Autodiscover Process in Hybrid with "internal" Exchange Servers
Hi everyone, i really need help about the EWS Autodiscover process in a specific hybrid Environment. Customer is starting to use Exchange Online. For Full Hybrid configuration there is a seperate new Exchange SE with a valid certificate, NAT for IP Ranges from M365 and public available URLs for Autodiscover,EWS,... There are internal Exchange Servers which are used only for internal access. Those are the servers with all mailboxes. All URLs are configured for internal use (mail.contoso.internal) Migration is working, access to own calender is working, mailfllow is working. But there are problems to access other users calender. If a user which is migrated to Exchange Online (or via Teams) try to access another calender which is onPrem, there is no access. So i tried to use connectivity analyzer for teams integration to find out whats the problem. Result: Autodiscover resolves, connects to Hybrid and gets EWS URL as answer. But it gets the internal EWS URL from the internal Exchange Servers, not from the public available URLs which are configured at the hybrid server. I visualised the two scenarios. Number1: Thats how i thought it would work Autodiscover to autodiscover.contoso.com Hybrid answers with EWS URL: hybrid.contoso.com Connect from EXO to hybrid EWS URL Proxy to Internal Exchange Number2 : Thats what really happens Autodiscover to autodiscover.contoso.com Hybrid relays request to internal Exchange (Mailbox Server) Server answers with internal EWS URL: mail.contoso.internal Connect from EXO to internal EWS URL (which is obviously not working) So as you can see, the autodiscover process asks the internal Exchange for its EWS URLs and not as i expected the hybrid server's URLs. I always thought, the hybrid server works as a sort of proxy for every external connection from EXO. But it seems that the hybrid just relays the autodiscover request to the server which holds the mailbox. And this servers in this scenario cannot change their EWS URLs to a public resolvable FQDN. So my question is: Is this correct? Does the process always works like this or did i do anything wrong in the configuration? I hope you understand my explanation. Thanks in advance!!!Removing Retention Holds from Exchange Mailboxes
A new Exchange Online feature allows administrators to remove multiple types of holds from mailboxes (usually inactive mailboxes). It’s a great way to release holds that might be keeping inactive mailboxes lingering in a tenant. The feature doesn’t remove holds used to retain items required for eDiscovery or other compliance purposes. Even so, this is definitely a feature that needs to be carefully tested. https://office365itpros.com/2025/12/18/remove-retention-holds/
o365 public folder migration
Hi All, I have began a migration from on-prem exchange 2010 to o365 using minimal hybrid method I need to consider how i'm going to migrate public folders. I refer to two MS docs links below The first article suggests this method should be used when using a cutover or staged method https://docs.microsoft.com/en-us/exchange/collaboration-exo/public-folders/batch-migration-of-legacy-public-folders The second article references a hybrid setup but fails to mention if this includes the minimal hybrid option https://docs.microsoft.com/en-us/exchange/collaboration-exo/public-folders/set-up-legacy-hybrid-public-folders Can anyone clarify? Kind regardsExchange Server SE Licensing, Part II
Since posting my previous article about licensing and product keys in Exchange Server SE, I’ve received a ton of follow-up questions. Many of them were public, and I answered them publicly. Many were sent privately and answered privately, but I wanted to publicly share that information because I think it may generally be helpful. Discrepancies on Microsoft’s web site There were questions were about Microsoft’s https://www.microsoft.com/en-us/microsoft-365/exchange/microsoft-exchange-server-licensing-licensing-overview, which talks about Server licenses and Client Access Licenses (CALs), but doesn’t mention anything about a subscription, or Software Assurance (SA), or cloud subscription licenses. If you look at the https://web.archive.org/web/20250309171415/https:/www.microsoft.com/en-us/microsoft-365/exchange/microsoft-exchange-server-licensing-licensing-overview of that page (before Exchange Server SE was released) you’ll notice that the SE version is simply a copy and paste of Exchange Server 2019 version. I’ve said and written many times that licensing for Exchange Server SE is the same as it was for Exchange Server 2019, and that is a true statement. There were also questions about Microsoft’s https://www.microsoft.com/en-us/microsoft-365/exchange/microsoft-exchange-licensing-faq-email-for-business, which still talks about Exchange Server 2019 licensing, and also fails to mention subscriptions or SA. So, how does my article reconcile with the information on Microsoft’s licensing pages? The answer is that, while Microsoft’s licensing pages are accurate, they are also incomplete because they don’t mention anything about a subscription, SA, or cloud licenses. The good news is that I’m told by Microsoft that they will be updating those pages with complete information (and perhaps consolidating them). I don’t have a timeline to share, but updates to those pages are coming. But I’m not sure those pages actually matter, given that the source of licensing truth is https://www.microsoft.com/licensing/terms/, which has three main areas: Product Terms that describe the license terms and Use Rights of Products and Services for VL programs; Other Documents related legal materials referenced in the Product Terms; and Licensing Resources, which are links to additional information. You can (and should) also review Microsoft’s https://www.microsoft.com/licensing/terms/product/ForallSoftware/all#clause-705-h3-1 (ULTs), which apply to all software products licensed through Microsoft Volume Licensing. Note that these may not be your only rights and the only terms to which you are bound. For example, SA grants additional rights and comes with additional terms. And your VL agreement may include additional rights and terms. One of the “code changes” in Exchange Server SE RTM was the updating of a rich text file that ships with Exchange Server. This file contains the Microsoft Software License Terms (MSLT), to which you must agree in order to install Exchange Server. The MSLT is displayed, however, only when using the GUI version of Setup. But you don’t need to run Setup to view the MSLT; the file—License.rtf—is localized in several languages in the Setup files under \Setup\ServerRoles\Common\Eula\<language>. Using the Trial Edition Beyond 180 days There were several questions about using a Trial Edition beyond 180 days after installing it. Microsoft’s ULTs explicitly https://www.microsoft.com/licensing/terms/product/ForallSoftware/all#clause-723-h3-1 that “An assigned product key is required for licensed use of the software.” It also talks about technical measures that Microsoft may use to enforce these terms, but as I mentioned in my previous article, Exchange Server implements product keys, but it does not implement any activation or validation of the software. The MSLT for Exchange Server SE states “If you do not have a product key, then Section 2 (Trial) applies to you.” Some (but not all) of Section 2 is shown below. Paragraph 2 of Section 2 makes it clear that the software rights are time-sensitive and limited to 180 days after installation (2a), that you may receive periodic reminders about this time limit (2b), and that you may not be able to access data when the license term ends (2c). The language in Section 2 is used in the MSLT for multiple products. In the case of Exchange Server SE, an admin will see a message in the Exchange admin center when the Trial period ends (as described in 2b), but the product remains fully functional, and data is fully accessible, contrary to the statements in 2c. More on License Terms Paragraphs 6 and 7 on Section 2 are also worth noting: Paragraph 6 states that Microsoft is not obligated to provide support for Trial Edition deployments. While Microsoft has no obligation to provide support, they will do so, even for Trial Editions. In fact, they likely won’t ask about licensing or product keys unless its germane to the support case (for example, you can’t mount more than 5 databases on a server because it is a Trial or Standard Edition). Paragraph 7 discusses software updates, which in the case of Exchange Server SE, includes CUs, SUs, HUs, and IUs. Exchange Server SE does not check for updates, does not download updates, and does not install updates. It does include the optional Exchange Emergency Mitigation service, but that applies mitigations and does not download updates. Exchange Server SE also includes Feature Flighting which will be used by Microsoft in the future to enable features or changes present in an update, but it won’t download or install those updates automatically. Windows Server has the ability to check for and install updates, and an Exchange admin can opt into these automatic updates which include Exchange Server SUs; however, it’s a best practice to control updates to Exchange Server by installing them manually or using controlled automation. If you do install an SU manually using the GUI, then you’ll see additional License Terms, as shown below, that state the license requirements for installing the SU. Based on the above License Terms, if you don’t have a valid license for Exchange Server SE, then you don’t have the right to install the SU. Again, though, Exchange Server uses the honor system, and there is nothing that blocks the install. Client Access Licenses and Management Licenses One of the three ways to allow users or devices to legally access Exchange Server SE is by using CAL or ML equivalency licenses (the other two ways are L+SA or Exchange Online licenses). CALs are used by a user or a device, and MLs are licenses that are used by management software. “Licensing software with CALs and MLs can be complicated due to the technical nature of server products and networks.” That’s a direct quote from Microsoft’s https://www.microsoft.com/en-us/licensing/product-licensing/client-access-license#tab-overview, and it’s very true. Microsoft has user CALs, device CALs, External Connector licenses, Server MLs for managing server operating systems (OSEs), OSE client MLs, user client MLs, and core-based licensing. Exchange Server SE (like SharePoint Server SE and Skype for Business Server SE) use the Server+CAL model (which is what the aforementioned Microsoft’s licensing pages are trying to convey). Microsoft also offers what are called CAL Suites, which is a single license that covers multiple products (e.g., one CAL that covers Exchange Server, SharePoint Server, Skype for Business Server, Windows Server, etc.). There is a Core CAL Suite and an Enterprise CAL Suite, and the Enterprise CAL Suite also includes licenses for online services such as Exchange Online Archiving for Exchange Server and Exchange Online Protection. If you have deployed on-premises and you do want to move to the cloud, Microsoft also offers CAL Suite Bridges, which is a subscription-based licensing path that moves you from L+SA to cloud subscription licenses. This is where things can get tricky when comparing licensing costs between on-premises and the cloud. Remember, cloud licensing is deployment-agnostic, so you can purchase cloud licenses and deploy solely on-premises. Ultimately, the most economical approach will depend on what you are buying and how much.
Exchange SE Transport Rule Query
I'm trying to use a transport rule to send a notification to an audit mailbox with a note of the names of all attachments being sent externally with From, To, CC, BCC details. It sort of works. Rule If message has an attachment that's larger than or equal to 0 bytes Do the following Set audit severity level to 'Not specified' and send the incident report to <audit mailbox>, include these message properties in the report: sender, recipients, subject, cc'd recipients, bcc'd recipients, severity, sender override information, matching rules, false positive reports, detected data classifications, matching content. If I send a message to: 'email address removed for privacy reasons', cc: 'email address removed for privacy reasons', bcc:'email address removed for privacy reasons' with 2 attachments the report includes the following: Sender: <sender> Recipient: To & CC Attachments: Only 1 attachment name i.e. Missing an attachment name and the BCC entry Is this a bug or a feature? I presume it is just flagging the first attachment greater than 0 bytes which is annoying but that wouldn't explain the missing BCC entry.
Hybrid Configuration Wizard fails to run – manifest download error on all machines
Hello, I am unable to run the Exchange Hybrid Configuration Wizard (HCW) for our Exchange 2016 environment. The issue occurs on multiple machines and networks, so it does not appear to be a local configuration problem. Environment: Exchange Server: 2016 CU23 Windows versions tested: Windows Server 2016, Windows 10 (all fully updated) .NET Framework: 4.8 (Release 528040 / 4.8.03761) TLS: TLS 1.2 enabled, SSL 3.0/TLS 1.0/1.1 disabled Network: No proxy, firewall, or other network restrictions; internet access available Problem: When attempting to run HCW via https://aka.ms/HybridWizard, the wizard fails to start. I have also tried to run HCW offline by downloading Microsoft.Online.CSE.Hybrid.Client.application, but it immediately fails. The error log shows the following repeated messages: Downloading file:///C:/Users/.../Application Files/Microsoft.Online.CSE.Hybrid.Client_17_1_3902_0/Microsoft.Online.CSE.Hybrid.Client.exe.manifest did not succeed. Could not find a part of the path 'C:\Users\...\Application Files\Microsoft.Online.CSE.Hybrid.Client_17_1_3902_0\Microsoft.Online.CSE.Hybrid.Client.exe.manifest' This occurs on all tested machines (three PCs across three different networks). ClickOnce cache has been cleared, root certificates are up-to-date, .NET is 4.8, and TLS 1.2 is active. Attempts to resolve: Ensured TLS 1.2 is enabled and default in .NET and OS Verified .NET 4.8 installation Cleared ClickOnce cache (rundll32 dfshim CleanOnlineAppCache) Updated root certificates Tried multiple machines and networks Tried to run offline using .application file and local copy of Application Files Result: HCW fails immediately with DeploymentDownloadException / DirectoryNotFoundException for the manifest. The issue is reproducible on all tested machines. Request: Please advise if there is an official offline installation method for HCW or a way to obtain a working manifest. If this is a temporary issue with the hosted distribution, please confirm expected resolution or workaround. Thank you for your assistance.
Exchange 2016 Mail Flow is Not Working
We had issues with updating to a latest Cumulative Update and messed up our EMS and some Web Config. It seems our Exchange Server is totally bricked. So, we decided to boot our Exchange Server from backup. The backup was dated September 2025. Unfortunately, after booting up the September 2025 backup, we noticed that the internal and external mail flow is not working (our Exchange 2016 is Exchange hybrid configured). The outgoing emails are stuck in Draft folder. The following troubleshooting steps have been done to no avail: -Checked if the port 25 is open -> This port is opened -Check the network settings if the Preferred DNS Address points to the correct DNS Server --> It points to the correct DNS Server -Modified the DNS lookup under Exchange Admin Center > Servers > DNS Lookups > Internal DNS Lookups --> Added the IP Address of the DNS Server -Modified the hosts file under System32 > drivers > etc --> Pointed the IP Address of the Exchange Server to the FQDN of the Exchange Server Currently, are not sure of the next steps to do in order to fix the issue. Any advice?Exchange Server SE Licensing and Product Keys
It seems that there’s a lot of confusion about licensing and product keys for Exchange Server SE; not just here on the Tech Community, but also on LinkedIn, on Reddit, and in the general Exchange community. So, I thought I would write an article to try to clear up that confusion. Licensing Let’s talk about licensing first. Undoubtedly, changing the name of the product to Exchange Server Subscription Edition caused some of the confusion. Some mistakenly believed it meant that cloud connectivity would now be required for the first time in Exchange Server history. Others thought this meant that Microsoft would start updating on-premises Exchange servers the same way they update Exchange Online. Neither of these things are true—as with all previous versions of Exchange Server, cloud (or Internet) connectivity is not required for Exchange Server SE (although there are some features that do require cloud connectivity to be used, such as the Exchange Emergency Mitigation service and Feature Flighting). Despite the name change, though, the reality is that the https://www.microsoft.com/licensing/terms/productoffering/ExchangeServer/all (and distributions channels) for Exchange Server SE are exactly the same as Exchange Server 2019: there are three licensing options: Server licenses and client access licenses (CALs) that have active Software Assurance (SA); Exchange Online licenses; or CAL equivalency licenses. Purchasing server licenses and CALs with SA is the traditional approach and something that can be done with Exchange Server SE; however, some customers have chosen to purchase cloud licenses or equivalency licenses to modernize their license acquisition and to better manage their licenses. Qualifying cloud licenses that satisfy the Exchange Server SE CAL requirement include https://www.microsoft.com/microsoft-365/exchange/exchange-online, which provides a license equivalent to an Exchange Server Standard CAL, and https://www.microsoft.com/microsoft-365/exchange/compare-microsoft-exchange-online-plans, which provides a license equivalent to an Exchange Server Enterprise CAL, which gives you the right to use advanced features, such as In-Place Archive, In-Place Holds, Information Protection and Compliance, Custom Retention Policies, Per User/DL Journaling, Site Mailboxes – Compliance, Data Loss Prevention, Exchange Online Protection, and Cloud Voicemail. At the higher end of cloud licenses are Microsoft 365 E3 (ME3) and Microsoft 365 E5 (ME5), both of which include https://www.microsoft.com/licensing/terms/productoffering/Microsoft365 for on-premises Office servers, namely Exchange Server, SharePoint Server, and Skype for Business Server, depending on the type of agreement you have with Microsoft. For example, customers with an Enterprise Agreement and ME3 or ME5 licenses can “install any number of copies of” Office server software. In this scenario, though, all users and devices accessing the on-premises Office servers must have an ME3 or ME5 license. Note though that you don’t directly assign the license in this case; you simply need to purchase it. In addition, there are similar https://www.microsoft.com/licensing/terms/productoffering/Microsoft365/MCA available with Microsoft 365 A3 and A5 under the Microsoft Customer Agreement (MCA) program. As I mentioned earlier, these are the same requirements as Exchange Server 2019. So, if you are running Exchange Server 2019 and you have active SA, then you likely already satisfy the license requirements for Exchange Server SE, and you can deploy it in your environment without any additional licensing costs. If you are running an earlier version of Exchange Server and you have active SA or qualifying cloud licenses, then you also likely satisfy the license requirements for Exchange Server SE. But if you don’t have SA or cloud licenses (or a Volume License Agreement), then you will need to purchase qualifying licenses and sign the right agreement to be entitled to Exchange Server SE and updates. However, there is one key difference. Downgrade (aka previous version) rights are no longer available. This is simply because there are no other supported versions, so there’s nothing to downgrade to. So, if you don’t maintain a subscription, you lose the right to install updates and run the product. Product Keys Now let’s talk about product keys. As with previous versions of Exchange Server, there is no product key or license activation. You simply purchase the required licenses (or maintain your existing subscription) to get the rights to use the software and install updates. A product key validates that you have purchased a Standard or Enterprise Edition server license for Exchange Server SE. Without a product key, a server is considered a Trial Edition. The Trial edition operates identically to a Standard Edition server and can be used to evaluate Exchange in a non-production setting for up to 180 days. To continue using the server beyond this period, you must enter a product key; otherwise, the Exchange admin center (EAC) will begin displaying reminders to enter a product key on the server, which you can do using the EAC or the Exchange Management Shell. Although the EAC will display a warning when the trial period expires, there’s no loss of functionality, and the software will continue to operate as if it were licensed (except for the warning messages). If you are doing an in-place upgrade of a running Exchange Server 2019 that has an existing valid product key, the RTM version of Exchange Server SE will continue to use that key. This was done on purpose to support a smooth in-place upgrade. If you are doing a fresh install of Exchange Server SE RTM (which includes legacy upgrades from Exchange Server 2016), you can also enter a product key Exchange Server 2019, which you can get from the Volume License page in the Microsoft 365 admin center (after you’ve signed your agreement with Microsoft). Exchange Server SE is available in four Editions: Enterprise, which supports a maximum of 100 mounted databases per server. Standard, which supports a maximum of 5 mounted databases per server. StandardEvaluation, which is a 180-day time-limited Standard Trial Edition. Coexistence (aka Hybrid Deployment), which maintains the hybrid relationship with Exchange Online. As an aside, a mounted database is a database that's in use (an active mailbox database that's mounted for use by clients or a passive mailbox database that's mounted for log replication and replay). While you can create more databases than the described limits, you can only mount the maximum number of databases that are allowed by the Edition of Exchange, as determined by the product key. Note that recovery databases don’t count towards these limits. When you enter a valid product key, the supported edition for the server is established. You can use a valid product key to move from the Trial Edition to either Standard Edition or Enterprise Edition. Again, no loss of functionality occurs after the Trial Edition expires, so you can maintain lab, demo, training, and other non-production environments beyond 180 days without having to reinstall the Trial Edition of Exchange or enter a product key. You can use a valid product key to move from Standard Edition to Enterprise Edition, but you can't use a valid product key to downgrade from Enterprise Edition to Standard Edition or revert to a Trial Edition. You can only do these types of downgrades by uninstalling Exchange, reinstalling Exchange, and entering the correct product key. Product keys also apply to Edge Transport servers. When you create an Edge Subscription, the Edition of Edge Transport server is captured (as determined by the presence or absence of a product key). Edge Transport servers support two Editions: Trial or Standard. Enterprise doesn’t apply because there are no Enterprise features or mailbox databases on Edge Transport servers. Hybrid doesn’t apply because you can’t use an Edge Transport server as a hybrid server. If you create an Edge Subscription for an Edge Transport server that is a Trial Edition, it will appear as unlicensed to the internal organization. If you then enter a product key on a subscribed Edge Transport server, the server will reflect the change to Standard immediately, but the internal organization will not. To update the internal organization information, you must remove and recreate the Edge Subscription. If you don’t, the internal organization will continue to see the Edge Transport server as unlicensed, which is only cosmetic in nature (e.g., no changes in functionality). However, for compliance, auditing, etc., it is considered a best practice to recreate the Edge Subscription. As in previous versions, the Hybrid Configuration Wizard (HCW) provides the license for Hybrid servers, so it is expected that you have not entered a product key on the server. To obtain the Hybrid server license, click license this server now in the HCW and authenticate to your tenant. The HCW will update the product key on the server and refresh the page, and depending on replication latency, it might not update the Version from StandardEvaluation Edition to Coexistence Edition (Hybrid Deployment). However, you can verify the license using Get-ExchangeServer or simply toggle between the two on-premises server options in the HCW, which triggers detection and should choose the same server with updated properties. Final Note Although the Exchange Server 2019 product keys work with Exchange Server SE RTM, it is expected that new product keys specific to Exchange Server SE will be made available with Exchange Server SE CU1, which is expected in H1 of 2026. When the new keys are issues, they will be available from the Volume License area of the Microsoft 365 admin center, along with the CU1 download. I hope this clears up any confusion regarding licensing and product keys for Exchange Server SE.Exchange Server SE Licensing and Product Keys
It seems that there’s a lot of confusion about licensing and product keys for Exchange Server SE; not just here on the Microsoft Tech Community, but also on Reddit, on LinkedIn, and in the general Exchange community. So, I thought I would write an article to try to clear up that confusion. https://www.linkedin.com/pulse/exchange-server-se-licensing-product-keys-scott-schnoll-qjhic/ If you're confused about licensing or product keys, this may help.
